Chicago · TOURS

The 15 Best Guided Tours & Day Trips in Chicago

260 tours  ·  from $5 a head

Everything with a guide, a boat or a bus attached, in one list. These 15 are the ones worth a whole afternoon, priced and timed, with the rest of the catalogue underneath.

Chicago River 90-Minute Architecture Tour - Following the river past the city’s landmarks
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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 a Wendella boat at the Michigan Avenue Bridge for a 90-minute narrated cruise along all three branches of the Chicago River. An expert local guide connects buildings such as Marina City, the Wrigley Building and Willis Tower to the city’s architectural story. Choose indoor or outdoor seating, and plan for weather: the best open-air views come with exposure to wind and cold.

“Great experience . Definitely would do it again. Trying to get to know me hundred characters and just made it.”

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Chicago: Gangsters and Ghosts Walking Tour - From Millennium Park to the Palmer House
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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, hearing stories of Al Capone, bootleggers, and reported hauntings at places such as the Palmer House and Congress Plaza Hotel. The tour lasts about two hours, with frequent stops and a refreshment and restroom break. A bus upgrade is available, with one stop at Harry Caray’s Italian Steakhouse.

“This was a very interesting and also funny tour! Our guide Tanner was amazing!!! We had a very good time”

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Chicago Crime and Mob Bus Tour - The Biograph Theatre and Dillinger’s last stop
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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

The Chicago Crime and Mob Bus Tour takes you from Pearson Street through River North, the Loop, Lincoln Park, and other neighborhoods tied to Chicago crime. An English-speaking guide shares stories of Al Capone, Bugs Moran, John Dillinger, and more, with photo stops at sites such as the Biograph Theatre and a visit to Harry Caray’s mini mob museum.

“Jamie was a great guide, very comedic, informed, prompt, and a great photographer too! It was nice being able to stop and learn about some of the history of Chicago. I highly recommend!”

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Chicago River 45-Minute Architecture Tour from Magnificent Mile - Marina City’s corn-cob towers from the water
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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 the Chicago River from the Wrigley Building for 45 minutes of live architecture commentary. You’ll pass the Riverwalk, Michigan Avenue Bridge, Merchandise Mart, Lyric Opera House, and Marina City’s corn-cob towers. Choose an open-air seat or a climate-controlled lounge; guides have included Tess, Zach, Alyssa, and Chris, though the guide varies.

“Great experience. The skyline was beautiful and the tour guide was awesome. This was the highlight of my trip.”

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Chicago Lake and River Architecture Tour - Spot the city-within-a-city buildings
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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

Board Wendella’s boat at the Wrigley Building for a 90-minute cruise along the Chicago River and Lake Michigan. A live guide points out landmark architecture, from the Wrigley Building to Marina City, while you get river-level views and photos of the skyline. Indoor climate-controlled seating and an outdoor deck are available, but spots are first come, first served.

“This was a great tour if you are wanting to many of the buildings and the skyline from the lake. The guide was knowledgeable with the history and construction of the buildings”

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Big Bus Chicago: Hop-On Hop-Off Sightseeing Tour, 24/48/72hr Pass - Museum Campus, the river, and Navy Pier
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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

Ride a 24-, 48-, or 72-hour Big Bus pass past the Riverwalk, Millennium Park, Navy Pier, and more. Use the app to track buses and find stops, then hop off to explore at your own pace. Digital commentary covers the city, while drivers such as Candace and Felicia have added local tips and personality.

“We loved it. Only thing was that it canceled for Dec 13th we planned on riding it another day for are 24 hrs pass. Candice was bad driver she was a 10 put of a 10”

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Chicago Favorites Ultimate Food and Walking Tour - Hot dogs, Italian beef and the art of eating neatly
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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 about 1.25 to 1.5 miles through downtown Chicago with a local English-speaking guide, stopping for deep-dish pizza, a Chicago hot dog, Italian beef, Garrett’s popcorn and a sweet treat. You’ll pass landmarks such as Millennium Park and the Chicago River. The tour lasts about three hours, includes food, and comes with a two-hour bike or kayak rental to use within three days before or after.

“Very fun, informative, and delicious tour of Chicago with our great guide Gabe, who was super personable and humorous. Highly recommend!”

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Chicago: Gangsters and Ghosts Guided Walking Tour - The Riverwalk and Death Alley
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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

Join an English-speaking historian guide for a 1.5-mile walk through Chicago’s South Loop, where Prohibition-era gangsters and ghost legends meet at landmarks including the Riverwalk, Palmer House and Congress Hotel. The $36 tour includes entry inside the Palmer House and Congress Hotel, plus a midway break at a former gangster hangout.

“Tanner was really nice Guide. It was a good interesting tour, with much of deap facts.”

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Chicago River 90-Minute Architecture Boat Tour - Reading the skyline from the Wrigley Building
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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

Spend 90 minutes on the Chicago River, hearing how the city’s buildings took shape as you pass landmarks such as the Wrigley Building, Willis Tower, Aqua Tower, and Merchandise Mart. A live guide narrates the route through all three river branches. Choose an open-air seat or settle inside, where there is air conditioning, windows, and a restroom.

“Amazing tour, handicap accessible, small business owned, Hillary was so knowledgeable and made the trip a great experience! Thanks for a memorable time!”

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Original Chicago Architecture Interiors Tour: Dazzling Interiors - Starting at the Chicago Board of Trade
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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

Walk the Loop with an English-speaking local guide, starting at 425 S Financial Pl and finishing at the Chicago Cultural Center. The two-hour route includes the Art Deco Chicago Board of Trade Building and other interiors that vary by tour. Guides have included Spencer, Kaylee, Adam, and Heath. Expect outdoor walks between indoor stops.

“Very fun tour guides, he was well educated about the city and knew a lot of minute details that you would miss out because you dont know what to look for. Excellent tour!”

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Delicious Donuts & City Sights: Chicago's Original Donut Tour - Sampling your way through the Loop
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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

Walk Chicago’s Loop with a guide such as Nick, Jackson, Lauren, or Lizzy, stopping at four donut shops for included samples and stories about the bakeries and nearby buildings. The tour lasts about two hours, starts at Doughnut Vault, and ends at Do-Rite on Erie Street. Doughnut Vault is listed as a Sunday stop, so check which route applies to your date.

“Fun facts, great donut flavors and hidden spots one would never find. Tour guide was great and did a great job of keeping us all moving. My only advice would be that these flits slots are small so there is only one stop where we actually stopped and sat down. The others were outside and standing majority of the time. Thankfully our weather was cool and overcast. Really enjoyed it.”

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Chicago: Hop-on Hop-off Sightseeing Tour by Open-top Bus - Museum Campus and the lakefront
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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 Big Bus Chicago’s open-top double-decker past Willis Tower, Millennium Park, Navy Pier, Museum Campus and the Magnificent Mile. Hop off to explore, then track buses in the app. Digital commentary is available in English and Spanish; selected tickets add self-guided walks or a river architecture cruise. Drivers such as Candace have also been praised for lively live commentary.

“Candice our driver made our journey around Chicago with her fun facts, ideas of things to do, safe driving and was just so motivating enjoyable route.”

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Chicago in a Day: Food, History & Architecture Walking Tour - Chicago River views and a stretch along the Mag Mile
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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

Walk about 3 to 4 miles over roughly 4.5 hours with a local guide and no more than 11 other people. You’ll pass the Chicago Theatre, the Riverwalk, the Wrigley Building and Millennium Park, with tastings of Chicago favorites along the way. Guides have included Dave, Rich and Dash. Food is meant to add up to a meal, but the main tastings may come later in the tour.

“Informative; our guide Dave was passionate and knowledgeable. It was great to try Chicago’s iconic foods too!”

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Chicago Loop District Food Tour with Deep Dish & Beef Sandwich - The Loop route, stop by stop
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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 local food guide, tasting deep-dish pizza, Italian beef, a Chicago-style hot dog, popcorn, brownie, and a secret dish. Along the way, see the Rookery, Willis Tower, Calder’s Flamingo, and other downtown landmarks. Groups are capped at 12, and you can choose a private option.

“The food was excellent; truly representative of Chicago. Info. regarding the food and city was really interesting. I would take this tour again!”

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Chicago: Mob and Crime Bus Tour - From Al Capone to Dillinger
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Chicago: Mob and Crime Bus Tour

15.Mob and Crime Bus Tour

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

This 90-minute Chicago crime tour pairs an English-speaking guide with a climate-controlled coach, photo stops and short walks. Hear stories about Al Capone, John Dillinger and other criminals, then see a mini mob museum featuring Frank Nitti’s safe and address book. Guides such as Jay and Katie have led engaging, story-rich tours.

“Myself, husband, and 11 year old had a great experience. Tour guide was informative and we saw sights around Chicago we wouldn't have. Just the right amount of on and off.”

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New in Tours

★ 5.0Skip the Line: Public Tour-Adult Admission Ticket (50 mins)12 reviews
★ 5.0Single Guided Kayaking Tour near ChicagoFrom $694 reviews
★ 4.5Tandem Guided Kayak Tour Near Chicago6 reviews
★ 5.0Cocktail Adventure Tour 21+From $709 reviews
★ 5.0Walking Tour: Historic Chicago Pubs in River North and the LoopFrom $659 reviews
★ 4.5The Devil in the White City: A Haunting History TourFrom $6417 reviews
★ 5.0The Deep Pockets Of Graceland Cemetery Walking TourFrom $459 reviews
★ 5.02 Hour Chicago Landmarks & Lakefront E-Bike TourFrom $724 reviews
★ 5.0Small Group Lake Michigan TourFrom $6013 reviews
★ 4.0Chicago Riverwalk Self-Guided Walking TourFrom $146 reviews
★ 5.0Self-Guided Chicago Loop Tour Explore the City at Your Own PaceFrom $93 reviews
★ 5.0Chicago Sunset Segway TourFrom $7526 reviews
★ 5.0Retro River North Walking TourFrom $04 reviews
★ 4.5Chicago Night Driving Tour with Skydeck and River CruiseFrom $18926 reviews
★ 5.0Private Holiday City Tour3 reviews

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