Recent Searches
Clear

Top Chicago Walking Tours

Saved to wishlist!
Dates
Select Dates
Architecture Tours
Architecture Tours
Half-day Tours
Half-day Tours
Hop on Hop Off
Hop on Hop Off
City Tours
City Tours
Private Sightseeing Tours
Private Sightseeing Tours
Night Tours
Night Tours
Audio Guides
Audio Guides
Historical Tours
Historical Tours
Food Tours
Food Tours
Private and Luxury
Private and Luxury
Sightseeing Tours
Sightseeing Tours
Skip-the-Line Tours
Skip-the-Line Tours
Adventure Tours
Multi-day Tours
Multi-day Tours
Shopping Tours
Shopping Tours
Photography Tours
Photography Tours
Water Tours
Water Tours
Culinary & Gourmet Tour
Culinary & Gourmet Tour
Crime Tours
Crime Tours
Rail Tours
Rail Tours
When are you traveling?
Select Dates
Popular
Search experiences that may have limited interaction with crowds.
Search experiences with increased health and safety practices.
Search tours and activities you can do from home.

You are viewing Virtual Experiences in Chicago. See more Virtual Experiences around the globe. 🌎

Price
$0
$500+
Duration
Time of Day
RatingClear
Specials

82 results | All Chicago Tours

Sort by: Featured

Gangsters and Ghosts Tour in Chicago

Gangsters and Ghosts Tour in Chicago

star-4.5
1941
  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$27.00
From
$27.00
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.
More

* A traveler said: "Kias energy was super fun and I learned a lot of tid bits and excited to learn more about the history of the city!!"


Chicago Architecture River Cruise

Chicago Architecture River Cruise

star-5
6493
  • 1 hour 15 minutes
  • Free Cancellation
  • Taking safety measures
From
$44.69
From
$44.69
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).
More

* A traveler said: "Great way to see the city and learn a little bit more about the beautiful buildings that make Chicago"


Chicago Favorites Ultimate Food & Walking Tour

Chicago Favorites Ultimate Food & Walking Tour

star-5
255
  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
$65.99
From
$65.99
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.
More

* A traveler said: "Loved all 4 places! The three beers were good also. Justin was an amazing tour guide. Only problem was locating were to meet. I didn't understand the directions that we were to meet on Beaubien Court, the first left going north on Randoff."


90-Minute Chicago River Architecture Tour

90-Minute Chicago River Architecture Tour

star-4.5
1153
  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$40.00
From
$40.00
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.
More

* A traveler said: "The tour was amazing and exceeded our expectations! The tour was on time and the hostess knowledge on Chicago’s history was thrilling!"


Underground Donut Tour: Chicago's First Donut Tour

Underground Donut Tour: Chicago's First Donut Tour

star-5
283
  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$30.00
From
$30.00
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.
More

* A traveler said: "Jackson was an incredible host. I really enjoyed the funny stories and the one on one conversations that he had with all of us on the tour. He was very interactive. In glad it a walk tour because it gave me an opportunity to see the different areas of downtown."


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

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

star-5
126
  • 5 hours
  • Free Cancellation
  • Taking safety measures
From
$104.00
From
$104.00
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.
More

* A traveler said: "Kelly, our guide was extraordinary. She was knowledgeable, patient and fun. The length of the tour was just right, and provided the perfect 1st day orientation of this amazing city"


Chicago Pizza Tour
Likely to Sell OutLikely to Sell Out

Chicago Pizza Tour

star-5
233
  • 3 hours 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$60.00
From
$60.00
Enjoy Chicago’s only bus guided neighborhood pizza tour.  Eat like a local as you travel off the beaten path into Chicago neighborhoods to savor the best pizza.  Your local guide will teach you the science behind ingredient selection and baking as you sample slices from historic pizzerias.  In just a few hours, you’ll leave stuffed, and with an understanding of why pizza is such an important part of Chicago’s culture.
More

* A traveler said: "Learned a lot about the pizza scene in Chicago from our tour guide, James. It was a very entertaining and fun time. Lots of delicious pizza, you won’t leave hungry."


45-Minute Chicago River Architecture Tour from Magnificent Mile
Likely to Sell OutLikely to Sell Out

45-Minute Chicago River Architecture Tour from Magnificent Mile

star-4.5
132
  • 45 minutes
  • Free Cancellation
  • Taking safety measures
From
$23.00
From
$23.00
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.
More

* A traveler said: "This tour was everything! Our tour guide was very knowledgeable and funny. The Chicago Skyline and building are beautiful. The drinks are very strong also and I can’t wait to come back and visit."


Chicago Crime and Mob Bus Tour

Chicago Crime and Mob Bus Tour

star-4.5
1046
  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$45.00
From
$45.00
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.
More

* A traveler said: "Liked it all. Second time we’ve went on the tour. Would tell anybody to go and it’s very interesting!"


Big Bus Chicago Hop-On Hop-Off Tour

Big Bus Chicago Hop-On Hop-Off Tour

star-4
873
  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$26.10
From
$26.10
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.
More

* A traveler said: "Convenient, clean, freindly. Actors giving the commentary were a little too cute for our taste. Pointing out landmarks, history and telling about a city doesn't have to be cutesy."


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

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

star-5
315
  • 4 hours
  • Free Cancellation
  • Taking safety measures
From
$84.99
From
$84.99
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 the Chicago neighborhoods of Wrigleyville, the Gold Coast, Old Town, Lakeview and Lincoln Park. Stop along the way at a popular downtown bakery, pizza shop, hot dog stand and two breweries for a taste of local flavors.
More

* A traveler said: "Enjoyed the casual bike ride through the city. We saw a lot. Julie, our guide, was great. Ate some delicious Lou malnatis pizza and drank beer. Had a hot dog and a delicious cupcake. Perfect afternoon."


Chicago Loop Secret Food Tour with Private Tour Option

Chicago Loop Secret Food Tour with Private Tour Option

star-5
253
  • 3 hours
  • Taking safety measures
From
$84.53
From
$84.53
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.
More

* A traveler said: "Deanise was very nice and knowledgeable. It felt like walking with. Friend from Chicago versus someone paid to show us around . The food places where delicious , would recommend taking this tour."


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

* A traveler said: "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."


Discovering Vintage Chicago: The Loop Walking Audio Tour by VoiceMap
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.
More

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

Chicago Walking Tour: Art Deco Skyscrapers

star-4.5
78
  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$30.00
From
$30.00
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.
More

* A traveler said: "David took us to a trip to the past. Art Deco can be hidden or glowing in front of you and David gave us tips on how to recognize it. He took us to amazing places around Downtown where this style exists. Thank you for sharing with us! We highly recommend this tour!"


Chicago Loop Walking Tour

Chicago Loop Walking Tour

star-5
38
  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$42.67
From
$42.67
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.
More

* A traveler said: "Kevin was a great guide! Knowledgeable and enthusiastic! We had a great tour inside many magnificent buildings! Definitely recommend this one!"


Holiday Hike Chicago-Style: Festive Food & Walking tour

Holiday Hike Chicago-Style: Festive Food & Walking tour

star-5
13
  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
$69.99
From
$69.99
Stroll through Chicago's winter streets, lit up for the holidays, on this gourmet walking tour. Learn about Chicago's celebrated holiday traditions like the European-inspired Christkindlmarket, the beautiful decor and windows on State Street, and ice skating at Millennium Park. Sample generous tastes of classic Chicago foods and holiday treats as you walk. Seasonal craft beer tastings help you stay warm and toasty; please note this tour operates in all weather conditions, so dress appropriately.
More

* A traveler said: "Noah, our guide, was informative, entertaining and a pleasure to hang with! The food stops were perfect and the day was fun!"


Chicago Walking Tour: Modern Architecture

Chicago Walking Tour: Modern Architecture

star-4.5
10
  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$30.00
From
$30.00
Embark on a walking tour of Chicago's more-recent architecture heritage with a 2-hour stroll highlighting the city's modern, postmodern, and international structures. Especially known for its architectural originality, Chi-town boasts everything from the elegant metal and glass tower of One South Dearborn to the Harold Washington Library, with its Beaux-Arts inspired exterior. Your guide will highlight these and other unique buildings, relaying background on their individual histories and construction en route.
More

* A traveler said: "A challenge during Covid 19 restrictions, the tour guide found good ways to share her excellent information and make us comfortable."


Chicago Architecture Walking Tour: Dazzling Interiors of the Loop

Chicago Architecture Walking Tour: Dazzling Interiors of the Loop

star-5
269
  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$33.00
From
$33.00
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.
More

* A traveler said: "Hillary did a great job showing us an out of the path Chicago. She is very knowledgeable of Chicago with focus in history and architecture. The selection of places gave us an amazing experience through styles and time. We highly recommend this tour! Thank you Hillary!"


Go Chicago Explorer Pass with SkyDeck and 360 Chicago
From
$59.00
The easiest and most affordable way to explore some of Chicago's top attractions at your own pace, the Go Chicago Explorer Pass saves you up to 45 percent on regular ticket prices. Create your own sightseeing itinerary by choosing 2, 3, 4, or 5 attractions, tours, and activities from among more than 30 top sites, including SkyDeck, 360 Chicago, the Field Museum, a shoreline sightseeing cruise, a hop-on hop-off Big Bus tour, Lincoln Park Zoo, Navy Pier, and LEGOLAND® Discovery Center. Please note: Enjoy the extra flexibility in case your travel plans need to change: All passes are valid for two year from purchase date and only become activated with your first attraction visit. After activation your pass will be valid for 60 days and/or the remaining number of attraction choices purchased.
More

* A traveler said: "So fun! The River architecture boat tour was my favorite. We saw the Field Museum as well and it took a whole day to attempt to see it all"


Famous Tastes of Chicago Food Tour

Famous Tastes of Chicago Food Tour

star-4.5
153
  • 3 hours
  • Free Cancellation
From
$70.00
From
$70.00
Discover Chicago’s food, history, architecture and culture on this 3-hour, small-group walking tour. Try six of the Windy City’s quintessential staples from local restaurants and specialty food shops like Pizano’s Pizza and the Berghoff, the oldest family run-establishment in Chicago. Taste local favorites including deep-dish pizza,  Chicago Italian Beef Sandwich and chocolates from Fannie May, just to name a few. Along the way, see and learn about the historical, cultural and architectural components that make up this legendary town.
More

* A traveler said: "Elizabeth was a great tour guide, she gave us time to explore and gave us so much information on the history of Chicago, the places we visited and made sure everyone was comfortable and even offered us seconds. The places we visited were uniquely Chicago. It was a comfortable walk and we were stuffed when we waddled off to the hotel!"


River North Food Walking Tour

River North Food Walking Tour

star-4.5
58
  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
$75.00
From
$75.00
Get to know the River North district of Chicago through its food on a culinary walking tour that takes you to five local food venues. You'll enjoy tastings of Mexican fare, Chicago deep dish pizza, and other items while learning about the neighborhood's history and food culture.
More

Chicago Style Food Tour

Chicago Style Food Tour

star-4.5
55
  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
$70.00
From
$70.00
Discover Chicago’s food, history, architecture and culture on this small-group walking tour. Try the Windy City’s quintessential staples from local restaurants and specialty food shops like Downtown Dogs and the world-famous Billy Goat Tavern. Taste local favorites including deep-dish pizza, a Chicago-style hot dog, and chocolates from Fannie May, just to name a few. Along the way, see and learn about the historical, cultural, and architectural components that make up this legendary town.
More

* A traveler said: "Tour guide very knowledgeable and friendly. Wish tour would have circled back closer to starting point. Great food selections and big servings."


Chicago's Chinatown Food and Walking Tour

Chicago's Chinatown Food and Walking Tour

star-4.5
47
  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
$65.99
From
$65.99
Explore Chicago's Chinese food scene on this walking tour in the Chinatown district. With a guide, learn about the cuisine of different regions of China and how Chinese culture has influenced Chicago and other areas. Enjoy included tastings from restaurants and other food venues in Chinatown—a great way to start a night out in the city.
More

* A traveler said: "Great food, great tour guide, and great people on our Chinatown walking food tour. We took the water taxi there and back, so it was like a mini-vacation. Highly recommend upgrading to the VIP option with enhanced beverages - definitely a delicious choice."


Filters
* How are review snippets generated?

Frequently Asked Questions

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