All tours (21–40 of 142 · from US$ 6)
Chicago: Art Institute Early Access Tour & Skip-the-Line Feel the quiet before the crowds at Chicago’s Art Institute. Early entry, skip-the-line tickets, and a small group with an art historian guide. Includes all admission fees. Every day except Tuesday · 10:30 · All ages ★ 4.97 (697 reviews) Duration: 2h 30m Live guide: EN ✓ Free cancellation. from US$ 71 per person
Chicago Small Group Tours: Museum Campus skyline views Small-group minibus tour of Chicago with expert guide, four photo stops at iconic landmarks, and skyline views from Museum Campus. Max 13 passengers. Every day · 10:00, 10:30, 13:00 and 13:30 · All ages ★ 4.87 (694 reviews) Duration: 2h Live guide: EN ✓ Free cancellation. from US$ 50 per person
Field Museum Chicago: SUE T. Rex & Egyptian Mummies Tickets Field Museum admission includes SUE the T. rex, Egyptian mummies, Gem Hall, and Dinosaur Hall. 40 million artifacts, free docent tours, wheelchair accessible. Hours 9am–5pm. Every day · No fixed time · From age 5 ★ 4.58 (602 reviews) Duration: 4h Live guide: EN ✓ Free cancellation. from US$ 29 per person
Chicago: Pedway Underground Tour & Loop Architecture Chicago's Pedway tunnel system connects 40 downtown blocks. Tour City Hall, Chicago Picasso, Marshall Field's interior, and Chicago Cultural Center with a local guide. Every day · 10:00 and 14:00 · All ages ★ 4.89 (597 reviews) Duration: 2h Live guide: EN ✓ Free cancellation. from US$ 35 per person
Chicago Night Crimes Tour: St Valentine's Day Massacre & Gangster Sites 2–2.5 hour bus tour of Chicago's mob history with stops at the St. Valentine's Day Massacre, Biograph Theater, and crime scenes. Includes video footage and souvenir pamphlet. Fri · 19:30 ★ 4.82 (526 reviews) Duration: 2h–2h 30m Live guide: EN ✓ Free cancellation. from US$ 55 per person
Chicago: Historic Fireboat River & Lake Cruise with Architecture Cruise Chicago's river and Lake Michigan aboard a retired 1937 fireboat. Expert narration on fire history and architecture. Onboard bathrooms, all fitness levels welcome. Next departure: 17 Apr 2027 · All ages ★ 4.92 (517 reviews) Duration: 2h Live guide: EN ✓ Free cancellation. from US$ 39 per person
Chicago: Gangster & Ghosts Walking Tour with Speakeasy Bars Feel Chicago’s haunted past on a walking tour with real crime stories, Prohibition speakeasy bars, and exclusive access to historic interiors. Includes expert guide. Every day except Wednesday · 11:00, 14:00, 17:00, 19:00 and 21:00 · All ages ★ 4.98 (506 reviews) Duration: 1h 30m Live guide: EN ✓ Free cancellation. from US$ 35 per person
Chicago: Neighborhood Pizza Bus Tour & Historic Pizzerias Eat your way through Chicago’s iconic neighborhoods with a local guide, sampling deep dish, tavern-style, and coal-fired pizza. Includes bus transport and four slices. Sat and Sun · 11:00 · All ages ★ 4.89 (489 reviews) Duration: 3h 30m Live guide: EN ✓ Free cancellation. from US$ 89 per person
Chicago: Mob & Ghost Walking Tour in the Loop at Night Wander Chicago’s shadowy alleys and haunted hotels on a true crime walking tour. Hear mob tales, ghost stories, and explore with a local guide, includes all stops. Every day · 16:00 and 19:00 · All ages ★ 4.72 (475 reviews) Duration: 1h 30m–2h Live guide: EN ✓ Free cancellation. from US$ 34 per person
Chicago Architecture Walking Tour: Burnham & Sullivan Landmarks Walking tour of Chicago's architectural landmarks on Michigan Avenue and State Street. Includes Chicago Cultural Center, Palmer House, Wrigley Building. 2.5 hours. Every day · 6 start times, 10:30 to 13:30 · From age 5 ★ 4.94 (465 reviews) Duration: 2h Live guide: EN ✓ Free cancellation. from US$ 35 per person
Escape Room Chicago: 5 Themed Puzzle Games in River North Solve puzzles and crack codes in one of five themed escape rooms near Michigan Avenue. Mission: Mars, Prison Break, The Heist, and more. Mon–Thu · 50 start times, 08:00 to 23:55 ★ 4.96 (445 reviews) Duration: 1h 15m Live guide: EN ✓ Free cancellation. from US$ 48 per person
Paint your own street art in Chicago: Spray paint workshop Learn spray paint, stencil and graffiti styles from local artists at Studio W.I.P. in Chicago, then take home a canvas you painted yourself in 90 minutes. Every day · 13:00, 15:30, 18:00 and 20:30 · From age 10 ★ 4.80 (439 reviews) Duration: 1h 30m Live guide: EN ✓ Free cancellation. from US$ 45 per person
Chicago Lakefront Segway Tour: Grant Park & Museum Campus 2-hour Chicago Segway tour covering 6-8 miles along the lakefront. Includes Buckingham Fountain, Field Museum, Shedd Aquarium, Soldier Field, guide and helmet. Max 8 people. Every day · 11:00, 13:30 and 14:00 · From age 12 ★ 4.96 (397 reviews) Duration: 2h Live guide: EN ✓ Free cancellation. from US$ 67 per person
Art Institute of Chicago Skip-the-Line Guided Tour Skip the entrance line at the Art Institute and spend 2.5 hours with a guide who knows where the masterpieces are: Paris Street Rainy Day, Nighthawks. Every day except Tuesday · 10:30, 14:00 and 17:00 · All ages ★ 4.99 (366 reviews) Duration: 2h 30m Live guide: EN ✓ Free cancellation. from US$ 90 per person
Lake Michigan Speedboat Ride Chicago: 30-Minute Skyline Tour High-speed boat tour departing Navy Pier with unobstructed views of Chicago's skyline and live guide commentary. 30 minutes on the water. Next departure: 1 May 2027 · All ages ★ 4.11 (360 reviews) Duration: 30m Live guide: EN ✓ Free cancellation. from US$ 45 per person
Chicago: Haunted Pub Crawl & Ghost Stories Walking Tour Follow a costumed guide through Chicago’s haunted bars, hear real ghost stories, and sip drinks in historic pubs. Includes walking tour with local expert. Fri and Sat · 16:30 and 19:30 · From age 21 ★ 4.91 (354 reviews) Duration: 2h 30m Live guide: EN ✓ Free cancellation. from US$ 36 per person
Chicago Gangsters and Ghosts Walking Tour: South Loop History Walk Chicago's South Loop with a historian guide through speakeasies, mob sites and haunted landmarks: Palmer House, Chicago Theatre, Congress Hotel. Every day · 13 start times, 09:00 to 20:00 · All ages ★ 4.82 (349 reviews) Duration: 2h Live guide: EN ✓ Free cancellation. from US$ 38 per person
Chicago Bike Tour: Downtown Landmarks & Lakefront Guided 3-hour Chicago bike tour covering Millennium Park, Grant Park, Museum Campus and the lakefront with bikes and helmets included. Every day except Tuesday and Thursday · 13:30 · All ages ★ 4.94 (281 reviews) Duration: 3h Live guide: EN ✓ Free cancellation. from US$ 59 per person
Chicago Lakefront Bike Tour: 3-hour neighborhood ride Bike tour of Chicago's North Side lakefront neighborhoods with guide, bike and helmet included: ride past Gold Coast mansions. Next departure: 2 Mar 2027 · All ages ★ 4.91 (268 reviews) Duration: 3h Live guide: EN ✓ Free cancellation. from US$ 59 per person
Chicago Walking Tour: Loop Architecture & Picasso Sculpture Downtown Chicago walking tour of the Loop's landmark buildings, Chagall mosaic, Picasso sculpture and Chicago Theatre. 2 hours, 2 miles. Mon, Tue, Thu and Fri · 10:00 and 13:00 · From age 10 ★ 4.98 (257 reviews) Duration: 2h Live guide: EN ✓ Free cancellation. from US$ 44 per person