Chicago
Culture & History

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Our most recommended Chicago Culture & History

Chicago River: 1.5-Hour Guided Architecture Cruise

1. Chicago River: 1.5-Hour Guided Architecture Cruise

Experience more of Chicago by boat than on any other architectural cruise. See architectural highlights and enjoy an open-air deck or climate-controlled interior as you travel the main River and its north and south branches. View all of Chicago's architectural highlights during this comprehensive sightseeing tour. Be entertained by the expert and friendly tour guides as they explain the 130 year-long history behind the skyline, while bartenders and staff keep you comfortable with refreshments.  Choose between the fresh air of the open-air decks or enjoy the comfort of the climate-controlled interiors during your cruise. The tour starts at the Michigan Avenue (DuSable) bridge and goes up the main branch of the Chicago River past Wolf Point. It then cruises along the north and south branches of the river, before heading back past the Chicago Riverwalk towards Lake Michigan. On the way, learn about ornate, historic early skyscrapers like the Wrigley Building and the Tribune Tower, the imposing art deco Merchandise Mart, mid-century skyscrapers like the Mies Van der Rohe AMA Building. Don't miss the circular Marina City Towers, the majestic Willis Tower (formerly the Sears Tower and the tallest building in Chicago) the soaring AON Center, and more modernist structures like Aqua, Trump Tower, Nuveen, and the new Vista Tower. During your cruise, have the opportunity to enjoy a full-service cash bar featuring authentic Chicago products, including local beer and spirits, and Garrett’s Popcorn. 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.

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Chicago: Field Museum of Natural History Ticket or VIP Tour

2. Chicago: Field Museum of Natural History Ticket or VIP Tour

Visit the Field Museum of Natural History, one of Chicago's great museums. With more than 35 world-renowned natural history exhibitions, there's something for everyone. Visit the Field Museum of Natural History, which holds over 35 world-renowned natural history exhibitions. Explore subterranean life in the Underground Adventure exhibit. Admire gemstones in the Hall of Gems and one of the largest collections of Chinese jade in North America in the Hall of Jades. Next, follow the stories of the Ice Age mammoth hunters and the temples of the Inca and Aztecs. Visit the Dinosaur Hall Evolving Planet exhibit to mingle with giant sloths, woolly mammoths, Sue, and Maximo. Upgrade to the All-Access Pass to see a 3-D movie and all 3 ticketed special exhibitions. Choose the Early Access VIP Tour option for a one-hour VIP tour of the museum's dinosaurs before the museum opens to the general public. Take pictures with Sue or Maximo without the crowds. Then explore the rest of the museum with an all-access ticket including a 3D movie titled "Waking the T-Rex."

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Chicago: Willis Tower Skydeck and The Ledge Ticket

3. Chicago: Willis Tower Skydeck and The Ledge Ticket

Enjoy an unrivaled view over the city of Chicago on a trip up the city's Willis Tower. This famous building, once known as the Sears Tower, is not only home to a Skydeck on the 103rd floor, but it also features The Ledge, a series of 4 glass-paneled boxes that extend out from the building's facade to give visitors a view straight down. As you wind through the ground levels of the Willis Tower, you will be surrounded by museum-quality exhibits highlighting the iconic tower. Learn about Chicago's rich history and culture through these informative visuals. Watch a video presentation, "Reaching for the Sky," where you will be briefed on the history of the building and of architecture in Chicago. Then step into your elevator and you will be amazed at how quickly it ascends. As you travel, your multimedia-equipped elevator will inform you about your vertical progress. Upon reaching the 103rd floor, step out onto the Skydeck, which offers views spanning over 50 miles and across 4 states. Then summon your courage to step out onto The Ledge, a glass balcony that hangs over the edge, for vertigo-inducing views 1,353 feet (about 412 meters) straight down to the city below! Download the Skydeck Mobile App for a free viewfinder which points out many of Chicago’s notable landmarks. Learn more about sights like Navy Pier, Wrigley Field, Grant Park, Art Institute of Chicago, Shedd Aquarium, and Field Museum of Natural History.

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Chicago River: 45-Minute Family-Friendly Architecture Cruise

4. Chicago River: 45-Minute Family-Friendly Architecture Cruise

Admire Chicago’s impressive architecture from a unique perspective aboard a 45-minute cruise sailing down the Chicago River, which features a full-service cash bar and live commentary tailored to entertain the whole family. Experience the best of the Chicago River from Lakeshore Drive to the Willis Tower, navigating along the South branch of the river, before heading back past the Chicago Riverwalk towards Lake Shore Drive and Lake Michigan. Be entertained by the fun and experienced tour guides as they explain the history behind Chicago’s buildings along the river and the exceptional architects who created this ever-changing skyline. Enjoy the most relaxing way to sightsee in Chicago- a perfect way to explore the city free of traffic noise and congestion. Make sure to visit the full-service cash bar featuring authentic Chicago products, including local beer and spirits. Explore the open-air decks that allow you to feel the cooling river breeze and see the city from many vantage points that provide perfect photo opportunities.

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Chicago: 90-Minute Mob and Crime Bus Tour

5. Chicago: 90-Minute Mob and Crime Bus Tour

Experience Chicago’s underworld of criminals and gangsters on a luxury 90-minute bus tour. Find out how some of the world’s most famous criminals, mobsters, and gangsters conned their way through the city. Ride comfortably in luxury, on a climate-controlled bus, as you see famous Chicago crime scenes that range from the 19th century through modern times. Unlike Chicago walking tours, this Mob and Crime Tour isn’t affected by the Windy City weather. Learn from a local expert tour guide giving interactive live commentary about Al Capone, the Untouchables, the Chicago Mob, John Dillinger, Terrible Tommy O'Connor, H. H. Holmes, the Chicago Black Sox, Leopold and Loeb, bank heists, Cap George Streeter, and more. Grab your camera for a drive-by shooting of the historic criminal courthouse, a Chicago architectural landmark where some of Chicago's most notorious cases were tried. You'll also view historic video footage, receive an informative pamphlet with photos, and can even take part in a crime quiz. Stake out crime scenes like the Biograph Theatre, Holy Name Cathedral, Clark Street Bridge, and other Chicago landmarks. See the site of the St. Valentine's Day Massacre, one of Chicago's most notorious murder scenes. Get off the bus and walk the path that notorious Chicago gangsters John Dillinger and Hymie Weiss followed just before their deaths. Travel into the criminal past of Chicago's River North, Gold Coast, Lincoln Park, Old Town, Loop, and Magnificent Mile neighborhoods.

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Chicago CityPASS®: Save 50% on 5 Top Attractions

6. Chicago CityPASS®: Save 50% on 5 Top Attractions

Take in incredible views, fascinating science, world-class art, and more with Chicago CityPASS® tickets that include premium admission to Chicago’s top attractions and save travelers 50% off the price of the same tickets purchased separately. The CityPASS system is simple. Simply present your mobile (or printed) ticket to be scanned at any 2 of the 5 attractions for entry. What exactly can you experience with the CityPASS ticket? One-stop is the Shedd Aquarium, where you can see otters, lizards, whales, and dolphins – and much, much more. Shedd Aquarium is home to more than 32,000 animals, housed under one octagonal dome. You can also take in breathtaking views at Skydeck, which stands 1,353 feet above the city. The Field Museum is on the list too, home of “Sue” the world’s largest T. Rex. This pass includes prepaid admission to 5 must-see attractions: 1. Shedd Aquarium From angelfish to zebra sharks, meet 32,000 animals from aquatic habitats around the world at Chicago’s “must-sea” destination! See penguins fly through chilly waters, dolphins leap high in the air, monkeys scamper through rainforest trees, and stingrays swim below your feet.  You’ll have all-access priority admission including permanent exhibits, animal presentations, special exhibit, and Stingray Touch (seasonal), plus a 4-D Experience. 2. Field Museum See the world’s wonders! Visit an ancient Egyptian tomb with 23 mummies, explore over 10,000 years of Chinese history and culture, and “Sue” the world’s largest T. Rex dinosaur. You’ll get an All-Access Pass (admission to all permanent and regularly-priced ticketed exhibitions, and your choice of one digital 3D film). Film selection subject to availability. Additional charges may apply for specially ticketed exhibitions outside of the All-Access Pass. 3. Skydeck Chicago (Reopening Spring 2021) Atop the Willis Tower, Skydeck, invites intrepid visitors to step onto The Ledge, four glass boxes jutting out from the observatory. Situated at 1,353 feet (412 meters), the boxes provide a jaw-dropping view of 103 stories above the city. Includes expedited Entry to Willis Tower’s 103rd floor. Your ticket includes expedited entrance to the Skydeck as well as to The Ledge. 4. Your choice of 2 from the following attractions: 4.1 Art Institute of Chicago Travel the globe through galleries featuring the art of ancient Greece, Japan, Africa, and the Americas. The museum also has one of the largest Impressionist collections outside France and features classic artists like Van Gough and Georges Seurat.  You’ll get Fast Pass Admission to the permanent collection and non-ticketed special exhibitions; including an audio tour. 4.2 Museum of Science and Industry Learn about the science of storms, tour a real World War II German submarine, and run on a human-sized hamster wheel. Chicago’s Museum of Science and Industry is the largest in the Western hemisphere. Includes museum entry, plus one timed-entry experience. 4.3 360 CHICAGO Observation Deck Experience magnificent views of Chicago’s skyline, beaches, and historic waterfront from 1000 feet up. Includes express entry admission.

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Chicago: Hop-on Hop-off Open Top Bus Tour

7. Chicago: Hop-on Hop-off Open Top Bus Tour

From your vantage point on the double-decker sightseeing bus you'll enjoy panoramic views of Chicago’s finest skyscrapers, including the 875 N Michigan, the Willis Tower and the Wrigley Building. Take in the city's impressive landmarks as your tour guide provides entertaining commentary and insight into Chicago's history. Enjoy exploring this dynamic city with the freedom to hop-on and hop-off as many times as you wish to visit attractions such as the Shedd Aquarium and the Field Museum. You’ll travel down the famous Magnificent Mile, considered one of the great avenues of the world, and continue across the Michigan Avenue Bridge over the Chicago River. The bridge connects the north and south sides of the city. This hop-on, hop-off bus tour of Chicago makes it easy for you to explore the city's sights at your own pace. There are 13 stops, where you can hop-off to visit attractions and explore places of interest. The stops are conveniently located to make navigating your way around the city easy, and with a choice of Classic, Premium or Deluxe tickets, you can take your time discovering Chicago. Be sure to take advantage of admission to the Chicago Architecture Center, included with the Premium and Deluxe tickets, to dive deeper into the city that invented the skyscraper. So don't wait, just hop-on an exciting journey through Chicago.

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Chicago River: Brunch, Lunch, or Dinner City Cruise

8. Chicago River: Brunch, Lunch, or Dinner City Cruise

Admire the unparalleled riverfront views as you enjoy a fine dining experience on the Chicago River. Arrive early for your 2-hour cruise, dressed to impress. Explore the beautiful Chicago Riverwalk when boarding the boat. The crew will welcome you aboard, and the ship's photographer will record the moment. You'll be escorted to your table in the dining area. With its gorgeous glass-enclosed design, you can enjoy Chicago's incredible architecture from your seat. Savor a delicious meal prepared freshly onboard, and choose to buy a cocktail from the bar.   To add to your enjoyment, the dinner cruise includes music provided by an onboard DJ. During the lunch and brunch cruises, occasional onboard narration will be provided about some of the architectural highlights along the river. On Wednesday and Saturday evenings throughout the summer, you'll have amazing views of the Navy Pier fireworks display. Sample dinner menu Choice of starter: Caesar salad Lobster soup Choice of main course: Jumbo lump crab cakes Maple and mustard glazed chicken breast Braised beef short rib Jumbo forest mushroom ravioli Choice of dessert:  Eli’s original cheesecake Duo seasonal sorbet Chocolate decadent cake Odyssey signature warm butter cake Sample Brunch Menu Choice of starter: Caesar salad Scottish smoked salmon toast Greek yogurt and granola parfait Fresh blueberries and strawberries Choice of main course: Cannellini bean shakshuka Maple and mustard glazed chicken breast Scrambled eggs  Raisin and cinnamon french toast Choice of dessert: Eli's New York style cheesecake Tres con leche flan Triple chocolate mud pie Freshly cut fruit and fresh strawberries Sample Lunch Menu Starter: Caesar Salad Choice of main course: Jumbo forest mushroom ravioli Maple and mustard glazed chicken breast Oven baked Atlantic salmon fillet Braised beef short rib Choice of dessert: Eli's New York style cheesecake Freshly cut fruit and fresh strawberries Duo of Sorbet

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Chicago: 45-Minute Private Helicopter Flight for 1-3 People

9. Chicago: 45-Minute Private Helicopter Flight for 1-3 People

Enjoy spectacular views of Chicago from an MD500 helicopter. This 45-minute helicopter flight over Chicago covers all the important highlights of the city from McCormick Place and Soldiers Field in the South to Wrigley Field in the North. Depart from Schaumburg Regional Airport and see some of Chicago's highlights including the Willis Tower, the John Hancock Building, Navy Pier, and Lake Michigan with its beaches and picturesque shoreline. Also see the Chicago River, Grant Park, Millennium Park, Buckingham Fountain, and Museum Campus. Make sure you also look out for Wrigley Field, home to the Chicago Cubs, and the United Center, where the Chicago Bulls and Blackhawks both play. This is a private helicopter experience for 1 to 3 passengers. Travel in complete safety with a professional pilot who will provide you with live commentary through noise-canceling headphones. In the summertime, have the added thrill of the doors being able to be off during the flight.

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

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

Pre-book and skip the lines to enter the Art Institute of Chicago, a world-class museum with hundreds of thousands of artworks. Here you can get an intimate view of some of the world's most famous art, from iconic contemporary and modern paintings to medieval masterpieces.  Experience the Institute’s vast collection of Impressionist and Post-Impressionist paintings, the largest outside The Louvre in Paris. See masterpieces such as Seurat's "A Sunday Afternoon on La Grand Jatte," Renoir's "Two Sisters (on the Terrace)”, and numerous paintings by Claude Monet first-hand. In the “Modern Art” collection, see iconic pieces such as Matisse's “Bathers by a River”, Brâncusi's “Golden Bird”, Magritte's “Time Transfixed”, O'Keeffe's “Black Cross, New Mexico”, Orozco's “Zapata”, Ivan Albright's “Picture of Dorian Gray”, and Lachaise's “Woman (Elevation)”. The “American Art” collection will show you work by renowned artists such as John Singer Sargent, James McNeill Whistler, Mary Cassatt, and Winslow Homer, as well as iconic Modernist holdings from Georgia O'Keeffe to the Mexican muralist Diego Rivera. In the “Contemporary Art” section, you will see ground-breaking works by Willem de Kooning, Eva Hesse, Jasper Johns, Ellsworth Kelly, Joan Mitchell, Bruce Nauman, Jackson Pollock, Gerhard Richter, and Cy Twombly. Use your pass to the full and browse the Institute’s other collections, including “European Painting and Sculpture Collection”, “Asian Collection”, “African Collection”, and “Medieval Collections”. As you walk through the halls, admire the museum’s architecture by Pritzker Prize-winning Renzo Piano, complementing the museum's original 1893 building, which was built for the World's Columbian Exposition of the same year.

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Other Sightseeing Options in Chicago

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What people are saying about Chicago

Overall rating

4.6 / 5

based on 1,407 reviews

Es un paseo muy bonito, bien explicado, las bebidas a bordo deliciosas, y las fotos que se pueden tomar en el paseo de las 5pm son increíbles, Chicago de noche se ve hermoso.

The tour guide, Jack, was the star of this trip- engaging, knowledgeable, and funny! I would highly recommend a tour with him!

A great way to figure out where you want to spend additional time. Canopy on the roof keeps you warm, even when chilly.

We had beautiful clear skies and really enjoyed the views and listening to the tour guide.

The tour guide for the 2pm sailing was out standing!!