March 23, 2023

The 6 Best Chicago Boat Tours

Note: Some tour providers on this list may have limited or ceased operations due to COVID-19. Check with your tour operator about availability before you book.

If you’re hoping to see as much of Chicago as you can in a short amount of time, you may want to sign up for a boat tour. During each tour, you’ll learn the historical significance of the skyline’s iconic buildings while enjoying breathtaking views of the city. Considering traveler reviews and expert opinion, U.S. News selected six of Chicago’s best boat tours, ranging from an architectural boat tour on the river to a thrilling speedboat ride on Lake Michigan.

Tall Ship Windy – Chicago Skyline Sail

Tall Ship Windy’s Chicago Skyline Sail introduces you to the beauty and splendor of Chicago’s famous buildings aboard the company’s four-masted schooner. On the 75-minute tour, you’ll learn interesting facts about the history of this renowned waterfront and its skyline, as well as the people who built it. Travelers love the experience, describing the crew and the schooner as incredible. Tickets start at $37 for adults 13 and older and $17 for kids 12 and younger. Tours depart from Navy Pier daily from May through September at 1, 3, 5 and 7 p.m. Tall Ship Windy also offers nighttime cruises on select days to correspond with Navy Pier’s seasonal Fireworks at the Pier show.

Chicago Architecture Foundation Center River Cruise

Hop aboard the Chicago Architecture Foundation Center River Cruise for a 90-minute tour of the Windy City’s spectacular skyline. With one of the Chicago Architecture Center’s volunteer docents guiding your trip, you’ll learn the architectural and cultural history of more than 50 of Chicago’s iconic buildings. Boats are equipped with open-air upper decks, climate-controlled lower cabins and full-service bars. Travelers say this architectural boat tour is not to be missed and describe it as a cool experience with spectacular views. They also rave about the insightful, entertaining guides who provide a wealth of information. Daytime cruise tickets cost about $50per adult and $24 per infant. Cruises generally depart Wednesday through Monday from 9 a.m. to 8 p.m., though exact times may vary by day. For an additional $5, you can gain access to the Chicago Architecture Center (which saves you $7 on center admission).

City Experiences by Hornblower – Chicago Seadog Lakefront Speedboat Tour

This speedboat tour departs from popular Navy Pier, taking travelers on a fast-paced, 30-minute ride along Lake Michigan’s shores. During the cruise, an expert guide will share the history of Chicago and the landmarks that created its iconic skyline. Along with the entertaining commentary, you’ll enjoy photo-worthy views of lakefront attractions. Reviewers rave about the tour, saying that the views are superb and the speedboat makes for a thrilling ride. Tickets start at about $30 for adults and $23 for kids ages 3 to 12; children 2 and younger can cruise for free with a paid adult. The tour, which operates from March through October, departs hourly every day from 10 or 11 a.m. until 9 p.m. Keep in mind that the tour is not recommended for pregnant women or people with neck or back injuries. Prefer a more low-key ride? The company also offers brunch, lunch and dinner cruises on larger vessels, along with architectural boat tours.

Urban Kayaks – Historic Chicago Tour

Travelers angling for an active way to see the Chicago River should book this guided kayak excursion. You’ll learn about Chicago’s contemporary urban landscape – and the historical significance of many of its buildings – while you paddle alongside an expert guide for 90 minutes. Reviewers enjoy seeing the city from their kayaks and say you’ll pass beautiful and romantic views along the way. What’s more, the tour is suitable for novice and experienced kayakers alike. According to travelers, you should expect to get wet and will want to dress accordingly. Single kayak tours start at $65, but you can book a double kayak for two people for about $130. Tours are available daily from May through mid-October, but exact departure times vary by day of the week. There are generally two to three tours offered each day. If you’d rather paddle the lake, consider signing up for Urban Kayaks’ tour along the lakefront, which leaves from Monroe Harbor.

Shoreline Sightseeing – Classic Lake Tour

Sit back, relax and take in the dramatic scenery of the Chicago skyline with this classic tour of Lake Michigan. The narrated journey, led by a local guide, will help you learn about Chicago’s most famous buildings and how they came to life. This tour lasts 40 minutes, which is just enough time to take in the views and enjoy a cocktail from the cash bar. Visitors love the tour for the views and history lesson. However, they advise future riders to bring a jacket because it gets cold on the water. Tickets cost approximately $25 for adults ages 13 and up and $10 for children ages 3 to 12. Infants 2 and younger ride for free. Tours depart daily in the spring, summer and fall multiple times a day. Shoreline Sightseeing also offers architecture tours and evening tours in the summer that end with the Navy Pier fireworks display.

Wendella Boats – Chicago River Architecture Tour

This 90-minute architecture boat tour makes it easy to learn about the buildings that make up Chicago’s skyline, proving once and for all that they’re more than bricks and steel. A professionally trained architectural expert will guide you through all three branches of the Chicago River while you discover the architectural mastery and design behind many classic Chicago landmarks. This boat boasts climate-controlled seating areas, a full-service bar with cocktails and snacks, and plenty of space to spread out and enjoy the views. Travelers rave about the tour, applauding the knowledgeable guides. Wendella Boats also offers sunset cruises and trips that tour the Chicago River and Lake Michigan. Tickets start at $40 for adults and $18 for children ages 4 to 12; kids 3 and younger ride for free. Tours are generally available daily from 9:30 or 10:45 a.m. to 6 or 8 p.m., depending on the month.

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