The Best Things to See and Do During Marathon Weekend

Welcome to Chicago! There are SO MANY fun and amazing things to do in The Windy City that it can be a real challenge to narrow the list of attractions down to the top few. That's we asked our Chicago Ambassadors for help. We tasked them with recommending their favorite three sites, tours or attractions—those experiences that are crowdpleasers and unique to this fine city.

Best Attractions Overall

See Chicago Architecture By Foot, Bus or Boat - Chicago Architecture Foundation
Chicago Architecture Foundation Tour Inside Chicago Board of Trade Building | Racertrips LLC
The Art Deco Skyscrapers tour takes you inside the Chicago Board of Trade Building.

The Chicago Architecture Foundation is renowned for its historical and architectural tours of the city. They have a whopping 85 tours to choose from, and you can go on foot or by boat, bus or bike. If you're a fan of architectural history, you'll be in your glory trying to choose the best tour for you. Even if you're not really "into" architecture, the tours offer interesting tidbits and history about Chicago and its buildings.

Here's info on just three of their most popular tours:

  • The River Cruise Aboard Chicago's First Lady—This tour has been called a “top tour in Chicago and one of the top ten tours in the U.S.” by TripAdvisor. It also comes recommended by Racertrips Ambassador Kristin. In 90 minutes, you'll cruise along the river while one of the CAF-Certified tour guides, called a docent, gives you the history on more than 50 buildings. If you're traveling with kids, they may not be as interested in the history, but they should enjoy the scenery and the experience of the boat ride.
  • Must-See Chicago—This one is for those of you who want to know more about Chicago's famous buildings, including the Wrigley Building, Tribune Tower, the Art Institute of Chicago, Willis (Sears) Tower and the Chicago Theatre. In abotu 90 minutes, the tour also covers Chicago landmarks like Millenium Park, the Chicago River and "the Loop." This is a hybrid walking/train tour. You'll need Ventra passes to get on and off the "El" (trains).
  • Historic Treasures of Chicago's Golden Age—This walking tour looks at the architectural landmarks along Michigan Avenue and State Street, highlighting buildings from the 1890s-1930s. You'll make stops at the Palmer House Hotel and the Chicago Cultural Center, while learning about some of Chicago's greatest architects, like Daniel Burnham, Louis Sullivan, Holabird and Roche.

Racertrips™ Tips

  • Considering you're in town for the Chicago Marathon, you'll want to consider the timing of the tour and the mode of transport. With the walking tours, you will be on your feet for at least 2 hours (walking and standing). If you'd like to do a tour the day before the marathon, we highly recommend choosing a boat or bus tour. However, if you choose a walking tour the day after, it may be an ideal way to loosen up those sore muscles. And while there is a good bit of walking, the tour groups tend to move along at a moderate pace.
  • One thing we love about the walking tours is that the CAF uses headsets to ensure everyone can hear. Have you ever been on a walking tour and had to strain to hear the tour guide? You won't have to do that here. Each person receives a set of headphones and a power "box" to control volume. The docent is then equipped with a microphone, which feeds directly into your headset. It makes it a cinch to hear the entire tour, even above loud city street noises and your restless toddler.

The Details

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See Chicago Architecture By Boat - Wendella Cruises

A Chicago family-owned business since 1935, Wendella comes recommended by Racertrips™ Ambassadors Shelly and Jared.

Shelly loves the great tours of the city they offer and finds the docents fun and informative. Jared says Wendella's cruises that combine architecture and wine tasting are a favorite in his household: They've taken out of town guests on those cruises about 15 times. (Unfortunately, the wine cruise don't run late into the fall.)

Here are two of Wendella's top tours:

  • Chicago's Original Architecture Tour—This 75-minute tour will take you up and down all three branches of the Chicago River, while your professional guide shares 130 years of Chicago history, innovation, architecture and architects with you.
  • Wendella's Signature Lake & River Tour—This is the tour that started it all way back in 1935. This tour tells the store of Chicago's social, cultural and political history, while also exploring more than 100 years of groundbreaking architecture. When you're on this tour, you'll start in the Chicago River and then venture through the Chicago Lock and out onto Lake Michigan with beautiful views of the Chicago skyline.
  • Chicago Sunset Cruise—If you'd like to get some time out on beautiful Lake Michigan but without an architectural lesson, consider Wendella's 90-minute sunset cruise.

Racertrips™ Tips

  • Most of the Wendella fleet offers indoor, climate-controlled seating with ample windows for those days when the Chicago weather is simply not cooperating with your tourism plans. If you want to see the city but don't have a fair-weather day, a Wendella boat cruise is one way to get out and about.
  • Feeling thirsty but can't book their wine cruise? Make one of your own! Each of the boats includes a snack and beverage bar with a selection of beer, wine, cocktails and soda. Cash and credit cards are accepted.

The Details

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Laugh Your Way through a Second City Show
Second City is a Chicago classic and comes highly recommended by Chicago Ambassadors Coach Denise, Jared, Kristen, Shelly and Angi. This is comedy and improv at its finest, and Second City helped to launch the careers of countless famous alumni, including Tina Fey, Gilda Radner, Jim Belushi, John Belushi, Dan Akroyd, Jane Lynch, Alan Alda, Steve Carell, Shelley Long, Bill Murray, Jordan Peele, John Candy, Tim Meadows, Joan Rivers, Amy PoehlerJulia Louis-Dreyfus and more. (Click the links on each name to see mugshots from their Second City days.) Shall we go on, or are you convinced that you can't go wrong with Second City? They do have several shows and multiple theaters. Their shows change regularly, so we recommend going to the newest show on the Mainstage Theater. As of September 2018, that is Dream Freaks Fall from Space. The theater itself is intimate with individual chairs placed around small cocktail tables. Expect to be sitting close to the people around you. While you can order food and drinks, you don't have to. (There is no food or beverage minimum.)

Racertrips™ Tips

  • This is probably not the best thing to do the night before the marathon. The 8 pm show runs for 2 hours plus a 10-minute intermission. That means you're getting back to your hotel well after 10 pm. If you really want to experience Second City but don't have another night available, consider The Best of Second City, which starts at 4 pm on Saturday and Sunday. It's a compilation of their best sketches, songs and improvisations from the company's 58-year history.
  • If you go to the 11 pm show, they will often do live improv after the main show for 20 or 30 minutes. This can be a treat if you really enjoy improv and are a night owl.
  • Kids must be at least 10 years old to attend and the shows are R-rated.
  • Buy tickets at least a week, if not 2 to 3 weeks in advance. The weekend shows sell out, especially the 8 pm ones.

The Details

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Sit Back and Relax for Some Chicago Blues or Jazz

The blues are an integral part of Chicago's rich history, and a trip to Chicago wouldn't be complete without checking out one of our blues clubs. Be forewarned, though, that some of these places don't get hopping until late in the evening. This is an ideal activity for a couple days before the marathon or, perhaps, a day or two after. (Although, we suspect these clubs are quieter early in the week.)

Once you've decided which evening you'll be heading out to a blue bar, you merely have to pick your venue. Here are some favorites from our Racertrips™ Amabassadors:

Kingston Mines

This venue had made a name for itself by having two different bands playing on two different stages 7 days a week. One band will play a set on one stage in one of the two main rooms. When they're done, the second band starts up on the other stage in the other room. The facility is fairly large compared to the many smaller, intimate blues bars. This can make it easier to get a seat (especially at the end of a set), although there's no guarantee. We're not sure how this fits into your plan to be well-rested for the marathon, but the music plays on into the wee hours. The cover charge is also fairly reasonable.

B.L.U.E.S.

If you want a cozy, intimate blues experience, this is the place to go. There isn't a bad seat in the house in this small, authentic venue, which has music 6 days a week (closed Mondays). Doors open at 8 pm, and the music starts at 9:30 pm. B.L.U.E.S. is also located across the street from Kingston Mines, so if you're up to for two places in one evening, it doesn't get any more convenient.

The Green Mill

Although the Green Mill serves up more jazz than blues, we have to include it here. The club and cocktail lounge opened its doors in 1907 and has a long history in Chicago, including gaining notoriety in the 1920s as a popular hangout for gangsters like Al Capone. As soon as you walk through the door, you'll feel like you've been transported back in time to a sophisticated speakeasy. The club has music 7 days a week, with some performances starting as early as 3 pm and 5 pm. (This may be a better fit for your marathon sleep needs than some of the clubs that start later.)

Andy's Jazz Club & Restaurant - Under 21 Permitted for the 5 pm & 7 pm Shows

If you're traveling with your family and want to hear Chicago blues or jazz, it can be tricky because of the age restrictions. However, Andy's welcomes under-21 guests at their 5 pm and 7 pm shows, provided you make dinner reservations and arrive by 6:45 pm. Their downtown location (near Michigan Avenue and the river) may be convenient to your marathon hotel, and a 5 pm showtime may be easier to fit into your schedule.

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Best Ways to Enjoy Chicago Outdoors

Kayaking the Chicago River

Kayaking the Chicago River, See the Loop, downtown | Racertrips LLCOne of our favorite ways to see this magnificent city is by kayak. There's something amazing about being in a kayak on the Chicago River—many feet below street level—and looking up at all of the buildings, bridges and people.

During the summer months, there are a number of places to rent kayaks on the river and on the lake. By October, your options will be somewhat weather-dependent.

For rentals, we suggest starting with Wateriders, which launches on the river just behind the East Bank Club and just north of the "Y" in the river where you can choose to go north, east or south. Wateriders charges $10 less per her hour than their nearby competitors (as of 8/7/18), and they launch at a prime spot.

However, if you're staying close to Michigan Avenue and Wacker Drive, you may want to rent from Urban Kayaks, which launches from the east end of the River Walk. You can still follow the route we recommend below: You just start at a different point.

Recommended Route for Novice Kayakers, Families or Those on a Time Crunch

Once you've launched your kayak, Wateriders asks you to paddle north up to the Grand Avenue bridge (just a short distance - the bridges are clearly marked) and then crossing the river. Then, you can head back south toward the heart of the action.

If you're newer to kayaking, paddling with kids or only have about an hour to spend on the water, we recommend continuing south to Wolf Point (or the "Y" in the river), crossing the river at the Lake Street bridge and then heading east toward Lake Michigan. This is the gem of the route and not to be missed. You'll paddle along the Chicago River Walk, which has been transformed in the past few years from plain slabs of concrete to an outdoor walking and eating hub. You'll see tons of scenic places to sit, as well as a wide selection of restaurants, cafes and places to grab a drink.

Above the River Walk, you'll see historical buildings and modern skyscrapers alike—Merchandise Mart, the Wrigley Building and Marina City, the "corn cob" shaped twin buildings made famous by The Blues Brothers. You can continue on to the bridge that crosses Lake Shore Drive, where you'll need to cross the river and head back toward your starting point. If you pass up the bridge, you'll head toward the lock system and the entrance to Lake Michigan. Wateriders specifically says at the beginning of your journey not to go to the locks or the lake.

Recommended Route for Experienced Kayakers

If you're experienced kayakers and have 2 hours to devote to the water, we recommend not turning east at Lake Street. Instead, continue south into the South Branch of the river and paddle down to the Jackson Street or Van Buren Street bridges. You'll pass restaurants along the river, Union Station and Willis Tower (or the Sears Tower for those of us who resist change). You'll also be able to see Ceres, the Roman goddess of agriculture, who adorns the top of the Chicago Board of Trade building. (If you do any architecture tours while you're here, you'll likely hear more about this statue.)

Then, after you paddle back north, you can head east into the river toward the River Walk and Lake Michigan. Going this way saves you 10-15 minutes of time waiting for a break in river traffic in order to cross.

Racertrips™ Tips

  • If you're traveling with young children, we recommend calling the kayak outfitter first to make sure they can accommodate you.
  • During nice weather, there is a LOT of traffic on the river. Be prepared to pay attention and to yield to approaching water taxis, tour boats and private boats. If you can kayak during the week, you'll find the experience more enjoyable because the river will be much less busy.
  • If Wateriders is closed for the season, check out Urban Kayaks or Kayak Chicago. Urban Kayaks launches from a prime spot along the river near Lake Michigan. You can easily do the same route we recommend here, just in a different order. Kayak Chicago launches farther north in the river, so you'd need to paddle south for 20-30 minutes to get to Wolf Point (or the "Y" in the river, where you could then head east to see the best sites).
  • If you're a novice kayaker and/or traveling with kids and aren't sure you're ready for the bustling river, consider kayaking farther north where you'll be able to relax and see more nature and less watercraft. Chicago River Kayak and Canoe launches at 3400 N. Rockwell. This is a scenic paddle; you just won't see the city sites.

Wateriders - The Details

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Bike, Walk or Jog along Lake Michigan

Montrose Harbor, Chicago, Lake Michigan | Racertrips LLC
See stunning views of Lake Michigan and the Chicago skyline when you bike, walk or jog along Lake Michigan.

One of the most beautiful places to go in Chicago is the lakefront, not only for the views of Lake Michigan but also for the spectacular views of the city skyline. And depending on where you go, it can also be extremely peaceful and relaxing.

The marathon route does not take you along the lake at any point, so you'll want to carve out time before or after the marathon to head over to the Lakefront Trail, a paved multi-use path that spans nearly 20 miles from Ardmore Avenue at the north edge of the city all the way south to 71st St. For many of you, the lakefront will be a short, easy walk from where you're staying.

To see the lakefront, you can take a leisurely walk, lace up your running shoes, rent a bike from one of the city's many vendors* or buy a day-pass for a Divvy bike. If you'd like to go point-to-point or aren't sure how far you want to go, a Divvy bike is a great choice because you can dock the bike at any of the numerous Divvy stations across the city and along the lakefront. (You don't have to return to where you started.)

Because you can see more by bike without tiring your legs too much, we're going to focus the rest of this post on suggested bike routes and our favorite scenic spots. The starting point for each is Grant Park/Millennium Park. If you are starting farther north or south of there, take a quick peak at a map to adjust your route accordingly. We also encourage you to pack snacks or a picnic lunch for a bit of a respite along the way!

To the South

Many of the most serene areas along the lake are south of the Loop, and Racertrips™ Ambassador Jared is a big fan of biking in this direction. Once on your bike, head east, cross over Lake Shore Drive at Monroe Street, Jackson Drive or Balbo Drive to the Lakefront Trail and then turn right to head south. You'll be biking along Monroe Harbor (which is where the swimming leg of Chicago's Triathlon takes place) toward The Field Museum, Shedd Aquarium and Adler Planetarium. As you approach the Field Museum, the lakefront trail turns left to take you beside and then behind the aquarium.

Photo Opp:
Stop beside the aquarium to look back and get beautiful views of the Lakefront and the skyline.

Once back on your bike, continue around to the back of the museum and into a short tunnel that crosses under the road going to Adler Planetarium. As you come out of the tunnel, look for a path on your left that will take you to Northerly Island, a tranquil, 91-acre peninsula that offers wide open green space, a beach and many great photo opps.

If you're a fan of "Chicago politics," you might get a kick out of the history behind the park area: From 1946 until 2003, Northerly Island was the site of Meigs Field, a small airport serving the city's business district. In 2003, Richard M. Daley had the runways torn up and removed illegally in the middle of the night in the name of homeland security. It was then converted into the park space that it is today.

After you leave Northerly Island, head back to the lakefront trail and continue south toward Solider Field, home of the Chicago Bears football team, and McCormick Place (site of the race expo). Just after McCormick Place, you'll pass Memorial Park, which is a tribute to fallen firefighters and paramedics, and then a bird sanctuary. We encourage you to take in all of the scenery, from the lake to the trees and flowers on both sides of the path. Continue on to 31st Beach, which is about 3 miles from where you started. This may be enough for you and your group!

If you want more, continue another 3.6 miles to Promontory Point, another scenic (and man-made) peninsula extending out into Lake Michigan. The Museum of Science and Industry is just south of here and an ideal place to turn around or wrap up your ride. If you've had enough biking, you can dock your Divvy at the museum, request an Uber/Lyft or take mass transit. If the latter, you'll want to take the number 6 bus north to the Loop or the South Short Line Metra train to Millennium Station (in the Loop).

To the North

The busiest part of the Lakefront Trail is to the north, primarily from Navy Pier to Addison Street. If you're comfortable dodging and weaving around walkers, runners and other bikers, there are plenty of beautiful things to see in this direction, too. From Grant Park, cross over Lake Short Drive and turn left on the Lakefront Trail. You'll pass the Columbia Yacht Club, a large ship that's permanently anchored in DuSable Harbor, and will catch site of Navy Pier.

If you want to see the view from the tip of Navy Pier, now would be an ideal time to do that. (Again, you'll probably have to do a lot of dodging and weaving, so bike carefully.) We also highly recommend taking a detour into Milton Lee Olive Park for a peaceful view of the city. This park is just to the north after you leave Navy Pier. (See our full description in the Navy Pier section of our guide.)

Once you exit Milton Lee Olive Park, continue north again and enjoy biking right along the water. You'll pass Oak Street Beach and, about a half mile later, the chess pavilion, which you've probably seen in B-roll footage of Chicago.

Photo Opp: As you near the chess pavilion, the path will split. The bike path continues to the left and the walking path to the right. If you stay to the right for abotu 50 feet past the chess pavilion, you can stop along the water and take a photo with the lake and city skyline behind you. This is a popular spot for wedding parties to take their group shots!

From here you have a choice: Continue north for a couple more miles to extend your ride, or cut it short in favor of the Lincoln Park Zoo, the nature boardwalk and one of our favorite photo spots.

Bike North or Hit the Zoo and Surrounding Nature Areas

If you're enjoying your ride, continue north on the path until you reach Belmont Harbor. This will give you continued scenery and a bike ride that's abotu 5.5 miles one way. Once at Belmont, you can dock your Divvy bike and grab a bite to eat or catch the Red Line back to the Loop.

If you'd like to check out the zoo, however, bike to North Avenue Beach and then look for the bridge that crosses over Lake Shore Drive. This will put you at the exit for the zoo parking lot. There are a couple of paths and sidewalks here that you can bike on. Head north until you pass the soccer field and then come upon a parking lot and a stone monument featuring Ulysses S. Grant on horseback. Not sure what Ulysses looks like? That's OK. It's the only monument right there. You'll know you're at the right place because there's a path that goes up behind it and a path beneath and archway that goes through it.

Take the path that winds up behind the statue, goes north for several feet and then heads west (away from the lake). You'll soon find yourself on a bridge overlooking the zoo's south pond, nature boardwalk, Cafe Brauer (which is on our restaurant guide)—and our next photo opp spot. This bridge is another popular spot for bridal parties and engagement pics. In one shot, you can get water, nature and a beautiful view of the city.

It's 1/4 mile from here to the nearest Divvy docking station. If you want to walk around just a little bit, you may just want to walk with your bike. If you're ready for some food or really want to explore the boardwalk, zoo and gardens north of the zoo, you may want to take the little trek and dock your bikes now.

When you're ready to continue on, head to the west side of the zoo and then follow the paved path that goes to your right (heading north). Depending on where you start, it will take you past the western entrance to the zoo, the gardens north of the zoo and to the Lincoln Park Conservatory. Once you pass the conservatory, turn to the right (don't cross Fullerton Avenue) and look for the entrance to the Alfred Caldwell Lily Pool.

After taking in the sites here, you can cross over Fullerton Avenue and do a loop around scenic North Pond, too. The path to the west of the pond is paved and suitable for bikes. If you stay along the pond on the east side, the path is not paved and not suited for bikes. You can dock your bike and walk at the Divvy station in front of the Peggy Notebaert Nature Museum.

To bike from here back to the Loop is about 4 miles. If you've had enough biking, you can pick up the Clark Street bus to get back to the Loop or walk 0.9 miles to the Fullerton Red Line station.

* We haven't reviewed any bike vendors yet for this guide. But you can generally find bike rentals at Navy Pier, Millenium Park, North Avenue Beach and Montrose Beach (north of the beach along the lakefront and just south of Foster Beach).

Stroll Michigan Avenue and Chicago Riverwalk

Chicago RIver Walk | Racertrips LLC
Just 2 years old, the Chicago River Walk offers a 1.25 stretch of places to eat, drink and relax along the scenic Chicago River.

When traveling, some of the best experiences come from those sites you see on foot—and without any admission fees. For one such experience in Chicago, Racertrips™ Ambassadors Shelly and Angi suggest a trip down The Magnificent Mile (Chicago's premiere shopping area), followed by lunch or dinner at the Chicago Riverwalk.

Even if you're not a shopper, we promise that there is a lot to see along the way, such as the Water Tower that survived the Chicago Fire of 1871, the historic Wrigley Building and Tribune Tower. And yes, this is a "touristy" thing to do, but it's worth check out at least once.

The Michigan Avenue Walk

Start at John Hancock Center, one of Chicago's iconic skyscrapers. From here, you can go up to the observation deck (for a fee), or depending on time of day, take the elevator up to The Signature Lounge on the 96th floor. You can enjoy spectacular views, light fare and drinks, all while skipping the line and the price of admission.

From the John Hancock Center, you can head to Water Tower Place on the next block south. If you are a shopper, you may want to cruise quickly through the multiple levels, which include most of the regulars you'd expect, plus some notables like American Girl Place and Vera Bradley. (If you don't get your fill here, you may want to head across the street to the 900 North Michigan Shops.)

Not a shopper? Skip this and go across the street to the actual Water Tower. This castle-like structure was built in the 1860s to pump and store water. It became a famous landmark when it was one of the few structures to survive the Great Chicago Fire of 1871. A modern day tourist stop, you can also wander inside to see work from local photographers and artists.

From the Water Tower or Water Tower Place, continue your walk south past everything from Tiffany & Co., Burberry and Salvatore Ferragamo to Nike Chicago, Under Armour and the Disney Store. You'll also pass a slew of well-known hotels and restaurants, including one of the Gino's East pizza locations we recommend and at least one of the Garrett Popcorn Shops that come recommended by Racertrips™ Ambassador Coach Denise.

As you approach the Chicago River, you'll find the historic Wrigley Building (built in 1924) on the west side of the street and the neo-Gothic Tribune Tower on the east side. From here, you can cross over the Chicago River to the River Walk. On your way, look down at the river and imagine it being an odd day-glo green. If you've ever heard the stories about Chicago dying the river green for St. Patrick's Day, this is where it happens.

The Chicago River Walk

Just a few years ago, this stretch along the Chicago River was nothing but a desolate stretch of concrete and boarding areas for boat cruises. (In fact, if you go to Google Maps and use the Street View, you can see what it used to look like.) But in 2016, the city officially opened this 1.25 mile long path as another urban outdoor space where residents and visitors alike can now walk, run, relax, eat or drink and enjoy the all-too-short summer season.

Once you're on the other side of the river, look for one of a few staircases taking you down to the river level. You can head east a short distance to Urban Kayaks (if you want to plan for another day) and the very laid back tiki bar that is Island Party Hut & Boat Charters. If you head west, you'll find several other restaurants and bars, along with a Vienam Veterans Memorial, a fountain and a floating garden.

If you've worked up an appetite during your walk along Michigan Avenue, there are plenty of places to choose from for a snack, hearty lunch or a cocktail. As you near the end of the River Walk, you'll come to a the "Y" in the Chicago River and several places to sit and lounge and take in the scenery.

Racertrips™ Tips

  • Instead of starting at the north end of Michigan Avenue, you could start with lunch at the River Walk and then end with cocktails at the Signature Lounge in the John Hancock Tower. This gives you spectacular views of the city with no lines and without the cost of admission you'd pay at the tower's 360 Degree Observation Deck or at Willis Tower.
  • This is ideal if the weather is mild, and you're up for some walking. You probably should avoid this the day before the marathon, unless you really limit the amount of time you're on your feet.

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Fun for Families

Navy Pier

Navy Pier comes recommended by Racertrips™ Ambassadors Coach Denise and Kristen. It's great for families not only because kids can be outside and moving around, but also because it is home to the Chicago Children's Museum and Pier Park with the Centennial (Ferris) Wheel, wave swinger and carousel rides. There are a number of shops and restaurants, including Coach Denise's favorite burger joint—DMK Burger Bar. And although the kids probably won't appreciate it, you can also seek out the statue of Bob Newhart from his TV days as a psychologist in the 1970s.

A number of boat tours go out of Navy Pier, too, including some of the architecture tours, speedboats and sunset dining cruises. (In October, some of these may depend on the weather.)

For a beautiful view of Lake Michigan, walk all the way to the end of Navy Pier. The wind picks up here, but it's worth the chill to take in the view. This end of the pier also features the 8-ton anchor from the U.S.S. Chicago, a warship that was funded by the citizens of Chicago and that saw action in World War II, Korea and Vietnam.

On the way back, you may want to stop for a beverage or listen to live music at the Miller Lite Beer Garden. This can be a beautiful spot to relax and see the city skyline. However, it will likely be more crowded on October 6 because of Oktoberfest, an all-you-can-eat, open bar event at the beer garden. (If loading up on beer and brats is the way you prep for a marathon, you're in luck!)

If the weather is dismal, Navy Pier is also home to the Chicago Shakespeare Theater and an IMAX theater.

Racertrips™ Tips

Milton Lee Olive Park Chicago | Racertrips LLC
Photo of Milton Lee Olive Park entrance courtesy of TripAdvisor.
  • There are free trolleys to Navy Pier from several downtown locations. In October, they only run on  on Saturdays and Sundays. (Download a trolley route map.) If you're going to Navy Pier on another day, you can get there by taking the Grand Avenue (#66) bus east or by walking, depending where you're staying and how much you want to be on your feet.
  • If you're walking to Navy Pier, we recommend taking a few minutes to visit Milton Lee Olive Park, which offers picturesque views of Lake Michigan, Lake Shore Drive, and part of the city skyline in peaceful, quiet surroundings. The park is located to the north of Navy Pier between Ohio Street Beach and the water treatment plant that is parallel to Navy Pier. If you follow the foot path in or out of Navy Pier from the north, look for a subtle gated entryway.

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Millennium Park, Maggie Daley Park and Buckingham Fountain

If you want to be outside and want a crowd pleaser for the whole family, we recommend Millennium Park and Maggie Daley Park, followed by a trek through Grant Park to Buckingham Fountain. Here's a rundown of what you can see and do...

Start at Crown Fountain

Often referred to in some fashion as "the faces" or "the face statue," this popular work of art is located at Monroe Street and Michigan Avenue, the fountain gets its nickname from the two 50-ft LED that project close-up images of human faces. They're on opposite ends of a reflecting pool, where scores of kids in the summer play, splash, run and jump through the water. If it's a nice day, you can probably lose an hour here while your kids play. Not traveling with kids? There's also good people watching.

Crown Fountain Chicago | Racertrips LLC
Kids love to splash and play in the reflecting pool at the Crown Fountain.

Continue on to The Bean

Walk north just a short distance to what is officially called the Cloud Gate, but which everyone calls The Bean. Why? Well, once you see it, you'll know why. It genuinely is a pretty cool sculpture—the smooth surfaces, the mirror finish, the reflection of the city skyline. And it's fun to try and figure out the best angle for a photo. You can even practice taking selfies in the reflection of the sculpture itself. This is a very popular spot with tourists so be prepared to have many strangers in the background of your photos.

Head Over to Lurie Garden and Maggie Daley Park via the BP Pedestrian Bridge

From The Bean, head east toward the band shell (Jay Pritzker Pavilion) and the large swath of green grass. Ultimately, you're heading to the large, winding pedestrian bridge that starts on the other side of the lawn. As you're walking, Lurie Garden will be on your right. If you're a plant and flower aficionado, take some time to stroll through here and take in the city garden's flowers, plants, water features and overall peacefulness. If you're traveling with youngsters, you may be lucky to catch a glimpse of the garden as they pull you toward Maggie Daley Park.

Maggie Daley Park

Maggie Daley Park Chicago | Racertrips LLC
You can rent scooters or rollerblades and then take a spin around the skating ribbon at Maggie Daley Park.

This gem on the lakefront offers an assortment of activities, but the highlights are the skating ribbon, the climbing wall and the 3-acre children's playground for kids ages 2-12. Let's start our trip with a visit to the skating ribbon and climbing wall. In the winter, the skating ribbon becomes one of Chicago's favorite outdoor ice skating areas. In the summer, the ribbon is open for rollerblading, scooters and even skateboards. Didn't pack your rollerblades for this trip? No worries. You can rent blades and scooters right there in 30-minute increments. This is a great way to tire out the little ones!

If you want to try rock climbing instead, you can rent all the equipment you need and then seek assistance from the instructors who are stationed out by the climbing walls. Kids as young as 4 years old can give this a whirl.When you're done scootering or climbing, we recommend taking a bathroom break before you head to the playground. We mention this because there are no real bathrooms by the playground, and it's a solid 10-minute walk with little ones.

Practical matters behind us, let's head over to the playground. It's an impressive size and offers everything from an Enchanted Forest to a toddler-sized ship and a long, swinging bridge to massive slides that start from towers approximately two stories up. There's simply a lot to see and do here, and part of the fun is going from one section of the playground to the next to see what is around the bend or on the other side of the trees.

Buckingham Fountain

If you have energy for one more site, let's make it Buckingham Fountain. Head south for about 1/2 mile by walking parallel to Lake Michigan and Lake Shore Drive. You'll exit Maggie Daley Park, cross Monroe Street and then head into Grant Park. As you walk, you can enjoy large fields of green grass, views of the lake and the park's beautiful plans and shrubs. The fountain is beautiful any time of day, but the highlight is the geyser of water that shoots 150 feet into the air for 20 minutes at the start of every hour (beginning at 9 am). Beginning at dusk, the jet of water is accompanied by a light and music display.

From Buckingham Fountain, it's a fairly quick walk back toward Michigan Avenue, where you can head to dinner, your hotel, etc.

Racertrips™ Tips

If you're going through Maggie Daley Park with young children, we recommend hitting a bathroom before you go to the park or, upon arriving at the park, taking a bathroombreak in the park building by the climbing wall. Once you're in the playground section of the park, the only "facilities" available are porta potties and it's a solid 10-minute walk back to the real bathrooms. (Yep, bit of an "oops" in the planning there.)

  • If the weather's nice, we recommending pickup up sandwiches and other provisions near your hotel and having a picnic in the park. There are plenty of places to sit in the shade in any area of the park. At Maggie Daley Park, there are plenty of picnic tables and several open grassy areas.
  • Doing this right before race day? It can be a lot of walking or time on your feet, but you can also take a load off on any number of benches and picnic tables. And if your kids are a bit self-sufficient, you can have a seat while they play.

Learn More

The Bean or Cloud Gate Chicago | Racertrips LLC
There are lots of ways to snap cool pics at "The Bean."

Chicago Museums

(Please note: We only feature sites and attractions that are recommended by our Racertrips™ Ambassadors. However, as a GetYourGuide.com partner, Racertrips LLC  may earn commision from qualifying ticket purchases.)

Art Institute of Chicago

Chicago has a number of world-class museums, and the Art Institute of Chicago just may top the list.

The Art Institute of Chicago is one of the top museums in the world and has an impressive array of art from many different periods and cultures. Some of the most famous works include:

  • Van Gogh’s The Bedroom
  • Georges Seurat’s A Sunday Afternoon on the Island of La Grande Jatte
  • Edward Hopper’s Nighthawks
  • Grant Wood’s American Gothic
  • Examples from Claude Monet’s Water Lilies,
  • Gustave Caillebotte’s Paris Street- Rainy Weather 1877
  • Pierre Auguste Renoir’s Two Sisters Aka On The Terrace

If you're a fan of modern art, you won't want to miss the Art Institute's galleries of contemporary art, which were just re-opened in December 2017 to unveil 44 iconic works by artists like Andy Warhol, Roy Lichtenstein and Jasper Johns. These 44 pieces were donated by Chicago collectors Stefand represent the largest gift in the museum's 136-year history.

Racertrips™ Tips

  • You can save money and time on admission if you purchase a Chicago Explorer Pass or Chicago Go Card in advance, since either will get you into the museum and many other attractions for a low fixed price.
  • Don’t miss Hans Haacke’s Gift Horse on the Art Institute’s Bluhm Family Terrace, which is the first time that the work will be seen in North America.
  • Kids may enjoy the Elizabeth Morse Touch Gallery in the Modern Wing, which features several sculptures that visitors can touch.

The Details

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The Field Museum

The Field Museum is one of the largest natural history museums in the world and has an interesting history on its own: It originated for the 1893 World’s Columbian Exposition and the artifacts displayed at the fair. In fact, Tiffany & Co's gem collection was a huge hit at the Exposition. When the exposition closed, the World's Fair President Harlo Higinbotham purchased the entire collection and donated it to the then-new museum. Today, this collection is part of the Grainger Hall of Gems, with more than 600 gemstones and 150 pieces of antique and contemporary jewelry.

In addition to the gem collection, the Field Museum offers something for every member of the family. Are you or one of your kids a fan of dinosaurs? At The Field Museum, you can see Maximo the Titanosaur, literally, the biggest dinosaur that scientists have discovered to date. This Patagotitan lived more than 100 million years ago in what is now Patagonia and weighed about 70 tons, the equivalent of 10 African elephants. The Field Museum's touchable cast of the dinosaur stretches 122 feet across Stanley Field Hall and stands 28 feet tall.

The Field Museum is also renowned for SUE the T. Rex, who unfortunately, is only partially visible right now. The museum is moving SUE to a new home on their second floor, and the exhibit is set to open later this year. According to the museum's website, you can see SUE on most days. But sometimes, the T. rex may be obscured due to the construction.

In addition to the dinos, the Field Museum has one of the largest collections of mummies in the United States and the Underground Adventure experience, where you shrink to 1/100th of a person’s actual size to get a bug’s eye view and explore giant worm tunnels and soil chambers.

Racertrips™ Tips

  • You can save money and time on admission if you purchase a Chicago Explorer Pass or Chicago Go Card in advance. Either card will get you into the museum and many other attractions for a fixed price.
  • October 8 is a free admission day. The good news: You can get your whole family in for free. The bad news: It's likely to be very busy with marathon visitors and school kids. Chicago Public Schools are closed Oct. 8, as are many private schools.

The Details

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Adler Planetarium
The Adler was the first planetarium in the United States and is part of Chicago's Museum Campus, which includes the Shedd Aquarium and The Field Museum. Adler's mission is to inspire exploration and understanding of the universe. The planetarium's Grainger Sky Theater offers audiences the most immersive, technologically enhanced theater experience ever developed. Twenty ultra-high definition projectors create the largest single seamless digital image in the world.

Racertrips™ Tips

  • The planetarium comes with a bonus: The American Institute of Architects says the Adler Planetarium has the "best view of the Chicago skyline." We agree! Be sure to snap some selfies before you leave.

The Details

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Shedd Aquarium
Racertrips™ Ambassador Jared loves the Shedd: He's a sponsor and a volunteer there. He points out that many of their mammals were injured in the wild and that the aquarium will rehab the mammals and re-release them if they can survive. If not, they remain at the Shedd as a permanent home. As you can imagine, the Shedd is a great place for kids, and they get to encounter 32,000 animals from the world’s aquatic environments, including sting rays you can touch and a live dolphin show. The Shedd was the first inland aquarium with permanent saltwater exhibits as well as freshwater habitats.

Racertrips™ Tips

  • If, by some miracle, you have time or energy the day of the marathon, you can gain free entry for 1 person by presenting a valid Bank of America/Merrill Lynch ATM, credit or debit card, along with photo identification.
  • Want a beautiful snapshot of Lake Michigan and the city skyline? Before or after your visit, head to the north side of the aquarium (by the lake and the Lakefront Trail).
  • This is a popular attraction for children.

The Details

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Museum of Science and Industry

Like the Shedd Aquarium, Racertrips™ Ambassador Jared also recommends the Museum of Science and Industry. "We have a history here that's a little more diverse," he says. "We had all these expositions that were big at the time. As technology advanced, we got to freeze those earlier moments in time and put that into a museum. It's just really neat." The museum features a lot of displays about Chicago technology, as well as the very Chicago-centric Columbia Exposition.

Popular permanent exhibits include Science Storms, The Great Train Story, The Idea Factory, Colleen Moore's Fairy Castle and the Baby Chick Hatchery. Popular special exhibits include the U-505 Submarine, the only German submarine in the United States, and the Coal Mine, which takes visitors through a mine shaft and helps them experience the dangerous and strenuous work of coal mining.

Racertrips™ Tips

  • If you have time after you see the museum, explore the lagoons and gardens of Jackson Park, which are directly behind (south of) the museum. These have been here since the 1893 Columbian Exposition and include the recently-restored Wooded Island and the Japanese-themed Garden of the Phoenix.
  • If you're full of energy and not worried about wearing out your legs, you can rent a Divvy bike near Grant Park/Buckingham Fountain and bike about 7 miles down the Lakefront Trail to at the museum. See our "Bike, Walk or Jog along Lake Michigan" recommendation for more details.

The Details

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Meet our Chicago Ambassadors

Jose Maria H. Gabriel, MD
Gaby ran his first marathon at age 50 in Bordeaux, France, and has since finished more than 64 marathons and 4 ultras. He's a qualifying member in both Marathon Maniacs and the 50 States Marathon Club.
Kristin Vilt
Kristin is a two-time Chicago Marathon finisher, and she'll add a third Chicago to her tally in 2018. She's also finished several half marathons in Chicago and Duluth, MN.
Coach Denise Sauriol
Coach Denise, aka "The Marathon Whisperer," has been running since the first grade and says running is still her BFF. The 2018 Chicago Marathon will be her 100th marathon and...
Jared Rummel
Jared is a three-time Chicago Marathoner and an avid triathlete, who qualified for the USA Triathlon National Championship every year from 2012 until 2018.
Shelly Hennig
Shelly is a proud member of the "One and Done" Marathon Club. She completed the Chicago Marathon in 2011 and counts it as a great achievement...
Lyman (Chip) Welch
Chip is a half-marathoner, triathlete and co-founder of Racertrips LLC. He's completed the Chicago Triathlon seven times, and he's run several half marathons...
Angi Semler Welch
Angi is a co-founder of Racertrips LLC and has completed four marathons, including the Chicago Marathon three times. Her fourth marathon was in D.C., and ...
Bryan O'Sullivan
Bryan is a half-marathoner and running enthusiast. Although these days, he logs more frequent flier miles than he does running miles...
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Bonus Touring Ideas

Want some additional ideas for things to do in Chicago? While we haven't yet reviewed the activities listed here, we wanted to share them with you...

Disclaimer: As a Get Your Guide partner, Racertrips LLC  earns from qualifying purchases.

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