Top Chicago Art & Culture - page 3

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Take in views of the Chicago skyline and its landmarks during this Lake Michigan sightseeing boat cruise. Enjoy a laidback ride, soaking up panoramic views from this unique perspective. Listen to audio commentary to give you fresh insight into the landmarks you see, like Navy Pier and the Willis Tower, and feel free to bring your own lunch or grab a drink at the onboard bar (own expense).

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Lake Michigan Skyline Cruise in Chicago

30 to 45 minutesFree Cancellation

4.4

(928)

from $33

Immerse yourself in the pizza culture of Chicago on this hearty lunch tour. Enjoy deep dish—and then go beyond it, with commentary from your food-loving guide and tastes of four different pizza varieties. Learn all about Chicago's history and culinary heritage as you go, and receive an introduction to the city's pizza scene that's more in depth than what other tours offer, with lunch included.

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Chicago West Loop Pizza Crawl

3 hours

5.0

(8)

from $79

Likely to Sell Out

Lake Michigan Fireworks Cruise in Chicago

2 to 3 hours

4.2

(130)

from $55

Total Chicago: From Architecture to Food

Experience Chicago like a true insider on this top-rated walking tour that blends the city’s most iconic food, awe-inspiring architecture, and rich history — all in one unforgettable day. From deep-dish pizza to legendary skyscrapers, you’ll taste, see, and learn what makes the Windy City a world-class destination. Led by expert local guides and limited to just 12 guests, this immersive, small-group tour is the perfect way to discover the real Chicago — not just the tourist spots.

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Chicago in a Day Walking Tour: Food, History & Architecture

4 hours 30 minutesFree Cancellation

4.9

(1,293)

from $101

Price varies by group size

Chicago Walking Tour: Art Deco Skyscrapers Loop

Admire the ornamental facades and intricate interiors of the Windy City's art deco buildings during this in-depth walking tour of the vibrant Loop. This small-group tour will introduce you to some of the city's highlight architectural landmarks and its rich history, all in a single excursion. As you go, get an up-close look at landmarks that many other tours overlook—and learn insider stories from your architecture-expert guide.

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Chicago Walking Tour: Art Deco Skyscrapers Loop

1 hour 30 minutesFree Cancellation

4.8

(186)

from $35

Likely to Sell Out

Get to know the Windy City the easy and comfortable way on a small-group minibus tour. Instead of long walks and navigating public transit, see major landmarks like Museum Campus, Buckingham Fountain, the Magnificent Mile, and Millennium Park from an uncrowded minibus with large picture windows. Your driver and guide knows where to find all the best views, and there are plenty of photo stops along the way.

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Chicago City Minibus Tour

2 hoursFree Cancellation

4.9

(607)

from $50

Likely to Sell Out

Experience Chicago in Style with Our Luxury City Sightseeing Minibus Tour. Indulge in the ultimate Chicago adventure on our top-rated, luxury sightseeing minibus tour. This 2-hour, expertly guided experience takes you through the vibrant heart of the city in a sleek, climate-controlled minibus designed for comfort and class. Marvel at iconic skyline views and the shimmering waters of Lake Michigan from panoramic windows, and enjoy curated photo stops at the city's most breathtaking landmarks. With engaging stories from your private guide and an intimate, upscale atmosphere, this tour offers an unmatched blend of elegance and exploration. Please note, infants 0-3 years old must sit on a lap.

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Luxury Minibus Chicago City Tour

2 hoursFree Cancellation

4.9

(8)

from $65

Likely to Sell Out

Taste deep-dish pizza, a Chicago-style hot dog, Italian beef, Garrett’s popcorn & the original 1893 brownie on our top-rated Chicago Food Tours—the ultimate Chicago Culinary Tour experience!

Eat your way through downtown Chicago on a walking food tour. Visit Millennium Park, the Palmer House Hotel, and other city landmarks and taste quintessential Chicago foods such as deep-dish pizza, hot dogs, and chocolate brownies. All food tastings are included, and the tour covers an easy 1.5 miles (2.4 km) suitable for most fitness levels. A bike or kayak rental is also included in the tour cost.

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Chicago Favorites Ultimate Food and Walking Tour

3 hoursFree Cancellation

4.9

(2,166)

from $85

Likely to Sell Out

The Chicago River, as seen from our stop on wacky Wacker Drive

Skip navigating around the city with a map and guidebook and explore Chicago's iconic landmarks in just a few hours on this sightseeing tour led by an expert guide. Board a comfortable, large-windowed minibus and explore Downtown and North Side neighborhoods, stopping to visit several locations and hear about the historical and cultural factors that make Chicago unique. Upgrade your tour with a popular open-top boat tour on the Chicago River that focuses on the city's renowned architecture.

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Chicago City Tour with Architecture River Cruise Option

2 to 4 hoursFree Cancellation

4.8

(728)

from $50

American Writers Museum Admission Ticket

Immerse yourself in American literary traditions, and enjoy a wide range of interactive exhibitions, during a visit to Chicago’s one-of-a-kind American Writers Museum. Conveniently located on Michigan Avenue, the museum was established in 2017, and is one of the city’s newest highlight institutions. Guarantee your admission, and prevent any travel hassles, by securing your tickets in advance. Once inside, you’ll have time to explore at your own pace.

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American Writers Museum Admission Ticket

1 to 5 hoursFree Cancellation

4.8

(74)

from $16

Medieval Torture Museum Ticket with Audio Guide and Ghost Hunting

Discover one of the Windy City’s most spooky, gruesome destinations when you book advance tickets to the Medieval Torture Museum. Perfect for Halloween—or any other creepy-crawly occasion—this museum includes a wealth of information about medieval torture practices and devices, plus realistic models to add a macabre edge. Book tickets before you travel for a seamless visiting experience, and make use of an audio guide and included ghost-hunting app.

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Medieval Torture Museum Ticket with Audio Guide and Ghost Hunting

1 hour 30 minutesFree Cancellation

4.9

(1,046)

from $36

2-Hour Chicago's Chinatown History and Culture Tour

Discover the heart of Chicago’s Chinatown with your authentic history and culture tours, exclusively offered by the official Chinatown Visitor Center. Led by experienced local guides, your tours dives deep into the neighborhood’s rich heritage, hidden landmarks, and cultural traditions. Unlike generic tours, we bring you behind the scenes with insider stories, community connections, and exclusive access to local favorites. Experience Chinatown through the eyes of those who know it best. A minimum of 2 participants is required for this experience. If the minimum is not met, the tour may be canceled, and you will receive a full refund.

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2-Hour Chicago's Chinatown History and Culture Tour

2 hoursFree Cancellation

3.8

(5)

from $30

City Cruises Chicago: Premier Lake Michigan Brunch Cruise

Enjoy waterfront views of downtown Chicago on a 2-hour brunch cruise through the heart of the city. Board a luxurious yacht at Navy Pier then relax on deck with a complementary mimosa. Find a comfortable spot on the three climate-controlled observation decks, and enjoy a sumptuous buffet while the onboard DJ spins a leisurely afternoon playlist. Capture unforgettable images of downtown skyscrapers and architectural landmarks as you navigate along the historic shoreline, then loop back and finish your outing at the bustling Navy Pier.

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City Cruises Chicago: Premier Lake Michigan Brunch Cruise

2 hoursFree Cancellation

3.9

(29)

from $105

Smiles ear to ear as you ride our Chicago Bike Tour through scenic Lakefront Neighborhoods. Fresh air, open paths, and lake views make this the ultimate Bicycle Tour in Chicago.

On this small-group Windy City bike tour, you won't just pedal past the lakefront neighborhoods of Chicago's North Side—you'll see more of the city than you could if exploring on your own. Follow a local guide along quiet streets, city parks, and scenic beaches, starting at Lake Shore Drive and continuing along Rush Street and the Magnificent Mile. As you go, glimpse offbeat attractions like the Playboy Mansion, Oprah’s penthouse, and the Victorian houses of Old Town.

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Bike Tour of Chicago's Lakefront Neighborhoods

3 hoursFree Cancellation

4.9

(250)

from $59

Likely to Sell Out

Offbeat Street Art Tour of Chicago: Urban Graffiti, Art, and Murals

Discover a side of the Windy City that many visitors overlook—and immerse yourself in its vibrant street art scene—on this urban walking tour. With your art-expert guide in the lead, you can focus on soaking up the city's ambiance, and spotting artworks and murals you may not have discovered on your own. As you go, listen to in-depth commentary about the artists and artworks, and explore some of the city's hippest neighborhoods.

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Offbeat Street Art Tour of Chicago: Urban Graffiti, Art, and Murals

2 hoursFree Cancellation

4.9

(205)

from $40

From deep-dish to hot dogs, taste Chicago Classic Dishes on our Chicago Food & Bike Tour. Ride by Bicycle, learn the stories, and savor every stop on the best Food & Bike Tour in Chicago.

Chicago dogs, deep-dish pizza, brownies, and craft beer are all sampled on this half-day bike tour through the Windy City. Cover about 13 miles (21 km), following your guide at a moderate pace through Chicago neighborhoods. On the day tour, ride through Wrigleyville, Old Town, Lincoln Park, and Gold Coast. On the night tour, visit Chicago’s Riverwalk, Millennium Park, Buckingham Fountain and the Lakefront Trail. As you go, stop for generous food and beer tasters.

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Chicago Bike & Classic Food Tour: Bikes, Bites & Views - Adults

4 hours 30 minutesFree Cancellation

4.9

(754)

from $89

Tourgoers in front of the Marshall Field Mansion

Considered Chicago’s original “Millionaire’s Row,” Prairie Avenue in the Near South Side is renowned for its Gilded Age mansions—and this tour makes exploring easy (and delightfully spooky). In the evening, meet your guide in front of the Glessner House, and set off with ghost-hunting gear to accompany you. In between spotting highlights including the Marshall Field Jr. Mansion and the Henry B. Clarke House, you’ll hunt for specters and hear ghost stories.

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Prairie Avenue Haunted History Tour and Ghost Hunt

2 hours 20 minutes

5.0

(12)

from $40

Discover Chicago architectural treasures—and immerse yourself in the Windy City's history—on this small-group walking tour. Your focus is the iconic stained glass pieces crafted and designed by the Tiffany Glass and Decorating Company. Following your guide from the Chicago Architecture Center, visit four late-19th-century landmarks that contain glass works by Louis Comfort Tiffany and his contemporaries. This in-depth, insider tour is a must-do for history and architecture fans.

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Chicago Walking Tour: Tiffany Treasures

1 hour 30 minutesFree Cancellation

4.7

(46)

from $35

Stop off the bus at Chicago Landmark Building with Prohibition Era History

Chicago Night Crimes Tour by Bus

2 hours to 2 hours 30 minutesFree Cancellation

4.8

(501)

from $55

Private 45-Minute Chicago Skyline Helicopter Tour

Take in sweeping views of Chicago from the air during a scenic helicopter flight that offers a premier experience of the Windy City. This private 45-minute flight provides an aerial look at landmarks such as Millennium Park, Navy Park, and Wrigley Field. Ideal for a special occasion, this helicopter tour accommodates up to three people and includes the use of noise-cancelling headsets to hear the pilot clearly.

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Private 45-Minute Chicago Skyline Helicopter Tour

45 minutesFree Cancellation

4.8

(129)

from $849

Per group

Travel through architectural history on this express, small-group walking tour, which covers Chicago's most famous buildings in chronological order (and which is speedy enough to cater to the most time-pressed travelers). With a guide in the lead, there's no need to fuss over maps or worry about directions. Simply stroll along and listen to the in-depth commentary on Chicago's architectural history; you'll learn about each building, and will have plenty of chances to stop for photos.

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Chicago Walking Tour: A Walk Through Time

1 hour 30 minutesFree Cancellation

4.9

(220)

from $35

Feel the presence of the unseen as we wander through haunted history under the moon's glow.

Discover some of the Windy City’s spookiest ghost stories—and step back in time to the era of gangsters, bootleggers, jazz performers, and more—on this small-group walking tour. Meet your guide in Chicago’s Lincoln Park neighborhood, and set off after dark. You’ll visit supposedly haunted former burial grounds, pubs, theaters, and more—and will hear about macabre legends and unexplained happenings as you go.

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Embers of the Windy City: Chilling Chicago Ghost Tours

1 hourFree Cancellation

4.4

(121)

from $26

Private Arrival Transfer from Chicago Airports (ORD) (MDW)

Ensure a hassle-free arrival at Chicago O'Hare International Airport (ORD) or Midway Airport (MDW) with this private transfer service to your downtown Chicago hotel (or farther-flung Chicagoland destination). Take the stress out of finding a taxi at Chicago's busy airports and book a private vehicle in advance. Travel in style by luxury sedan or SUV that can accommodate up to six passengers.

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Private Arrival Transfer from Chicago Airports (ORD) (MDW)

1 hourFree Cancellation

3.7

(201)

from $90

Per group

Lakefront Segway Tour in Chicago

1 hour 30 minutesFree Cancellation

4.6

(146)

from $70

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Top Chicago Art & Culture - page 3

200+ results

Top Attractions in Chicago

Art Institute of Chicago

Chicago Theatre

Skydeck Chicago at Willis Tower (Sears Tower)

Chicago River

Chicago Riverwalk

The Magnificent Mile

Art Institute of Chicago

Chicago Theatre

Skydeck Chicago at Willis Tower (Sears Tower)

Chicago River

Chicago Riverwalk

The Magnificent Mile

Art Institute of Chicago

Chicago Theatre

Skydeck Chicago at Willis Tower (Sears Tower)

Chicago River

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