Chicago · CANOES & KAYAKS
The 11 best canoes & kayaks tours you can book right now, with what each costs, how long it runs and who it suits. Number one is top for a reason; start there.
3-hour Chicago food walk with 5 iconic bites, downtown landmarks, and a free 2-hour bike or kayak rental for $84.
“AMAZING! Dylan our tour guide made the day so much fun! The food was amazing and I was so full by the end of the tour but completely satisfied. As a solo traveler I couldn’t rate it anymore.”
Kayak calm Lake Michigan from Ohio Street Beach near Navy Pier for 1 or 2 hours, with skyline views and easy downtown access.
“No hassle, Evan was great helping us get started. He was very accommodating and felxible. Great experience.”
Kayak the Chicago River downtown for 2 hours with a safety lesson, single or tandem boats, and skyscraper views for $62.
“The person checking us in and giving us our kayaks gave the worst advice on where to kayak. Also, there were so many dead fish and birds floating and a lot of trash. My husband who ended up finishing it and going the opposite way, said it was much better and cleaner.”
Moonlight kayak on the Chicago River for 1.5 hours, $58. See Willis Tower and Marina City lit up, with a guided night route.
“Kayaking at night was great, but the activity details were misleading. There were at least 30 participants (even though the activity states that it is limited to 6 participants). We received a notice to check in by 19:30 for this activity to start at 20:00. We were not in the water until a few minutes past 20:30 and docked back at 21:52. This was hardly a tour as the guide did not provide any info and were mainly there to herd us to the sides or cross the river. There was very little kayaking done. We would have preferred renting but unfortunately, this was the only company I found that…”
Kayak Chicago River at sunset for 90 minutes, gliding past Willis Tower and Merchandise Mart, with guides and great golden hour skyline views.
“This was a fun activity that puts you right in the middle of Chicago! All of the guides are great and take their time to make sure you are comfortable before the fun starts. Highly recommend!”
2-hour Chicago attractions walk with a local guide, plus a free bike or kayak rental within 3 days. See the Bean and more.
“Bobby’s Bike Hike Tours was amazing! Thanks so much for accommodating my daughter and I on the Chicago Favorites Food & Walking Tour! Our Tour Guide James was very knowledgeable, energetic, and entertaining! This tours is the absolute BEST way to see and taste Chicago!”
Chicago highlights in 2 hours: Millennium Park, Riverwalk, Magnificent Mile, art and more, plus a free 2-hour bike or kayak rental.
“Food was great, learning the history from our tour guide Mickey was fun. Our kids love history and they really enjoyed it!”
Two-hour small-group kayak on the Chicago River, learning reverse flow and drawbridges, with skyline views.
5-hour Chicago food and walking tour with five iconic bites, top landmarks, and a free 2-hour bike or kayak rental.
“My booking was moved to a different tour called “Chicago Favourites” as the one I originally booked was undersubscribed. It wasn’t really worth the money -the additional $20 for the “3 craft beer pairing” and the recommended $10-15 tip taking it over $100. For that price we got a slice of pizza, a small hot dog, half an Italian beef sandwich, a one inch piece of brownie and a small serve of popcorn. The guide, Gregg, was clearly new to the tour and, while he knew about the city and the food, he didn’t order my beer in the first restaurant until I asked for it, so when it eventually…”
Five hours of Chicago classics on foot, deep dish, hot dogs, Italian beef, brownie, plus free 2-hour bike or kayak rental.
“Quinn injected a lot of humor into his history that we enjoyed. Loved the small local places we went to for a few of the yummy bites. Would have never found/gone on our own.”
Rent a kayak for 2 hours on Chicago’s Bubbly Creek from Bridgeport. Spot wildlife, enjoy calm water, and learn stockyard history for $48.
Every kind of day out in the city, and the best of each.
