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Chicago Culture & history

Our most recommended Chicago Culture & history

Chicago: 1.5-Hour Lake and River Architecture Cruise

1. Chicago: 1.5-Hour Lake and River Architecture Cruise

Experience an architecture cruise along the Chicago River and Lake Michigan, a family tradition since 1935. Admire Chicago’s historic and ever-changing skyline with a local expert guide as you cruise through the city. Choose between the open-air decks or the comfort of the climate-controlled interiors during the cruise. Start the cruise at Michigan Avenue (DuSable) bridge and go up the main branch of the Chicago River to Wolf Point before heading back past the Chicago Riverwalk towards Lake Michigan. Learn about historic skyscrapers like the Wrigley Building and the Tribune Tower, the deco Merchandise Mart, mid-century skyscrapers like the Mies Van der Rohe AMA Building, the circular Marina City Towers, the AON Center, and modernist structures like Aqua, Trump Tower, Nuveen, and the Vista Tower. After passing through the Chicago Lock and cruising past Navy Pier, admire the Chicago skyline from Lake Michigan, one of the largest bodies of fresh water in the world. Here you can also see the twin super-skyscrapers, the famous Willis (formerly Sears) Tower, and the John Hancock Building. See the majesty of Grant Park with its famous Buckingham Fountain, and iconic Chicago venues such as Soldier’s Field, Adler Planetarium, and the Shedd Aquarium. Enjoy several vantage points for memorable pictures throughout, and finally arrive back at Du Sable Bridge on Michigan Avenue.

Chicago: Museum of Ice Cream Entry Ticket

2. Chicago: Museum of Ice Cream Entry Ticket

The world-famous ice cream attraction is now open in Chicago. Step into an ice cream wonderland that is bound to ignite your senses through a theatrical experience with unlimited ice cream treats as you journey through 14 installations. Ride on the pink Sprink-L line, put your golf skills to the test on the Putt-Putt course, or take a dip in a pool filled with millions of sprinkles. Come with an empty stomach and get ready to make unforgettable memories. When you finish your experience, be sure to explore the museum's whimsical shop. The Museum of Ice Cream is not a traditional museum — every installation is interactive. This means touching isn't only allowed, it's encouraged.

Chicago: Art Institute of Chicago Skip-the-Line Ticket

3. Chicago: Art Institute of Chicago Skip-the-Line Ticket

Pre-book and skip the lines to enter the world-renowned Art Institute of Chicago. Experience the museum’s vast collection spanning 5,000 years of art from around the world. See iconic works like Seurat's "A Sunday Afternoon on La Grand Jatte," Renoir's "Two Sisters (On the Terrace),” several works by Van Gogh, and more than 25 paintings by Claude Monet. Must-sees also include paintings like Edward Hopper's “Nighthawks'' and Grant Wood's “American Gothic,” as well as unforgettable works by Georgia O’Keeffe, Pablo Picasso, Henri Matisse, Salvador Dalí, Andy Warhol, Alma Thomas, Cindy Sherman, and Kerry James Marshall. Continue your museum journey around the world and through the centuries with the museum’s outstanding collection of works—from ancient Egyptian objects through 5,000 years of Asian art, a rich selection of works from across Africa, and onto the wide-ranging holdings of arts of Europe and the Americas. Families won’t want to miss favorites like the armored knights and armor collection or the wonders of our 68 Thorne Miniature Rooms. Plus, a stop in the museum’s Ryan Learning Center offers art-making activities and the chance to create your very own custom adventure-filled tour of the galleries with the interactive JourneyMaker. Enjoy an expertly guided experience of the museum at one of our free daily tours, or take it at your own pace with the engaging audio tours available on the museum’s free app.

Chicago: Gangsters and Ghosts 2-Hour Walking Tour

4. Chicago: Gangsters and Ghosts 2-Hour Walking Tour

See a different side of Chicago on a family-friendly guided tour and hear the tales of the ghosts that haunt the city. Explore the famous Chicago Loop district with your historian guide revealing the many interesting stories hidden behind each turn. Explore the Chicago Loop, known as the vice district during the 1920s and 30s, once the home of speakeasies, secret tunnels and bootleggers. See the places where gangsters such as Al Capone used to party, make deals, and carry out business. Visit haunted locations and old crime scenes including Chicago Riverwalk, Death Alley, and the Chicago Theatre. Peak inside the haunted Palmer House. Finish up at the Congress Hotel, one of the most haunted places in Illinois. Enjoy frequent stops along the way, including a refreshment stop and a restroom break.

Chicago: 1.5-Hour Romantic Sunset Cruise

5. Chicago: 1.5-Hour Romantic Sunset Cruise

Relax as you glide over the Chicago River and into Lake Michigan on this cruise. Enjoy the glow of the sunset on Chicago's sparkling skyline. Have the option to purchase delectable drinks and snacks at the onboard bar as you sail. Start your sunset cruise on the Chicago River at Michigan Avenue. Make your way along the main branch of the river towards Lake Michigan before entering the Chicago Locks, a modern engineering marvel, that will transfer the vessel onto the great Lake Michigan. The vessel will cruise along Lake Michigan as the sun sets behind the wonderful skyline offering several amazing views. Your local tour guide will give a very brief commentary along the Chicago River and entrance to Lake Michigan, but most of the 1.5-hour cruise is spent without narration, leaving you to watch the sun put on a beautiful display with the City skyline. Admire the many angles of the Chicago skyline from Lake Michigan, one of the largest bodies of fresh water in the world. Capture magical views of Chicago's twin super-skyscrapers, the famous Willis (formerly Sears) Tower and the John Hancock Building. You'll also get to admire the majesty of Grant Park with its famous Buckingham Fountain, and iconic Chicago venues such as Soldier’s Field, Adler Planetarium, and the Shedd Aquarium. During your cruise, treat yourself at the full-service cash bar featuring authentic Chicago products. Try local beer and spirits and Garrett’s Popcorn. Choose between the fresh air of the open-air decks or enjoy the comfort of the climate-controlled interiors during your cruise. Don’t forget to take a selfie at the Grand Staircase at the front of the boat or pose for photos at the picturesque stern or bow of this classic vessel.

Chicago Lakefront: Seadog Speedboat Ride

6. Chicago Lakefront: Seadog Speedboat Ride

This half-hour Seadog Speedboat ride along Chicago’s lakefront is one of the best ways to view the city’s skyline while learning about the city. Combine an exciting speedboat ride with informative and amusing stories about the world-famous Windy City. As you depart Chicago's Navy Pier, your captain will tell you interesting facts about the pier and the lakefront as he cranks up the music and races to key lakefront landmarks. Stop near the picturesque lakefront park of the Chicago Museum campus, where you’ll learn about the architecture and history of Chicago. Admire views of the Magnificent Mile neighborhood, including the Buckingham Fountain, Sears Tower, Grant Park, and Chicago's largest shopping district. Listen to the thrilling sound of the turbo engines as you race around the Lake Michigan waterfront and back to the Navy Pier. Upgrade to the Extreme Thrill Ride Option and experience exhilarating speeds and full 360° spins. This jet-propelled ride blasts off to start and splashes down to stop. Experience full-throttle slalom runs, sharp twists and turns, and the raw power of Seadog Extreme's 1400 HP engines.

Chicago: Beautiful Lakefront and Museum Campus Segway Tour

7. Chicago: Beautiful Lakefront and Museum Campus Segway Tour

Segways are amazingly fun and there is no better way to tour a world-class city like Chicago than on your own personal set of wheels--a Segway! Our eight-mile Lakefront Chicago Segway tour lets you learn about and view and many Chicago's attractions in a highly unique way. As you glide effortlessly and enjoy the lakefront, you can learn the history of our city from your friendly and professional tour guide. Immerse yourself in the area's countless attractions, gorgeous parks and gardens, and stunning photo opportunities. See sights like Grant Park, the BP Bridge, the Bean, and the Buckingham Fountain, as well as generous views of Lake Michigan and the majestic skyline. Segways are safe to use, easy to learn, and fun to ride. We offer a thorough training session from our certified guides before we begin the tour.

Chicago: Museum of Illusions Timed Entrance Ticket

8. Chicago: Museum of Illusions Timed Entrance Ticket

Experience the impossible with an entry ticket to the Museum of Illusions Chicago. Immerse yourself in a world where your eyes will be in a constant battle with your brain. Located in the heart of the Chicago Loop, this brain-boggling museum is a one-of-a-kind destination all about optical illusions. Illusions challenge you to see things differently and reveal a lot about how your brain interprets reality. Experience more than 60 visual and educational exhibits featuring holograms, stereograms, optical illusions, and immersive rooms that are designed to tease the senses and trick the mind. Illusions include: defying gravity in the Tilted Room; growing and shrinking in the Ames Room; walking on walls in the Rotated Room; experiencing infinite space in the Infinity Room; confusing your mind in the Vortex Tunnel; posing in the Beuchet Chair; meeting your doppelgangers at the Clone Table. Then spend some time in the Smart Playroom with games that will stimulate and challenge your mind. Enjoy some friendly competition with friends and family while simultaneously improving your cognition, problem-solving skills, and memory. Overall, the museum is designed to encourage you to have fun while learning the mechanics behind each and every illusion you experience. And don't forget your camera or smartphone when you visit as there are eye-fooling photo-ops around every corner.

Amazing Lakefront Segway Tour of Chicago

9. Amazing Lakefront Segway Tour of Chicago

Glide around the streets and parks of Chicago on a leisurely guided Segway tour. Perfect for Chicago newbies and veterans alike, the tour uncovers quirky facts about one of America’s most energetic destinations. Begin with a training session to become familiar with the unique self-balancing Segways, before exploring the Windy City in a fun and futuristic fashion. Start your Segway experience at Millennium Park and continue to Grant Park to stop and admire the famous Buckingham Fountain Ride to Museum Campus to soak up spectacular views of the Chicago skyline and beautiful lakefront. Capture pictures to share of the expansive views of the sea-like Lake Michigan. Return to your meeting point at the end of your tour.

Chicago: Art Institute Skip-the-Line Tour with Guide

10. Chicago: Art Institute Skip-the-Line Tour with Guide

Experience a guided tour around some of the world’s greatest and most iconic art pieces at the Art Institute of Chicago. Avoid the crowds and lines and meet your expert guide at the Institute 30 minutes before opening time. Explore the expansive collection, learning more about both contemporary and classic pieces. Although the museum usually hosts 1.79 million people per year, you will be able to stroll among the pieces at leisure, getting up close and personal with works by famous and infamous artists like Edward Hopper, Pablo Picasso, Salvador Dali, and Andy Warhol. The Art Institute of Chicago is home to the greatest collection of Impressionist artwork in the world. Your guide will provide expert information on the collection and the museum’s history and hidden gems.

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Frequently asked questions about Chicago Culture & history

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What people are saying about Chicago

Overall rating

4.6 / 5

based on 1,407 reviews

Awesome tour with an awesome guide ! Baylor’s enthusiasm and friendliness really sold it and she even managed to give me goosebumps with the way she told some of the stories! :)

Our guide Ty was super cool and handled the whole tour well. I'll definitely tell all my friends who visit Chicago to take this tour.

Great tour for newcomers! Our guide was knowledgeable and resourceful. Great experience!

Conor was very knowledgeable and the tour was a great pace with lots of info!

Our docent was extremely knowledgeable and the tour was well worth it.