Why You Need to See Chicago by Kayak

Kayaking the Chicago River, See the Loop, downtown | Racertrips LLCOne of our favorite ways to see the beautiful city of Chicago is by kayak. There’s just something special 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 marathon weekend in October, your options will be weather-dependent. If it’s been a warm fall, a few places will still be open.

We suggest first checking to see if Wateriders is open. This kayak outfitter 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 prefer 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 from the eastern most point and paddle west.

Recommended Route for Experienced Kayakers

If you’ve rented from Wateriders, they’re going to instruct you to paddle north up to the Grand Avenue bridge (just a short distance – the bridges are clearly marked) and then cross the river. Once you’ve safely crossed the river at the bridge, you can head south toward the heart of the action.

If you’re experienced kayakers and have 2 hours to devote to the water, we recommend continuing south into the South Branch of the river. This route allows you to see more of the city and minimizes the number of times you have to cross the river, thereby saving you 10-15 minutes waiting for a break in river traffic.

As you head south, you’ll pass river-side restaurants, 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 in honor of the commodities exchanged there. (If you do any architecture tours while you’re here, you’ll probably hear more about this iconic statue.)

A good turnaround point in this direction is the Jackson Street or Van Buren Street bridge. Head north again until you reach the “Y” in the river. From here, turn right to head east toward the River Walk and Lake Michigan. Continue your trip by following the route we outline in the next section.

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

If you’re newer to kayaking, paddling with kids or only have about an hour to spend on the water, we recommend skipping the South Branch and heading east right away.

Once you’ve turned around at the Grand Avenue bridge and are heading south, continue to Wolf Point (or the “Y” in the river) and then cross the river at the Lake Street bridge. This will point you toward Lake Michigan. This is the gem of the route and a must-see. 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 east to the bridge that crosses Lake Shore Drive, where you’ll need to cross the river again 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. We don’t recommend that, and Wateriders specifically says at the beginning of your journey not to go to the locks or the lake.

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. You’ll need to pay attention and yield to approaching water taxis, tour boats and private boats. If you can kayak during the week, 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.
  • 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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