Chicago Theatre Tours & Attractions

Interested in exploring Chicago from the perspective of ghosts and gangsters? Want to really immerse yourself in the history of this great American city, right from the locations that started it all? This tour visits the locations frequented by some of Chicago's most notorious gangsters along with many of the most haunted locations in Chicago!

You can get the best of both worlds with this 2 in 1, history-based guided walking tour of Chicago’s gangsters and ghost stories, right from the famous Chicago Loop Vice District! Upgrade to the bus tour option to experience the same spine-chilling stories by minibus. Includes one stop for an immersive experience.
Duration: 2 hours.

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.
Duration: 2 hours.

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.

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.

Discover Chicago's captivating past on our top-rated Gangsters and Ghosts luxury minibus tour, exploring the iconic Loop and River North neighborhoods, once dominated by notorious Italian and Irish gangs during Prohibition.

Delve into the city's infamous organized crime history and hear spine-chilling tales from our expert guide about the ghosts that still roam these streets. The tour features 1 stop for an immersive experience, allowing you to witness Chicago's history firsthand.

Interested in exploring Chicago from the perspective of ghosts and gangsters? Want to really immerse yourself in the history of this great American city, right from the locations that started it all? This tour visits the locations frequented by some of Chicago's most notorious gangsters along with many of the most haunted locations in Chicago!
Duration: 2 hours.

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!
Duration: 3 hours.

Experience the magic of Chicago at dusk on a 90-minute live guided panoramic adventure that captures the city in its most captivating light. Watch the entire skyline come to life, from Magnificent Mile to Museum Campus and beyond. From the top deck of an open-top double decker, you’ll have a perfect vantage point to see the best of Chicago.

Witness the vibrant nightlife of River North brim with energy, trendy bars, and eclectic dining options. Your knowledgeable guide will provide fascinating insights and stories into the history and hidden stories of Chicago.

Next, the journey takes you along the legendary Michigan Avenue. From the upscale shopping and historic architecture of The Magnificent Mile to the cultural treasures of State Street Theater District, you’ll experience the diverse facets of Chicago’s most famous avenues. See renowned attractions like the Wrigley Building, Tribune Tower, and the Art Institute of Chicago, all beautifully illuminated against the evening sky.
Duration: 1 hour 30 minutes.

Create your own sightseeing itinerary with the Chicago Explorer Pass, saving up to 50%* off compared to buying individual attraction tickets. This multi-attraction pass, valid for 60 days after your first use, provides admission to your choice of up to seven attractions, tours or activities - all one one pass. Select from more than 25 top sites and things to do, including SkyDeck Chicago, Navy Pier and a Shoreline Architecture River Cruise. It's the easiest and most affordable way to explore the Windy City at your own pace. Simply save your pass on your mobile device (available as your 'ticket' after purchase) and go – no voucher redemption required! With Go City you can see more, do more, and save more.

*Savings based on sample itineraries on the Go City website
Duration: 1 to 60 days.

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 amazing art and architecture along the way as we uncover how it all came to be. Expect an engaging, entertaining and wide-eye-opening tour du jour of my sweet home, Chicago.
Duration: 2 hours.

Experience the best travel stories for yourself! Join a local expert and uncover hidden gems. Join us for the ultimate foodie adventure in Chicago’s historic River North area alongside a local guide who can show you the best spots for some of the city’s best-loved dishes. From deep-dish pizza to Chicago-style hot dogs, this tour will leave you filled with delicious local foods as well as some insider knowledge into the city’s culinary history and culture.
Duration: 2 hours.

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.

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!
Duration: 2 hours.

Enjoy admission to more than 30 of Chicago's most popular attractions with Go City's All-Inclusive Pass. Go City lets you create your own itinerary and save far more than if you were to purchase individual attraction tickets. Take a hop-on hop-off bus tour of the Windy City, admire the stunning views from SkyDeck Chicago, and much more. You can visit as many attractions as you like over the course of 1, 2, 3 or 5 days.

Access your Pass in the Go City App and simply simply show it at the gate or ticket office to gain admission. The App acts as your digital guidebook including attraction information and details on which attractions require reservations in advance.
Duration: 1 to 5 days.

Enjoy and appreciate Chicago with your private transportation and guide. Customize your tour and visit the most important sites and landmarks of the Windy City. Be satisfied that you experienced the most important and beautiful sites, taking the most memorable tour of the city.
Duration: 3 hours.

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.

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.
Duration: 4 hours.

Discover Chicago's captivating past on our top-rated Gangsters and Ghosts minibus tour + Riverboat Architecture Cruise. Explore the iconic Loop and River North neighborhoods, once dominated by notorious Italian and Irish gangs during Prohibition. Seamlessly transition to the Riverboat Cruise, where you'll glide along the Chicago River and learn about the city's rich history and iconic architecture

Delve into the city's infamous organized crime history and hear spine-chilling tales from our expert guide about the ghosts that still roam these streets. The minibus tour features 1 stop for an immersive experience, allowing you to witness Chicago's history firsthand.

Interested in exploring Chicago from the perspective of ghosts and gangsters? Want to really immerse yourself in the history of this great American city from the water? This pass includes the top two most famous tours in Chicago!
Duration: 3 hours.

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.

Fell the tug of history and dive into the breathtaking events of the past. On this intriguing and unusual tour, you will explore another side of famous locations and get acquainted with haunted places filled with a spirit of gangsters and speakeasies of the roaring 20s.

Hear the captivating stories of Chicago’s past and feel the curiosity level rising as you immerse yourself into those times.

Discover the dark and mysterious history of the Chicago downtown
Be entertained by the expert local guide who knows the true history of the city
Get to know what lies beyond the famous Chicago facades and what is hidden from the mainstream tours
Visit the most impressive and exciting sites.
Duration: 2 hours.

Insta Walk offers you a lot of stylish photos, shooting angles and ideas. This easy, relaxed and friendly walk will open Chicago for you from a new perspective!

Throughout the tour, I'll use iPhone and Polaroid cameras to capture your perfect shot. You'll receive approximately 100 digital photos, 10 of which will be color-corrected to make them truly pop. And for a unique and timeless souvenir, I'll also give you 5 Polaroid prints that you can treasure forever.
Duration: 1 hour.

Discover Chicago by private boat with a local Chicagoan to highlight its fascinating history and architectural marvels along the way!

Before we board, we’ll take a short walk in the Chicago Loop, a bustling area filled with gems like the ostentatious Marshall Field building, the stained-glass-domed Cultural Center, and the Chicago Theatre, adorned with its emblematic marquee.

After arriving at the dock, you’ll board your own private boat and set sail along the Chicago River. As we glide along, your guide will point out some of the city’s most fascinating landmarks. Stare up in awe at Willis Tower, once the world’s tallest building. Spot Union Station, which you might recognize from several famous films. And gaze upon a behemoth Art Deco building so large it once had its own zip code!

We’ll also pass by Wolf Point, formerly occupied by Native Americans and later by many of Chicago’s first commercial buildings. Afterwards, you might want to explore all these sites and more on foot!

Duration: 2 hours 30 minutes.

This Chicago food tour gives you the chance to explore the city’s foodie scene to its fullest. Explore legendary bakeries in neighborhoods around the city. You'll discover Chicago’s immigrant roots with incredible food from around the world, including Italian, Polish, and German cuisines. Let your local tour guide take you to their favorite candy shop in town, meet interesting shop owners, and hear the stories of restaurants that have been local favorites for generations. We can even include a tour stop to sample some of Chicago’s amazing craft beer from a local brewery! In between food tour stops, we’ll show you the iconic historic and architectural sights of the city as well as a wonderful variety of neighborhoods, and you’ll get your fill of the city’s
Duration: 2 hours 1 minute.

There’s nothing more magical than downtown Chicago during the holiday season. 2-hour guided walking tour through the Chicago Loop, Millennium Park and the Magnificent Mile. This tour is brought to you, internationally recognized tour company headquartered right here in Chicago. Our entertaining guides will get your holiday spirit primed with plenty of fun facts, general knowledge, and the best of Chicago holiday decor. Did you know Rudolph the red-nosed reindeer was a story created in Chicago? You’ll see the fabulous 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. This tour is a walking tour only. No food/drinks on this particular tour.
Duration: 2 hours.

Ready for the ultimate day out in Chicago? We’ll embark on an unforgettable Chicago journey, where iconic flavors like Chicago Pizza, Hot Dogs, Italian Beef, Chicago-mix Popcorn, and the original Brownie await. Opt for the VIP Craft Beer package for a heightened experience. Beyond bites, our expert-guided tour explores Millennium Park, the Chicago Riverwalk, Michigan Avenue, Cloud Gate, Chicago Theater, and more. Enjoy a 5-hour walking tour and receive a bonus 2-hour FREE bike or kayak rental, adding value to your experience. Maximize your day by biking along the scenic Lakefront Trail or kayaking on Lake Michigan. Leave the planning to the local experts. Bobby’s Bike Hike was awarded the following three awards just this year: “Top 10 Food Tours in America” by USA Today, “Top 20 Food Tours in the World” by TripAdvisor, and “Top 15 Vacation Ideas in USA” by Entrepreneur Magazine. Seize the opportunity for the ultimate Chicago fusion of flavors and sights in a single, unforgettable day!
Duration: 5 hours.

Discover a new side of Chicago with Insta Walk! I offer stylish photos, cool angles, and creative ideas during our relaxed and friendly stroll.

I'll use both iPhone and Polaroid cameras to capture your best shots. You'll get about 50 digital photos, with 5 of them color-corrected for a pop of vibrancy. Plus, you'll take home 5 Polaroid prints for a unique and timeless memento.
Duration: 30 to 40 minutes.

The perfect tour for first timers to Chicago or those who want to explore Chicago's top attractions and highlights. Stroll through the beautiful streets of downtown Chicago and learn about the City’s rich history, colorful characters, and get insider tips. Enjoy a 2hr walking tour & receive a bonus FREE 2hr bike or kayak rental, adding value to your experience. Enjoy biking along the scenic Lakefront Trail or kayaking on Lake Michigan. Bobby's Bike Hike walking tours have been recognized nationally by National Geographic, USA Today, and Conde Nast Magazine. Explore the amazing sites that Chicago made famous; Millennium Park, Chicago Riverwalk, amazing Architecture of the Wrigley Building and Chicago Theater, & Michigan Avenue dubbed ‘the Magnificent Mile’ for it’s world-renowned shopping. Bobby’s local expert guides lead you through downtown Chicago’s most iconic landmarks and share their knowledge about the City along the way. The tour covers 1.5 miles(2.25km) on easy, flat terrain.

Duration: 2 hours.

Take a spin through the Windy City on a bike tour and discover the most remarkable and world-famous sights. Hit the streets like a local with your guide, dive into the bustling life of the business districts, be welcomed by the soothing green of the parks, and admire the lake scenery as you ride along the shore.
The city boasts plenty of attractions and landmarks to discover, so the bike is a perfect way to save time to get there.

Visit the most important landmarks of the city following your guide. Enjoy a safe bike trip around the city and get experience mainstream tours can’t offer. Be entertained with historical and cultural insights from your guide. The tour is great for families
Duration: 3 hours.

Our Chicago Walking Instagram Tour will take you to the most Instagrammable spots in Chicago all in one day. If you are looking for a little bit of culture, some amazing architecture, & a ton of great photos then this is the tour for you.
The morning will start with meeting with your friendly local guide at the meeting point. From there your tour will begin as you start your day walking throughout Chicago and exploring the most famous locations in the city.
This half-day tour will be fully packed with famous landmarks, vintage architecture, secretly located spots and much much more!
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Full schedule
10:00 AM- Meet your Guide at the Grand Subway Station
10:10 AM- Walk along Magnificent Mile
10:20 AM- Stop at Wrigley Building & admire Tribune Tower
10:50 AM- Explore Pioneer Court
11:20 AM- Explore Millennium Park & see Cloud Gate
11:55 AM- Check out an Iconic fountain
12:20 AM- Chicago Riverwalk
1:00 PM- Explore Navy Pier
2:00 PM- Get dropped off by your guide at Millennium station
Duration: 4 hours.

Are you looking for a way to see Chicago without joining a tour group? Explore at your own pace with this affordable walking tour.

• Take in Chicago’s concrete giants and hear fascinating stories about quirky artworks, local tragedy, and the city’s journey to revitalisation
• Hear from producer Phil Biedron, an actor and tour guide whose passion for storytelling lead him to create this VoiceMap tour
• Do it all in two hours or linger at stops along the way with complete control over when you start and finish
• Get unlimited use before your booking date and after it
• Use the virtual tour option at home

Once you’ve booked, you’ll receive a ticket with instructions and a unique code listed under “Before You Go”. Then simply install the VoiceMap app and enter your code.

The app displays directions to the starting point, and when you’re in the right place, just pop in your headphones and tap start. VoiceMap has automatic GPS playback, with turn-by-turn directions. It also works offline.
Duration: 120 to 150 minutes.

In this photoshoot you will have most iconic and important places in downtown Chicago, places where you need to have a photo with , and in a unique way with your own personal photographer.
We will have the most photogenic and beautiful places in millenium park like the pavilion, the cloud gate, also known like “the bean”, one of the bridges with skylines view, as well as the famous chicago sign, in Chicago theater, and we will ended in the vibrant river walk.
I will make you feel like a super model, and realy confident in front of the camera and you will take home amazing edited memories of your trip (50+ edited photos )
Duration: 1 hour.

Enjoy this 2 hour walking tour around Chicago, a city full of art and unique buildings. Discover why there is a sculpture by Picasso or why there is a flamingo in the middle of the city.

Get to know a city full of history and stories behind its skyscrapers.
Also, here you can find the start of a famous route, do you want to know which one?

Duration: 2 hours.

Chicago has long been the culinary and cultural capital of the United States. Visitors come to Chicago to enjoy the city's delicacies, while chefs come to establish culinary empires and legacies. Come join us and experience some of the Windy City's tastiest offerings.
Duration: 2 hours 45 minutes.

If you're looking for an exciting and stress-free day exploring the wonders of Chicago, then this is the tour for you. We can’t wait to show you around!

The morning will start with a private pickup from your hotel by one of our friendly, local guides. From there your tour will begin as you start your drive in one of our comfortable and spacious vehicles.

This full-day tour will be fully packed with famous landmarks, vintage architecture, secret spots and much much more!
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Full schedule
10:00 AM – Pick up from Hotel
10:15 AM – Check out Buckingham Fountain
10:45 AM – Arrive at Michigan Avenue Bridge
11:15 AM – Awe at the Chicago Cultural Center
12:15 PM – See Cloud Gate and explore Millennium park
1:00 PM – Lunch time
2:00 PM – Go to Chicago Theater
2:30 PM – See Garfield Park Conservatory
3:00 PM – Check out the Greetings from Chicago mural
3:30 PM – Snap a cool pic outside of Wrigley Field
3:45 PM – Return to hotel
4:00 PM – Arrive at hotel
Duration: 6 hours.