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116 results | All Chicago Tours

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Gangsters and Ghosts Tour in Chicago

Gangsters and Ghosts Tour in Chicago

star-4.5
2885
Experience a colorful side of Chicago history with this Gangsters and Ghosts Tour. With a historian as your guide, you’ll step back to the roaring 20’s, when the Chicago Loop was a hub for bootleggers, speakeasies, and gangsters like the infamous Al Capone. Visit onetime gangster hangouts and haunted sites like the Palmer House, Congress Hotel, and Death Alley.
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  • 2 hours
  • Free Cancellation
From
USD35.00
From
USD35.00

Chicago Favorites Ultimate Food & Walking Tour

Chicago Favorites Ultimate Food & Walking Tour

star-5
474
Stroll through downtown Chicago on this walking food tour. Visit Millennium Park, the Palmer House Hotel and other city landmarks. Taste quintessential Chicago foods such as deep-dish pizza, hot dogs, plus chocolates and pastry. All food tastings are included, and the tour covers an easy 1.5 miles (2.4 km) suitable for most fitness levels. Upgrade your tour to include three pours of local craft beer.
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  • 3 hours
  • Free Cancellation
From
USD74.99
From
USD74.99

Chicago Architecture Walking Tour: Dazzling Interiors™ of the Loop

Chicago Architecture Walking Tour: Dazzling Interiors™ of the Loop

star-5
371
See the overlooked highlights of Chicago’s Loop district with a 2-hour walking tour that takes in the best of the bustling, vibrant neighborhood’s inside spaces. Get behind the façades to explore stunningly designed interiors as you follow a specially-designed route with an experienced guide. Learn about the city’s architecture, art and history while visitng a side of Chicago that’s beyond the tourist trail, and experience the Windy City with a local perspective.
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  • 2 hours
  • Free Cancellation
From
USD35.00
From
USD35.00

Chicago Walking Tour: Historic Treasures of Chicago

Chicago Walking Tour: Historic Treasures of Chicago

star-5
68
Get an insider's introduction to Chicago's most celebrated buildings during this architecture-focused walking tour of Michigan Avenue and State Street. Revisit the heyday of the skyscraper and visit stunning, Art Deco-era interiors, from the Palmer House Hotel to the Chicago Cultural Center. Admission to the Chicago Architecture Center is included, with an introduction by the docent.
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  • 2 hours
  • Free Cancellation
From
USD30.00
From
USD30.00

Chicago in a Day: Food, History and Architecture Walking Tour
Likely to Sell OutLikely to Sell Out

Chicago in a Day: Food, History and Architecture Walking Tour

star-5
295
An excellent choice for first-time visitors, this tour provides a comprehensive overview of the city and hits on both classic attractions and little-known sites. Beginning at the Chicago Theatre, work your way to the Chicago Pedway, an elaborate network of underground tunnels used by locals and commuters. Stroll the Chicago Riverwalk and the Magnificent Mile, then embark on a food tour to taste some of the city’s famous foods.
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  • 5 hours
  • Free Cancellation
From
USD104.00
From
USD104.00

Chicago Architecture River Cruise

Chicago Architecture River Cruise

star-5
8492
Cruise down the Chicago River to see the city's famous architecture on this boat tour. With commentary from your onboard guide, watch the spectacular skyline glide by, including more than 40 notable buildings like Navy Pier, the Wrigley Building, and the John Hancock Building. Cover all three branches of the Chicago River, passing the East Bank Club, the old Post Office Building and the Willis Tower (formerly known as the Sears Tower).
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  • 1 hour 15 minutes
  • Free Cancellation
From
USD46.87
From
USD46.87

90-Minute Chicago River Architecture Tour
Likely to Sell OutLikely to Sell Out

90-Minute Chicago River Architecture Tour

star-4.5
2176
Discover the architectural gems of the Windy City from an ideal vantage point on a cruise down the Chicago River. Offered several times throughout the day, it’s easy to fit the leisurely excursion into your itinerary. Covering more than 130 years of architectural history, the tour is the perfect opportunity to see a huge area of the city without the hassle of taxis and public transit.
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  • 1 hour 30 minutes
  • Free Cancellation
From
USD42.00
From
USD42.00

Chicago Crime and Mob Bus Tour

Chicago Crime and Mob Bus Tour

star-4.5
1508
Explore Chicago's gangster past on this mafia tour in a coach vehicle. Drive around the Windy City to see where Al Capone, The Untouchables, Hymie Weiss, and John Dillinger, among other thugs hung out. A history-savvy guide introduces you to some of the most storied locations of Chicago’s criminal past, including Holy Name Cathedral, Biography Theatre, and the site of the bloody St. Valentine’s Day Massacre. You'll be able to get out and pose for pictures in front of a historic courthouse, among other infamous sites.
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  • 1 hour 30 minutes to 2 hours
  • Free Cancellation
From
USD46.00
From
USD46.00

Skyline Tour Aboard 148 Ft. Schooner Windy - Chicago's Official Tall Ship

Skyline Tour Aboard 148 Ft. Schooner Windy - Chicago's Official Tall Ship

star-4.5
290
Escape the bustle of the city on a sailboat tour through Lake Michigan with a convenient departure from Navy Pier. The cruise offers plenty of frame–worthy photo opportunities, including sweeping views of the Chicago skyline rarely seen by visitors. As a popular choice for both locals and visitors, your experience is guaranteed to be family–friendly and tailored to your needs. Select from Pirates and Maritime Stories Sail at 1pm, Skyline/Architectural Theme at 3pm and 5pm, and Skyline Sunset Sail at 7pm. This sail is approximately 75 minutes. The ship leaves promptly at the scheduled time, please allow for time to park, off the pier if necessary.
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  • 1 hour 15 minutes
  • Free Cancellation
From
USD49.00
From
USD49.00

Lake Michigan Sightseeing Cruise

Lake Michigan Sightseeing Cruise

star-4.5
447
Take in iconic views of the beautiful Chicago lakefront and its many landmarks during this Lake Michigan sightseeing boat cruise. Climb aboard your vessel for a laid-back ride, enjoying panoramic views of the Windy City's skyline from a unique perspective. Along the way, you'll listen to informative commentary and take in views of the John Hancock Center and Willis Tower, along with many other landmarks. Plus feel free to bring your own lunch or grab a drink at the onboard bar, during your ride.
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  • 40 minutes
  • Free Cancellation
From
USD28.34
From
USD28.34

Bikes, Bites, and Brews: Chicago's Signature Dishes Bike Tour

Bikes, Bites, and Brews: Chicago's Signature Dishes Bike Tour

star-5
385
Chicago dogs, deep-dish pizza, cupcakes and craft beer are all sampled on this half-day bike tour through the Windy City. Cover about 13 miles (21 km), following an informative guide at a moderate pace through Chicago neighborhoods. On the day tour, ride through Wrigleyville, Old Town, Lincoln Park, and Gold Coast. On the night tour, visit Gold Coast, Chicago’s Riverwalk, Millennium Park, Buckingham Fountain and Chicago’s Lakefront trail. Stop along the way at a popular downtown bakery, pizza shop, hot dog stand and two breweries for a taste of local flavors.
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  • 4 hours
  • Free Cancellation
From
USD89.99
From
USD89.99

Chicago Lake and River Architecture Tour
Likely to Sell OutLikely to Sell Out

Chicago Lake and River Architecture Tour

star-4.5
860
Step aboard a boat for a comprehensive cruise that details the history of Chicago's architecture. Enjoy views of the Chicago skyline accompanied by architecture-focused commentary that points out each of the landmark buildings. As you cruise through Lake Michigan, snap photos of you and your party against the stretch of Chicago's 26-mile shoreline.
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  • 1 hour 30 minutes
  • Free Cancellation
From
USD42.00
From
USD42.00

Underground Donut Tour: Chicago's First Donut Tour
Likely to Sell OutLikely to Sell Out

Underground Donut Tour: Chicago's First Donut Tour

star-5
465
Sample some of the Windy City’s tastiest donuts on this Underground Donut Tour, celebrating the magic of Chicago’s tastiest sugar-filled concoctions. Donut-lovers are sure to enjoy this visit to some of Chicago’s tastiest donut purveyors, offering a chance to savor all of your favorite varieties, on the city's only donut-themed excursion. All tastings are included, and vegan, gluten-, and nut-free options are also available.
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  • 2 hours
  • Free Cancellation
From
USD40.00
From
USD40.00

45-Minute Chicago River Architecture Tour from Magnificent Mile

45-Minute Chicago River Architecture Tour from Magnificent Mile

star-4.5
233
Get a front row perspective on the exquisite buildings that line the Chicago River during a 45-minute architecture cruise. Hear live commentary about the history and architectural heritage of Chicago on this family-friendly tour, which highlights landmarks such as the Chicago Riverwalk, Michigan Avenue Bridge, Wrigley Building, and Willis Tower. Sit on the open-air top deck or the sheltered bottom deck for the ultimate view of Chicago.
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  • 45 minutes
  • Free Cancellation
From
USD25.00
From
USD25.00

Chicago Sunset Cruise

Chicago Sunset Cruise

star-4.5
372
Drink in a one-of-a-kind perspective on the Windy City when you go for an evening cruise, perfectly timed to coincide with the sunset. Hop aboard your open-top vessel in the heart of the Magnificent Mile, and cruise along the Chicago River, where your guide will point out architectural highlights. Then, see the skyline from a distance, and watch the skyscrapers light up, when you continue to Lake Michigan for a sunset viewing.
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  • 1 hour 30 minutes
  • Free Cancellation
From
USD40.00
From
USD40.00

Chicago Walking Tour: Art Deco Skyscrapers Loop
Likely to Sell OutLikely to Sell Out

Chicago Walking Tour: Art Deco Skyscrapers Loop

star-5
89
Admire the incredible façades and intricate interiors of the Windy City's 1920s art deco and art moderne buildings during this architecture walking tour of Chicago. Uncover the history of Chicago art deco architectural along with the city's influential role in the development of this iconic artistic style, as you get an up close and personal look at its wealth of gorgeous period buildings. This art deco Chicago walking tour also includes a certified guide.
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  • 1 hour 30 minutes
  • Free Cancellation
From
USD30.00
From
USD30.00

Big Bus Chicago Hop-On Hop-Off Tour

Big Bus Chicago Hop-On Hop-Off Tour

star-4
1120
Don’t spend time figuring out what to see in Chicago and how to get there—this hop-on hop-off tour provides a mapped-out itinerary of the city's top sights. With several strategically located stops, the tour allows you to explore the Windy City at your own pace. See the world-class Art Institute and landmark skyscrapers, while audio commentary onboard gives you insight into the city's colorful history.
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  • 2 hours
  • Free Cancellation
From
USD44.99
From
USD44.99

Chicago Loop Walking Tour

Chicago Loop Walking Tour

star-5
48
Step into the heart of Chicago with this 2-hour walking tour of the Loop. You’ll meet your local guide at the Chicago Cultural Center and make your way through the city’s downtown. Stop to check out the elevated “L” train, buildings by Burnham and Sullivan, busy commercial centers and lesser-known quiet corners of this vibrant area. You’ll come away with a deeper sense of Chicago’s rich history and architecture.
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  • 2 hours
  • Free Cancellation
From
USD60.00
From
USD60.00

Chicago Night Crimes Bus Tour

Chicago Night Crimes Bus Tour

star-5
177
Discover the ‘dark side’ of the Windy City thanks to this 2.5-hour, bus-based, nighttime crime history tour of Chicago. Explore the lives of notorious mobsters like Al Capone, Frank Nitti, Bugs Moran, and more as you explore infamous crime scenes like the St. Valentine’s Day Massacre, learn about ‘The Enforcer’s Safe,’ and stop by local watering holes.
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  • 2 hours to 2 hours 30 minutes
  • Free Cancellation
From
USD52.00
From
USD52.00

Art Institute of Chicago Skip-the-Line Small-Group Guided Tour

Art Institute of Chicago Skip-the-Line Small-Group Guided Tour

star-5
56
Explore one of the country’s great art museums—and discover many of its collection highlights—on this small-group Art Institute of Chicago tour. Meet your guide right out front, and see works from artists the likes of Picasso, Chagall, Seurat, O’Keeffe, and many more. As you go, your guide will share the stories behind the masterpieces, and will help bring the history of the museum and its collection to life.
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  • 2 hours 30 minutes
  • Free Cancellation
From
USD115.54
Price varies by group size
From
USD115.54
Price varies by group size

Chicago Premier Dinner Cruise on Lake Michigan
Likely to Sell OutLikely to Sell Out

Chicago Premier Dinner Cruise on Lake Michigan

star-3.5
192
Take a gourmet dinner cruise on a high-end luxury yacht with the stunning skyline of Chicago serving as your backdrop. Climb aboard your recently renovated vessel, featuring a sumptuously-appointed rooftop lounge and stylish interior design, for your cruise along Lake Michigan. Then sit down for a 3-course dinner, informed by some of the world’s top celebrity chefs and composed of fresh ingredients cooked right on-board. After dinner, enjoy coffee and tea, captivating views of Chicago landmarks like the Willis (formerly Sears) Tower and Navy Pier, plus musical entertainment provided by the onboard DJ.
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  • 2 hours 30 minutes
From
USD180.18
From
USD180.18

Chicago's Gold Coast Hidden History: A Self-Guided Audio Walk

Chicago's Gold Coast Hidden History: A Self-Guided Audio Walk

star-4.5
4
Amy Bizzarri, author of 111 Places in Chicago That You Must Not Miss, takes you on a fascinating self-guided audio tour of hidden historical spots in Chicago's gilded Gold Coast. Peep behind the gates of the original Playboy Mansion, walk along a wooden block-paved alley, sip a Faster Pussycat in Chicago's oldest piano bar and more as you enjoy a delightful walk through time in this exclusive Chicago neighborhood. The starting point is the Chicago History Museum, located at 1601 N. Clark Street. The tour is ready whenever you are and the audio plays automatically at exactly the right time and place using your smartphone's GPS and the VoiceMap mobile app, which also works offline.
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  • 50 minutes
From
USD5.34
From
USD5.34

Discovering Vintage Chicago: A Self-Guided Audio Tour of the Loop

Discovering Vintage Chicago: A Self-Guided Audio Tour of the Loop

star-1
1
Take a walk back in time through the history of Chicago's Loop on this app-enabled tour. After downloading the app and tour to you smartphone, you and your party will listen to author Amy Bizzarri, an author and expert in Chicago history, as she leads you through walking tour of the city. The GPS-enabled tour will trigger commentary at just the right times, and you can stop and start whenever you like for a flexible experience that lets you move at your own pace. Highlights include Daley Plaza, the Chicago Theater, Berghoff Restaurant, and the Art Institute of Chicago.
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  • 50 minutes
From
USD5.34
From
USD5.34

Chicago Loop Secret Food Tour with Private Tour Option

Chicago Loop Secret Food Tour with Private Tour Option

star-5
274
Explore Chicago's buzzing food scene with a small group on this small group walking tour. Stroll around the 'Loop', stopping at hidden gems and hearing tales of the city from your guide. Taste classic Chicago foods, from deep-dish pizza to dipped Italian beef sandwiches.
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  • 3 hours
From
USD87.00
From
USD87.00

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What people are saying about Walking Tours in Chicago

star-5
Gangsters and Ghosts Tour in Chicago
"Our tour guide did a great job! Temperature were very high and he was very considerate and checked repeatedly if my 84 year old Mom was doing okay."..."
star-5
Chicago Favorites Ultimate Food & Walking Tour
"The deep dish pizza was amazing. We really enjoyed the history along the tour. Our tour guide was very high energy and knew an amazing amount of information about the city. It was a great experience."..."
star-5
Chicago Architecture Walking Tour: Dazzling Interiors™ of the Loop
"Kylie was a lovely tour guide! She was friendly & engaging, answering questions as they arose. She gave us a lot of time to just soak up the beauty we were seeing, before she would share the historical & personal tales that bring these beautiful interiors to life! Highly recommend the Dazzling Interiors tour!"..."
star-5
Chicago Walking Tour: Historic Treasures of Chicago
"Thank you Laurel for a great insight to this wonderful city. I was amazed at your knowledge and ease of sharing this with the group"..."
star-5
Chicago in a Day: Food, History and Architecture Walking Tour
"Spectacular tour, our guide Dave is extremely knowledgeable and taught us a lot about the history of Chicago. This tour hands down checks all the boxes. Loved everything about it and highly recommend this experience."..."
star-5
Chicago Architecture River Cruise
"Guide had a good sense of humor, enjoyed the history, view of the city from the boat is remarkable. The description of the many unique buildings old and new was very interesting. I also appreciated the fact that he mentioned the many neighborhoods to explore."..."
star-5
90-Minute Chicago River Architecture Tour
"Lovely way to spend an afternoon. Interesting facts learned from very good tour guide. Thank you!!!!!"..."
star-5
Chicago Crime and Mob Bus Tour
"Mike was great! Learned a lot. He was fun and informative. It was nice to have a bus after walking all over town for a few days."..."
star-5
Skyline Tour Aboard 148 Ft. Schooner Windy - Chicago's Official Tall Ship
"What a fabulous experience on Tall Windy! Beautiful memory. 🙏🏽 Crew did a great job! Thank you! Perfect weather."..."
star-5
Lake Michigan Sightseeing Cruise
"A nice daytime activity that me and my girlfriend both enjoyed while waiting for our dinner reservation."..."
star-5
Bikes, Bites, and Brews: Chicago's Signature Dishes Bike Tour
"Such a great way to learn about the city and enjoy the view and amazing food! If in Chicago I definitely recommend Bobby’s bikes, bites and brew tour. So FUN!!"..."
star-5
Chicago Lake and River Architecture Tour
"This tour was fantastic. Our guide, Kenneth was the right balance of being both knowledgeable and entertaining. This was hubby's 1st trip to Chicago and although I have been to this lovely city many times, I'd never done a river tour so we had a. blast. Highly recommend"..."
star-5
Underground Donut Tour: Chicago's First Donut Tour
"We had a blast! Great idea! It was a fun tour! Our tour guide Max was wonderful! He was very knowledgeable about the donuts and the history behind them."..."
star-5
45-Minute Chicago River Architecture Tour from Magnificent Mile
"Great information! Very engaging tour guide! Really enjoyed the tour! I did the tour before, and it was not as enjoyable as this tour!"..."
star-5
Chicago Sunset Cruise
"Took a birthday cruise and everyone in our party loved it!! Our host was enthusiastic and taught us a lot about Chicago history. We will definitely do another cruise when we visit again!!"..."
star-5
Chicago Walking Tour: Art Deco Skyscrapers Loop
"Jonelle was an amazing guide! She gave a great educational tour of the pivotal Chicago Art Deco skyscrapers and I’m so glad we went. Highly recommended!"..."
star-5
Big Bus Chicago Hop-On Hop-Off Tour
"Candace was an excellent tour guide. She cracked jokes, gave us plenty of history about the sites & gave us time to take quick pics! We had a great time!!"..."
star-5
Chicago Loop Walking Tour
"Kevin gave us an amazing tour of the El. We would never have found the sites on our own. Highly recommend this for culture, history or architecture buffs. Kevin covered it all. He is very dedicated to Chicago. Hope to be back for a tour with him in the future."..."
star-5
Chicago Night Crimes Bus Tour
"Superb tour guide and must do tour when in Chicago !!! Very interesting history and masterfully told"..."
star-5
Art Institute of Chicago Skip-the-Line Small-Group Guided Tour
"The stories our guide Mandy told about all the artists - she was very good and knowledgeable. Made getting through the museum very easy."..."
star-5
Chicago Premier Dinner Cruise on Lake Michigan
"It was my husband's birthday and we both really enjoyed it. It was very nice and serene and the view was spectacular can't wait till we do it again"..."
star-5
Chicago's Gold Coast Hidden History: A Self-Guided Audio Walk
"I generally don't like group tours, so having this option is wonderful. It felt like having your own private tour guide. In this time of Covid-19, this gae us a nice way to get out of the house. The Zebra Lounge wasn't open, but just around the corner there was a street closed off to allow for outdoor dining/social distancing. The museum of surgery was open, and we spent time there as well as Restoration Hardware."..."
star-5
Chicago Loop Secret Food Tour with Private Tour Option
"Eddie was a wonderful tour guide! He was very educated on Chicago's architectural history as well as the history behind the food (gyros, hotdogs, brownies, etc). Definitely bring your appetite - the "samples" were large and delicious! Definitely a "must do" in Chicago."..."
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Frequently Asked Questions

The answers provided below are based on answers previously given by the tour provider to customers’ questions.
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What are the best Walking Tours in Chicago?
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What Walking Tours in Chicago are 1 hour or less?
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What Walking Tours in Chicago are taking additional safety precautions?
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What Walking Tours in Chicago are good for avoiding crowds?