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    Kayak Chicago

    4.1 (218 reviews)
    Closed 10:00 am - 7:00 pm
    Updated over 3 months ago

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    Cassie E.

    We did the firework kayaking. EXPERIENCE: They warn you to bring water and/or food because it's a long ride, and they aren't kidding. We got there at 7:30pm and we got back to our car at like 11:30 pm. My poor boyfriend did a shoulder workout earlier in the day and we definitely recommend against that since it's definitely a workout. It's very long and tiring. They give you training before you take off. It didn't feel rushed, so I wasn't nervous and I had never kayaked before. The views are fantastic. Be prepared for your phone to get wet because the paddles splash water into the kayak (they warn you about this when you sign up as well). I wished I had an action camera, but I was still able to take decent pics. KAYAKS: They have lights that go on the front and the back of the kayaks so it's easy to see. The lights kept going out for my time slot, but they said it was a brand new box that they just opened. So they didn't know it was going to do that, so I am not holding that against them. They have different types of kayaks and have some for folks that have a wider stature. CREW: The crew are very helpful, lively, and friendly. Some of them also do the tour guides so they are also very knowledgeable and were telling me about the history. There was a concert near where we were departing, so the crew texted us ahead of time to warn us to get there early to park and offered to help us find parking. They also let us know where the free parking was and yelled at people trying to charge for parking when they shouldn't be. I found them extremely helpful in terms of parking. When you are kayaking, they don't rush you if you are in the back of the pack. They go at your pace. They wear head lights so it's easy to see where/who they are. OVERALL: The pictures we got from the experience were great. I had a lot of people asking me how they could do it and what company I used. I definitely wish I had a DJI Action 4 (like a go pro, but better for low light scenarios). Just be prepared for a workout!

    Kayak Chicago
    Ernie H.

    Excellent crew really great lead guide - Matt. Equipment set up and orientation was thorough and help ease our concerns as first timers. So why 4 stars? Well you start around Goose Island which is NOT close to downtown. So you do a LOT of paddling just to get the Nuveen building. We turned around before the Marina Towers meaning we never got passed the Michigan ave and missed a lot of buildings and views. We also did not venture south of the river pass the nuveen building to see the civic opera or by the Sears tower. I almost get that because it would have been physically too much. Which goes back to the location issue and the distance just to get there.

    Kayak across the city on the Chicago River during this energizing adventure tour
    Sabrina C.

    If you are nervous about going kayaking for your very first time - this is definitely the place to do it. After you fill out your waivers and your group arrives, you are fitted to the proper boat and ensured that you understand the basic instructions. The route that you will take starts to be explained and then you head off to the water! At the water, initially getting in your kayak can be kind of scary, but once you're in, YOURE IN! There are workers that are around to help you in for your initial boarding because it will be a little shaky. After everyone is in you spend some time getting used to how you steer your boat, then everyone takes off! The sights are so dope to see from the River. We did the a tour on the Chicago River that went into the early evening hours and were able to learn so much on our architecture tour. The guides were very knowledgeable and the two that we had were sure to stay along helping everyone, since there were different levels of experience. It was definitely a workout but absolutely something I will be doing again with this company!

    Kayaking at night
    Jim R.

    Kayak Chicago is such a great time! Great value too. My girlfriend and I took the City Lights Night Paddle tour. We were the only 2 people on the tour with the guide. It felt a little awkward as it was such a small private tour but Mike ("Magic Mike") gave us a tour we'll never forget! He was very knowledgeable about the city buildings, history of the Chicago river, goose island area and everything in between. We got to see the blue river cranes as Mike pointed them out. What a great experience :)

    Kayak across the city on the Chicago River during this energizing adventure tour
    Julie L.

    Evan was the best! So funny and knowledgeable. He made sure everyone had a great time! Highly recommend this business!

    Starting/ending spot, with Wrigley research building in the back and our awesome tour guide in the front!
    Ivonnie S.

    We booked the architecture kayak tour for 2 through Groupon, which came out to be about $50/person for 3 hours, including a short lesson and getting on/off the water. Tl;dr: it was lots of fun and I'd highly recommend checking out this company, whether you're a tourist briefly visiting the city or a local who's never been on an architecture tour here. Some deets: the tours will happen rain or shine, unless there is potentially dangerous weather (i.e. lightning/thunder). Weather calls are made at the time that the tour starts, so I'd recommend showing up regardless of what the fickle weather report says. When we showed up for our 10am start time, it was starting to rain with a few flashes of lightning, so we couldn't go out onto the water and were feeling pretty disappointed. The staff were quite accommodating though, and we chose to wait it out a bit and see if the lightning died out. 45 minutes later, the rain had ended and they started the tour, yay! Our guide (sorry I forgot your name) inserted several dad jokes and interesting stories into the tour, including one about Dave Matthews and "Poopgate". Not sure if the boat architecture tours would be as entertaining haha. Plus, what's the fun in just sitting on a boat and passively listening for the duration of the tour? Might as well get in some good exercise - and then reward yourself afterwards with some of Chicago's deeelicious food! Also, if you're worried about the river water cleanliness, it's no chlorinated pool water, but the city has been cleaning up and beautifying the area recently and it's no longer as contaminated as it used to be. Just don't drink the water directly and wash your hands before eating! Last tips on things to bring: + A bottle of water to put behind your kayak seat! The tour goes at an easy pace, but it's still an arm/core workout + Phone or small camera to take lots of cool pics! They have Ziploc bags and waterproof boxes to store your phone while paddling + A change of clothes if you'd like; you'll probably splash a little bit of river water onto your legs and arms during the 3 hours + Leave everything else you don't need in one of the cubbies in the office, unless you don't care about it getting wet + Your excitement and sense of adventure! :) Have fun!

    By the riverwalk
    Peter T.

    I took my gf and I to this place and did the Sunset Tour. We enjoyed it but we're gonna try the Fireworks tour next. We gave it five stars becuase the orientation was short and the staff was super friendly and funny (well 5th grade teacher funny - LOL). I liked how they were patience with us, especially sinced we never kayaked before and the views were amazing. Only thing bad is water smells nasty like a hamster cage.

    Geese
    Molly A.

    I went with a group of ladies from Chicago and we all had varying levels of experience with kayaking (some had no experience, some kayak a lot) and we all really enjoyed the trip. The staff was incredibly helpful and walked us through the entire process. The route was easy to maneuver and it made for a really fun activity for us. I'd never kayaked before and it was such a good time that I was thinking about getting a ten hour punch card to use for the summer.

    Beautiful day in Chicago to kayak ...

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    16 years ago

    Did the Wednesday night trek to (and from) the fireworks. What a great workout, but you can still go at your own pace. A fun time!

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    Ask the Community - Kayak Chicago

    Is there free parking?

    yes along moyne theres plenty, please be cautious since there have been some breakins

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    Review Highlights - Kayak Chicago

    My hubby surprised me with the architecture tour on kayaks and it was the best way to spend a Sunday.

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    Chicago Food & City Tours - Urban Belly caramelized chicken dumplings

    Chicago Food & City Tours

    4.8(692 reviews)
    2.5 miRiver East, Near North Side

    Amazing amazing amazing! My best friend and I absolutely loved the "Yes Chef! Chicago: A Bear…read moreInspired Food Tour". Casey, our guide, was phenomenal. So fun and witty, and he really went above and beyond to make sure we had a great experience. All the places we visited were very special and iconic, including a bakery that's 115 years old and an ice cream shop that's 105 years old. It was really fun remembering where these places appeared in the show. Another perk of the tour was skipping lines and having special areas and service just for us. And not having to drive and look for parking. The air conditioned bus was lovely and comfortable, and it was fabulous to be driven around different neighborhoods. We went to so many great places and it's a fun way to get to know the city better. We ate so much good food!!! Italian beef sandwich, charcuterie, pepperoni pizza, hot fudge sundae, strawberry donut and more. Great drinks too! Beer and cocktails, or soda. I didn't need to eat for the rest of the day! Everything was delicious! I highly recommend this tour! It was exceptional and worth every penny.

    What a fun and filling afternoon! We went to restaurants associated with The Bear, ate delicious…read morefoods, and learned fascinating back stories about the show, the restaurants, and Chicago. Our tour director, Casey, and our driver, Joe, set the mood for fun and community. Definitely recommend!

    Photos
    Chicago Food & City Tours - Mr. Beef beef sandwich with hot peppers

    Mr. Beef beef sandwich with hot peppers

    Chicago Food & City Tours - Pizza Lobo pepperoni pizza

    Pizza Lobo pepperoni pizza

    Chicago Food & City Tours - Our tour guide in a local temple.

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    Our tour guide in a local temple.

    Chicago Detours - Beyond dates and names of architects, we dig into the ways in which we interact with architecture.

    Chicago Detours

    4.9(273 reviews)
    0.9 miRiver West, Noble Square, West Town

    During Parents' Weekend at the University of Chicago, the university offered tours of the…read moreneighborhood through Chicago Detours. My wife did this tour a couple years ago and highly recommended it, but I wasn't especially interested because I had also gone to school here and figured I knew enough about Hyde Park already. However, she insisted that it would be worth our while and so I agreed to climb on the bus. And it was the absolutely right decision, because the tour was excellent. In fact, it wasn't just a tour of Hyde Park. It included the surrounding neighborhoods of Washington Park, Kenwood, Jackson Park, and Woodlawn. Since this was a UChicago sponsored event much of the information related to the University's investment and involvement in the area. Our tour guide and founder of Chicago Detours, Amanda, is herself a graduate of UChicago and thus she had some additional insight into the relationship with the community. Though the 75-minute tour felt a little slow-going at times, there was much to learn about the vibrant but sometimes troubled history of the area. Amanda has tremendous knowledge and the excursion was both fascinating and entertaining. I can imagine that Chicago Detours would have equally interesting tours of other neighborhoods in this diverse city.

    Virtual tours are such a cool thing to do right now. I attended a Yelp Elite event that was a…read morevirtual food tour of Chicago. It was incredibly informative and a good balance of history and current trends. Looking forward to attending more virtual tours, like the World's Fair and the Cruise From Your Couch Boat Tour. I loved seeing the pictures of the in-person tours and can't wait to attend some of those too.

    Photos
    Chicago Detours - On an architecture tour, you'll venture into spaces many locals don't know

    On an architecture tour, you'll venture into spaces many locals don't know

    Chicago Detours - Enjoy drinks in opulent settings like the Chicago Athletic Association Hotel on the 1893 World's Fair Walking Tour with Bars and Food.

    Enjoy drinks in opulent settings like the Chicago Athletic Association Hotel on the 1893 World's Fair Walking Tour with Bars and Food.

    Chicago Detours - Historic Walking Tour with Bars- drink, learn, eat, explore.

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    Historic Walking Tour with Bars- drink, learn, eat, explore.

    Shoreline Sightseeing - Chicago Fire Department near Navy Pier

    Shoreline Sightseeing

    4.7(1.9k reviews)
    2.8 miNear North Side

    A river tour is a must when visiting Chicago! We decided to do Shoreline Sightseeing, and it was…read moresuch a great experience. We were nervous because my mom gets motion sickness easily, and we weren't sure she'd be able to enjoy the tour. Thankfully, the water was calm enough, and she absolutely loved it! The views were beautiful, and we learned so many fun facts about the city along the way. Definitely recommend adding this to your Chicago itinerary!

    This tour was on the top 10 list of our things to do in Chicago. I researched all the boat…read morecompanies that offered the Chicago architecture boat cruises and Shoreline Sightseeing came out hands down #1 for us in tour length, type of cruises, accessibility and in price for what you got. Best deal. Our tour guide was happy, energetic, and very knowledgeable about Chicago because he was born and raised there. We chose the 75 minute, 4pm Chicago River tour and it covered a lot! We never lost interest and learned about Chicago's history. It is well worth it! Our Architecture River Tour boat departed from the dock at Navy Pier. We learned that their boats are the most accessible at this location. Their boats can accommodate wheelchairs up to 30-inches wide. Your wheelchair must be able to navigate a ramp with a 2-inch step at one end. I needed one that was kind to my knees. Best to call them for more details. They were very helpful whenever we called them. Their boats are both double-decker and single-level boats, and there is generally no protection from the sun, rain, or wind. There is a small bar on the main level. Restrooms are located on the lower deck, which is accessible only via stairs from the upper deck. Enjoy! It's amazing!

    Photos
    Shoreline Sightseeing - The Chicago Architecture Tour boat cruise was amazing!

    The Chicago Architecture Tour boat cruise was amazing!

    Shoreline Sightseeing - Top deck - guide Joe

    Top deck - guide Joe

    Shoreline Sightseeing - View of (former) Sears Tower  See the Chicago's architectural landmarks on this relaxing river tour

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    View of (former) Sears Tower See the Chicago's architectural landmarks on this relaxing river tour

    Kayak Chicago - boating - Updated September 2026

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