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 Windy City. Considering traveler reviews and expert opinion, U.S. News selected seven of the best Chicago boat tours, ranging from an architectural boat tour on the river to a thrilling speedboat ride on Lake Michigan.
Note: Some tour providers on this list may be running more limited operations due to COVID-19 or may impose testing or vaccine requirements. Check with your tour operator about availability before you book.
Tall Ship Windy – Chicago Skyline Sail
Price: Adults from $39; kids from $29
Duration: 75 minutes
Tall Ship Windy’s Chicago Skyline Sail introduces you to the beauty and splendor of Chicago’s world-famous buildings aboard the company’s four-masted schooner. On the 75-minute sightseeing 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 $39 for adults 13 and older and $29 for kids 12 and younger. Tours depart from Navy Pier daily from May through September at 1, 3, 5 and 7 p.m. Note that the 1 p.m. sail is all about the history of piracy in the area. 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
Price: Adults from $50; kids from $25
Duration: 1.5 hours
Hop aboard Chicago’s First Lady 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, full-service bars and restrooms. Travelers say this architectural boat tour is not to be missed and describe it as a family-friendly experience with spectacular views. They also rave about the insightful, entertaining tour guides who provide a wealth of information.
Daytime cruise tickets cost about $50 per adult and $25 per infant; fees are slightly higher for nighttime cruises. Cruises generally depart daily from 9 a.m. to 7:30 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
Price: Adults from $30; children from $23
Duration: 30 minutes
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 or early November, departs hourly every day from 11 a.m. until 11 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
Price: Singles from $70; tandems from $140
Duration: 1.5 hours
Travelers angling for an active way to see the Chicago River should book this guided kayak outing. 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. What’s more, the tour is suitable for novice and experienced kayakers alike. According to the company, you should expect to get wet and will want to dress accordingly. Reviewers enjoy seeing the city from their kayaks and say you’ll pass beautiful and romantic views along the way.
Single kayak tours start at $70, but you can book a tandem kayak (which accommodates two people) for about $140. Tours are available daily at 11 a.m. and 3 p.m. from May through September. If you’d rather paddle the lake, consider renting a kayak from the company or signing up for its paddleboarding class.
Shoreline Sightseeing – Skyline Lake Tour
Price: Adults from $27; kids from $10
Duration: 40 minutes
Sit back, relax and take in the dramatic scenery of the Chicago skyline with this tour of Lake Michigan. The prerecorded narration will help you learn about Chicago’s most famous buildings, such as the Willis Tower, 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, though some complain it was difficult to hear the narration. They also advise future riders to bring a jacket because it gets cold on the water.
Ticket fees start at $27 for adults and $10 for children. Infants 2 and younger ride for free. Tours depart daily in the spring, summer and early 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
Price: Adults from $42; kids from $19
Duration: 1.5 hours
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. An 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 $42 for adults and $19 for children ages 4 to 12; kids 3 and younger ride for free. Tours are generally available daily beginning at 9:30 a.m., with multiple departures throughout the day and night. Cruises depart from Michigan Avenue at the Wrigley Building.
Tours & Boats – 90-Minute Architecture Boat Tour
Price: Adults from $49; kids from $25
Duration: 1.5 hours
Tour-takers say this boat ride is entertaining and educational thanks to the informed guides. In 90 minutes, you’ll see Chicago’s gorgeous buildings up close as guides tell stories of the city’s history. Plus, the tour takes you to the locks on the river’s main branch, Chinatown in the south and Goose Island in the north.
Tickets start at $49 for adults, $25 for kids 4 to 17. There’s no cost for children 3 and younger, but they will need a ticket. Tours depart Wednesday to Monday at multiple times each day. Boats depart from River City Marina, which is about a mile west of Grant Park. Tours & Boats also operates private tours.