16 Products

Chicago Food Tour: 6 Dishes with Deep Dish Pizza & Beef Sandwich

Chicago Food Tour: 6 Dishes with Deep Dish Pizza & Beef Sandwich

3 hrsEco-FriendlyFree cancellationLikely to sell out
$85
Book now
Chicago Food Tour: 6 Dishes with Deep Dish Pizza & Beef Sandwich
Summary

On our Secret Food Tour: Chicago, you'll enjoy a variety of foods with culinary influences from the people who built this city. You'll experience all the city's biggest food hits, many dishes with roots dating back over 150 years. This moving feast incorporates a walk through some of the city's wor...

Inclusions
  • Fudgy Brownie
  • Chicago-style Hot Dog
  • Local Foodie Guide to show you Windy City
  • Italian Beef Sandwich
  • Deep Dish Pizza with Sausage
  • Our delicious Secret Dish (to be revealed on the day)
  • Gourmet Popcorn
Exclusions
  • Hotel pickup and drop-off
  • Gratuities (optional)
Itinerary
  • Chicago Public Library - Hall Branch
  • Financial District
  • Calder’s Flamingo
  • The Rookery Building
  • Palmer House Hilton Historic Lobby
Good to know
  • Not recommended for travelers with poor cardiovascular health, Suitable for all physical fitness levels, * Please note: the itinerary and menu is subject to change, based on the locations' availability, weather, and other circumstances., * Please ensure to contact us in advance of the tour for any dietary requirement, to ensure we can cater for them the best we can., * This tour involves a fair amount of walking; comfortable shoes are recommended.
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
Book now
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.

Chicago Architecture and True Crime History Tour

Chicago Architecture and True Crime History Tour

1.8 hrsEco-FriendlyFree cancellation
$35
Book now
Chicago Architecture and True Crime History Tour
Summary

Get the best of both worlds: explore Chicago’s stunning architecture while uncovering its dark past. Inspired by Devil in the White City, this expert-led walking tour reveals the secrets of the city’s skyline and its shadowy history. If it’s raining the tour is almost all INDOOR. Led by a passionate...

Inclusions
  • Local guide
Exclusions
  • Gratuity
Itinerary
  • Palmer House Hilton Historic Lobby
  • Downtown / The Loop
  • Chase Tower
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, Suitable for all physical fitness levels
Cancellation Policy

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

Chicago Walking Tour: Historic Treasures of Chicago

Chicago Walking Tour: Historic Treasures of Chicago

2 hrsEco-FriendlyFree cancellation
$35
Book now
Chicago Walking Tour: Historic Treasures of Chicago
Summary

Learn about the great architectural landmarks of Michigan Avenue and State Street. The 40 years between 1890 and 1930 saw the creation of some of Chicago’s the most memorable buildings, many of which are featured on this tour. After the World's Columbian Exposition of 1893, Chicago was determined t...

Inclusions
  • Admission to the Galleries of the Chicago Architecture Center
  • Narration by a professional and certified guide
  • Walking tour of Chicago Architecture
Exclusions
  • Hotel pick-up or drop-off
  • Storage for luggage or strollers
  • Coat check
Itinerary
  • Wrigley Building
  • Palmer House Hilton Historic Lobby
  • Carbide and Carbon Building
  • Reliance Building
  • 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, Access to building interiors featured on this tour may be subject to change, due to weekend and holiday schedules or unforeseen closures., Pets are not allowed.
Cancellation Policy

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

Private Chicago Food Tour with Deep Dish and Beef Sandwich

Private Chicago Food Tour with Deep Dish and Beef Sandwich

3 hrsPrivate tourEco-FriendlyFree cancellationLikely to sell out
$225
Book now
Private Chicago Food Tour with Deep Dish and Beef Sandwich
Summary

On our Secret Food Tour: Chicago, you'll enjoy a variety of foods with culinary influences from the people who built this city. You'll experience all the city's biggest food hits, many dishes with roots dating back over 150 years. This moving feast incorporates a walk through some of the city's wor...

Inclusions
  • Fudgy Brownie
  • Chicago-style Hot Dog
  • Local Foodie Guide to show you Windy City
  • Italian Beef Sandwich
  • Deep Dish Pizza with Sausage
  • Our delicious Secret Dish (to be revealed on the day)
  • Gourmet Popcorn
Exclusions
  • Hotel Pick Up and Drop Off
  • Gratuity
Itinerary
  • Chicago Public Library - Hall Branch
  • Financial District
  • Calder’s Flamingo
  • The Rookery Building
  • Palmer House Hilton Historic Lobby
Good to know
  • Public transportation options are available nearby, Infants are required to sit on an adult’s lap, Not recommended for travelers with poor cardiovascular health, Suitable for all physical fitness levels, Please note: the itinerary and menu is subject to change, based on the locations' availability, weather, and other circumstances., Please ensure to contact us in advance of the tour for any dietary requirement, to ensure we can cater for them the best we can., This tour involves a fair amount of walking; comfortable shoes are recommended.
Cancellation Policy

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

History and Architecture of Chicago Loop Walking Tour
$30
Book now
History and Architecture of Chicago Loop Walking Tour
Summary

Discover the rich history and architecture of downtown Chicago with local expert Dave Lineal. Walking underneath the soaring buildings, we will learn how Chicago grew to become a global force in culture, commerce, and architecture. How did this roaring city come to be? We will hear the tales of Chic...

Itinerary
  • Chicago River
  • Cloud Gate
  • The Picasso
  • Chicago Pedway
  • City of Chicago - City Hall
  • Palmer House Hilton Historic Lobby
  • 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, Suitable for all physical fitness levels
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
Book now
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 Walking Tour of Highlights with Free Bike or Kayak Rental
$45
Book now
Chicago Walking Tour of Highlights with Free Bike or Kayak Rental
Summary

This tour is ideal for first-time visitors or anyone eager to discover the city’s most iconic Top Attractions and Highlights on a guided Chicago Walking Tour. During this 2-hour Walking Tour of Chicago, stroll through downtown’s beautiful streets as expert local guides share rich history, colorful c...

Inclusions
  • Explore Millennium Park’s iconic art and architecture with stories that reveal its deeper meaning.
  • Stroll the Magnificent Mile as your guide shares the history, style, and stories behind every block.
  • Discover Cloud Gate’s reflective magic as your guide reveals the meaning behind the iconic sculpture
  • Enjoy a FREE 2-hour Bike Rental or Kayak Rental as an added bonus (weather permitting)
  • See Chicago’s top sights up close, with rich stories that deepen every landmark you visit.
  • See the Art Institute through a new lens as your guide reveals the stories behind its masterpieces.
  • Walk the Riverwalk’s scenic edge as history, architecture, and culture come to life around you.
  • Walking Tour of Chicago's Top Highlights and Attractions
  • Your local guide brings Chicago’s stories to life with personality, insight, and charm.
  • Step beneath the Chicago Theatre marquee as your guide shares the dazzling history behind its glow.
  • Marvel at the Wrigley Building’s stunning architecture as your guide unveils its rich history.
Itinerary
  • Millennium Park
  • The Magnificent Mile
  • Chicago Riverwalk
  • Crown Fountain
  • The Chicago Theatre
  • Historic Water Tower
  • Cloud Gate
  • The Art Institute of Chicago
  • Holy Name Cathedral
  • Jay Pritzker Pavilion
  • Daley Bicentennial Plaza
  • Palmer House Hilton Historic Lobby
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, Suitable for all physical fitness levels, 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
Cancellation Policy

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

Chicago Seasonal Stroll Walking Tour of Holiday Attractions
$45
Book now
Chicago Seasonal Stroll Walking Tour of Holiday Attractions
Summary

There’s nothing more magical than Christmas in Chicago, & this 2hr guided Chicago Walking Tour takes you straight into the heart of it. Journey through the Chicago Loop, Millennium Park, & the Magnificent Mile with an internationally recognized tour company proudly headquartered right here in Chicag...

Inclusions
  • Walk beneath millions of glittering lights as the Magnificent Mile glows for the season.
  • Skip the Lines—enjoy festive, VIP front-of-line access to Christkindlmarket’s holiday magic.
  • Stroll through Millennium Park as it sparkles with lights and joyful holiday energy.
  • Watch skaters glide under the skyline as Millennium Park transforms into a holiday wonder.
  • Experience State Street’s festive shops bursting with lights, dĂ©cor, and holiday cheer.
  • See Chicago’s soaring Christmas tree glowing with festive lights—pure holiday magic.
  • See the Wrigley Building glow with festive lights—an elegant icon shining bright for Christmas.
  • Join a lively local guide who brings Chicago’s holiday spirit to life with every story.
  • Marvel at Macy’s iconic holiday windows—sparkling scenes that capture pure Christmas joy.
Exclusions
  • Optional gratuity: $6 per person (or more) suggested guide gratuity (via Cash, Venmo and PayPal)
  • Hotel pickup and drop-off
  • This is purely a walking tour, no food or drink offered on this tour
Itinerary
  • Christkindlemarket
  • Cloud Gate
  • Macy's on State Street
  • The Magnificent Mile
  • Millennium Park
  • Michigan Avenue Bridge
  • Daley Bicentennial Plaza
  • Jay Pritzker Pavilion
  • The Chicago Theatre
  • Palmer House Hilton Historic Lobby
Good to know
  • Service animals allowed, Public transportation options are available nearby, Infants and small children can ride in a pram or stroller, All areas and surfaces are wheelchair accessible, Transportation options are wheelchair accessible, Wheelchair accessible, Suitable for all physical fitness levels, All of our walking tours at the present moment do allow for ADA compliant and wheelchair accessible., Operates in all weather conditions, please dress appropriately, TripAdvisor rated Bobby’s Bike Hike its highest-level Traveler’s Choice Award each year since 2002., 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., Our groups have exclusive VIP access to locations we visit, including VIP access to Christkindlmarket.
Cancellation Policy

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

Luxury Minibus Chicago City Tour

Luxury Minibus Chicago City Tour

2 hrsFree cancellationLikely to sell out
$65
Book now
Luxury Minibus Chicago City Tour
Summary

Experience Chicago in Style with Our Luxury City Sightseeing Minibus Tour. Indulge in the ultimate Chicago adventure on our top-rated, luxury sightseeing minibus tour. This 2-hour, expertly guided experience takes you through the vibrant heart of the city in a sleek, climate-controlled minibus desig...

Inclusions
  • Luxury Minibus
  • Live Tour Guide
Itinerary
  • Palmer House Hilton Historic Lobby
  • Soldier Field
  • Field Museum
  • Museum Campus
  • Clarence F. Buckingham Fountain
  • Cloud Gate
  • The Magnificent Mile
  • Water Tower Place
  • The Rookery Building
  • Lake Shore Drive
Good to know
  • Infants and small children can ride in a pram or stroller, Service animals allowed, Public transportation options are available nearby, Infants are required to sit on an adult’s lap, Suitable for all physical fitness levels, Infants (0-3 years) must sit on a lap
Cancellation Policy

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