Recent Searches
Clear

Top Chicago Unique Experiences

Travel update: We’re doing our best to help keep you safe and your plans flexible. Learn more.

Read More
When are you traveling?
Select Dates
Popular
Search experiences that may have limited interaction with crowds.
Search experiences with increased health and safety practices.
These experiences are highly rated by travelers and have met our top quality standards.
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

Travel update: We’re doing our best to help keep you safe and your plans flexible. Learn more.

Read More
Select Dates
Today
Tomorrow

25 Chicago Unique Experiences | All Chicago Tours

Sort by:Featured

Gangsters and Ghosts Tour in Chicago

Gangsters and Ghosts Tour in Chicago

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

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.
More
  • 4 hours
  • Taking safety measures
From
$79.99
From
$79.99
Taking safety measures

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.
More
  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$30.00
From
$30.00
Taking safety measures

Hey, nice badge.
Experiences with this badge meet our highest quality standards and are loved by travelers like you.
Learn more
Chicago Favorites Ultimate Food & Walking Tour

Chicago Favorites Ultimate Food & 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.
More
  • 2 hours 30 minutes
  • Taking safety measures
From
$62.99
From
$62.99
Taking safety measures

Chicago Loop Secret Food Tour w/ Private Tour Option

Chicago Loop Secret Food Tour w/ Private Tour Option

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.
More
  • 3 hours
  • Taking safety measures
From
$193.20
From
$193.20
Taking safety measures

Available now


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.
More
  • 3 hours
  • Free Cancellation
From
$74.67
From
$74.67

Underground Donut Tour of Chicago's Wicker Park

Underground Donut Tour of Chicago's Wicker Park

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.
More
  • 2 hours
  • Free Cancellation
From
$35.00
From
$35.00

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.
More
  • 3 hours 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$89.60
From
$89.60
Taking safety measures

30 Minute Private Vacation Photography Session with Local Photographer in Chicago

30 Minute Private Vacation Photography Session with Local Photographer in Chicago

star-5
Go beyond the selfies and smartphone shots—and walk away from your Chicago vacation with professional-quality photos—when you book this private photo shoot experience. Meet your professional photographer guide at a time and place of your choosing and practice your poses: they’ll capture upwards of 15 high-resolution digital photos of you and your party, with Chicago’s majestic scenery as your backdrop. Your guide will also share insider knowledge and tips about the Windy City’s key attractions and eateries.
More
  • 30 minutes
  • Free Cancellation
From
$272.44
per group
From
$272.44
per group

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.
More
  • 4 hours
  • Free Cancellation
  • Taking safety measures
From
$74.95
From
$74.95
Taking safety measures

Private Pontoon Boat Rental with Pizza Included

Private Pontoon Boat Rental with Pizza Included

star-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.
More
  • 2 hours
  • Free Cancellation
From
$297.60
per group
From
$297.60
per group

Chicago West Loop Pizza Crawl

Chicago West Loop Pizza Crawl

star-5
Immerse yourself in the pizza culture of Chicago with this tour de force of the city's 10 pizza styles. Go beyond deep dish with commentary from your food-loving guide and tastes of four different types over the course of the half-day tour. Learn about some of the most interesting Chicago neighborhoods and their culinary history.
More
  • 3 hours
  • Taking safety measures
From
$52.00
From
$52.00
Taking safety measures

Chicago Bucktown-Wicker Park Pizza Crawl

Chicago Bucktown-Wicker Park Pizza Crawl

star-5
Immerse yourself in Chicago’s bounty of pizza offerings, and learn about the Windy City’s pizza traditions beyond the classic deep-dish, on this small-group walking tour. Designed by a James Beard Award-winning food journalist, this tour takes place in the city’s vibrant and hip Bucktown and Wicker Park neighborhoods. Meet your group prior to lunch, and be sure to come hungry: you’ll visit four different pizzerias, and will enjoy tastes at each one. As you go, meet the chefs behind the pizza, and learn about Chicago’s culinary traditions.
More
  • 3 hours
  • Taking safety measures
From
$52.00
From
$52.00
Taking safety measures

Chicago Architecture Crash Course Walking Tour

Chicago Architecture Crash Course Walking Tour

star-5
See Chicago from a new perspective with this art- and pop culture-themed architectural walking tour. Follow an informative guide through the city’s streets, from the Michigan Avenue Bridge to the new Maggie Daley Park, while learning about the city’s history, architecture, and the fascinating connections between art history and Chicago architectural styles. Enrich your understanding of this beautiful American city with this fun and affordable outing.
More
  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$28.00
From
$28.00
Taking safety measures

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.
More
  • 1 hour 30 minutes
From
$66.87
From
$66.87

Chicago Scavenger Hunt Adventure

Chicago Scavenger Hunt Adventure

Discover Chicago in a fun new way on this 3-hour scavenger hunt. Jump into the middle of an exciting adventure around the Chicago Loop — to the historic buildings, famous streets and plethora of real-life locations around town. Discover both well-known and overlooked sites, solving clues and completing challenges via smartphone while learning the local history of the Windy City. Teams of 2- to 5-people are welcome.
More
  • 3 hours
  • Free Cancellation
From
$20.52
Price varies by group size
From
$20.52
Price varies by group size

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.
More
  • 2 hours
  • Free Cancellation
From
$53.34
From
$53.34

60 Minute Private Vacation Photography Session with Local Photographer in Chicago

60 Minute Private Vacation Photography Session with Local Photographer in Chicago

Flytographer 60 Minute Vacation Photoshoot Connect with a local professional photographer in Chicago and capture your most memorable moments during this private photoshoot. Get insider tips on the best things to do in Chicago, including where to eat and what to see from your vacation photographer.  Return from your trip with beautiful, high-quality, vacation photos. The best souvenir ever.
More
  • 1 hour
  • Free Cancellation
From
$350.00
per group
From
$350.00
per group

120 Minute Private Vacation Photography Session with Local Photographer in Chicago

120 Minute Private Vacation Photography Session with Local Photographer in Chicago

Flytographer 120 Minute Vacation Photoshoot Connect with a local professional photographer in Chicago and capture your most memorable moments during this private photoshoot. Get insider tips on the best things to do in Chicago, including where to eat and what to see from your vacation photographer.  Return from your trip with beautiful, high-quality, vacation photos. The best souvenir ever.
More
  • 2 hours
  • Free Cancellation
From
$708.34
per group
From
$708.34
per group

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.
More
  • 1 hour 30 minutes
  • Free Cancellation
From
$46.67
From
$46.67

90 Minute Private Vacation Photography Session with Local Photographer in Chicago

90 Minute Private Vacation Photography Session with Local Photographer in Chicago

Flytographer 90 Minute Vacation Photoshoot Connect with a local professional photographer in Chicago and capture your most memorable moments during this private photoshoot. Get insider tips on the best things to do in Chicago, including where to eat and what to see from your vacation photographer.  Return from your trip with beautiful, high-quality, vacation photos. The best souvenir ever.
More
  • 1 hour 30 minutes
  • Free Cancellation
From
$544.88
per group
From
$544.88
per group

Chicago Pizza Coach Tour

Chicago 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.
More
  • 3 hours
  • Taking safety measures
From
$75.00
From
$75.00
Taking safety measures

Private 2-hour Boat Rental with Pizza Included

Private 2-hour Boat Rental with Pizza Included

star-5
Please note: Chicago's reopening plan requires that we limit capacity on all boats to 4 adults and 2 children (6 total). We cannot allow any exceptions. 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.
More
  • 2 hours
  • Free Cancellation
From
$286.94
per group
From
$286.94
per group

Private Luxury Boat Rental with Pizza Included

Private Luxury Boat Rental with Pizza Included

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.
More
  • 2 hours
  • Free Cancellation
From
$318.94
per group
From
$318.94
per group