Sightseeing Tours in Chicago

If you only book one tour in Chicago, make it an architecture cruise on the river. After that, you can see the city by boat, bus, bike, Segway or on foot, and one of the best walking options is free. Prices below come from each company's own site in September 2026 and change with the season, so treat them as a starting point.

By boat

The Chicago Architecture Center river cruise

This is the one locals send their visitors on, and plenty of locals have done it more than once. The Chicago Architecture Center River Cruise runs aboard Chicago's First Lady boats, and it's led by the center's volunteer docents, who go through a long training program before they lead a tour. That's the difference from the cheaper cruises. You get a person who can answer your question about the building you're passing, not a recording.

The cruise lasts 90 minutes and starts at $57 for adults. The season runs from mid-March to late November. Boats leave from the southeast corner of the DuSable (Michigan Avenue) Bridge at Wacker Drive (112 E. Wacker Dr.), and the center asks you to show up 30 minutes early. Book ahead for summer weekends and anything around sunset. The boats have heated and cooled cabins, but sit on the open upper deck if the weather lets you. The First Lady fleet also runs other cruises of its own, but the docent-led one is the reason to come.

Other river and lake cruises

Wendella has been running boats since 1935 from 400 N. Michigan Ave., at the river. It has a 90-minute and a 45-minute architecture tour, plus a 90-minute Lake & River Architecture Tour that adds time out on Lake Michigan. Wendella also runs sunset and fireworks cruises.

Shoreline Sightseeing has an Architecture River Tour of 60 to 75 minutes from $39. Its Skyline Lake Tour leaves from Navy Pier, lasts about 45 minutes with recorded narration, and costs $34 for adults and $13 for kids 3 to 12. It runs daily from spring through fall, weather permitting. That's the quick, cheap way to see the skyline from the water, and the view back at the city from the lake is the best one you'll get. Shoreline also runs the water taxis between Navy Pier, Michigan Avenue, the Museum Campus and Union Station, which are a handy way to get around in summer.

If you'd rather eat on the water, City Cruises runs brunch, lunch and dinner cruises on the lake from Navy Pier and on the river. For more ideas, see five ways to get out on the water in Chicago.

On foot

Chicago Greeter (free)

Still running, still free, and still one of the best deals in town. Chicago Greeter is run by Choose Chicago, the city's tourism office, and pairs you with a volunteer local for a two- to four-hour walk around a neighborhood of your choice. Groups are capped at six, visits are offered in more than a dozen languages, and you can shape it around what you care about. You do need to plan ahead, since they ask you to register at least two weeks before you arrive.

No plan that far ahead? The InstaGreeter walks need no booking. They're about an hour long, and the Loop walk leaves from the Randolph Street entrance of the Chicago Cultural Center on Fridays, Saturdays and Sundays at 11:30am and 1:30pm, year-round. There's also a Riverwalk walk on the same days at 11:30am from May 22 to October 18, meeting at the Vietnam Veterans Memorial.

Chicago Architecture Center walking tours

The Chicago Architecture Center runs dozens of walking tours, from the Loop's first skyscrapers to the underground Pedway, Wicker Park and Frank Lloyd Wright's houses in Oak Park. The ones I checked run an hour and a half to just under two hours. The Intro to Chicago Architecture walk is a good first one (1.75 hours, ending at the Marquette Building). The Pedway tour is the one to book in January, since you spend it indoors. Its ticket also gets you into the center at 111 E. Wacker Dr. within seven days.

Private walks and food tours

Walk Chicago Tours only does private tours, for groups of two or more, across about 16 routes covering architecture, history and neighborhoods like Pilsen and Chinatown. You book by phone or email, and prices are on its FAQ page.

If you care about food, Chicago Food & City Tours (the company this page once linked as Chicago Food Planet) has walks from $65 for a two-hour Lincoln Park tour to $85 for three hours on its Iconic Foods of Chicago or Street Foods of Pilsen tours. The Chinatown tour starts at $99, the West Loop at $129, and there's a 3.5-hour tour inspired by the TV show The Bear from $139. Our own unusual tours in Chicago page has more niche options.

By bike or Segway

The old Bike Chicago is now Bike & Roll Chicago, with shops at Millennium Park (34 S. Michigan Ave., at Monroe) and Navy Pier (600 E. Grand Ave.). Tours run daily in spring, summer and fall and include a Lakefront bike tour, a Lincoln Park ride and a night ride. Bike & Roll also runs lakefront, skyline and sunset Segway tours from its two shops. A Segway tour is worth it if you want to ride a Segway or have trouble walking long distances. If you plan to go inside the museums on the route anyway, skip it and walk.

Bobby's Bike Hike, which started in 2002, runs bike, walking and food tours of two to four hours from 540 N. Lake Shore Dr. in Streeterville (entrance on Ohio Street), and rents bikes and kayaks too. Check its site for current tours and prices.

Or skip the guide and take a Divvy bike down the Lakefront Trail yourself. A day pass is $19.90.

By bus

The Chicago Trolley & Double Decker Co. that this page used to recommend is gone. Its web address now points to an unrelated site. The hop-on, hop-off option today is Big Bus Chicago. Its open-top Red Loop has 11 stops near the main downtown sights, with audio guides, and runs from 10am to 5pm every 20 to 30 minutes. A Yellow Shuttle heads to the South Side, with a stop at the Presidential Center. Adult tickets start at $39 on its site, and several packages bundle in a boat tour or the 360 CHICAGO observation deck. Before you buy, compare against Go City and CityPASS on our city pass page.

You can also build your own version on the CTA with a $5 1-day pass. A ride around the elevated Loop on the Brown Line gets you a window seat among the buildings. Our transportation guide explains how.

The Chicago Architecture Center also runs bus tours, including Frank Lloyd Wright and Historic Route 66, for when the thing you want to see is too far to walk.

Photo by Smart Destinations