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Chicago, United States

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Popular Chicago tours & activities

discover Chicago with one of these popular guided tours

Chicago River 90 Minute Architecture Tour (opens in a new tab)

11,318 1 h 30 min

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.

from$45

Chicago Architecture River Cruise (opens in a new tab)

17,212 1 h – 1 h 15 min

Experience the stunning beauty of Chicago on a captivating cruise along the historic Chicago River. This architectural tour takes you down the main branch of the river, up the north branch to the East Bank Club, and then south past the iconic Willis Tower (Sears Tower) to the historic Old Post Office Building. Marvel at the magnificent city skyline as you pass by over 40 notable buildings, including: John Hancock Center: An iconic skyscraper that defines the Chicago skyline. Wrigley Building: Known for its distinctive white facade and clock tower. As you sail, an expert architecture guide will provide fascinating insights into the distinctive designs and history of these architectural marvels. Whether you're a local or visiting for the first time, this tour offers a unique perspective on one of the world's most beautiful cities. Sit back, relax, and let the architectural wonders of Chicago unfold before your eyes.

from$39

Chicago River 45-Minute Architecture Tour from Magnificent Mile (opens in a new tab)

3,780 45 min

Experience Chicago's legendary architecture and the exceptional architects who created this ever-changing legacy for all to admire. This family-friendly introduction to the Windy City's rich history and architectural heritage features highlights from Wendella's full-length architecture tours. Hop aboard our world class vessels as our local authentic tour guides showcase our amazing city.

from$28

Chicago Architecture Center River Cruise aboard First Lady (opens in a new tab)

7,643 1 h 30 min

The Chicago Architecture Center River Cruise aboard Chicago's First Lady has long been the gold standard among all Chicago tour experiences, and is the only Chicago architecture boat tour led by highly trained expert docents. On this 90-minute cruise, you will enjoy an overview of historic and modern architectural styles including stories about the people who designed and built Chicago. As a certified nonprofit, all ticket purchases directly support education efforts and community engagement projects. No visit to Chicago is complete without experiencing this award winning tour, so accept no substitutes.

from$57

Flyover in Chicago (opens in a new tab)

784 30 min

The Flyover experience takes 30 minutes from beginning to end. First, on-the-ground stories connect you with the spirit of the Windy City. Then, you’ll discover Chicago from a whole new perspective, as Flyover transports you over, around and through remarkable locations. You'll explore in motion with scenes captured by an award-winning creative team using custom-made drones and helicopter-mounted cameras, while scents, sounds and music deepen the immersion. It’ll take your breath away (we promise you’ll get it back).

from$27.95

Prices and availability are confirmed with our booking partner when you book.

Popular Chicago itineraries

discover Chicago with one of these self-guided tours

3 Days in Chicago: Top Attractions

Use this 3-day plan to see Skydeck Chicago at Willis Tower, Art Institute of Chicago, Chicago Architecture River Cruise, Millennium Park and more without rushing.

See Full Itinerary >
4 Days in Chicago: Landmarks & Local Life

Use this 4-day plan to see Skydeck Chicago at Willis Tower, Art Institute of Chicago, Chicago Architecture River Cruise, Millennium Park and more without rushing.

See Full Itinerary >
5 Days in Chicago: Must-Sees & Day Trips

Use this 5-day plan to see Skydeck Chicago at Willis Tower, Art Institute of Chicago, Chicago Architecture River Cruise, Millennium Park and more without rushing.

See Full Itinerary >

Choose your Chicago guide

Tours & sightseeing

Chicago River 90 Minute Architecture Tour (opens in a new tab)

11,318 1 h 30 min

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.

from$45

Chicago Architecture River Cruise (opens in a new tab)

17,212 1 h – 1 h 15 min

Experience the stunning beauty of Chicago on a captivating cruise along the historic Chicago River. This architectural tour takes you down the main branch of the river, up the north branch to the East Bank Club, and then south past the iconic Willis Tower (Sears Tower) to the historic Old Post Office Building. Marvel at the magnificent city skyline as you pass by over 40 notable buildings, including: John Hancock Center: An iconic skyscraper that defines the Chicago skyline. Wrigley Building: Known for its distinctive white facade and clock tower. As you sail, an expert architecture guide will provide fascinating insights into the distinctive designs and history of these architectural marvels. Whether you're a local or visiting for the first time, this tour offers a unique perspective on one of the world's most beautiful cities. Sit back, relax, and let the architectural wonders of Chicago unfold before your eyes.

from$39

Chicago River 45-Minute Architecture Tour from Magnificent Mile (opens in a new tab)

3,780 45 min

Experience Chicago's legendary architecture and the exceptional architects who created this ever-changing legacy for all to admire. This family-friendly introduction to the Windy City's rich history and architectural heritage features highlights from Wendella's full-length architecture tours. Hop aboard our world class vessels as our local authentic tour guides showcase our amazing city.

from$28

Chicago Architecture Center River Cruise aboard First Lady (opens in a new tab)

7,643 1 h 30 min

The Chicago Architecture Center River Cruise aboard Chicago's First Lady has long been the gold standard among all Chicago tour experiences, and is the only Chicago architecture boat tour led by highly trained expert docents. On this 90-minute cruise, you will enjoy an overview of historic and modern architectural styles including stories about the people who designed and built Chicago. As a certified nonprofit, all ticket purchases directly support education efforts and community engagement projects. No visit to Chicago is complete without experiencing this award winning tour, so accept no substitutes.

from$57

Flyover in Chicago (opens in a new tab)

784 30 min

The Flyover experience takes 30 minutes from beginning to end. First, on-the-ground stories connect you with the spirit of the Windy City. Then, you’ll discover Chicago from a whole new perspective, as Flyover transports you over, around and through remarkable locations. You'll explore in motion with scenes captured by an award-winning creative team using custom-made drones and helicopter-mounted cameras, while scents, sounds and music deepen the immersion. It’ll take your breath away (we promise you’ll get it back).

from$27.95

Prices and availability are confirmed with our booking partner when you book.

Chicago top attractions & all things to do

make the most out of your time in Chicago

Things to do in Chicago

Chicago travel tips

learn more about Chicago

Budget & costs

Chicago is moderate to expensive, but many attractions have free options.

Read More >>

Getting around

The 'L' trains and buses are efficient.

Read More >>

Safety & scams

Central Chicago is generally safe; use normal city precautions.

Read More >>

Best time to visit

May to October for warm weather, festivals and lakefront activity.

Read More >>

3 days Chicago top attractions

see the best of Chicago

Day 1

  1. 09:00Skydeck Chicago at Willis TowerVisibility is best on clear days; book an early morning or late afternoon slot.
  2. 12:30LunchWalk a couple of streets away from the main sight – prices drop and quality rises.
  3. 14:00Art Institute of ChicagoAllow three hours. Free-entry days for residents are crowded.About 12 min on foot
  4. 19:00Chicago Architecture River CruiseDaytime departures give the clearest views. Book ahead for summer afternoons.About 17 min on foot
SEE FULL ITINERARY >>

Cultural & theme tours

Chicago River 90 Minute Architecture Tour (opens in a new tab)

11,318 1 h 30 min

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.

from$45

Chicago Architecture River Cruise (opens in a new tab)

17,212 1 h – 1 h 15 min

Experience the stunning beauty of Chicago on a captivating cruise along the historic Chicago River. This architectural tour takes you down the main branch of the river, up the north branch to the East Bank Club, and then south past the iconic Willis Tower (Sears Tower) to the historic Old Post Office Building. Marvel at the magnificent city skyline as you pass by over 40 notable buildings, including: John Hancock Center: An iconic skyscraper that defines the Chicago skyline. Wrigley Building: Known for its distinctive white facade and clock tower. As you sail, an expert architecture guide will provide fascinating insights into the distinctive designs and history of these architectural marvels. Whether you're a local or visiting for the first time, this tour offers a unique perspective on one of the world's most beautiful cities. Sit back, relax, and let the architectural wonders of Chicago unfold before your eyes.

from$39

Chicago River 45-Minute Architecture Tour from Magnificent Mile (opens in a new tab)

3,780 45 min

Experience Chicago's legendary architecture and the exceptional architects who created this ever-changing legacy for all to admire. This family-friendly introduction to the Windy City's rich history and architectural heritage features highlights from Wendella's full-length architecture tours. Hop aboard our world class vessels as our local authentic tour guides showcase our amazing city.

from$28

Chicago Architecture Center River Cruise aboard First Lady (opens in a new tab)

7,643 1 h 30 min

The Chicago Architecture Center River Cruise aboard Chicago's First Lady has long been the gold standard among all Chicago tour experiences, and is the only Chicago architecture boat tour led by highly trained expert docents. On this 90-minute cruise, you will enjoy an overview of historic and modern architectural styles including stories about the people who designed and built Chicago. As a certified nonprofit, all ticket purchases directly support education efforts and community engagement projects. No visit to Chicago is complete without experiencing this award winning tour, so accept no substitutes.

from$57

Flyover in Chicago (opens in a new tab)

784 30 min

The Flyover experience takes 30 minutes from beginning to end. First, on-the-ground stories connect you with the spirit of the Windy City. Then, you’ll discover Chicago from a whole new perspective, as Flyover transports you over, around and through remarkable locations. You'll explore in motion with scenes captured by an award-winning creative team using custom-made drones and helicopter-mounted cameras, while scents, sounds and music deepen the immersion. It’ll take your breath away (we promise you’ll get it back).

from$27.95

Prices and availability are confirmed with our booking partner when you book.

Walking & biking tours

Chicago River 90 Minute Architecture Tour (opens in a new tab)

11,318 1 h 30 min

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.

from$45

Chicago Architecture River Cruise (opens in a new tab)

17,212 1 h – 1 h 15 min

Experience the stunning beauty of Chicago on a captivating cruise along the historic Chicago River. This architectural tour takes you down the main branch of the river, up the north branch to the East Bank Club, and then south past the iconic Willis Tower (Sears Tower) to the historic Old Post Office Building. Marvel at the magnificent city skyline as you pass by over 40 notable buildings, including: John Hancock Center: An iconic skyscraper that defines the Chicago skyline. Wrigley Building: Known for its distinctive white facade and clock tower. As you sail, an expert architecture guide will provide fascinating insights into the distinctive designs and history of these architectural marvels. Whether you're a local or visiting for the first time, this tour offers a unique perspective on one of the world's most beautiful cities. Sit back, relax, and let the architectural wonders of Chicago unfold before your eyes.

from$39

Chicago River 45-Minute Architecture Tour from Magnificent Mile (opens in a new tab)

3,780 45 min

Experience Chicago's legendary architecture and the exceptional architects who created this ever-changing legacy for all to admire. This family-friendly introduction to the Windy City's rich history and architectural heritage features highlights from Wendella's full-length architecture tours. Hop aboard our world class vessels as our local authentic tour guides showcase our amazing city.

from$28

Chicago Architecture Center River Cruise aboard First Lady (opens in a new tab)

7,643 1 h 30 min

The Chicago Architecture Center River Cruise aboard Chicago's First Lady has long been the gold standard among all Chicago tour experiences, and is the only Chicago architecture boat tour led by highly trained expert docents. On this 90-minute cruise, you will enjoy an overview of historic and modern architectural styles including stories about the people who designed and built Chicago. As a certified nonprofit, all ticket purchases directly support education efforts and community engagement projects. No visit to Chicago is complete without experiencing this award winning tour, so accept no substitutes.

from$57

Flyover in Chicago (opens in a new tab)

784 30 min

The Flyover experience takes 30 minutes from beginning to end. First, on-the-ground stories connect you with the spirit of the Windy City. Then, you’ll discover Chicago from a whole new perspective, as Flyover transports you over, around and through remarkable locations. You'll explore in motion with scenes captured by an award-winning creative team using custom-made drones and helicopter-mounted cameras, while scents, sounds and music deepen the immersion. It’ll take your breath away (we promise you’ll get it back).

from$27.95

Prices and availability are confirmed with our booking partner when you book.

Top-rated Chicago tours

the highest-rated experiences from traveller reviews

Private Sailing on Beautiful Lake Michigan - Navy Pier, Chicago (opens in a new tab)

73 2 h

Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefront. Kick back, relax, and let the US Coast Guard licensed captain treat you to stunning views of Chicago’s spectacular skyline. Make the experience your own. The flexibility of a private charter allows customization of virtually any aspect of the sailing adventure from guest list to music selection to sailing route. Three departure times offered daily. This experience is not meant to be an in-depth guided tour; however, our captain is always happy to point out interesting sights with anecdotes and historical information. Just ask you captain. Looking for a sunset sail, see our other product listing "Come Sailing with us at Navy Pier - Sunset Sail on Lake Michigan". Looking to watch the Navy Pier Fireworks from a private sailing charter, see our other product listing "Come Sailing with us at Navy Pier - Saturday Fireworks Sail". All charters are NON-SMOKING experiences.

from$508

Chicago Walking Tour: Connecting Past and Present (opens in a new tab)

44 1 h 45 min

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.

from$35

Chicago Haunts and Hooligans Tour (opens in a new tab)

42 1 h 30 min

Nightly Spirits’ Haunts and Hooligans Tour will illustrate Chicago’s haunted history of secret parlors, underground tunnels, murderous movie theaters and supernatural speakeasies. Whether you’re a recent transplant to Chicago or have lived among the Windy City’s ‘others’ for years, you’re about to get a haunted history that may leave you with more memories than you dare to retain.   Tours begin at the haunted Harry Caray’s Italian Steakhouse in downtown Chicago. A costumed guide will lead tour goers on a walking journey exploring the creepy past of one of Chicago’s most famous bootleggers, offering glimpses into the past and revealing the stories of long-dead phantoms and specters who still call Chicago home.

from$34.77

Chicago Shoreline Adventure Boat Tour (opens in a new tab)

40 1 h 30 min

This tour is the perfect way to experience the shoreline of Chicago in a new and exciting way! Our tour vessel is a former military Williard Marine, which provides a unique and interesting touch to the normal tour experience. Being both sturdy in the water, and fast! Reaching up to speeds of 35 Knots! We work hard to provide historical context for our great city, as well as provide an exhilarating experience through the use of high speed runs and spins!

from$90

Chicago Photo Walk to Bean and Landmarks (opens in a new tab)

32 1 h

We’ll begin our photo walk in Millennium Park with portraits at Cloud Gate (The Bean), one of Chicago’s most iconic landmarks. During our time together, we’ll visit a rooftop spot for skyline views, cross the scenic DuSable Bridge, and stop by the elegant Wrigley Building - all perfect for beautiful photos. Along the way, I’ll guide you with natural poses and creative ideas, helping you feel relaxed and confident. By the end of this walk, you’ll not only have a beautiful photo gallery - you’ll have also visited many of the MUST-SEE places in downtown Chicago.

from$169

Prices and availability are confirmed with our booking partner when you book.

Chicago day trips & excursions

Chicago-Milwaukee Small Group Tour (opens in a new tab)

6 h – 7 h

Discover the charm of Milwaukee on a small group day trip from Chicago! Enjoy a guided city tour, explore iconic landmarks, and experience the legendary Miller Brewery with exclusive behind-the-scenes access and tastings. With comfortable transport, expert local insights, and a friendly group atmosphere, this all-inclusive adventure is perfect for curious travelers. Book now for a memorable escape to Milwaukee's culture and flavors!

from$485

Chicago to Milwaukee Day Trip with Brewery Tour & City Highlights (opens in a new tab)

13 8 h – 10 h

Escape Chicago for a day and experience Milwaukee’s culture, food, and legendary beer scene. This curated day trip includes highlights such as the Harley-Davidson Museum, free time at the Milwaukee Public Market, and an optional Miller Brewery tour and tasting. Enjoy scenic views along the lakefront and an outside visit to the Milwaukee Art Museum before returning to Chicago. Ideal for travelers looking for a relaxed, well-rounded introduction to Milwaukee.

from$125

Chicago City's Iconic Sights and Suburb Gems Tour (opens in a new tab)

5 h – 10 h

This tour offers a refreshing blend of Chicago’s iconic sights and hidden suburban gems, giving travelers a unique perspective on the city's diverse culture, history, and architecture. Start by marveling at Chicago’s world-renowned skyline, exploring its legendary landmarks, and soaking in the vibrant energy of the city. Then, step beyond the usual tourist path to uncover the hidden treasures nestled in the suburbs. Discover the BAPS Shri Swaminarayan Mandir, an architectural masterpiece showcasing intricate carvings and spiritual serenity; visit the quirky Leaning Tower of Niles, a charming replica of Italy’s famous landmark; experience the awe-inspiring Bahá’í House of Worship, known for its breathtaking design and peaceful ambiance; and stroll through Westfield Old Orchard, a stylish open-air shopping destination offering a blend of modern luxury and relaxed charm. This thoughtfully curated journey bridges the gap between city excitement and suburban surprises. Ready to explore?

from$299

Chicago to Mackinac Island Scenic Tour (opens in a new tab)

16 h – 17 h

Explore the charm of Mackinac Island on this delightful journey from Chicago. Experience a blend of history, culture, and stunning landscapes as you travel through the Great Lakes region. Discover the island's unique features, where cars are absent, allowing horse-drawn carriages to roam freely among Victorian architecture and beautiful scenery. Enjoy iconic sites like Fort Mackinac and Arch Rock while wandering through quaint downtown shops and savoring famous fudge. This tour is designed for families, couples, and solo travelers looking for a serene getaway filled with natural beauty and cultural richness. - Scenic travel through the picturesque Great Lakes region - Discover Mackinac Island's charm without car traffic - Visit Fort Mackinac, Arch Rock, and local boutiques - Ideal for families, couples, and solo adventurers seeking relaxation

from$685

Chicago VIP Private Tour (opens in a new tab)

2 h – 7 h

Discover the very best of New York City in one unforgettable experience! From the majestic Statue of Liberty and the historic Brooklyn Bridge to famous neighborhoods, hidden gems, and picture-perfect skyline views — this tour captures it all. Enjoy guided stops at iconic landmarks, learn fascinating stories from your local guide, and experience the true energy of the city that never sleeps. Perfect for first-time visitors or anyone wanting to see it all, this experience blends history, culture, and unbeatable photo ops at every turn. Come ready to explore, snap amazing pictures, and make lasting memories on the ultimate NYC adventure!

from$499

Prices and availability are confirmed with our booking partner when you book.

Food, wine & nightlife in Chicago

Chicago Favorites Ultimate Food and Walking Tour (opens in a new tab)

2,405 3 h

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!

from$84.99

Museum of Ice Cream Chicago Admission Ticket (opens in a new tab)

478 1 h 30 min

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.

from$43

City Cruises Chicago: Premier Plus Brunch Cruise on Chicago River (opens in a new tab)

89 2 h

Sail along the magnificent skyline on our Premier Plus Chicago Brunch Cruise. A chef-curated menu of plated brunch specials will delight your palate while unparalleled panoramas of the city’s iconic architecture are marveled at from our glass-enclosed vessel. Enjoy the awe-inspiring views of landmarks such as the Willis Tower, Navy Pier, and the Old Chicago Post Office in the comfortable interior or from the open-air spaces. This upscale experience on the Chicago River is complete with bottomless mimosas and a fully stocked cash bar, light architectural narration, masterful DJ entertainment, and exceptional service. Elevate your weekend with an unforgettable afternoon brunch cruise against a backdrop of Chicago’s most spectacular scenery.

from$111

Chicago's Chinatown Food and Walking Tour (opens in a new tab)

851 3 h

Chicago's Chinatown: Few neighborhoods in America combine such delicious cuisine with fascinating history. Join Bobby’s Bike Hike & Food Tours, whose food tours have ranked Top 10 in America by USA Today & Top 20 in the world by Tripadvisor, for a day of interesting stories and scrumptious eats on this delicious Food Tour in Chinatown. This 3-hour Walking and Chintown Food Tour, you’ll see the bustling Chinatown Square, then get to sampling some of the richest cuisine around; including Cantonese dim sum, Portuguese-Chinese bakery treats, Szechuan style, and even Xi'an cuisine, all while learning about the history of how these foods & culture arrived in Chicago. This is a totally unique culinary tour experience, and not to be missed! Upon arrival to the tour, you can add a VIP Drink option for alcoholic and ethnic drink pairings! Chinatown can be challenging to navigate on your own, so let our expert local guides show you the way & discover 5 of our all-time favorite dishes.

from$79.99

Chicago: Gangsters and Food Tasting Walking Tour (opens in a new tab)

49 2 h

Taste some of Chicago's most iconic foods while walking through one of the Prohibition Era’s most fashionable and notorious neighborhoods. Learn about Chicago's world-famous cuisine and the gangsters who ate it all in one special unique tour! Sample Chicago’s deep dish – as well as prime steak and the world famous “Chicago hot dog" all while treading the streets of Capone’s closest friends and dreaded enemies. Highlights include a visit to an old tunnel used by prohibition gangsters in the basement of one of the establishments; a mansion once used as a brothel for gangsters; the Cathedral where gangsters were gunned down by Capone’s men; and a restaurant owned by the man who brought down what was left of the Chicago mafia in the early 2000’s. Gluten-free/vegan/vegetarian options are available (please reach out prior to the tour to inform us of any dietary requirements.)

from$79.99

Prices and availability are confirmed with our booking partner when you book.

Cruises & water tours in Chicago

Chicago River 90 Minute Architecture Tour (opens in a new tab)

11,318 1 h 30 min

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.

from$45

Chicago Architecture River Cruise (opens in a new tab)

17,212 1 h – 1 h 15 min

Experience the stunning beauty of Chicago on a captivating cruise along the historic Chicago River. This architectural tour takes you down the main branch of the river, up the north branch to the East Bank Club, and then south past the iconic Willis Tower (Sears Tower) to the historic Old Post Office Building. Marvel at the magnificent city skyline as you pass by over 40 notable buildings, including: John Hancock Center: An iconic skyscraper that defines the Chicago skyline. Wrigley Building: Known for its distinctive white facade and clock tower. As you sail, an expert architecture guide will provide fascinating insights into the distinctive designs and history of these architectural marvels. Whether you're a local or visiting for the first time, this tour offers a unique perspective on one of the world's most beautiful cities. Sit back, relax, and let the architectural wonders of Chicago unfold before your eyes.

from$39

Chicago River 45-Minute Architecture Tour from Magnificent Mile (opens in a new tab)

3,780 45 min

Experience Chicago's legendary architecture and the exceptional architects who created this ever-changing legacy for all to admire. This family-friendly introduction to the Windy City's rich history and architectural heritage features highlights from Wendella's full-length architecture tours. Hop aboard our world class vessels as our local authentic tour guides showcase our amazing city.

from$28

Chicago Architecture Center River Cruise aboard First Lady (opens in a new tab)

7,643 1 h 30 min

The Chicago Architecture Center River Cruise aboard Chicago's First Lady has long been the gold standard among all Chicago tour experiences, and is the only Chicago architecture boat tour led by highly trained expert docents. On this 90-minute cruise, you will enjoy an overview of historic and modern architectural styles including stories about the people who designed and built Chicago. As a certified nonprofit, all ticket purchases directly support education efforts and community engagement projects. No visit to Chicago is complete without experiencing this award winning tour, so accept no substitutes.

from$57

Chicago By Night River and Lake Cruise (opens in a new tab)

468 1 h 30 min

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!

from$50

Prices and availability are confirmed with our booking partner when you book.

Tickets & passes for Chicago

Flyover in Chicago (opens in a new tab)

784 30 min

The Flyover experience takes 30 minutes from beginning to end. First, on-the-ground stories connect you with the spirit of the Windy City. Then, you’ll discover Chicago from a whole new perspective, as Flyover transports you over, around and through remarkable locations. You'll explore in motion with scenes captured by an award-winning creative team using custom-made drones and helicopter-mounted cameras, while scents, sounds and music deepen the immersion. It’ll take your breath away (we promise you’ll get it back).

from$27.95

360 CHICAGO Observation Deck Admission (opens in a new tab)

1,328 1 h – 4 h

The best views of Chicago can be yours at 360 Chicago Observation Deck! Perched 94 stories above the Windy City in the former John Hancock Building, 360 Chicago provides commanding views of Lake Michigan and Chicago’s towering skyscrapers. Located in the heart of downtown on Michigan Avenue, the observatory is steps away from other top Chicago attractions. It will be the high point (literally) of your Chicago trip! Upgrade to the Sip and View ticket, which includes one drink at the newly renovated CloudBar. The Sip menu includes a rotating selection of beer, wine and cocktails. Once onsite, you can purchase tickets to TILT, a thrill ride that offers visitors unique, downward facing views from 1,030 feet. You may also choose to upgrade your Sip and View ticket from the Sip Menu to the Elevated Menu for an additional $8. *TILT not included in purchase

from$27

Skydeck - Willis Tower Admission (opens in a new tab)

1,957 30 min – 1 h 30 min

Gaze upon the city sights from the pinnacle of Chicago, the Skydeck. Located on the 103rd floor of Willis Tower, formerly Sears Tower -- the third-tallest building in the world -- the Skydeck offers spectacular sweeping views and is full of interactive exhibits. To complete your exciting Chicago experience, head to the Ledge, a glass balcony showcasing unbeatable views of Chicago’s top attractions like Wrigley Field and the Navy Pier. We added a brand new Chicago Experience that you start with by the box office prior taking the elevator trip to the 103rd floor. It is a 45,000 sq ft. museum of today. The New Experience is part Chicago History, part Architecural tour, part Selfie Museum and part Children's Museum. This is fun and interactive for all ages. Ride our "L" Train, see our infinity pizza bed, take pictures ontop of Willis Tower and so much more! This is the best way to see Chicago in one setting. With mobile tickets, simply scan your phone for direct entry into the SkyDeck

from$44

Museum of Ice Cream Chicago Admission Ticket (opens in a new tab)

478 1 h 30 min

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.

from$43

Field Museum of Natural History Admission Tickets (opens in a new tab)

602 4 h

Explore over 40 million artifacts, including SUE, the world’s largest, most complete T. rex ever discovered! Discover 23 mummified remains in a recreated Egyptian tomb, our dazzling Gem Hall or journey to the powerful Aztec empire! Meet Maximo our newest titanosaur at over two stories tall! The health of our guests and staff is always our top priority and we welcome you back to safely explore nearly half a million square feet of open gallery space.

from$29

Prices and availability are confirmed with our booking partner when you book.

Shows & concerts in Chicago

Trickery Chicago Magic Show (opens in a new tab)

116 1 h – 2 h

Chicago’s most entertaining magic show! Fun, intimate, sometimes outrageous, and always hilarious. Theater is located at 3453 N Halsted Street (near the SE corner of Cornelia Ave). Door opens 15 minutes before showtime and seating is general admission. Venue is BYOB for guests 21+. Cups and bottle openers are available if needed. We do not stock ice but there is a 7-Eleven just down the street (3407 N Halsted). Performance runs approximately 1 hour.

from$42

The Infinite Wrench: Experimental theater in Chicago (opens in a new tab)

1 1 h 20 min

Every Friday & Saturday at 10:30pm, Sundays at 7:00 at The Neo-Futurist Theater, the Neo-Futurist Ensemble attempts to perform 30 original, handcrafted, radically honest plays in the ever-shrinking span of 60 minutes. Each play offers something different, be it funny, profound, elegant, disgusting, topical, irreverent, terrifying, or musical; all are ORIGINAL, truthful and tackle the here-and-now, inspired by the lived experiences of the performers. With new plays every week, THE INFINITE WRENCH is The Neo-Futurists’ ongoing and ever-changing attempt to shift the conventions of live performance and speak to those unreached or unmoved by traditional theater. Masking is optional on Friday and Saturdays. Masks are required on Sundays.

from$20

Winter Fireworks Cruise (opens in a new tab)

1 1 h

Travel on a piece of history! We travel on the Chicago River seeing the sights after watching the Holiday Fireworks Show. Perfect for Fire enthusiasts, families and everyone in between! Our flagship vessel is a retired Chicago fire boat, the Fred A Busse, Engine 41, which served Chicago from 1937 to 1981. Firefighter patches from around the world and memorabilia from Engine 41's time in service, adorn the walls inside the cabin.

from$44.30

Prices and availability are confirmed with our booking partner when you book.

More ways to book in Chicago

Other tickets and tours for the same sights

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About Chicago

Skyscraper architecture, deep-dish pizza and a lakefront skyline

Chicago is the birthplace of the skyscraper, and the best way to understand it is from the river. Its Loop district packs in landmark towers, great museums and Millennium Park, all on the edge of Lake Michigan.

It is also a food city, famous for deep-dish pizza, Italian beef sandwiches and a serious fine-dining scene, and a music city with blues and jazz clubs on most nights of the week.

Best time
May to October for warm weather, festivals and lakefront activity. Summers are lively; winters are cold and windy but the museums and restaurants are warm.
How long
Three days.
Getting around
The 'L' trains and buses cover the centre and reach both airports. The Loop and the lakefront are easy to walk, and bike shares are popular in summer.

Best time to visit Chicago

The most comfortable months with manageable crowds are Apr, Sep, Oct. These are broad seasonal patterns, not forecasts.

  1. Jan
    Cold
    Crowds: quiet
  2. Feb
    Cold
    Crowds: quiet
  3. Mar
    Cool
    Crowds: busy
  4. Apr
    Mild
    Crowds: busy
  5. May
    Warm
    Crowds: peak
  6. Jun
    Hot
    Crowds: peak
  7. Jul
    Hot
    Crowds: peak
  8. Aug
    Hot
    Crowds: peak
  9. Sep
    Warm
    Crowds: busy
  10. Oct
    Mild
    Crowds: busy
  11. Nov
    Cool
    Crowds: quiet
  12. Dec
    Cold
    Crowds: quiet

Best months Peak crowds and harsh weatherBars show how busy it is: taller means more visitors.

Where to stay & explore in Chicago

The Loop

Downtown, with landmark buildings and Millennium Park.

River North

Restaurants, galleries and the Riverwalk.

Lincoln Park

A leafy neighbourhood with the zoo and lakefront.

Chicago on the map

Chicago travel questions

How many days do I need in Chicago?

Three days cover the architecture cruise, Millennium Park, the Art Institute and a food tour, with room for a baseball game or a show.

Is Chicago-style pizza really different?

Yes. Deep-dish has a tall crust filled with cheese and toppings, with sauce on top, and it takes about 45 minutes to bake.

Is Chicago safe for tourists?

The central areas, the Loop, the Magnificent Mile and the lakefront are well patrolled. Use common sense at night like in any large city.