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Chicago Archiecture Center boat tour
Photograph: Courtesy Chicago Architecture Foundation

The 15 best Chicago boat tours

See the skyline from dazzling new vantage points aboard the best boat tours in Chicago

Written by
Emma Krupp
Rhys Thomas
Lindsay Eanet

Sure, walks along Michigan Avenue and State Street are nice and rooftop bars offer plenty of pretty sights—but the best way to see downtown Chicago is from the water. Both Chicago River and Lake Michigan offer unparalleled vantage points for taking in the city’s world-famous architecture and the breathtaking Chicago skyline, with many of the tours providing unique insights into the city’s culture and history. From architecture tours and history lessons to straightforward sightseeing affairs, or from romantic excursions to pirate-themed family fun, there's a Chicago cruise for every groove. Below we’ve got the essential list of the city’s finest waterborne tours, including tall-mast ships and glitzy speed boats. Bon voyage!  

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Best Chicago boat tours

Chicago Architecture Foundation Center River Cruise
Photograph: Barry Butler

1. Chicago Architecture Foundation Center River Cruise

There's a reason the Chicago Architecture Foundation's beloved tour has been named the Best Boat Tour in the U.S. The center’s official tour goes into detail on more than 50 buildings both on the riverfront and beyond. In doing so, they give a fascinating history of the city and those that built it—plus you can easily upgrade your ticket to include entry to just Chicago Architecture Center itself. It’s a proper design enthusiasts’ dream. This one leaves from the Chicago First Lady Cruises dock and lasts around 90 minutes. For a real treat, gather friends for the serene evening cruise for just a few dollars more.

Shoreline Sightseeing Skyline Lake Tour
Photograph: Courtesy Navy Pier

2. Shoreline Sightseeing Skyline Lake Tour

Want to see Chicago from the water but don't have much time to spare? You can peep the skyline in just 30 minutes on Shoreline's Classic Lake Tour, which departs from Navy Pier and boasts some of the best views you'll find on Lake Michigan. The commentary on the city's architecture and history is pre-recorded, so you won't miss out on any information because your guide ran out of time (and if you've heard it before, you can sit back and enjoy those sweet, sweet sights).

Seadog Lakefront Speedboat Tour
Photograph: Courtesy Seadog

3. Seadog Lakefront Speedboat Tour

If you balk at the idea of traipsing around museums and galleries all day with just your legs for locomotion, this whistle-stop boat ride is the tour for you. See every worthy Chicago landmark in 30 minutes on Seadog’s speedboat, which can sometimes feel like a floating rollercoaster. Launching from Navy Pier, the captain will efficiently guide you (with a running commentary) around Lake Michigan, past Museum Campus, Magnificent Mile, Grant Park and more.

Odyssey Lake Michigan Dinner Cruise
Photograph: Courtesy Entertainment Cruises

4. Odyssey Lake Michigan Dinner Cruise

Enjoy a leisurely dinner on the water in the Odyssey Chicago, where you can enjoy breathtaking views of the skyline surrounding you. Departing from Navy Pier, this cruise includes a dinner buffet with freshly-prepared entrées, salads and desserts. The 2.5-or-3-hour ride takes you around Lake Michigan, with a cash bar and a DJ-led dancefloor to keep you entertained.

Shoreline Sightseeing Architecture River Tour
Photograph: Courtesy Shoreline Sightseeing

5. Shoreline Sightseeing Architecture River Tour

Departing from Navy Pier's Polk Bros Park or the northeast corner of the Michigan Avenue Bridge, this 60-minute trip packs in all of the architectural sights that visitors want to see. Tour guides highlight more than 40 towering Chicago landmarks, including the Tribune Tower, the Wrigley Building, and Marina City (a.k.a. "The Corncobs" or "The Wilco Building"). 

Chicago Skyline Sail
Photograph: Chuck Eckert

6. Chicago Skyline Sail

Let the wind carry you to stunning views of the city from aboard the Tall Ship Windy, a four-masted, 148-foot topsail schooner. The 75-minute trip cruise brings guests on a scenic route running along the Lake Michigan shoreline, where you can take in lovely skyline vistas and glimpses of the sunset. Head to the aft salon of the boat to find snacks and drinks for sale. Bring the kids for the special 7pm pirate-themed cruise, featuring tales of swashbuckling on the Great Lakes. 

Spirit of Chicago Dinner Cruise on Lake Michigan
Photograph: Courtesy City Cruises by Hornblower

7. Spirit of Chicago Dinner Cruise on Lake Michigan

If you're looking for dinner with a view, you could do worse than watching the sunset against the skyline aboard this 2.5-or-3-hour Lake Michigan dinner cruise. Grab a group of friends book a table—ideally one with a window-facing view—for a buffet-style meal before making your way to the dancefloor for an evening of DJ-curated music. Unlimited coffee, tea and water will be on hand, but you can also visit the bar for some stronger libations, including some creative signature cocktails.

Wendella Chicago's Original Architecture Tour
Photograph: Courtesy Wendella

8. Wendella Chicago's Original Architecture Tour

If you're weighing your options, Wendella's architecture tour (which it claims is Chicago's original) is another way to explore all of the beautiful structures that line the river. Over the course of the 90-minute tour, you'll navigate all three branches of the Chicago River, while your guide fills you in on the stories behind some of the skyline's most prominent edifices. This tour departs from the Wendella Dock, located at the northwest corner of the Michigan Avenue Bridge at the foot of the Wrigley Building.

Lady Grebe Chicago River Experience
Photograph: Courtesy Chicago's First Lady Cruises

9. Lady Grebe Chicago River Experience

Want to feel extra posh? Grab a group of up to six friends and book a private cruise aboard Lady Grebe, a 48-foot vintage yacht that can be reserved for 90-minute trips along the Chicago River. The reservation comes with non-alcoholic drink service but you can also opt to kick things up a notch with various beverage package options (or, for an educational twist, book a Chicago Architecture Center docent to give a guided tour).

Odyssey Lunch Cruise
Photograph: Courtesy City Cruises by Hornblower

10. Odyssey Lunch Cruise

Why settle for lunch at a land-lubbing restaurant when you could eat your meal on Lake Michigan? The Odyssey's lunch cruise includes a lunch buffet and all the coffee, hot tea, iced tea and water you can drink. Visit the cash bar to buy wine, beer and cocktails and enjoy the views on this two-hour tour.

Chicago Electric Boat Company Tour
Photograph: Courtesy Chicago Electric Boat Company

11. Chicago Electric Boat Company Tour

Go your own way. Be your own captain. That’s what’s on offer with this Chicago River tour. The Chicago Electric Boat Company lets passengers steer the ship themselves (if they’ve got a valid drivers’ license and watched a 10-minute tutorial, that is), allowing total freedom on the Windy City’s waterways. If you’re looking to still have some kind of tour, you can hire a personal tour guide—and we haven’t even gotten to the best bit. These boats are all electric, so they’re that little bit more environmentally-friendly, too.

12. Chicago Fireboat Tours Historical and Architectural Cruise

Hosted on the bright red Fred A. Busse Fireboat—which served the Chicago Fire Department until 1981—this architectural tour of the Chicago River lasts anywhere from 90 minutes to two hours. A docent will fill you in on the history of buildings lining the river as well as the story of the boat you've boarded, which formerly traveled the city's waterways to fight fires. Departing from DuSable Harbor, the fireboat doubles as a floating museum, packed with vintage firefighting artifacts and photos.

Seadog River and Lake Architectural Tour
Photograph: Courtesy Seadog

13. Seadog River and Lake Architectural Tour

There are few more iconic Chicago sights than seeing the bright yellow Seadog speeding around town. Combining speed and sightseeing, Seadog’s Architectural Tour whizzes guests past the likes of the Willis Tower and Lyric Opera, all while arming you with an impressive load of facts about the Windy City. And after this blustery 75-minute tour has finished traversing the Chicago River, it ends with a thrilling whizz across Lake Michigan, past Museum Campus and Grant Park. This one departs from Seadog’s dock at Navy Pier throughout the summer months.

Wendella Chicago Sunset Cruise
Photograph: Jordan Avery

14. Wendella Chicago Sunset Cruise

How do you end the perfect day of sightseeing? With the perfect sunset, obvs. Setting off from Wendella Dock (at the northwest corner of the Michigan Avenue Bridge at the foot of the Wrigley Building), this 90-minute cruise will breeze along Lake Michigan as the glint of the sun on Chicago's skyscrapers is replaced by twinkling city lights. Wine, local beer and cocktails will be available onboard, too.

GYG Chicago TTD

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