Chicago · TOURS

The 15 Best Tours & Day Trips in Chicago

102 tours  ·  from $6

Everything with a guide, a boat or a bus attached, in one list. The 15 here are the ones worth building a day around, priced and timed, with the rest of the catalogue below.

Chicago River 90-Minute Architecture Tour - The first views: Michigan Avenue and the Wrigley Building
Chicago Architecture River Cruises, Chicago Architecture Tours, Tour Reviews, Tours

Chicago River 90-Minute Architecture Tour

1.Chicago River 90-Minute Architecture Tour

★★★★★★★★★★4.5 · 9,629 reviews · 1 hour 30 minutes (approx.) · from $45Our pick

Board Wendella near the Wrigley Building for a 90-minute cruise along all three branches of the Chicago River. Your guide explains Chicago’s architectural story as you pass Marina City, Willis Tower, the Merchandise Mart, the Wrigley Building, and more. Choose outdoor views or a climate-controlled lounge.

“Super informative, beautiful deep-dive into the architectural history of this great city. Would definitely recommend. Dress more warmly than you think you need to!”

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Chicago: Gangsters and Ghosts Walking Tour - Starting with gangsters, tunnels, and Prohibition
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Chicago: Gangsters and Ghosts Walking Tour

2.Gangsters and Ghosts Walking Tour

★★★★★★★★★★5.0 · 7,155 reviews · from $52Top rated

Walk about 1.5 miles through Chicago’s Loop with a historian guide such as Taka, Sophia, Tanner, or Avery. Hear true crime tales, ghost stories, and Al Capone lore while visiting the Palmer House, Riverwalk, Chicago Theatre, and Congress Plaza Hotel. A minibus upgrade is also available.

“Tour guide (Sophia) was fantastic. Not only did she have great stories to share, she shared them in a theatrical way that made them more interesting and entertaining! I was with my 18 year old son and we both enjoyed it equally!”

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Chicago Crime and Mob Bus Tour - The Magnificent Mile, Streeterville, and Lincoln Park
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Chicago Crime and Mob Bus Tour

3.Chicago Crime and Mob Bus Tour

★★★★★★★★★★4.5 · 3,186 reviews · 1 hour 30 minutes to 2 hours (approx.) · from $49

Ride a climate-controlled coach through Chicago’s mob past with an entertaining local guide. You’ll see Capone and Dillinger sites, stop at the Biograph Theatre and Harry Caray’s mini museum, and hear crime stories from River North to Lincoln Park.

“We had so much fun and learned a lot! Our tour guide Mike was informative and hilarious! Would do this again!”

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Chicago River 45-Minute Architecture Tour from Magnificent Mile - The Main Chicago River and Riverwalk
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Chicago River 45-Minute Architecture Tour from Magnificent Mile

4.Chicago River 45-Minute Architecture Tour from Magnificent Mile

★★★★★★★★★★4.5 · 2,924 reviews · 45 minutes (approx.) · from $28Best value

Cruise from the Wrigley Building along Chicago’s main and south river branches. Hear guides such as Tess, Chris, Zach, and Alyssa explain the city’s buildings, bridges, and past while you choose open-air or climate-controlled seating. It is a compact, family-friendly introduction at $28.

“Went in January when it was 20 degrees but it was worth every penny and shiver. The tour guide was amazing she really made every minute enjoyable and had great knowledge! (I apologize for forgetting her name but she did mention she was a 7th grade teacher, hope that helps lol)”

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Chicago Lake and River Architecture Tour - Meeting at the Wrigley Building
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Chicago Lake and River Architecture Tour

5.Chicago Lake and River Architecture Tour

★★★★★★★★★★4.5 · 2,308 reviews · 1 hour 30 minutes (approx.) · from $45

Sail from Wendella’s Michigan Avenue dock along the Chicago River and Lake Michigan. Expect lively architecture commentary, skyline photos, possible lock action, indoor and outdoor seating, and guides such as John, Kenny, Tess, and Lucas. Arrive 30 minutes early for the best seats.

“Our tour guide Kenny was excellent! Very knowledgeable and funny! He made it fun and of course the architecture was fabulous.”

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Big Bus Chicago: Hop-On Hop-Off Sightseeing Tour, 24/48/72hr Pass - Stops 3 and 4 connect the Loop with Chicago’s green spaces
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Big Bus Chicago: Hop-On Hop-Off Sightseeing Tour, 24/48/72hr Pass

6.Big Bus Chicago: Hop-On Hop-Off Sightseeing Tour, 24/48/72hr Pass

★★★★★★★★★★4.0 · 2,191 reviews · 2 hours (approx.) · from $45

See Chicago from an open-top double-decker bus on a 24-, 48-, or 72-hour pass. Ride past Millennium Park, Navy Pier, Grant Park, and the Magnificent Mile, using the app to track buses and plan stops. Digital commentary, WiFi, and four self-guided walks are available with selected tickets.

“We had an excellent few hours riding around Chicago and learning about the various spots. Our driver was very knowledgeable and the journey was really comfortable. Headphones were awful but plenty of stops and chances to grab a few pictures.”

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Chicago Favorites Ultimate Food and Walking Tour - The Chicago hot dog and the no-ketchup rule
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Chicago Favorites Ultimate Food and Walking Tour

7.Chicago Favorites Ultimate Food and Walking Tour

★★★★★★★★★★5.0 · 1,962 reviews · 3 hours (approx.) · from $84

Walk 1.5 miles through Chicago’s Loop with an English-speaking guide such as Gabe, Fran, Jessika, or Kevin. Taste deep-dish pizza, a Chicago hot dog, Italian beef, Garrett popcorn, and a brownie or gelato. Your ticket also includes a two-hour bike or kayak rental, with seasonal limits.

“A great opportunity to taste local cusine which was all fantastic, also there was opportunity to buy drinks in the venues but water was also provided. Jessika's knowledge of the city was great and the opportunity to see the city sights during the tour as we walked was great, we all had a great evening😃👍”

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Chicago: Gangsters and Ghosts Guided Walking Tour - Chicago Riverwalk: crime beside the water
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Chicago: Gangsters and Ghosts Guided Walking Tour

8.Gangsters and Ghosts Guided Walking Tour

★★★★★★★★★★4.7 · 1,697 reviews · 2 hours · from $36

Spend two hours with an English-speaking historian guide such as Max, Baylor, Tanner, or Sophia, tracing Chicago’s gangster past and ghostly legends. Walk about 1.5 miles through the South Loop, visit Palmer House and Congress Hotel, and pause at a former gangster hangout.

“Great! Even in cold winter the walk was very enjoyable. Our guide Max was also very attentive and cheerful; We will ask for her again in our next visit soon. Hopefully not so cold!”

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Chicago River 90-Minute Architecture Boat Tour - Willis Tower and Chicago’s Vertical Ambition
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Chicago River 90-Minute Architecture Boat Tour

9.Chicago River 90-Minute Architecture Boat Tour

★★★★★★★★★★5.0 · 1,635 reviews · 1 hour 30 minutes (approx.) · from $37

This 90-minute Chicago River cruise combines open-air skyline views with a covered, air-conditioned cabin. Guides such as David, Hillary, Heath, and Colleen bring Chicago architecture to life with history, engineering facts, humor, and local detail. The boat visits all three major river branches and returns to the starting point.

“I have been on other Chicago River tours, but we covered parts I had not seen before, the southern end towards Chinatown. Having lived in the area and worked in town, I learned new things about my beloved Chicago. Our tour guide was exceptional- a young man from Traverse City, MI. GREAT experience and well worth the price.”

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Original Chicago Architecture Interiors Tour: Dazzling Interiors - The Loop buildings you might otherwise pass
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Original Chicago Architecture Interiors Tour: Dazzling Interiors

10.Original Chicago Architecture Interiors Tour: Dazzling Interiors

★★★★★★★★★★5.0 · 1,489 reviews · 2 hours (approx.) · from $35

Follow a local guide through Chicago’s Loop, beginning at the Art Deco Board of Trade and visiting remarkable lobbies, mosaics, and overlooked interiors before ending at the Cultural Center. Guides such as Spencer, Adam, Heath, Kaylee, and Katrina bring the city’s architecture and stories to life.

“If you do one tour in Chicago, this is THE one to do. Spencer was our inspiring guide…passionate, brilliant, informative and honestly proud of his wonderful city! He introduced us to hidden magical treasures of Chicago architecture: do not miss it.”

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Delicious Donuts & City Sights: Chicago's Original Donut Tour - Starting at Doughnut Vault on Franklin Street
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Delicious Donuts & City Sights: Chicago’s Original Donut Tour

11.Delicious Donuts & City Sights: Chicago’s Original Donut Tour

★★★★★★★★★★5.0 · 1,389 reviews · 2 hours (approx.) · from $70

Meet your guide at Doughnut Vault and walk through Chicago’s Loop to Firecakes, Stan’s, and Do-Rite. You’ll sample several styles, learn about donut shops and city landmarks, and finish near Michigan Avenue. Guides may include Nick, Lauren, Jackson, or Lizzy. Vegan and gluten-free options require advance notice.

“This is my favorite tour! I’ve booked it 3 times in the past year and brought new people. It’s always a hit and everyone’s favorite. Aside from the amazing Chicago doughnuts, you get a history of the shops and some of the local building’s you pass on the way. I particularly like that history is more personal and includes nuanced stories that you don’t hear on other tours. I’ve had the same guide all 3 times, Nick, and he is GREAT. He’s funny, personable and makes a point to talk with everyone in the group as we walk around. I highly recommend this tour.”

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Chicago: Hop-on Hop-off Sightseeing Tour by Open-top Bus - Starting along the Chicago Riverwalk
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Chicago: Hop-on Hop-off Sightseeing Tour by Open-top Bus

12.Hop-on Hop-off Sightseeing Tour by Open-top Bus

★★★★★★★★★★4.3 · 1,349 reviews · 1 - 3 days · from $45

Ride Chicago’s open-top Big Bus for 24, 48, or 72 hours, passing Willis Tower, Millennium Park, Navy Pier, Museum Campus, and the Magnificent Mile. Use live bus tracking, digital commentary in English or Spanish, and optional walking tours or an architecture cruise to shape your own day.

“It was fun because it was very informative and interactive at the same time! I liked the music that they were playing between stations.”

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Chicago in a Day: Food, History & Architecture Walking Tour - Finding the Chicago Pedway below street level
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Chicago in a Day: Food, History & Architecture Walking Tour

13.Chicago in a Day: Food, History & Architecture Walking Tour

★★★★★★★★★★5.0 · 1,153 reviews · 4 hours 30 minutes (approx.) · from $100

Spend about 4.5 hours walking from the Chicago Theatre through the Pedway, Riverwalk, Magnificent Mile, and Millennium Park. Guides such as Dave, Dash, Rich, and John mix Chicago history with deep-dish pizza, popcorn, hot dog, and Italian beef tastings. Expect 3 to 4 miles on foot and a full meal’s worth of food.

“Dave was very knowledgeable & friendly. Freezing outside but still was able to provide a great experience both inside & outside! I would do this tour again.”

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Chicago Loop District Food Tour with Deep Dish & Beef Sandwich - Deep dish, Italian beef, and the rest of the menu
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Chicago Loop District Food Tour with Deep Dish & Beef Sandwich

14.Chicago Loop District Food Tour with Deep Dish & Beef Sandwich

★★★★★★★★★★5.0 · 870 reviews · 3 hours (approx.) · from $84

Spend about three hours walking Chicago’s Loop with a guide such as Danny, Lance, Eliot, or Mike. Taste deep-dish pizza, Italian beef, a Chicago hot dog, popcorn, brownie, churro, and a secret dish while visiting the Rookery, Willis Tower, Federal Plaza, and Millennium Park.

“Come hungry!! Wonderful food and great choices!! We enjoyed all the history about Chicago’s different foods and learning a bit about the building they were houses in. Light walking around the loop area and a great kid of mains and sweets. Danny was a wonderful guide and was very knowledgeable! He kept the tour on a great schedule and had our food ready at each stop so no time was wasted. There was a bit more time to savour the food at the mains which was wonderful - highly recommend!!”

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Chicago: Mob and Crime Bus Tour - Starting beside the Water Tower
Chicago Bus Tours, Chicago Gangster Tours, Tour Reviews, Tours

Chicago: Mob and Crime Bus Tour

15.Mob and Crime Bus Tour

★★★★★★★★★★4.4 · 859 reviews · 1h 30m · from $49

Ride an enclosed, climate-controlled bus through Chicago’s crime past, from H. H. Holmes and Leopold and Loeb to Al Capone and John Dillinger. You’ll stop for photos, visit a mini mob museum, see Frank Nitti’s safe, and hear live English commentary from guides such as Jay, Katie, and Jamie.

“Guide-Dane-was great, really enthusiastic. Loved seeing Nittis secret room.”

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New in Tours

★ 4.5Chicago Helicopter 25-Mile Tour for up to Three Passengers11 reviews
★ 4.5Chicago Helicopter 10-Minute Tour for up to Three Passengers32 reviews
★ 3.52-Hour Chicago’s Chinatown History and Culture TourFrom $304 reviews
★ 4.6Helicopter Tour of Chicago SkylineFrom $18838 reviews
★ 4.0Chicago Riverwalk Self-Guided Walking TourFrom $146 reviews
★ 5.0Chicago Fire TV Show Set Tour68 reviews
★ 5.0Ferris Bueller Movie Tour at the Art Institute of ChicagoFrom $4926 reviews
★ 4.5Downtown Chicago TV and Movie Sites Guided Walking TourFrom $4423 reviews
★ 5.0Downtown Loop & Millennium Park 2 Hour Walking TourFrom $495 reviews
★ 5.0Chicago Walking Tour: The Magnificent MileFrom $3534 reviews
★ 5.0Oktoberfest Walking Brewery Tour in Malt RowFrom $3928 reviews
★ 4.5Chicago Millennium Park Self-Guided Walking TourFrom $145 reviews
★ 4.2Chicago to Milwaukee Day Trip: City Tour with Miller BreweryFrom $12516 reviews
★ 4.2Sunset Kayak Tour on the Chicago RiverFrom $575 reviews
★ 4.9Chicago Fire TV Show Set Tour43 reviews

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