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Skydeck - Willis Tower Admission

Visit the Skydeck, located on the 103rd floor of the Willis Tower (formerly the Sears Tower), with ease thanks to this prebooked ticket option. Avoid long lines at the ticket office and enter directly to access the highest point in Chicago. Peruse interactive displays and exhibits showcasing Chicago's history. Then walk out on to the Ledge, a glass balcony that offers unimpeded views of Navy Pier and Wrigley Field.

Skydeck - Willis Tower Admission

30 minutes to 1 hour 30 minutesFree Cancellation

Vito's Vault Chicago Speakeasy Dinner Theatre

Vito's Vault Chicago Speakeasy Dinner Theatre

3 hoursFree Cancellation

Price varies by group size

BYOB Spray Paint and Sip at Studio W.I.P.

BYOB Spray Paint and Sip at Studio W.I.P.

1 hour 30 minutesFree Cancellation

Chicago Hop-On Hop-Off Sightseeing Tour by Open-top Bus

Skip the hassle of planning your Chicago itinerary with this convenient hop-on hop-off tour, covering the city's must-see sights. With multiple strategically located stops, explore the Windy City at your own pace, hopping off to visit top attractions like the iconic Art Institute and famous skyscrapers. Enjoy insightful audio commentary as you cruise through the city, learning about its rich history and vibrant culture. Perfect for first-time visitors or those short on time, this tour offers flexibility and ease, ensuring you don’t miss any of Chicago’s highlights. Book your ticket today and experience the best of Chicago hassle-free!

Chicago Hop-On Hop-Off Sightseeing Tour by Open-top Bus

2 hoursFree Cancellation

Likely to Sell Out

This tour cruises the Chicago River and Lake Michigan.

Chicago Lake and River Architecture Tour

1 hour 30 minutesFree Cancellation

Premium Chicago City Tour Small Group ICONIC Landmarks & Skyline

Discover the architectural soul of Chicago on a thoughtfully curated half-day city tour. Travel through the city’s most influential districts, from historic riverfront landmarks to groundbreaking modern skyscrapers. Explore the Loop’s civic, financial, and architectural core, admire world-renowned towers, and experience Chicago’s most celebrated public spaces. This small-group tour offers a comprehensive introduction to Chicago’s skyline, history, and urban design, concluding with a panoramic skyline view before returning guests to the original pickup point. Ideal for first-time visitors and architecture enthusiasts alike. Explore Chicago’s iconic riverfront skyscrapers and historic bridges See legendary architecture including Willis Tower and Marina City Discover the heart of Chicago’s financial, civic, and architectural power Pass by Millennium Park and spend time at Cloud Gate (The Bean) Enjoy a panoramic Chicago skyline view, included for all guests

Premium Chicago City Tour Small Group ICONIC Landmarks & Skyline

3 hoursFree Cancellation

Chicago's Original Gangster Tour by Bus

Book in advance to take this popular tour that details the mob history of Chicago during the Prohibition Era (1920s-1930s). Learn about the exploits of gangsters like Capone, Dillinger, Moran, and others as you travel by minibus to sites like the Biograph Theater, Holy Name Cathedral, and St. Valentine's Day Massacre. Your guide adopts gangster attire and characteristics that add dramatic flair to the historical commentary.

Chicago's Original Gangster Tour by Bus

1 hour 45 minutesFree Cancellation

Likely to Sell Out

Chicago City Minibus Tour

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.

Chicago City Minibus Tour

2 hoursFree Cancellation

Likely to Sell Out

Guide discussing Nighthawks

The Art Institute of Chicago is home to over 300,000 works of art by local and international artists. With so much to explore, it’s easy to get overwhelmed by all of the options during a visit. Sit back and let an expert guide handle the planning as they take you through the museum’s major pieces. Learn about the history and context behind each piece in this culturally enriching experience.

Art Institute of Chicago Private Expert Guided Tour

2 hoursFree Cancellation

Price varies by group size

Chicago Architectural River Cruise

See the towers, piers and iconic landmarks along the Chicago River on an architectural cruise through the heart of the city. Enjoy complimentary refreshments on deck as you cruise down the historic waterway, while listening to fun stories and facts throughout the tour. Spot gargoyles that keep watch high above the city, and buildings that range from Neoclassical to Art Deco. Take in over fifty sites from Lake Point Tower to the Navy Pier, and see the Second City from the water.

Chicago Architectural River Cruise

1 hour 30 minutesFree Cancellation

Chicago Candle Making Class On Magnificent Mile

Chicago Candle Making Class On Magnificent Mile

1 hour 15 minutesFree Cancellation

City Cruises Chicago: River Architectural Lunch Cruise

Get a fresher perspective on the Windy City—and a traffic-free one—with this Chicago River architecture cruise. As you pass by some of Chicago's most notable buildings, you'll dine on a 3-course lunch, listening to onboard narration about the city's architecture and history along the way. Unlike your standard walking tour, you can expect comfort, great food, and endless photo opportunities.

City Cruises Chicago: River Architectural Lunch Cruise

2 hoursFree Cancellation

Likely to Sell Out

Skip the Line Art Institute of Chicago Tour Semi-Private 8ppl Max

Explore one of the country’s great art museums—and discover many of its collection highlights—on this small-group Art Institute of Chicago tour. Meet your guide right out front, and see works from artists the likes of Picasso, Chagall, Seurat, O’Keeffe, and many more. As you go, your guide will share the stories behind the masterpieces, and will help bring the history of the museum and its collection to life.

Skip the Line Art Institute of Chicago Tour Semi-Private 8ppl Max

2 hours 30 minutesFree Cancellation

Price varies by group size

Likely to Sell Out

Chicago Architecture Tour and Speedboat Ride and Lake Michigan

Discover Chicago's world-renowned architecture during this sightseeing cruise. Board a comfortable riverboat for a trip down the Chicago River, viewing landmarks like the Willis Tower and the Tribune Tower while listening to in-depth commentary from your guide. Then board a speedboat for an exciting ride up the shore of Lake Michigan for views of Grant Park, the Museum Campus, and other top sights.

Chicago Seadog River & Lake Architectural Tour

1 hour 15 minutesFree Cancellation

Likely to Sell Out

Amazing skyline and lakefront views await on our Chicago Bike Tour. Experience the city’s beauty up close on a Bicycle Tour in Chicago that blends culture, history, and unforgettable scenery.

Chicago's Ultimate City Bike Tour of Top Downtown Attractions

3 hoursFree Cancellation

Daley Plaza Picasso

Chicago Walking Tour: Must-See Chicago

1 hour 30 minutesFree Cancellation

Chicago Walking Tour: Historic Treasures of Chicago

Get an insider's introduction to Chicago's most celebrated buildings during this architecture-focused walking tour of Michigan Avenue, State Street, and the vibrant Loop area. Revisit the heyday of the skyscraper and visit stunning, art deco-era interiors, from the Palmer House Hotel to the Chicago Cultural Center. Admission to the Chicago Architecture Center is included, with an introduction by the docent.

Chicago Walking Tour: Historic Treasures of Chicago

2 hoursFree Cancellation

Chicago Mobs and Haunts Walking Tour

Chicago Mobs and Haunts Walking Tour

1 hour 30 minutes to 2 hoursFree Cancellation

Chicago CityPASS®

Get the most out of your trip to Chicago as you enjoy discount access to five of the city’s top attractions with the CityPASS®. This easy-to-use mobile ticket grants you free entry into top-tier sights including the Chicago's most famous aquarium and Skydeck Chicago, plus your choice of admission to three of the following attractions: Field Museum, Art Institute of Chicago, Museum of Science and Industry, 360 CHICAGO Observation Deck, Adler Planetarium, or Shoreline Sightseeing Architecture River Tour.

Chicago CityPASS®

See Chicago's magnificent skyline at night!

Discover the beauty of Chicago at night during a 1.5-hour cruise on the Chicago River and Lake Michigan. Watch the city sparkle as you pass landmarks such as Museum Campus, Willis Tower, Aon Center and the John Hancock Building, and the illuminated waters of Buckingham Fountain. You'll learn about the history of the city from live commentary by your knowledgeable guide as you glide along the waterfront of Chicago.

Chicago By Night River and Lake Cruise

1 hour 30 minutesFree Cancellation

360 CHICAGO Observation Deck Admission

Tower above the Windy City’s world-famous skyline with pre-booked admission to 360 Chicago—a great way to avoid long ticket lines. Ascend one of the tallest buildings in North America aboard its lightning-fast elevator, and be rewarded with bird’s-eye views of Chicago and Lake Michigan. You can also upgrade to the Sip and View ticket, which includes one drink at the newly renovated CloudBar. Once onsite, you can purchase tickets to TILT, 360 Chicago's top attraction.

360 CHICAGO Observation Deck Admission

1 to 4 hoursFree Cancellation

Likely to Sell Out

The Chicago Theatre Tour Experience

Enjoy the opportunity to go behind-the-scenes at one of the Windy City's most storied venues on this insider tour of the Chicago Theater. Let your guide lead the way, as you hear about the theater's architecture, history, and famous performers throughout the years. Stand on the famed stage and take in the atmosphere, and see artist signatures from notable performers, including Frank Sinatra and Dolly Parton. A great activity for fans of music and live performance.

The Chicago Theatre Tour Experience

1 hour to 1 hour 15 minutes

Likely to Sell Out

Lake Michigan Sunset Cruise in Chicago

Drink in a one-of-a-kind perspective on the Windy City when you go for an evening cruise, perfectly timed to coincide with the sunset. Hop aboard your open-top vessel (with an enclosed and climate-controlled lounge) in the heart of the Magnificent Mile, and cruise along the Chicago River. Then, see the skyline from a distance, and watch the skyscrapers light up, when you continue to Lake Michigan for a sunset viewing.

Lake Michigan Sunset Cruise in Chicago

1 hour 30 minutesFree Cancellation

Frank Lloyd Wright Robie House Admission

Discover one of Chicago’s top architectural marvels when you explore Frank Lloyd Wright’s UNESCO-listed Frederick C. Robie House, located right on the University of Chicago’s campus. Considered a masterpiece of Prairie School architecture, the building is famed for its cantilevered roof and rich wood details. Save money when you book tickets to the house in advance; call ahead to reserve a space on one of the museum’s frequent, small-group public tours.

Frank Lloyd Wright Robie House Admission

1 hourFree Cancellation

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Top Attractions in Chicago

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The statue of a lion at the entrance to Art Institute of Chicago, USA

Attractions

Art Institute of Chicago

Tour boats running on Chicago River on a sunny day

Attractions

Chicago River

Chicago Navy Pier on the Lake Michigan on a sunny day.

Attractions

Navy Pier

Wrigley Building and Tribune Tower on Michigan Avenue, Chicago.

Attractions

Tribune Tower

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People Also Ask

What are the best art and culture tours in Chicago?

There are plenty of high-quality Chicago art and culture tours to choose from. Looking at ratings and reviews given by previous customers, these are the best tours available right now:

What are the most affordable art and culture tours in Chicago?

Chicago art and culture tour prices vary depending on duration and inclusions. If you're looking for high-quality experiences on the lower end of the price range, these are the best tours to book now:

Are guided art and culture tours in Chicago worth it?

Yes, guided art and culture tours in Chicago are considered worth it by travelers. They provide an engaging way to explore the city's diverse neighborhoods, world-class museums, and iconic architecture with insights from knowledgeable local guides. Whether you're cruising the river, touring the Art Institute, or sampling food in Chinatown, these tours offer a deeper understanding of Chicago's creative and cultural identity.

Per one customer who booked the Chicago in a Day: Food, History & Architecture Walking Tour, "David was an awesome guide of the city. Chicago is an amazing town and we learned so much. The food and architecture is top-notch. We had a great time and our group was fun!"

What should I know before booking art and culture tours in Chicago?

What are the best tips for enjoying art and culture tours in Chicago?

What Chicago art and culture tours are one hour or less?

Even if you're short on time, you can find fun Chicago activities to fit your schedule. Here are some of the best Chicago art and culture tours to enjoy in an hour or less:

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