The Best Chicago Boat Tours

Posted by Lexington Square

Chicago is one of those wonderful cities that was both designed and built with existing natural waterways in mind. These waterways offer some of the most iconic views of the city, so experiencing a trip through Chicago via the three branches of the Chicago River and Lake Michigan is something every visitor, or resident for that matter, should do at least once in their lives.

With waterways being instrumental to the development and eventual rise of Chicago, there are many companies that offer boating tours through the city. Each of these operations approaches the city and its landmarks a bit differently, so we’ve put together a list of what we feel are the best Chicago boat tours to see the city from the water.

Chicago’s First Lady Cruises

112 E. Wacker Drive
Chicago, IL 60601
(847) 358-1330
Email: chartersales@cruisechicago.com
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It would be difficult to find a boat tour anywhere that can compare to the Chicago Architecture Foundation River Cruise provided by Chicago’s First Lady Cruises. Consistently ranked as one of the best things to do when in Chicago by numerous travel publications, the architectural cruise offered by Chicago’s First Lady is the premiere way to experience Chicago; whether it’s your first time in the city or you’ve lived here all your life.

Departing from below Michigan Avenue, the 90-minute tour showcases the significant architecture of the city through stories related to their construction and historical uses. You’ll see the Wrigley Building, the Centennial Fountain, the Tribune Tower, and much, much more. Tours are led by docents from the Chicago Architecture Foundation so you’re sure to learn far more than you ever thought possible in 90 short minutes. Tickets for the tour can be purchased through Ticketmaster online for $50.87 (including tax), or at the kiosk under the blue awning on the southeast corner of the Michigan Avenue Bridge for $44. Tours run until late November and pick up again in the Spring.

Shoreline Sightseeing

Navy Pier – Michigan Avenue
Chicago, Illinois
(312) 222-9328
Email: info@shorelinesightseeing.com
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One of the best combination tours in the country, Shoreline Sightseeing’s Architecture River Tour followed by the fireworks at Navy Pier is a 90-minute adventure you’ll never forget. Two of Chicago’s greatest treasures – the city’s architecture and its Navy Pier pyrotechnics – all rolled into one incredible experience. Unlike the tour offered by Chicago’s First Lady, Shoreline Sightseeing lets you take in the beauty of the city’s architecture as the sun set paints the picturesque Chicago skyline. It’s a sight unlike any you’ve seen before and that can only be experienced from the decks of the 200-passenger Voyageur.

Departing from two locations – Navy Pier’s Polk Bros. Park and the northeast corner of the Michigan Avenue Bridge – the combination architecture and fireworks cruise is offered on Wednesday and Saturday evenings all summer long. Tickets are $36 for seniors and boarding begins 15 minutes before scheduled departure. There are cash bars available on each boat so enjoy a cocktail as you see the city and its exciting fireworks display. With the third generation of family ownership running the tours, you’ll be in good hands with Shoreline Sightseeing!

Seadog Cruises

455 N. Cityfront Plaza Drive, Suite 2600
Chicago, Illinois 60611
(866) 391-8439
Email: Cruise.Chicago@entertainmentcruises.com
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Unlike any other tour in Chicago, Seadog Cruises’ Lakefront Speedboat Tour is the ultimate 30-minute introduction to the city and its beautiful lakeshore. Riding along in a giant speedboat with 110 other passengers, you’ll see all the sights and as you hear some interesting facts, but the real appeal here is the speed. It’s never uncomfortable or frightening, (you can find that from Seadog’s Extreme Thrill Ride) and it offers an experience most people will never have.

Departing from Navy Pier, the 30-minute excursion highlights all of the city’s landmarks, from Chicago’s Museum Campus to the Magnificent Mile and Buckingham Fountain. Once the cruise through the city is completed, you’ll speed north past Navy Pier on your way back to the dock. Tours run during the warmer months with some special tours during the holidays. You can find all of the dates available using their handy calendar. Tickets for this experience are $21.95 for seniors and dogs are allowed, so put Fido’s leash on and get ready for a ride of a lifetime!

Wendella Sightseeing Boats

400 North Michigan – 100-Concourse
Chicago, IL 60611
(312) 337-1446
Email: tours@wendellaboats.com
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Wendella is the originator of the Chicago Architectural Cruise, and they still offer an excellent take on the city’s buildings, but the real game-changer in their catalog is their Chicago River Bridges Tour. This amazing 2-hour experience will show you a side of Chicago that is too often overlooked – its 38 bridges.

Noted author Patrick McBriarty leads the tour which focuses on the beautiful architecture and historic importance of the city’s unique and
varied collection of bridges. The sheer volume of information you can learn is staggering, or you can simply gaze at the structures as you sip a cocktail or soda from the bar located on the lower deck. Tickets for seniors are $32 with tours beginning in March and going through December. If you take a tour later in the year, call ahead to make sure the boat has a climate-controlled lounge!

Tall Ship Windy

600 E Grand Avenue
Chicago, IL 60611
(312) 451-2700
Email: tickets@tallshipwindy.com
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With an appeal that speaks to history buffs, romantics, and anyone looking for inspiration, the Tall Ship Windy is one of Chicago’s real treasures – and an amazing way to experience the city! The Tall Ship Windy is a 148-foot traditional four-mast schooner built from the finest modern materials, but with all the feel and ambience of the great Age of Sail. As the flagship of the City of Chicago fleet, this ship’s Skyline Tour is world-renowned for its singular views and unique experience.

Docked at Navy Pier, Windy’s Skyline Tour will take you out onto the peaceful waters of Lake Michigan where you’ll have 75-minutes to admire the views and enjoy the peace and quiet. You can also join in with the amazingly talented crew for some interesting stories about maritime lore, the history of the lake, and the part sailing ships played in the birth and rise of Chicago. Tickets are $30 for seniors with tours running until December. You can check availability with the helpful calendar on their website. If the ship and its nautical theme have you thirsting for some rum, you’re in luck – there’s a fully stocked bar on board!

Chicago Line Cruises

465 North McClurg Court
Chicago, IL 60611
(312) 527-1977
Email: tickets@chicagoline.com
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While many companies offer architectural cruises along the Chicago River, only Chicago Line Cruises has partnered with the Chicago History Museum to create the stunning “Chicago Along the River” cruise. This really is a cruise unlike any you’ve ever imagined. As a passenger, you’ll have access to images from the museum’s archive giving you a remarkable then and now perspective you can’t find anywhere else. Each docent who narrates the tour has an average 17 years of experience giving guiding tours through the city, so you’ll never see the sights with a more qualified guide. Their knowledge is worth the price of admission all by itself.

Departing from a hidden branch of the Chicago River called the Ogden Slip, passengers on the 90-minute cruise are treated to incredible views and valuable knowledge, along with complimentary Starbucks coffee, Twinings Tea, Coca-Cola soft drinks, and muffins or cookies depending on the time of day your tour begins. There is also a full bar if you’d rather enjoy a cocktail while hearing the history of this great city. Tickets are $36 for seniors while the touring season is open. You can find tour dates and times using the calendar on their website. No matter how much you think you know about Chicago, this is one tour that will teach you something new!

Mercury, Chicago’s Skyline Cruiseline

P.O. Box 68
Palatine, IL 60078
(312) 332.1353
Email: contactus@mercurycruises.com
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While taking a boat tour of Chicago is an excellent way to see the city, there are few views during the day that can compare to Chicago after dark. That’s when the electric heart of the city comes alive, and Mercury, Chicago’s Skyline Cruiseline’s “Chicago by Night” absolutely shines. You’ll be amazed and enthralled by the slow shift from urban business center to glittering twilight jewel. It happens every single night and we barely take notice. As soon as this tour leaves the dock, you’ll begin to see this beautiful city in a whole new light.

Departing from the Chicago Riverwalk just 3 blocks from Millennium Park, the 90-minute tour showcases landmarks ranging from Buckingham Fountain’s light display to the extraordinary beauty of the skyscrapers at night. Beverages are sold onboard – ranging from soda to beer – but food is unavailable, so bring a lunch or snack of your own if you’d like. Tickets are $35 when purchased online or at the dock, and tours are active during the warmer months. You can find a full schedule of tours on their website, as well as any current specials they may be offering. Make sure you bring a coat as it does get chilly in Chicago after dark!

Spirit of Chicago

455 N. Cityfront Plaza Drive, Suite 2600
Chicago, Illinois 60611
(866) 391-8439
Email: Cruise.Chicago@entertainmentcruises.com
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One of Chicago’s best kept secrets is the Brunch Cruise aboard the Spirit of Chicago Charter. Brunch is one of the city’s calling cards, and there is no other brunch in the entire region to compare with this one. The Spirit of Chicago offers the same majestic views and thrilling perspectives, but aims to entertain and delight passengers with the food and ambience as well as the skyline. It’s also quite an amazing ship with climate-controlled decks and a professional, friendly staff.

Departing from Navy Pier, the Spirit of Chicago Brunch Cruise is a full two hours in length and sails along the shoreline of Lake Michigan and as far as one mile out into the lake. The menu for the Brunch Cruise is outstanding and can be viewed on their website in advance of your tour. They offer unlimited coffee, tea, and water and you’ll have access to shared spaces, interactive games, and a DJ who will take your requests for musical selections. Tickets are $41.90 and you can upgrade your experience for a few dollars more to include their famous “Build Your Own Bloody Mary” cocktail special. Don’t forget to request a window table to ensure you don’t miss a second of the amazing views!

Whether you’re looking for the most iconic views of the city, an educational experience second-to-none, or a spectacular meal served in a most unique space, Chicago has a boat tour that’s exactly what you’re looking for. Each of these tours are so different, you could take them all and never feel you’re recycling old views. No matter which Chicago boat tour you choose, you’ll walk away from the experience with a smile on your face and memories that will last a lifetime. So what are you waiting for?