1.Classic Food & Walking Tour with Free Bike or Kayak

★★★★★★★★★★4.9 · 145 reviews · 3 hours · from $84Our pick

A 3-hour Chicago food and walking tour with 5 classic bites plus free 2-hour bike or kayak rental along Lake Michigan.

“Our guide Jeff was incredibly knowledgeable, not only about the food we tried but about the history of the city, as well as the architecture. Jeff kept things moving and very upbeat throughout! I would rate Jeff as a five star guide! My husband and I just finished a two week tour of Greece and had many great guides during that time but Jeff was by far the best! Thank you Jeff from Rob and Shannon.”

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2.Starved Rock State Park: Guided Kayaking Tour

★★★★★★★★★★4.9 · 26 reviews · 2 hours · from $74

Guided Starved Rock kayaking on the Illinois River, 2 hours of cliff views, wildlife, lotus flowers, easy pace, gear included.

“Lot's of fun and guide tells funny jokes and is very informative of the area.”

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3.Chicago’s Lake Michigan Downtown Kayak Rental at Ohio Street Beach

★★★★★★★★★★5.0 · 22 reviews · 1 to 2 hours (approx.) · from $39Best value

Kayak Lake Michigan from Ohio Street Beach by Navy Pier. Calm, skyline views, and 1 or 2 hours on the water for $39.99.

“Evan was waiting for us! He was prepared and very friendly! He really helped us and got us off on the right foot (or should I say paddle?)! We came to Evan very stressed out and left with a wonderful memory! We loved paddling around the point to see Navy Pier and then when we were returning the city scape view was stunning! We loved Kayaking in Lake Michigan! Bucket list: kayaking in Lake Michigan: check!!”

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4.2-Hour Downtown Kayak Rental

★★★★★★★★★★4.5 · 19 reviews · 2 hours · from $62

Kayak the Chicago River downtown for 2 hours with a paddling lesson and safety briefing. Choose single or tandem 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.”

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5.Moonlight Paddle Tour on the Chicago River

★★★★★★★★★★4.2 · 9 reviews · from $58

Glide through the Chicago River at night on a 1.5-hour moonlit kayak tour, with skyline views of Willis Tower and Marina City.

“If you are considering this activity and you have no experience just keep in mind that there are breaks but if you cannot keep up there is no break for you. If you are mildly scared of the dark I recommend to do it during the day. That being said, it was a good experience and the staff organising and helping along the way were great. The young lady kept by my side and never made me feel uncomfortable or that I was taking too long. I only took a star off because it’s stated to come 30 minutes early, which I did but I was told to come back…”

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6.Tandem Guided Kayak Tour Near Chicago

★★★★★★★★★★4.5 · 6 reviews · 2 hours (approx.)

Tandem kayak near Chicago at Starved Rock, paddling past sandstone bluffs, 18 canyons, and wildlife with guides Rich and Dave in 2 hours.

“Rich and his partner were the best tour guides! We had so much fun and saw so many great things! We would totally recommend this trip!”

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7.Best of Attractions Walking Tour +Bike/Kayak Rental

★★★★★★★★★★5.0 · 5 reviews · 2 hours · from $44

A 2-hour guided Chicago highlights walk with entry included, plus a free 2-hour bike or kayak rental within 3 days.

“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!”

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8.Chicago Walking Tour of Highlights with Free Bike or Kayak Rental

★★★★★★★★★★5.0 · 5 reviews · 2 hours (approx.) · from $44

A 2-hour Chicago highlights walk with tight insider stories and VIP access, plus a free 2-hour bike or kayak rental within days.

“I appreciated being able to see the sites. Even more, however, I appreciated learning more about Chicago’s history and people, past and present. Thanks, Mikey, for a great tour. The bonus of the bike rental was also appreciated. We had a nice ride along the lake and even a short visit to the Lincoln Park Zoo.”

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9.Sunset Kayak Tour on the Chicago River

★★★★★★★★★★4.2 · 5 reviews · 1h 30m · from $57

Sunset kayak on the Chicago River for $57, 90 minutes with a guide, skyline views at golden hour past Willis Tower and Merchandise Mart.

“Eindrückliche Kanu-Tour inmitten von Chicago beim Einnachten… Leider etwas chaotisch organisiert mit Kanus, die viele Reparaturen nötig hätten. Von den Guides keine Hinweise/Erklärungen zur Tour 😳”

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10.Single Guided Kayaking Tour near Chicago

★★★★★★★★★★5.0 · 4 reviews · from $69

Guided 2-hour kayaking near Chicago through Starved Rock bluffs, birds overhead, and a lotus flower field. $69 with a mobile ticket.

“We ended up with beautiful weather, and our guide "Turtle Rick" was very knowledgeable about the area as well as personable.”

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11.Canoe/Kayak Day Tour of Mississippi Wildlife & Fish Refuge

★★★★★★★★★★5.0 · 3 reviews · 2 to 4 hours (approx.) · from $120

Kayak or canoe Mississippi backwaters from Galena, IL on a 2-4 hour wildlife tour with slow current, bald eagles, and a sandy beach.

“We booked this last minute when coming into the area. Quick response and accommodated us next day. What a piece of heaven the backwaters are. Roger guided us out to the Mississippi to a beautiful sandy beach. Haven never been on the Mississippi, I really enjoyed the water and the views. Highly recommend having him accompany you to help with navigation and info on the area. Great guy, loves what he’s doing and goes out of his way to make sure you enjoy the experience on the water. Great experience.”

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12.History and Architecture Guided Kayak Tour

★★★★★★★★★★5.0 · 3 reviews · 2 hours · from $64

Paddle Chicago River downtown for 2 hours, guided by pros who explain bridges, engineering, and the skyline, plus wildlife spotting.

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13.Chicago in a Day: Food & Walk Tour+Free Bike or Kayak Rental

★★★★★★★★★★4.2 · 3 reviews · 5 hours · from $99

A 5-hour Chicago food walk with five iconic bites, major landmarks, and a free 2-hour bike or kayak rental within 3 days.

“We had a terrific time exploring the food and city with an excellent guide.”

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