Explore the charm and hidden treasures of Chicago Pedway through tailored tours with Tours To Go. Whether you’re a first-time visitor or revisiting the city, we create unforgettable experiences with customizable itineraries. Reserve your Chicago tours today for an insider’s perspective on the top sights and attractions!
Chicago Favorites Ultimate Food and Walking Tour
The perfect tour for first timers to Chicago or those who want to explore Chicago's famous foods along with the city's top attractions, all on one tour. Stroll the beautiful streets of downtown Chicago & taste the Windy City’s favorite eats! Bobby’s Bike Hike, whose food tours are ranked Top 10 in America (USA Today) & Top 20 in the world (Tripadvisor), offers this ultimate food & walking tour to explore the hard-working, salt-of-the earth foods Chicago made famous; a slice of deep-dish pizza, a Chicago-style hotdog, Italian beef, popcorn & brownies. Bobby’s expert guides will lead you through downtown Chicago’s most iconic landmarks; Millennium Park, State St, Chicago Theatre, Riverwalk, Michigan Ave, & the Wrigley Building, all the while explaining the tales from Chicago’s rich food-centric history. Enjoy your food tour & receive a bonus 2-hour FREE bike or kayak rental for each ticket bought, adding value to your experience. Bike along the Lakefront Trail or kayak on Lake Michigan.
Duration: 3 hours.
Duration: 3 hours.
Chicago in a Day: Food, History and Architecture Walking Tour
Ready to discover some of the best Chicago has to offer with a local by your side? Join us on an epic tour of some of the city’s greatest hits: incredible architecture both old and new, delicious local treat and iconic Chicago dishes, a uniquely Chicago transit ride, stunning river views and much more!
Duration: 5 hours.
Duration: 5 hours.
Chicago Architecture Tour: Underground Pedway and the Loop
This tour explores some of the best hidden details, secret buildings and spaces, and untold stories that add wonderful bits of color and texture to the overall narrative of Chicago. On this tour, we will explore the famous and mysterious Chicago Pedway, a system of underground tunnels connecting 40 blocks downtown, popping in and out of buildings to see beautiful and fascinating interior spaces. You'll learn to use this system that most locals don't even fully know or use, and you'll be encouraged to continue exploring Chicago on your own after the tour!
Duration: 2 hours.
Duration: 2 hours.
Chicago Walking Tour: Legacy of the Prohibition Era
Tour the streets of Chicago to see the beauty and legacy left behind by the Prohibition Era. See the amazing architecture, iconic sights (both old and new), the city's best spots and try a local sweet treat along the way as you explore on foot.
Duration: 2 hours 30 minutes.
Duration: 2 hours 30 minutes.
Chicago History and Architecture Walking Tour with Boat Cruise
Park with the iconic Cloud Gate sculpture. Wander through lush gardens and public art, then delve into the Chicago Pedway's hidden gems.
Enjoy breathtaking views on the Chicago Riverwalk, admire the Wrigley Building and Tribune Tower on the Magnificent Mile, and cross the historic Michigan Avenue Bridge.
Learn about the Chicago Fire and have the opportunity to enjoy a classic Chicago savory treat (additional cost). Visit Starbucks Reserve Roastery, savoring the flavors that are as rich as the city’s heritage.
Pass by several landmarks like the Tribune and Wrigley buildings. Gain a deeper appreciation of Chicago's spirit.
At the end, hop aboard the Shoreline Architecture Cruise to enjoy a narrated boat tour and marvel at the breathtaking views of over 40 Chicago iconic landmarks, from hidden architectural features to the Windy City's most famous monuments.
Duration: 3 hours 30 minutes.
Enjoy breathtaking views on the Chicago Riverwalk, admire the Wrigley Building and Tribune Tower on the Magnificent Mile, and cross the historic Michigan Avenue Bridge.
Learn about the Chicago Fire and have the opportunity to enjoy a classic Chicago savory treat (additional cost). Visit Starbucks Reserve Roastery, savoring the flavors that are as rich as the city’s heritage.
Pass by several landmarks like the Tribune and Wrigley buildings. Gain a deeper appreciation of Chicago's spirit.
At the end, hop aboard the Shoreline Architecture Cruise to enjoy a narrated boat tour and marvel at the breathtaking views of over 40 Chicago iconic landmarks, from hidden architectural features to the Windy City's most famous monuments.
Duration: 3 hours 30 minutes.
Small Group History And Architecture Walking Tour of Chicago
Explore Chicago's rich history and vibrant culture on a walking tour starting at Millennium Park with the iconic Cloud Gate sculpture. Wander through lush gardens and public art, then delve into the Chicago Pedway's hidden gems. Enjoy breathtaking views on the Chicago Riverwalk, admire the Wrigley Building and Tribune Tower on the Magnificent Mile, and cross the historic Michigan Avenue Bridge. Learn about the Chicago Fire and have the opportunity to enjoy a classic Chicago savory treat (additional cost). Visit Starbucks Reserve Roastery, savoring the flavors that are as rich as the city’s heritage. Pass by several landmarks like the Tribune and Wrigley buildings. Gain a deeper appreciation of Chicago's spirit.
Duration: 2 hours 30 minutes.
Duration: 2 hours 30 minutes.
Chicago Food Tour with The Magnificent Mile and Millennium Park
Wander through Chicago downtown exploring and gaining new food experience on this walking trip. Dive into the hospitable and authentic atmosphere of the city encountering interesting sights and visiting the principal city landmarks.
Be welcomed by the unique culinary tastes of the Windy City and fall in love with iconic treats, listening to the interesting historical and cultural facts from your guide.
On this walking tour of Chicago, revel in the incredible climate while visiting the most important landmarks of the city following your guide. You will also dive into the diversity of tastes exploring some typical Chicago food and drinks and enjoy a pleasant walk in good company, choosing your path depending on the weather.
Duration: 3 hours.
Be welcomed by the unique culinary tastes of the Windy City and fall in love with iconic treats, listening to the interesting historical and cultural facts from your guide.
On this walking tour of Chicago, revel in the incredible climate while visiting the most important landmarks of the city following your guide. You will also dive into the diversity of tastes exploring some typical Chicago food and drinks and enjoy a pleasant walk in good company, choosing your path depending on the weather.
Duration: 3 hours.
Best of Chicago: Architecture & Highlights City Private Tour
Get the best of Chicago with a local guide on this walking tour featuring the city’s best neighborhoods, top attractions, and the Chicago ‘L’!
We’ll start by exploring the Chicago Loop, home to an array of mind-blowing architecture. See the Willis Tower, Union Station just across the river, and admire the Beaux-Arts beauty of the Art Institute of Chicago. No downtown Chicago experience is complete without a stop at Millennium Park’s Cloud Gate, AKA The Bean.
We’ll then head north to stroll along the Chicago Riverwalk before exploring the River North neighborhood, home of the iconic Wrigley Building.
Over in the Magnificent Mile district, grab post-tour tickets for the Museum of Contemporary Art or brave the 94 floors up to 360 CHICAGO observation deck. End your tour here or nearby in the attraction- and entertainment-filled Navy Pier.
During your tour, your guide will treat you to a local snack as well as a $5 train pass so we can really maximize our time sightseeing in Chicago!
Duration: 2 hours.
We’ll start by exploring the Chicago Loop, home to an array of mind-blowing architecture. See the Willis Tower, Union Station just across the river, and admire the Beaux-Arts beauty of the Art Institute of Chicago. No downtown Chicago experience is complete without a stop at Millennium Park’s Cloud Gate, AKA The Bean.
We’ll then head north to stroll along the Chicago Riverwalk before exploring the River North neighborhood, home of the iconic Wrigley Building.
Over in the Magnificent Mile district, grab post-tour tickets for the Museum of Contemporary Art or brave the 94 floors up to 360 CHICAGO observation deck. End your tour here or nearby in the attraction- and entertainment-filled Navy Pier.
During your tour, your guide will treat you to a local snack as well as a $5 train pass so we can really maximize our time sightseeing in Chicago!
Duration: 2 hours.
Chicago in a Day: Food and Architecture Private Walking Tour
Get the whole Chicago experience combining our Chicago Architecture & Highlights Tour and Chicago Food Tour: Deep Roots to Deep Dish!
Our two-part tour begins by exploring the heart of downtown Chicago - with its iconic architecture, both old and new, views of the Chicago River, Millenium Park, and bustling city avenues (plus, a couple tasty local treats along the way).
From there, we’ll hit the Central Loop, where locals go to grab their favorite foods, day and night. Try the best of Chicago fare and get to know the history and how-tos (and how-not-tos) behind iconic street and comfort food staples - from the infamous deep dish pizza to sandwiches to a loaded hot dog!
Your local guide will entertain with fascinating stories and the everyday immigrant chefs and vendors responsible for Chicago’s eclectic food scene. By the end of the tour, you’ll have a deep appreciation for both the evolution of this excellent city and the role food has played in the lives of all Chicagoans!
Duration: 5 hours.
Our two-part tour begins by exploring the heart of downtown Chicago - with its iconic architecture, both old and new, views of the Chicago River, Millenium Park, and bustling city avenues (plus, a couple tasty local treats along the way).
From there, we’ll hit the Central Loop, where locals go to grab their favorite foods, day and night. Try the best of Chicago fare and get to know the history and how-tos (and how-not-tos) behind iconic street and comfort food staples - from the infamous deep dish pizza to sandwiches to a loaded hot dog!
Your local guide will entertain with fascinating stories and the everyday immigrant chefs and vendors responsible for Chicago’s eclectic food scene. By the end of the tour, you’ll have a deep appreciation for both the evolution of this excellent city and the role food has played in the lives of all Chicagoans!
Duration: 5 hours.
Walking Tour: Underground Chicago via the Pedway System
Take a tour of Chicago's Pedway system, a network of underground tunnels that allows pedestrians to pass from one end of the Loop to the other without encountering weather or traffic.
Our tour begins in the lobby of the Swissotel where we descend into the Pedway. After a tour of the Chicago Cultural Center and its famous Tiffany Dome, we return to the Pedway for a short walk to Macy's department store. There, we'll view the famous Tiffany ceiling from two unique perspectives, and make a quick stop the iconic Walnut Room.
We return to the Pedway and follow it to Civic Center Plaza for a quick look at a famous Picasso sculpture and view the Chicago Temple and it's famous Sky Chapel. Back down to the Pedway, we'll visit to City Hall followed by a short walk to a nearby L station.
A quick train ride takes us to the origin/terminus of Route 66, the Art Institute’s lion statues, and to Millennium Park to view the famous "Bean" sculpture, Lurie Gardens and Crown Fountain.
Duration: 2 hours 30 minutes.
Our tour begins in the lobby of the Swissotel where we descend into the Pedway. After a tour of the Chicago Cultural Center and its famous Tiffany Dome, we return to the Pedway for a short walk to Macy's department store. There, we'll view the famous Tiffany ceiling from two unique perspectives, and make a quick stop the iconic Walnut Room.
We return to the Pedway and follow it to Civic Center Plaza for a quick look at a famous Picasso sculpture and view the Chicago Temple and it's famous Sky Chapel. Back down to the Pedway, we'll visit to City Hall followed by a short walk to a nearby L station.
A quick train ride takes us to the origin/terminus of Route 66, the Art Institute’s lion statues, and to Millennium Park to view the famous "Bean" sculpture, Lurie Gardens and Crown Fountain.
Duration: 2 hours 30 minutes.
Chicago Scav Hunt
Take your shot at completing this Chicago Scavenger Hunt around the Loop and River North neighborhoods including the Riverwalk.
Complete this solo or build a ScavSquad of up to 5 people and discover the city like never before!
Use clues and hints within the app to complete the objectives (if you get stuck, you can skip and go back later).
Some objectives have prizes so do your best to complete as many objectives correctly.
Once complete, you can view the Leaderboard to see how you did against others.
Duration: 3 hours.
Complete this solo or build a ScavSquad of up to 5 people and discover the city like never before!
Use clues and hints within the app to complete the objectives (if you get stuck, you can skip and go back later).
Some objectives have prizes so do your best to complete as many objectives correctly.
Once complete, you can view the Leaderboard to see how you did against others.
Duration: 3 hours.
