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 through 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 by USA Today and Top 20 in the world by Tripadvisor, offers this ultimate food & walking tour to explore the foods Chicago made famous; a slice of deep-dish pizza, a Chicago-style hotdog, Italian beef, & brownies. Bobby’s expert guides will lead you through downtown Chicago’s most iconic landmarks; Millennium Park, State Street, Chicago Theatre, Chicago Riverwalk, Michigan Avenue, & 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 calm, clear Lake Michigan.

Taste all of Chicago’s classic eats on this 4 1/2 hour guided bicycle tour! Join the expert tour guides of Bobby’s Bike Hike, America’s longest-running city bike tour company, on this exciting and informative adventure which recently ranked Top 20 in the World by TripAdvisor. The journey is 13 miles (at a leisurely pace) and includes deep dish pizza, a gourmet brownie, a Chicago-style hot dog, and samples of local craft beer! On the daytime version of the tour, you’ll drink in the sights of Chicago’s beautiful northside neighborhoods, including the Lakefront and Wrigleyville, home to our Chicago Cubs baseball team. On the nighttime version, you'll ride through the party districts of downtown and see the lights of Buckingham Fountain, Millennium Park and the glorious skyline. Cruise the Lakefront Trail, one of the most popular waterfront bike paths in the country. Don’t miss out on this fun tour! You’ll leave with a profound understanding of our town, even if you only came for the beer.

Enjoy Chicago’s famous sights and fabulous views on this award-winning small-group sightseeing tour of the city. On this tour, you will travel through Chicago with an expert guide in a comfortable minibus, enjoy world renowned architecture including the world's first skyscrapers, Museum Campus (for the BEST skyline view in town), Millennium Park (Home of "The Bean"), Buckingham Fountain, The Magnificent Mile, Lincoln Park, Chicago River, The Gold Coast, Lake Shore Drive and more! Along the way, your guide will provide historical, informational and at times humorous commentary about the area. Four photo stops are a part of each tour. The small-group atmosphere with a maximum of 10 people ensures a more personal experience.  You also have the option to upgrade to include THE most popular Architecture River Cruise in Chicago! For good reason, our partner Shoreline Sightseeing, has been the most booked tour on TripAdvisor for the last 5 years! And yes, there is a bar on the boat.

Enjoy Chicago’s famous sights and fabulous skyline views on this award-winning small-group sightseeing tour of the city. Travel through Chicago with an expert guide on a comfortable minibus, stopping at iconic locations like early skyscraper "The Rookery" (Frank Lloyd Wright architecture), Museum Campus (for the BEST skyline view in town) and The Buckingham Fountain. You'll also see The Magnificent Mile, Lincoln Park, The Chicago River, Millennium Park, The Gold Coast, Lake Shore Drive and more! Along the way, your guide will provide historical and informational and at times humorous commentary about the area and its many attractions. The small-group atmosphere with maximum of 10 people ensures a more personal experience.  

2 hours of being a kid again!!! Take a Segway tour with us and discover how beautiful Chicago truly is. Ride through some of Chicago's most popular destinations with an experienced guide. We will glide through scenic and historic downtown Chicago and explore the beautiful Grant Park, around the Buckingham Fountain, near the Museum Campus and near the lakefront. Or take our Riverwalk tour to explore the Chicago River to view Navy Pier and famous Chicago bridges, traveling up historic Michigan Avenue and passing by Millennium Park. No matter which tour you choose, it will be a memory lasting a lifetime!

PRICE IS PER VEHICLE AND YOU MAY BRING UP TO 5 PASSENGERS.  Thank you for contacting Chicago Private Tours! We would love to help your group discover Chicago.  Our services include pick up from your downtown Chicago hotel, a 3-4 hour private City Tour in a chauffeured vehicle, and the services of one of our knowledgeable guides. This means you will have two people working with you the entire time, allowing you to get out of the vehicle with your guide at several stops. These stops include, but are not limited to Millennium Park, Lincoln Park Conservatory, Museum Campus, and more.  The tour will be interactive and entertaining, covering history, architecture and culture.  We share stories to bring Chicago's rich history to life. Once the tour concludes, we will drop your group off at your preferred, downtown Chicago location.

Get acquainted with Chicago’s most iconic landmarks on this riotous guided 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 leisurely pace), you’ll get up close and personal with Chicago’s legendary Museum Campus, Grant Park, and Millennium Park. You’ll become intimately familiar with Soldier Field, The Adler Planetarium, Buckingham Fountain, The Pritzker Pavilion, and Cloud Gate (the formal name of Chicago’s dearly-beloved “Bean”). This tour is perfect for first time visitors looking to see all of the classic hotspots, and for returning guests looking to understand more about the landmarks they know and love. Hop on two wheels, and come make memories that are sure to last a lifetime!

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.

This lively overview of Chicago architecture explores iconic buildings from the 1890s to present. We'll compare and contrast a wide range of buildings with varying architectural styles and see how older structures connect to new skyline additions. On this tour, we'll make seven stops in downtown Chicago where we can compare the histories and styles of buildings located within sight of each other. The tour features 19th-Century Commercial, Beaux-Arts, Mid-Century Modern and Postmodern buildings, as well as the latest in architecture from Frank Gehry, Renzo Piano and Adrian Smith. At each stop, we’ll look at the connections between the past and present and discover what inspires design today. The tour culminates with a visit to Millennium Park, where world-class art and architecture combine, creating a unique urban fabric. As a certified nonprofit, all CAC ticket purchases directly support our education efforts and community engagement projects.

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!

Must-See Chicago is a fast-paced, 90-minute introductory tour to Chicago featuring some of its most famous buildings, including the Wrigley Building, Tribune Tower, the Art Institute of Chicago, Willis (Sears) Tower, the Chicago Theatre and more! Get a brief overview of more than a dozen buildings—as well as Chicago landmarks like Millennium Park, the Loop and the Chicago River—on this whirlwind tour. There are lots of photo opportunities along the way, so be sure to bring your camera! As a certified nonprofit, all CAC ticket purchases directly support our education efforts and community engagement projects.

This is a tour like no other! Our newest Segway adventure is completely unique and will cover the good, the bad, the ugly and the totally weird stories of Chicago. We will travel back through the ages as you discover the city through the lens of the Chicago Syndicate, hear the whispers of the city’s elite (or politicians), and be entertained by stories that are rarely told. You’ll think “No, really I never would have known!” Glide around Millennium Park, through the new neighborhood of Lakeshore East, and along the Lakefront as we unveil Chicago’s forgotten past in two hours! Your imagination will come alive as you hear stories of the Chicago Mob, the truth behind the 1968 Democratic National Convention, innovations that changed history, and so much more!

Chicago is often defined by its wild architecture, satisfying staples such as its famous deep dish pizza, and iconic sculptures like “The Bean” of Millennium Park. But how do you get from one attraction to another with ease? The Chicago “L”! With your included all-day pass in hand, you’ll receive a true local experience as we cruise from station to station on Chicago’s elevated train. You’ll learn how these tracks shaped the city, from its steam locomotive days to its current electrified system. Among the neighborhoods we’ll tour is the Chicago Loop, thronged with Chicagoans commuting to its financial, federal, and theater districts. We’ll stop at one of the oldest surviving stations on the L system as well as the impressive main hub of the Chicago Public Library. We’ll hop off the train to enjoy a small Local treat before boarding the L to explore more of Chicago’s history and enjoy some spectacular skyline views. And by the end of your tour, you’ll be an expert CTA rider!

There’s nothing more magical than downtown Chicago during the holiday season. Bobby’s Holiday Hike is a 3hr guided walking and food tour through the Chicago Loop, brought to you by Bobby's Bike Hike, internationally recognized for their tours. You’ll get to sample the Windy City’s favorite winter treats; including a slice of deep dish pizza, Chicago-style hot dog, Italian Beef, chocolate brownie, and hot apple cider. Upon arrival, you can add a VIP holiday craft beer package for $19.99/person. Our entertaining guides will get your holiday spirit primed with plenty of food and knowledge. Did you know Rudolph the red-nosed reindeer was a story created in Chicago? You’ll see the Christmas window displays at the original Marshall Field’s department store, Chicago's city Christmas tree, the ice skating rink at Millennium Park, and the legendary Christkindlmarket, a traditional German Christmas Market. No other tour offers such an all-inclusive experience of Chicago during the holidays!

Explore Chicago at your own pace on an independent bike tour. With your full-day bike rental, pedal along Lake Michigan and visit top Chicago attractions such as Lincoln Park, Navy Pier, Millennium Park, Wrigley Field and the Shedd Aquarium. This is a fun and active way to experience the city with the whole family, and you can enjoy the flexibility to create your own itinerary with the help of your provided map.

Chicago is defined by its wild architecture, staples such as its famous deep dish pizza, and “The Bean” of Millennium Park. But how do you get from one attraction to another with ease?The Chicago “L”!

This 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 easy connections between attractions. We’ll be sampling from each of Chicago’s well known and unique foods -- deep dish pizza, a true Chicago hot dog, and a dessert for good measure. You’ll learn the history behind the foods and also get a taste for some of Chicago’s most popular downtown districts as we cruise through the Gold Coast, Chicago Riverwalk, Millennium Park, Buckingham Fountain, Museum Campus, Navy Pier and along the Lakefront. Whether day or night, you'll get fantastic views of the skyline and feel the city's vibrant energy. Veggie options available.

Ease into the evening with a relaxing glide through the parks and lakefront in Chicago. This evening ride offers cooler temperatures and beautiful sunset views as well as views of Chicago's world-famous skyline and graceful lakefront. This segway tour departs near Millennium Park as dusk arrives and passes sights like Buckingham Fountain, Chicago’s majestic lakefront, and the Museum Campus.

Discover Chicago's best on our Big Bus tour. Board our open-top, double-decker bus and see the city's iconic landmarks, from the Magnificent Mile to Millennium Park. Utilize our convenient stops to explore vibrant neighborhoods and attractions, including Willis Tower, the Chicago Riverwalk, and more. Spend your day shopping on Magnificent Mile, enjoying Navy Pier's Ferris Wheel, or tasting authentic Chicago Deep Dish Pizza. Our flexible tour lets you create your own itinerary, with a free app to track bus arrivals. Listen to digital commentary in multiple languages, offering expert insight into Chicago's history and culture, while recommending the best places to eat, drink, and shop. Offering comfortable seating and panoramic views, our Hop-On Hop-Off Sightseeing Tour is an ideal way to explore the city. Hop off as often as you like within your ticket's validity period, and simply hop on again when ready to continue.

Discover Chicago’s Millennium Park by solving clues and unlocking stories on your phone. Play the engaging exploration game to learn about the iconic works of art that populate the area on your way to riches beyond your imagination.