Boat Tours & Water Sports in Chicago
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Chicago’s First Lady Cruises
5,220 reviews
#1 of 91 Boat Tours & Water Sports in Chicago
"The river tour was fabulous, our guide Judith, so knowledgeable and passionate about the city, boat was very comfortable and had rest rooms and a full working bar, a truly wonderful way to spend a couple of hours,...""If you really want to hear about Chicago Architecture from (in our experience) a truly knowledgable, engaging and entertaining tour guide, be sure to find this tour, run by the Chicago Architecture Foundation."
Shoreline Sightseeing
5,378 reviews
#3 of 91 Boat Tours & Water Sports in Chicago
"We took this tour on our first trip to Chicago Tour guide Brigid was excellent very engaging with everyone & extremely informative We thoroughly enjoyed the trip it was well worth the cost & got lots of photos of...""The staff are friendly and enthusiastic and our guide Blake on the Bright Spark was very knowledgeable and funny and made the time pass very quickly with varied stories about the various buildings and the city its..."
Seadog Cruises
2,927 reviews
#4 of 91 Boat Tours & Water Sports in Chicago
"My husband and I went on Seadog Boat Tour with tour guide, Billy, Captain Swag and First Mate Jarion: PHENOMENAL! Amazing!! WORTH IT!! Billy was extremely knowledgeable of the history and fun facts about Chicago.""The Extreme Thrill Ride was so much fun!! Gorgeous views, great crew, flying through the water and even a bit through the air, getting soaked, learning a few interesting points about Chicago - it was awesome!"
Chicago River Boat Architecture Tours
430 reviews
#5 of 91 Boat Tours & Water Sports in Chicago
"She was fun and funny, and so very informative about all things Chicago and Chicago River, and it’s history and architecture, and she clearly loves her city and her volunteer job.""However, for a chance to see Chicago from the water with expert commentary from a well versed docent guide makes it seem a bargain in a lot of ways Do bring a hat if you plan to sit on the outside top deck- which..."
See it All Chicago Tours
500 reviews
#6 of 91 Boat Tours & Water Sports in Chicago
"Told us all about the city, neighborhoods, must-see area, etc. Interactive and answered all questions the group had, even about where to eat! Rick truly cares about the folks on his tour and wants them to enjoy th...""We are thankful to Rick for giving us a tour that perfectly matched our expectations in terms of narrating the history of the several tourist spots and the iconic architecture, in a manner that was humorous, lucid..."
Wendella
2,527 reviews
#7 of 91 Boat Tours & Water Sports in Chicago
"... a great up close look at several cool Chicago skyscrapers, and the lake portion offered great views of the entire skyline and included some great factoids about the Chicago river lock and other cool city history.""A really good way to see the delightful architecture of Chicago with a well informed guide David who was both amusing and interesting- we saw many great views and buildings from throughout the centuries and I woul..."
Urban Kayaks
486 reviews
#8 of 91 Boat Tours & Water Sports in Chicago
"We had our two children 11 and 13 in tandem kayaks with a great guide Spencer who was superb, very friendly and great as a tour guide telling us about the buildings as well as life in Chicago.""Whether a beginner, intermediate or experienced kayaker, you will have a great time and thoroughly enjoy the architecture that surrounds the Chicago River."
Chicago Line Cruises
805 reviews
#10 of 91 Boat Tours & Water Sports in Chicago
"We went on the architectural cruise, which is led by an historian so this cruise blended city history, architecture history, current history and the city's plans for the future.""We booked through groupon which ended up being a great deal, but even at regular price, the incredible knowledge our guide had of the city's buildings and history, the friendliness of the staff, and the length of..."
Tall Ship Windy
1,321 reviews
#11 of 91 Boat Tours & Water Sports in Chicago
"Great night time view of the skyline - crew was helpful and great Quiet and peaceful ride - so much fun to be on a sail ship rather than the traditional cruise boat""The tall ship windy located on Navy pier in Chicago Il, we had 41 guests for our wedding aboard the ship for a evening sail, the saff and captain were amazing, They aere all friendly, personable and helpful."
Odyssey Chicago River
72 reviews
#14 of 91 Boat Tours & Water Sports in Chicago
"The new boat by Chicago River is very clean, safety and elegant 🛳🛳🛳❤️❤️❤️ This was our visit number 13 since 2006, yesterday in Odyssey Chicago River and the others in Odyssey Lake Michigan at Navy Pier 😍😍😍...""The top and sides of the boat are entirely glass so the scenery was awesome... such interesting architecture and the guide provided lots of insight into the buildings as we passed."
Kayak Chicago
174 reviews
#15 of 91 Boat Tours & Water Sports in Chicago
"The Fireworks paddle is very long and novice kayakers will tire easily I recommend sunset paddles or renting at their lake locations if you're just looking to paddle around and have some fun.""Super fun tour down the river with Brian & David our knowledgable guides- stops on the way to explain architectural points of interest & facts about the city."
The Salty Dog Sailing Co.
32 reviews
#18 of 91 Boat Tours & Water Sports in Chicago
"We went on a perfect evening for sailing with the Salty Dog Co. Captain Kirk and his trusty mate “woody” welcomed us and made us feel comfortable and relaxed.""The sail was awesome, as the boat is was built with racing in mind so it’s fast and stable, making for some great memories for our first “real” sailing experience."
Chicago River Boat Architecture Tours
26 reviews
#25 of 91 Boat Tours & Water Sports in Chicago
"Hope and I were blessed with an absolutely gorgeous summer day, The trip departs from Wacker Drive and Michigan Ave in the heart of the city, and lasts 90 minutes, covering the Chicago River's main branch, as well...""This 2 hour boat tour of Chicago as seen from a boat on the river, provides an informed and fascinating overview of Chicago architecture from many decades, including award wining architects that have been building..."
ChicaGo By Boat
12 reviews
#29 of 91 Boat Tours & Water Sports in Chicago
"Captain Conway hooked us up with a parking pass right next to the pier, had a bottle of champagne waiting on board for us, and took us out on a great cruise along the north shore.""Sometimes my guests and I enjoy a cocktail skyline sail, other times it's water, Pellegrino and an athletic day finding the best wind."
Boat Tours & Water Sports in Chicago
Boat Tours Boat Rentals Fishing Charters & Tours Kayaking & Canoeing Surfing, Windsurfing & Kitesurfing Scuba & Snorkeling Stand-Up Paddleboarding Water Sports Waterskiing & JetskiingFrequently Asked Questions about Chicago
- Chicago Architecture River Cruise
- Chicago Odyssey Dinner Cruise
- Chicago Odyssey Lake Michigan Brunch Cruise
- Private Chicago City Mini Bus Tour
- Lake Michigan Sightseeing Cruise
- See it All Chicago Tours
- Chicago’s First Lady Cruises
- Shoreline Sightseeing
- Seadog Cruises
- Chicago River Boat Architecture Tours
- See it All Chicago Tours
- 3rd Coast Charters
- Chicago’s First Lady Cruises
- Tours and Boats
- Shoreline Sightseeing
- See it All Chicago Tours
- 3rd Coast Charters
- Chicago’s First Lady Cruises
- Shoreline Sightseeing
- Seadog Cruises
- See it All Chicago Tours
- Chicago’s First Lady Cruises
- Shoreline Sightseeing
- Seadog Cruises
- Chicago River Boat Architecture Tours
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