Chicago’s Best City Tours

Walk through underground tunnels with a subterranean city, discover hidden gems and historic landmarks, taste iconic foods, and step into the shadier side of the city’s history on a Windy City tour. Experienced guides lead visitors (and residents) on tours in the air, on land and on water.

Fly Heli (10-mile city skyline tour, minimum two people, max three people, take off and land at Vertiport Chicago, 1339 S Wood St.) Other tours: 30-mile shoreline tour from the Griffin Museum of Science and Industry to Wrigley Field; a 45-mile grand tour, north to Evanston, the Baha’i Temple and shoreline; and a 23-mile Diamond Tour of Chicago’s major sports stadiums: Guaranteed Rate Field, Wrigley Field, Soldier Field and the United Center. 

• Chicago River Boat Architecture Tours (90 minutes, depart from 465 N. McClurg Ct.)  On-board docents chat about bridges and skyscrapers, just some of the 50 landmarks you’ll see. 
• Seadog River and Lake Architecture (75 minutes, depart from Navy Pier) This narrated cruise starts in the lake and includes a short speedboat ride on your way to Willis Tower. The boat is BYOB and dog-friendly.
• Wendella Tours and Cruises (45 or 90 minutes, depart from the Wrigley Building, 400 N. Michigan Ave.) Tours and cruises include the Chicago River and Lake Michigan aboard a full-service, climate-controlled boat with a snack bar and restrooms. This family-owned and -operated company operates year-round. 

• Chicago Architecture Center, Evening River Cruise (90 minutes, Chicago’s First Lady, depart 112 E. Wacker Dr.) Cruise with trained and enthusiastic volunteer docents on board.
• Seadog Extreme Thrill Ride (30 minutes, depart from Navy Pier) Sharp twists and turns guarantee passengers (48 inches and taller) will get wet while reaching speeds up to 45 mph.
• Seadog Lakefront Speedboat Tour (30 minutes, depart Navy Pier) Facts are interspersed with bursts of speed on this BYOB, dog-friendly tour.
• Shoreline Sightseeing, Skyline Lake Cruise (30 minutes, depart Navy Pier) This prerecorded tour cruises past the skyline, where passengers see some of the city’s tallest buildings, such as the Willis Tower, Aqua Tower and The St. Regis Chicago, while hearing the history. 

• Chicago Boat Company (One to four hours, multiple departure locations: Marina City, 300 N. State St.; City Winery, 11 W. Riverwalk S.; Chicago Water Plaza, 151-155 W. Wacker Dr.; North Branch 3057 N. Rockwell St.; Lakefront, 400 E. Monroe) Be the captain of a Duffy electric boat as you navigate the river moving between 3 to 6 mph. Captains and tour guides cost extra. 
• Island Party Boat (90 minutes, depart Chicago Riverwalk, 355 E. Riverwalk South) Come board the tiki-themed river boat and tour the Chicago River and Lake Michigan. The boats are pet-friendly. There is a bar on board, but no guide. 

• Inside Chicago Walking Tours (Two hours, with 1.25 to 1.75 miles of walking, multiple tours: The World Within, tour the interior of Chicago Loop buildings, start near the Chicago Board of Trade, end three blocks away from Millennium Park (exact address sent with ticket purchase); Open Your Eyes, tour the pedway, a labyrinth of underground tunnels and corridors. Note: this tour includes several sets of stairs. Start near City Hall on LaSalle St. and end within a block of Millennium Park (exact address sent with ticket purchase).
• Wild Onion Walks (Multiple tours: Chicago Loop, 11 a.m. and 2 p.m., Monday through Saturday, 2 hours, start at the bronze cow outside of the Chicago Cultural Center, Washington St. and Michigan Ave.; Let’s Go to the Parks, 2 p.m. Monday, 2.5 hours, start at the big boulder next to Agora, 1135 S. Michigan Ave.; Strolling Around the Chicago River, 11 a.m. Wednesday and Saturday, 2 hours, start Anita Dee Yacht Charters, 200 N. Breakwater Access.; A Most Magnificent Mile, 2 p.m. Thursday, 2 hours, start at the Chicago Architecture Center, 111 E. Wacker Dr.; Exploring Lincoln Park, 2 p.m. Tuesday, 2 hours, start at the entrance of the Chicago History Museum, 1601 N. Clark St.) A Chicago native shares his love for the city on these tours. 

• Chicago Food and City Tours (Multiple tours: Iconic Foods of Chicago includes five must-eat Chicago dishes, 3 hours, 1.4 miles of walking. Yes, Chef!, inspired by the TV show, “The Bear,” 3.5 hours, 9 miles by bus. The tour ends with a hot fudge sundae at Margie’s Candies. Gateway to the West Loop, 3 hours, 0.6 miles, five stops. Stroll along Randolph Street in the West Loop, drink pairings available. Stops include hidden gems, tacos and pizza. Other food tours available.
• Pizza City, USA Tours (Multiple times and locations: Saturdays 11 a.m. to 2:30 p.m, start at Labriola (bus tour), 535 N. Michigan Ave., Friday 5-7:30 p.m. (walking tour) start at Robert’s Pizza and Dough Company, 465 N. McClurg Ct., also West Loop walking pizza tours). Learn fun facts while tasting pizza.
• Secret Food Tours (3 to 3.5 hours with a total of 45 minutes of walking, look for the guide holding an orange umbrella at the Harold Washington Library Center, 400 S. State St.) The Loop tour included six stops for tastes of iconic foods like popcorn, a Chicago-style hot dog, Italian beef, deep-dish pizza and the signature brownie from the Palmer House hotel. 

• Chicago Foodways Tours Go into neighborhoods and discover their history and taste their food on any of these tours. (Global Street Foods of Uptown: Friday at 2 p.m., 2.5 hours, 1-mile walk, six dishes; Lincoln Square: West Meets East, Sunday at 11:30 a.m., 3 hours, 1.5 miles, taste food from Austria, the Balkans, Germany, Greece and Kyrgyzstan; Saigon to Stockholm Food Tour, Saturday at 11 a.m., 3 hours. Argyle and Andersonville neighborhoods start at Nha Hang Viet Nam, 1032 W. Argyle St., and end at 5357 N. Ashland Ave., 1 mile from the starting point)  
• Spice of Life Tours (Saturday and Sunday, 12 p.m., 4 hours, start at Kamdar Plaza, 2646 W. Devon Ave.) Delve into West Rogers Park on the Little India Tour. Stops include a temple, spice stores, henna tattoos and South Asian cuisine.

• Chicago Gangsters and Ghosts Tour (Walking tours: 11 a.m., 1 p.m., 4 p.m., 8 p.m.; 2 hours, 1.5 miles walking, start at The Royal Sonesta Hotel Chicago Downtown, 71 E. Wacker Dr.) Historians share spooky tales of the city’s ghosts and gangsters at each famous location; family-friendly. Bus tours: Chicago Loop Vice District: 2 p.m., 4 p.m., 6 p.m., 8 p.m.; 1.5 hours, starts at Palmer House, 17 E. Monroe St.) Tour the Loop and River North neighborhoods, once dominated by notorious Italian and Irish gangs during Prohibition. One of the stops is an immersive experience.
• Untouchable Tours (11 a.m. and 1 p.m. tours—daily in summer; Thursday, Friday, Saturday and Sunday in springtime; Saturday and Sunday in winter. One to 1.5- hour bus tour, starting at Clark St. between Ohio and Ontario). Actors take on the persona of a 1920’s gangster, presenting an accurate account of the city’s crimes and activities during the Prohibition Era.

• Chicago Greeter Two to 4 hours, customized based on your interests and offered in more than a dozen languages. Book two weeks in advance.
• InstaGreeter Walks Memorial Day through the end of September; one hour, no reservations necessary for these two tours. Explore the must-see spots and top attractions of Chicago’s downtown (The Loop, Cultural Center, 11:30 a.m. and 1:30 p.m. Friday, Saturday, Sunday). Discover public art, outdoor cafes and scenic views along the banks of the Chicago River (Chicago Riverwalk at the Vietnam Veterans Memorial, 11:30 a.m. Friday, Saturday, Sunday). Self-Guided Tours via a Smart Phone 
• Urban Adventure Quest (Two to 2.5 hours, 2 miles. Start at The Westin Chicago River North, end at Monroe at Dearborn St.) Use your smartphone to get and solve clues as you traverse the city, see the sites and complete 19 challenges and three bonuses on this scavenger hunt. 

• City Fit Tours, Chicago Highlights Running Tour (3.5 miles, 1 hour, 7 a.m. Monday to Friday and 8 a.m. Saturday and Sunday, starting and ending at The Apple Store on Michigan Ave. or depending on your hotel, the group can pick you up upon request) A casual pace run allows guides to share interesting facts at designated stops, such as the Lakefront Trail, Navy Pier, Mag Mile and Wrigley Building.
• On Location Tours (10 a.m. Friday, Saturday, and Sunday, 2 hours). Explore downtown Chicago with a local actor who shares interesting facts, insider scoops, and behind-the-scenes stories from TV and movie sites such as Ferris Bueller’s Day Off, The Untouchables, The Dark Knight and The Bear.
• Soldier Field Stadium Tours (11-12:15 p.m., Monday and Saturday, Soldier Field, 1410 S. Museum Campus Dr.) Two tours: The Classic tour takes guests through a tour of the south courtyard, visitors’ locker room and interview room, the skyline suite, the colonnades, and the field. The VIP tour includes all of the Classic stops as well as a 15-minute on-field experience and a look inside the stadium video control room.
• Tour Through a Lens Select from 3-, 5- or 9-hour custom photography tours, then complete the pre-tour questionnaire.
• Wrigley Field Tours Tours last 75 to 90 minutes, starting at Gallagher Way gate. Public tour/nongame day tour: seating bowl, bleachers, outfield ivy, press box, visiting clubhouse, dugout and field. Public game-day tour: seating bowl, bleachers, upper deck and field.