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Chicago

Chicago, IL, USA

Chicago

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Chicago

Chicago, the Windy City! This vibrant metropolis has it all. Marvel at the stunning architecture, from the magnificent Willis Tower to the iconic Cloud Gate. Get your taste buds tingling with deep-dish pizza and Chicago-style hot dogs. Immerse yourself in the city's rich history at the Art Institute and explore the lively neighborhoods. Prepare to be blown away by the infectious energy of this city that never sleeps!

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Recommendations

Stays

Things To Do
Provided byViator

4.9/5

Chicago Private Custom City Tour with Hotel Pick Up

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.

$539.00
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4.9/5
3 h

Chicago Favorites Ultimate Food and Walking Tour

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 rank Top 20 worldwide on Tripadvisor, offers this ultimate walking & food experience featuring the hard-working, salt-of-the-earth classics Chicago made famous: a slice of deep dish pizza, a Chicago-style hot dog, Italian beef, popcorn & dessert. Expert guides lead you through downtown’s most iconic landmarks on our Day tours—Millennium Park, Chicago Theatre, Riverwalk, Michigan Ave—Night tours go a different route, please check itinerary for details-we share Chicago’s rich, food-loving history. It’s one of the tastiest Things to Do in Chicago! Enjoy your tour & get a BONUS 2-hour FREE bike or kayak rental gift per ticket. Cruise the Lakefront Bike Trail or paddle Lake Michigan for extra fun!

$84.99
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4.6/5

Chicago City Private Tours

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 captures the heart and soul of this incredible city. I’ll also capture professional photos along the way, so you can take home memories of your adventure. With flexible pickup options, including quick tours during layovers at O'Hare, I make it easy to see the best of Chicago, no matter how much time you have. Book your tour today and let me show you the Windy City through the eyes of a local!

$199.00
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4.9/5
3 h 30 mins

Chicago Pizza Tour

Enjoy Chicago’s only bus guided neighborhood pizza tour.  Eat like a local as you travel off the beaten path into Chicago neighborhoods to savor the best pizza.  Your local guide will teach you the science behind ingredient selection and baking as you sample slices from historic pizzerias.  In just a few hours, you’ll leave stuffed, and with an understanding of why pizza is such an important part of Chicago’s culture.

$89.00
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4.5/5
4 h

Chicago Tour South Side

The Blue-Collar side of Chicago many call it! This tour will show The Ford Factory, home of the steel mills, the blue-collar neighborhoods and many places on the South Side, home to the 44th President of The United States, Barack Obama. We tour Bronzeville! A historical African American neighborhood and early business district as well as Hyde Park, home of the World renowned University of Chicago (the spot where the atomic bomb was born and yes we show the spot!) We explore South Lake Drive and life along the lake. Chicago has a border with Indiana, we show how that special dynamic works. We visit Beverly Hills, Chinatown, and the large and highly populated Puerto Rican Neighborhood “Little Village”. We also pass through Pilsen, a proud Mexican community. Cook County jail, we pass by it too! We go thru Little Italy Greektown. It’s blue-collar! We visit a lime quarry in the Bridgeport neighborhood. After this tour you will know tons about The Southside of Chicago.

$125.00
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4.9/5
2 h

Chicago City Minibus Tour

Uncover the Windy City on Chicago’s premier guided minibus tour! Discover 20+ top landmarks with curated photo stops at Cloud Gate ("The Bean"), Museum Campus, and the historic Palmer House. Begin outside the Palmer House, birthplace of the brownie, and see Frank Lloyd Wright’s design at the Rookery. View icons like Willis Tower and Soldier Field while your guide shares local history. Step off at Buckingham Fountain and Museum Campus for skyline panoramas over Lake Michigan and Navy Pier. Pass cultural sights like Shedd Aquarium and the Field Museum. Capture photos beneath "The Bean," see the Chicago River, and drive down Michigan Avenue past the historic Water Tower, Gold Coast brownstones, and Playboy Mansion.

$49.95
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5/5

The Bear Private Pedicab Food Tour of Chicago

If you want culture, history, food, cinema and film and a heavy dose of all things Chicago this is your tour! Get ready to EAT. We are true fans of Chicago, The Bear and good food which is why we start our tour at the world famous Pequod's pizza where a hot pie will be ready waiting for us to pickup and try. Enjoy this in the pedicab as we begin our leisurely ride through the city getting an open air view of some of Chicago's cutest neighborhoods. Next up we go to Margies Candies for a Banana Split before embarking on a ride all the way from the west side to River North, crossing the Chicago River and getting some photos at the iconic LaSalle Flowers. End your epic Chicago adventure at Mr. Beef or Kasama! Your tour vehicle will be a decorated 6 seat pedicab driven by one of our knowledgeable tour guides. Comfortable for up to 4-5 adults, 6 if kids/teenagers are in the mix. Look at the photos of the cab and feel free to reach out with any questions.

$200.00
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3 h

Bike Tour in Chicago

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

$129.00
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2 h

Private Architectural Walking Tour in Chicago Loop Landmarks

Skip the crowds this is a private tour for your group only! Embark on a captivating journey through the Loop’s architectural wonders with our Loop Architecture Tour in Chicago. Explore the iconic Chicago Board of Trade Building and the historic Rookery Building, steeped in timeless elegance. Marvel at the striking Calder sculpture in Federal Plaza, a highlight of the city’s public art scene. Admire the innovative design of the Marquette Building, a masterpiece of the Chicago School of Architecture. Step into the luxurious Palmer House, a landmark boasting historical significance. Discover the rich legacy of the Marshall Field and Company Building, a symbol of Chicago’s commercial prowess. Finally, delve into the cultural richness of the Chicago Cultural Center, showcasing the city’s artistic diversity. Join us on this unforgettable journey through Chicago’s architectural gems in the heart of the Loop.

$869.00
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4.7/5
1 h 30 mins

Chicago River 90 Minute Architecture Tour

Be inspired by the captivating, visual art that is Chicago’s legendary architecture, and the exceptional architects who created this ever-changing, dynamic legacy for all to enjoy and admire. This comprehensive 90 minute tour will navigate through the heart of the city on all three branches of the Chicago River while your professionally-trained architectural guide tells the story of more than 130 years of innovation in design, style and technique and why it is important today. The Chicago River Architecture Tour is the most authentic and encompassing Chicago experience the city has to offer.

$45.00
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4.8/5
3 h

Private Chicago Architecture Walking Tour

Discover the heart of Chicago’s architectural legacy on this guided walking tour through the historic Loop District. Step back in time as you explore some of the world’s first skyscrapers and venture inside a collection of the city’s most influential and iconic buildings. Your expert local guide will share captivating stories about the rise of Chicago, the Great Fire, and the visionary architects whose bold designs shaped the skyline we know today. This tour offers the perfect mix of history, design, and city energy—a must for architecture lovers and curious travelers alike. - Explore the birthplace of the modern skyscraper - Step inside landmark buildings like The Rookery and the Palmer House - Learn about the Great Chicago Fire and its lasting impact on the city - Enjoy a relaxed pace through Chicago’s vibrant downtown Loop

$211.00
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4.9/5
1 h 30 mins

Chicago Walking Tour: Modern Architecture

Looking for iconic Mid-Century Modern architecture? What better place than Chicago with its triumvirate of modern architects (Mies van der Rohe, Bertrand Goldberg and SOM) and a city ready and willing to accept them. Find out what set these buildings apart from their predecessors and how they helped set the stage for the future. If you’re interested in iconic buildings, public art, urban planning or government this is your tour. Find out the stories behind inland steel, Marina city, the IBM building and other "Mad Men" worthy skyscrapers. As a certified nonprofit, all CAC ticket purchases directly support our education efforts and community engagement projects.

$35.00
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4.5/5
1 h 30 mins

Chicago By Night River and Lake Cruise

Glide along the Chicago River and Lakefront as you're dazzled by the sparkle of the city at night! Enjoy breathtaking views of the dramatic skyscrapers and Buckingham Fountain's spectacular light display. Hear lively commentary as you feel the night breeze and see Chicago’s skyline transformed into a glittering jewel. A one-of-a-kind experience to scratch off your Chicago bucket list. Family-friendly cruises are our specialty!

$50.00
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4.4/5

Lake Michigan Skyline Cruise in Chicago

Embark on an unforgettable journey along Lake Michigan and marvel at Chicago's iconic lakefront sights and attractions. Cruise along Lake Michigan and enjoy stunning views of Chicago's renowned skyscrapers from a unique vantage point. This tour offers an amazing opportunity to admire the city's breathtaking skyline and architectural wonders. Sunday – Friday Cruises departing prior to 8:00pm feature recorded narration of the city’s skyline, cruises departing after 8:00pm enjoy some music and the sounds of Lake Michigan aboard our Groove Cruise. November - April 9 tours are 30 minutes. Highlights: Spectacular views of Chicago's famous skyscrapers Onboard bar serving refreshing drinks Relaxing and enjoyable sightseeing cruise Experience Chicago like never before on this serene and scenic Lake Michigan boat tour. Remember to bring your camera to capture those social media worthy photos!

$34.00
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4.9/5
1 h 30 mins

Chicago Sunset Segway Tour

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.

$75.00
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4.5/5
1 h 30 mins

Lake Michigan Sunset Cruise in Chicago

The Lake Michigan Sunset Cruise departs near the DuSable (Michigan Avenue) Bridge on Wendella's world class tour boats. The Cruise will navigate from the Chicago River, through the Chicago Lock and out onto Lake Michigan. Watch the sun slowly set behind the city from the tranquil waters of Lake Michigan on this serene and romantic cruise.

$48.00
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3.4/5
1 h 30 mins

Museum of Ice Cream Chicago Admission Ticket

Step into a world of color, creativity, and sweetness at the Museum of Ice Cream in Chicago! This immersive, Instagram-worthy experience brings together art, interactive exhibits, and, of course, ice cream. Wander through vibrant rooms filled with unique, larger-than-life installations, from sprinkle-filled pools to playful, ice cream-inspired art. Indulge in a variety of delicious ice cream treats throughout the tour, including exclusive flavors that change seasonally. With engaging activities designed to spark joy and creativity, the Museum of Ice Cream is a fun, family-friendly adventure for all ages. Whether you’re a dessert lover, an art enthusiast, or simply looking for a fun outing, this experience promises a memorable, sweet escape. Don't forget your camera – every corner is a photo op! Reserve your spot today for a sugar-filled journey like no other.

$43.00
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4.4/5
216 h

Chicago CityPASS®

Experience 5 top attractions and save up to 50% with Chicago CityPASS® tickets. One simple purchase removes the stress of planning, so you can relax and enjoy your memories in the making. With 9 days to use your tickets, you’ll have plenty of time to explore the best sights. Chicago CityPASS® bundles one-time admission to 5 attractions. Includes: • Chicago's Famous Aquarium • Skydeck Chicago Plus choose 3 more attractions. • Shoreline Sightseeing Architecture River Tour • Field Museum • 360 CHICAGO Observation Deck • Griffin Museum of Science and Industry • Art Institute of Chicago • Adler Planetarium

$144.00
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4.9/5
2 h

Chicago Loop Walking Tour

The Loop is the heartbeat of downtown Chicago! It is filled with great architecture, drop-dead gorgeous interiors and fantastic works of art from famous artists. Along the way, we'll discuss some of the people, and people groups, that have helped to make this one of the "must see" communities, in Chicago!

$60.00
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5/5
2 h

BYOB Chicago River Guided History Tour

Discover the fascinating history of Chicago from a whole new perspective — on the water! This 120-minute Guided History Tour along the Chicago River brings the city’s past to life through captivating stories, iconic landmarks, and little-known facts that shaped the Windy City into what it is today. • Chicago’s transformation from swamp land to industrial hub to the modern metropolis it is today • The dramatic story of the Great Chicago Fire of 1871 and how the city rebuilt stronger than ever • Tales of Chicago’s most infamous gangsters and Prohibition-era legends • The groundbreaking 1893 World’s Fair and the inventions it introduced to the world • The incredible reversal of the Chicago River — its purpose and lasting impact on the city’s future Step aboard and experience how history, architecture, and innovation flow together on this unforgettable journey through Chicago’s past and present.

$65.00
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