26 Products

Chicago in a Day Walking Tour: Food, History & Architecture
$101
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Chicago in a Day Walking Tour: Food, History & Architecture
Summary

Immerse yourself in Chicago's rich history and vibrant culinary scene on this captivating walking tour. Discover the city's iconic architecture and Prohibition-era charm while indulging in delectable local cuisine. From deep-dish pizza to hidden gems, savor the flavors of Chicago as a knowledgeable ...

Inclusions
  • Hear stories of Chicago’s past from Prohibition to the Great Fire and immigrant history
  • Led by expert local guides, passionate storytelling from true Chicago insiders
  • Visit Millennium Park and snap photos at the famous Bean
  • Explore top sights & hidden gems like Riverwalk, Magnificent Mile, Pedway, Wrigley Building
  • Taste Chicago’s iconic eats, including deep‑dish pizza, Chicago‑style hot dogs, and Italian beef
  • Enjoy a relaxed, small‑group experience (maximum 12 travelers)
  • Travel with purpose on a tour operated by a certified B Corp committed to responsible tourism
Exclusions
  • Gratuity
  • Drinks and additional food
Itinerary
  • The Chicago Theatre
  • Chicago Pedway
  • Chicago River
  • Wrigley Building
  • Tribune Tower
  • Millenium Park
  • Cloud Gate
  • The Loop
Good to know
  • Wheelchair accessible, Infants and small children can ride in a pram or stroller, Service animals allowed, Public transportation options are available nearby, Transportation options are wheelchair accessible, Suitable for all physical fitness levels, Is this tour child-friendly? Yes! This tour is suitable for families. Children under 4 years old can join free of charge. A reduced child price applies for children aged 4 to 11., Will food options or portion sizes very? Food offerings and portion sizes may vary depending on the season and the stops visited on the day of the tour. However, the total amount of food included is always designed to equal a full meal., Is this tour suitable for all ages and fitness levels? Yes! This tour is suitable for guests of all ages and fitness levels. Please note that it includes approximately 4.8 to 6.4 km (3-4 miles) of walking. at a relaxed pace with regular stops., Can dietary requirements be accommodated? Vegetarian options are available. Unfortunately, we are unable to accommodate other food allergies or dietary preferences. Please let us know in advance if you require a vegetarian option so we can plan accordingly., What happens if the weather isn’t great? Experiences run rain, shine, or snow, so please dress appropriately for the weather on the day of your tour.
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Chicago Favorites Ultimate Food and Walking Tour

Chicago Favorites Ultimate Food and Walking Tour

3 hrsEco-FriendlyFree cancellation
$85
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Chicago Favorites Ultimate Food and Walking Tour
Summary

The perfect Food Tour of Chicago for first timers or anyone eager to explore Chicago's famous foods & top attractions—all in one tour. Stroll the beautiful streets of downtown & taste the Windy City’s favorite eats on this iconic Chicago Food Tour! Bobby’s Bike Hike & Food Tours, whose food tours ra...

Inclusions
  • Deep Dish Pizza slice: Thick, hot, cheesy, saucy, and baked to perfection!
  • Garrett’s Popcorn Chicago sample mix—sweet-salty, cheesy-caramel bliss in every crunchy bite.
  • Italian Beef Sandwich sample—slow-roasted beef, rich au jus, classic peppers, pure Chicago.
  • Led by a local English-speaking guide who’s passionate about Chicago’s eats, streets, & stories!
  • Receive insider tips on must-see attractions, activities, and culinary delights for your stay
  • See iconic Chicago architecture—from historic gems to modern marvels—while tasting city classics.
  • Enjoy a Free 2-hour Bike Rental or Kayak Rental as an added bonus (weather permitting)
  • Indulge in the original brownie—rich, fudgy, and born in Chicago(AM only). Other dessert on PM Tours
  • Full Chicago-style hot dog with mustard, relish, onions, pickle, peppers—no ketchup allowed!
Exclusions
  • Hotel pickup and drop-off
  • $10 per person (or more) recommended gratuity for guide (Cash, Venmo and PayPal)
Itinerary
  • Palmer House Hilton Historic Lobby
  • Millennium Park
  • Cloud Gate
  • The Chicago Theatre
  • The Magnificent Mile
  • Historic Water Tower
  • Crown Fountain
  • Wrigley Building
  • Holy Name Cathedral
  • Jay Pritzker Pavilion
  • The Loop
  • Chicago Pedway
Good to know
  • Wheelchair accessible, Infants and small children can ride in a pram or stroller, Public transportation options are available nearby, Transportation options are wheelchair accessible, All areas and surfaces are wheelchair accessible, Suitable for all physical fitness levels, If you have dietary restrictions, please add a note in the special requirements section when booking, and email us after booking to confirm they can accommodate., Tour Operator can accommodate vegetarians or those who don’t eat beef or pork but can’t cater for gluten-free (limited options) or vegan (extremely limited options) diets., VIP Adult Beverage upgrade (3 samples) available upon arrival for $19.99 per person extra (Ages 21+), TripAdvisor rated this tour its highest-level Traveler’s Choice Award each year since 2002., Our groups have exclusive VIP access to locations we visit., Operates in all weather conditions, please dress appropriately, Chicago's famous foods are built on grit, hard work, and on the backs of labor. They are not for everyone, so come with an open mind as we visit Chicago hot dog stand, Deep dish pizza joint, Italian Beef sample, and the original brownie..
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Walkin' with Colin: Chicago History-Mystery-Comedy-Tragedy Tour
$44
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Walkin' with Colin: Chicago History-Mystery-Comedy-Tragedy Tour
Summary

Embark on a profound, downtown walk-around, to discover incredible stories and secrets of the city on this not to miss feet on the street experience! During our loop around "Da Loop" we will peel back the layers of this Great Big Onion Town, going in and out of extraordinary buildings, admiring amaz...

Inclusions
  • All Fees and Taxes
Itinerary
  • Chagall's Four Seasons
  • Marquette Building
  • Calder’s Flamingo
  • The Rookery Building
  • The Picasso
  • The Chicago Theatre
  • Macy's on State Street
  • Chicago Cultural Center
Good to know
  • Wheelchair accessible, Service animals allowed, Public transportation options are available nearby, All areas and surfaces are wheelchair accessible, Not recommended for travelers with spinal injuries, Not recommended for pregnant travelers, Not recommended for travelers with poor cardiovascular health, Travelers should have at least a moderate level of physical fitness, Please bear in mind that this tour is an adventurous 2-hour, 2-mile, indoor/outdoor, downstairs/upstairs, elevator/escalator experience.
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Chicago's Ultimate City Bike Tour of Top Downtown Attractions
$59
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Chicago's Ultimate City Bike Tour of Top Downtown Attractions
Summary

Get acquainted with Chicago’s most iconic landmarks on this riotous guided Chicago bicycle tour! Join the expert guides of Bobby’s Bike Hike, America’s longest-running city bicycle tour company, on this exciting and informative adventure. Over the course of a 3-hour bike ride (traversed at a nice le...

Inclusions
  • Named Top 20 Tour in the World by TripAdvisor—experience why guests rave about Bobby’s Bike Hike!
  • Bikes, helmets, child equipment, and all gear included on your Chicago Bike Tour
  • Fun, local guides share insider tips, history, food, & hidden gems for an unforgettable experience.
  • See the best of Chicago's downtown attractions & architecture on this scenic, culture-packed ride.
Exclusions
  • $10 per person suggested guide gratuity. (via Cash, Venmo and PayPal)
  • Food and drinks
Itinerary
  • Millennium Park
  • Clarence F. Buckingham Fountain
  • Lakefront Trail
  • Museum Campus
  • Navy Pier
  • Northerly Island
  • Soldier Field
  • Chicago Riverwalk
  • The Chicago Theatre
  • Shedd Aquarium
  • Grant Ulysses Park
  • Field Museum
  • Cloud Gate
  • Jay Pritzker Pavilion
  • Crown Fountain
  • Adler Planetarium
  • Daley Bicentennial Plaza
Good to know
  • Public transportation options are available nearby, Suitable for all physical fitness levels, This Chicago Bike Tour is appropriate for most ages and fitness levels. Professional guides blend quality information, group interaction, and most of all, fun, to create an unforgettable Chicago experience. Bikes are provided, TripAdvisor rated Bobby’s Bike Hike its highest-level Traveler’s Choice Award each year since 2002., Operates rain or shine, please dress appropriately. If extreme weather forces cancellation there will be options to change tours or refund., Minimum numbers apply. There is a possibility of cancellation after confirmation if there are not enough guests to meet requirements. In the event of this occurring, you will be offered an alternative or full refund., Please note: children must be strong, capable riders and be able to bike for 9 miles, All equipment included: Bicycles, Helmets, and Child Equipment
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Chicago Crime and Movies Tour

Chicago Crime and Movies Tour

1.5 hrsEco-FriendlyFree cancellation
$35
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Chicago Crime and Movies Tour
Summary

Mobsters and Movies takes you through the real haunts of Capone, Dillinger, and The Outfit—then shows you how the very same streets turned into movie magic. Walk the same corners seen in 'The Untouchables' and 'Public Enemies,' and hear how Chicago wrote the script for American gangster history. Thi...

Inclusions
  • Souvenir Photos
Exclusions
  • Tip/Gratuity for Tour Guide
Itinerary
  • River North
  • The Picasso
  • The Rookery Building
  • The Art Institute of Chicago
  • The Chicago Theatre
  • Chicago Cultural Center
Good to know
  • Wheelchair accessible, Infants and small children can ride in a pram or stroller, Service animals allowed, Public transportation options are available nearby, Transportation options are wheelchair accessible, All areas and surfaces are wheelchair accessible, Not recommended for travelers with poor cardiovascular health, Suitable for all physical fitness levels, This is a walking tour—no vehicles are provided. The route is fully accessible, and we welcome all guests who can comfortably join at a walking pace.
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Chicago Family Food and Bike Tour with Top Attractions

Chicago Family Food and Bike Tour with Top Attractions

4 hrsFree cancellationLikely to sell outFamily friendly
$79
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Chicago Family Food and Bike Tour with Top Attractions
Summary

This Chicago Food & Bike tour is perfect for the entire family, put on by Bobby’s Bike Hike, whose food tours in just the past year have ranked as Top 10 in America by USA Today and Top 20 in the world by Tripadvisor. Biking is easy in Chicago because of it's miles of bike trails, flat terrain and e...

Inclusions
  • Bikes, helmets, and all gear included on your Kid-Friendly Chicago Food and Bike Tour
  • Fun, local guides share insider tips, history, food, & hidden gems for an unforgettable experience.
  • Rated Top 20 Food Tours in the World on TripAdvisor
Exclusions
  • $10 per person (or more) suggested guide gratuity. (via Cash, Venmo and PayPal)
Itinerary
  • Millennium Park
  • Lakefront Trail
  • Clarence F. Buckingham Fountain
  • Navy Pier
  • Chicago Riverwalk
  • Grant Park
  • North Avenue Beach
  • Gold Coast
  • Oak Street Beach
  • The Art Institute of Chicago
  • Lincoln Park
  • The Chicago Theatre
  • Cloud Gate
  • Crown Fountain
  • Jay Pritzker Pavilion
Good to know
  • Public transportation options are available nearby, Specialized infant seats are available, Suitable for all physical fitness levels, If you have dietary restrictions, please add a note in the special requirements section when booking, and contact us after booking to confirm they can accommodate., Tour Operator can accommodate vegetarians or those who don’t eat beef or pork but can’t cater for gluten-free (limited options) or vegan (extremely limited options) diets., VIP Adult Beverage upgrade (3 samples) available upon arrival for $19.99 per person extra (Ages 21+), TripAdvisor rated Bobby's Bike Hike its highest-level Traveler’s Choice Award each year since 2002., Our Family-Friendly Chicago Food & Bike Tour groups have exclusive VIP access to locations we visit., Operates rain or shine, please dress appropriately. If extreme weather forces cancellation there will be options to change tours or refund., Minimum numbers apply for the Kid-Friendly Chicago Food & Bike Tour. There is a possibility of cancellation after confirmation if there are not enough guests to meet requirements. In the event of this occurring, you will be offered an alternative or full refund., Please note: children must be strong, capable riders and be able to bike for 9 miles. There are frequent stops for rest, All Equipment included (bicycles, helmets, child equipment) in the Family Friendly Chicago Food & Bike Tour.
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

The Chicago Theatre Tour Experience
$30
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The Chicago Theatre Tour Experience
Summary

Unlock the secrets of Chicago's most-photographed venue with The Chicago Theatre Tour Experience. Marvel at the grandiose architecture and walk in the footsteps of legends on this exclusive tour.

Chicago Loop Food Tour: Taste the Most Iconic Local Eats
$87
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Chicago Loop Food Tour: Taste the Most Iconic Local Eats
Summary

Join a local guide for the ultimate foodie adventure in Chicago’s historic Loop, tasting classics like deep‑dish pizza and Chicago‑style hot dogs while discovering insider stories behind the city’s rich food culture.

Inclusions
  • Explore the historic Loop District, one of the city’s top dining and cultural hubs
  • Receive insider tips on the best places to eat, drink, and explore during your stay
  • Enjoy tastings of Chicago’s most iconic foods at three popular local spots
  • Sample a Chicago‑style hot dog, a slice of deep‑dish pizza, and a classic Italian beef sandwich
  • Be guided by a friendly, English‑speaking local expert
Exclusions
  • Gratuity
  • Additional Food and Drinks
Itinerary
  • The Chicago Theatre
  • The Loop
Good to know
  • Wheelchair accessible, Infants and small children can ride in a pram or stroller, Service animals allowed, Public transportation options are available nearby, Transportation options are wheelchair accessible, Suitable for all physical fitness levels, Is this tour child-friendly? Yes! This tour is suitable for families. Children under 4 years old can join free of charge. A reduced child price applies for children aged 4 to 11., Can dietary requirements be accommodated? Vegetarian options are available. Unfortunately, we are unable to accommodate other food allergies or dietary preferences. Please notify us in advance if you require a vegetarian option so we can plan accordingly., Will food options or portion sizes vary? Food offerings and portion sizes may vary depending on the season and the stops visited on the day of the tour. However, the total amount of food included is always designed to equal a full meal., What happens if the weather isn’t great? Experiences run rain, shine, or snow, so please dress appropriately for the weather on the day of your tour., Is this tour suitable for all ages and fitness levels? Yes! This tour is suitable for guests of all ages and fitness levels. Please note that it includes approximately 2.4 km (1.5 miles) of walking, at a relaxed pace with regular stops.
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Chicago City Private Tours

Chicago City Private Tours

8 hrsPrivate tourFree cancellation
$199
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Chicago City Private Tours
Summary

Ready to explore Chicago like never before? Whether you have just a couple of hours or a full day, my personalized city tours offer a unique and unforgettable experience, customizable from 2 to 8 hours. From the iconic skyline to hidden gems off the beaten path, I’ll take you on a journey that captu...

Itinerary
  • Holy Name Cathedral
  • 360 Chicago Observation Deck
  • The Magnificent Mile
  • Chicago Riverwalk
  • The Chicago Theatre
  • Chicago Cultural Center
  • Millennium Park
  • The Art Institute of Chicago
  • Palmer House Hilton Historic Lobby
  • Marquette Building
  • The Rookery Building
  • Chicago Board Of Trade Building
  • Chicago Fed's Money Museum
  • Skydeck Chicago - Willis Tower
  • Union Station
  • Chinatown
  • Jackson Park's Japanese Garden
  • Obama Presidential Library
  • Frank Lloyd Wright Trust - Frederick C. Robie House Tour
  • University of Chicago
  • Museum Campus
  • Field Museum
  • Clarence F. Buckingham Fountain
  • Navy Pier
  • Lincoln Park Conservatory
  • Lincoln Park
  • Elks National Memorial
  • Wrigley Field
Good to know
  • Infants and small children can ride in a pram or stroller, Service animals allowed, Public transportation options are available nearby, Specialized infant seats are available, Suitable for all physical fitness levels
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Chicago: Must See Chicago 90 minute Walking Tour
$35
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Chicago: Must See Chicago 90 minute Walking Tour
Summary

This introductory tour to Chicago, features some of its most famous buildings, including the Wrigley Building, Tribune Tower, the Chicago Theatre, and more