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35 Chicago Unique Experiences

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Free Cancellation:Get a full refund up to 24 hours in advance on most experiences.See Details

Gangsters and Ghosts Tour in Chicago

Gangsters and Ghosts Tour in Chicago

star-4.5
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  
US$27
From  
US$27
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  • 2 hours
  • Free Cancellation

Famous Tastes of Chicago Food Tour

Famous Tastes of Chicago Food Tour

star-4.5
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.
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  • 3 hours
From  
US$64
From  
US$64
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  • 3 hours

Private Chicago City Sights Helicopter Tour

Private Chicago City Sights Helicopter Tour

star-5
You and a guest will soar above Chicago’s skyscapers, shoreline and iconic sights on a private, 15-minute helicopter tour of the city. Communicate with your personal pilot through a two-way headset, and personalize your flight to your interests. Capture extraordinary aerial images of the city scape as you fly past Lincoln Park and Lake Michigan, then spot Willis Tower, the John Hancock Building and the gleaming Trump Tower. Bank high above Millennium Park and enjoy views of the Windy City from the comfort of a climate-controlled private helicopter. Tour route is subject to change.
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  • 15 minutes
  • Free Cancellation
From  
US$175
From  
US$175
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  • 15 minutes
  • Free Cancellation

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

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

star-5
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.
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  • 4 hours
From  
US$78
From  
US$78
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  • 4 hours

Chicago Loop Secret Food Tour

Chicago Loop Secret Food Tour

star-5
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  
US$78
From  
US$78
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  • 3 hours

Chicago Pizza Tour

Chicago Pizza Tour

star-5
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.
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  • 3 hours 30 minutes
  • Free Cancellation
From  
US$60
From  
US$60
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  • 3 hours 30 minutes
  • Free Cancellation

Chicago Favorites Food and Walking Tour

Chicago Favorites Food and Walking Tour

star-5
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.
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  • 2 hours 30 minutes
From  
US$60
From  
US$60
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  • 2 hours 30 minutes

Underground Donut Tour - Chicago's First Donut Tour

Underground Donut Tour - Chicago's First Donut Tour

star-5
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  
US$30
From  
US$30
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  • 2 hours
  • Free Cancellation

Chicago Craft Brewery Barrel Bus Tour

Chicago Craft Brewery Barrel Bus Tour

star-4.5
Learn about Chicago’s brewpub scene and taste different types of craft beer on this guided brewery tour. Visit unique breweries for craft beer samples plus an additional brewing production facility for an in-depth tour. Discover the science behind the brewing process, complete with step-by-step procedures, and enjoy plenty of beer samples throughout the tour. Round-trip transportation in a Prohibition-era-styled barrel bus is included.
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  • 3 hours 30 minutes
  • Free Cancellation
From  
US$84
From  
US$84
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  • 3 hours 30 minutes
  • Free Cancellation

Chicago City Sights Helicopter Tour

Chicago City Sights Helicopter Tour

star-5
Soar above the incredible skyline of Chicago during this 15-minute helicopter flight above the Windy City. Climb aboard your high-tech helicopter for a ride like no other, admiring views of Lake Michigan plus iconic city sights like Millennium Park, Lincoln Park, Navy Pier, the Shedd Aquarium and the Willis Tower. Along the way you'll hear informative details about the various landmarks from your pilot, who will provide commentary during the flight. Tour route is subject to change.
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  • 15 minutes
  • Free Cancellation
From  
US$149
From  
US$149
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  • 15 minutes
  • Free Cancellation

Chicago Style Food Tour

Chicago Style Food Tour

star-4.5
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.
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  • 3 hours
From  
US$64
From  
US$64
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  • 3 hours

Small-Group Chicago Food Tour: Gold Coast and Old Town

Small-Group Chicago Food Tour: Gold Coast and Old Town

star-5
Savor the flavors of the Gold Coast and Old Town neighborhoods on this 3-hour Chicago food walking tour, led by an expert guide. You’ll stop at seven popular shops and eateries, including a specialty tea merchant, confectioner, European bakery and — of course — Chicago-style pizzeria. Explore these culture-rich neighborhoods just north of the downtown and learn about their architecture and history along the way. Numbers are limited to 18 participants for a small-group experience.
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  • 3 hours
  • Free Cancellation
From  
US$70
From  
US$70
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  • 3 hours
  • Free Cancellation

Private Chicago Craft Beer and Pizza Tour

Private Chicago Craft Beer and Pizza Tour

Visit three of Chicago’s top craft breweries on a customizable 4-hour tour. Bring your own group of 4 to 11 people on this all-inclusive tour led by a private guide, who shares details about Chicago’s craft brewing scene. Choose the breweries you wish to visit, and pair those suds with an included pizza dinner as well. You’ll learn how these hand-crafted beers are produced, and tour one of the brewery facilities (if available). No need to worry about getting from place to place: Transportation and hotel pickup and drop-off has included, so all you'll have to worry about is which beer to try first.
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  • 3 hours
  • Free Cancellation
From  
US$99
From  
US$99
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  • 3 hours
  • Free Cancellation

Private 2-hour boat rental aboard New York Style for 8 people ~ Free pizza!

Private 2-hour boat rental aboard New York Style for 8 people ~ Free pizza!

star-4.5
Set your own course on this private self-guided cruise along the Chicago River. You're the captain for your group of just eight people, steering the boat wherever you like and getting epic views of the towering buildings along the river. When the munchies hit, grill up the provided pizza on the boat's barbecue and dig in.
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  • 2 hours
  • Free Cancellation
From  
US$279
From  
US$279
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  • 2 hours
  • Free Cancellation

Chicago Crime and Pizza Walk

Chicago Crime and Pizza Walk

star-5
Explore the River North and Gold Coast neighborhoods in Chicago during a 2-hour walking that focuses on the city's famous deep-dish pizza and most notorious criminals.
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  • 2 hours
  • Free Cancellation
From  
US$48
From  
US$48
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  • 2 hours
  • Free Cancellation

Private 2-hour boat rental aboard Deep Dish for 9 people ~ Free pizza!

Private 2-hour boat rental aboard Deep Dish for 9 people ~ Free pizza!

star-5
Step aboard an easy-to-maneuver pontoon boat for a private cruise on the Chicago River. You and your private group of up to nine people will enjoy having the boat to yourselves, as well as captaining the ship. You can choose your own itinerary and move at your own pace, pausing to cook the included pizza on the boat's built-in pizza grill.
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  • 2 hours
  • Free Cancellation
From  
US$299
From  
US$299
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  • 2 hours
  • Free Cancellation

Best of Chicago Tour Including a Deep-Dish Pizza

Best of Chicago Tour Including a Deep-Dish Pizza

star-2.5
Tour Chicago's sights aboard a luxury coach and enjoy some Chicago-style deep-dish pizza on this 5.5-hour guided tour. Visit sites like the Hancock Tower, the Lincoln Park Conservatory and the Loop. Pass through neighborhoods such as Wrigleyville, Lincoln Park and Gold Coast. Top off your tour with a visit to one of Chicago's most popular pizza restaurants to sample the famous Chicago-style deep dish pizza.
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  • 4 hours
  • Free Cancellation
From  
US$75
From  
US$75
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  • 4 hours
  • Free Cancellation

Pizza City USA Pizza Coach Tour

Pizza City USA Pizza Coach Tour

star-5
Take a deep dive into the deep dish and beyond with this pizza tour of Chicago. On a comfortable tour bus, run around town tasting four different pizza styles and learning about their differences. Meet some chefs and owners and learn about how the pizzas are made and Chicago's pizza history. You won't leave hungry.
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  • 3 hours
From  
US$69
From  
US$69
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  • 3 hours

Underground Donut Tour - Wicker Park Edition

Underground Donut Tour - Wicker Park Edition

star-5
Wicker Park is one of Chicago’s coolest and most food-oriented neighborhoods—and on this one-of-a-kind walking tour, you’ll see the sights while seeking out the best donuts that the area has to offer. Meet your guide in the morning in Wicker Park, and set out on foot. You'll visit four popular cafes and bakeries, will sample numerous creative donut flavors, and will learn more about the neighborhood. Additional drinks and treats are also available for purchase, if you wish.
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  • 2 hours
  • Free Cancellation
From  
US$35
From  
US$35
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  • 2 hours
  • Free Cancellation

Valerie's Chicago Chocolate Tours

Valerie's Chicago Chocolate Tours

Satisfy your sweet tooth on a 2.5-hour chocolate tour of Chicago. Follow your cocoa connoisseur guide through the Magnificent Mile neighborhood to four of the city’s top bakeries and chocolate shops. Meet some of the store owners to learn what makes their sugary products so delicious. Enjoy a variety of samples and learn about the city's history and top attractions between bites.
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  • 2 hours
  • Free Cancellation
From  
US$50
From  
US$50
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  • 2 hours
  • Free Cancellation

Tour Chinatown With Miss China!

Tour Chinatown With Miss China!

Tour Chicago’s Chinatown with local celebrity Jennifer Zhang. Crowned Miss Chicago Chinese 2015, and Miss China International 2017, Jennifer is also a model, actress, singer, social media influencer, and award-winning travel writer. She has written extensively about Chicago’s Chinatown and shares her inside knowledge with you on this tour. Stop to taste local specialities, and to explore significant landmarks on a one and a half hour-tour.
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  • 1 hour 30 minutes
From  
US$59
From  
US$59
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  • 1 hour 30 minutes

Valerie's Chicago Chocolate Tours - Seated Tasting Edition

Valerie's Chicago Chocolate Tours - Seated Tasting Edition

There is a time tested connection between love, romance, and the most delicious dessert in existence—chocolate. That's why true chocolate lovers shouldn't miss this Chicago Valentine's Day seated tasting experience, where you get to enjoy a chocolate tasting at Hannah's Bretzel. As you taste, hear about the history and health benefits of this amazing treat.
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  • 1 hour 30 minutes
  • Free Cancellation
From  
US$45
From  
US$45
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  • 1 hour 30 minutes
  • Free Cancellation

Soap Making the Old Fashioned Way (private Lesson)

Soap Making the Old Fashioned Way (private Lesson)

star-5
Making soap is a really fun activity. Once you learn how to do it it can become a lifelong hobby. I provide you with instructions and take home notes with lots of information for you to consult if you decide to make soap on your own in the future. This class takes place in my home, which is a 100 year old building in the charming Ukrainian Village neighborhood. Our home is filled with lots of interesting art and books and is a very unique place to visit.
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  • 2 hours
From  
US$60
From  
US$60
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  • 2 hours

Private 2-hour boat rental aboard Plain Slice for 8 people ~ Free pizza!

Private 2-hour boat rental aboard Plain Slice for 8 people ~ Free pizza!

Rent with us and you can take a private, self-guided cruise along the Chicago River where you’re the captain! No strangers tag along. It’s just you, kicking back with some good friends, great food and awesome views! All cruises come with free pizza that you cook on the boat's special pizza grill.
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  • 2 hours
  • Free Cancellation
From  
US$269
From  
US$269
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  • 2 hours
  • Free Cancellation


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(888) 651-9785
(888) 651-9785