Chicago Tours

Cruise down the Chicago River to see the city's famous architecture on this boat tour. With commentary from your onboard guide, watch the spectacular skyline glide by, including more than 40 notable buildings like Navy Pier, the Wrigley Building, and the John Hancock Building. Cover all three branches of the Chicago River, passing the East Bank Club, the old Post Office Building and the Willis Tower (formerly known as the Sears Tower).

Discover the architectural gems of the Windy City from an ideal vantage point on a cruise down the Chicago River. Offered several times throughout the day, it’s easy to fit the leisurely excursion into your itinerary. Covering more than 130 years of architectural history, the tour is the perfect opportunity to see a huge area of the city without the hassle of taxis and public transit.

Get a front row perspective on the exquisite buildings that line the Chicago River during a 45-minute architecture cruise. Hear live commentary about the history and architectural heritage of Chicago on this family-friendly tour, which highlights landmarks such as the Chicago Riverwalk, Michigan Avenue Bridge, Wrigley Building, and Willis Tower. Sit on the open-air top deck or the sheltered bottom deck for the ultimate view of Chicago.

Explore Chicago's gangster past on this mafia tour in a coach vehicle. Drive around the Windy City to see where Al Capone, The Untouchables, Hymie Weiss, and John Dillinger, among other thugs hung out. A history-savvy guide introduces you to some of the most storied locations of Chicago’s criminal past, including Holy Name Cathedral, Biography Theatre, and the site of the bloody St. Valentine’s Day Massacre. You'll be able to get out and pose for pictures in front of a historic courthouse, among other infamous sites.

Don’t spend time figuring out what to see in Chicago and how to get there—this hop-on hop-off tour provides a mapped-out itinerary of the city's top sights. With several strategically located stops, the tour allows you to explore the Windy City at your own pace. See the world-class Art Institute and landmark skyscrapers, while audio commentary onboard gives you insight into the city's colorful history.

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.

Experience a colorful side of Chicago history with this Gangsters and Ghosts Tour. With a historian as your guide, you’ll step back to the roaring 20’s, when the Chicago Loop was a hub for bootleggers, speakeasies, and gangsters like the infamous Al Capone. Visit onetime gangster hangouts and haunted sites like the Palmer House, Congress Hotel, and Death Alley.

Stroll through downtown Chicago on this walking food tour. Visit Millennium Park, the Palmer House Hotel and other city landmarks. Taste quintessential Chicago foods such as deep-dish pizza, hot dogs, plus chocolates and pastry. All food tastings are included, and the tour covers an easy 1.5 miles (2.4 km) suitable for most fitness levels. Upgrade your tour to include three pours of local craft beer.

Enjoy a unique creative outlet—and learn the ins and outs of graffiti and street art—during this hands-on urban art workshop. Pick from multiple class times, and make your own way to the Chicago studio. You’ll learn different styles and techniques from your instructors (including guest artists), can try out stenciling and spray-painting, and can even create your own work of art on canvas to bring home at the end of class.

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 Shedd Aquarium, Skydeck Chicago (Opening with reimagined experience in Spring 2021), and the Field Museum plus your choice of admission to 3 of the following attractions: Adler Planetarium, Art Institute of Chicago, Museum of Science and Industry, Chicago, and the 360 CHICAGO Observation Deck. Also enjoy a wealth of useful Chicago tips and savings at a variety of other venues and retailers. Attractions may be required to verify proof of full COVID-19 vaccination (14 days past final vaccine dose) before allowing entry. Please review attraction requirements before visiting Chicago.

An excellent choice for first-time visitors, this tour provides a comprehensive overview of the city and hits on both classic attractions and little-known sites. Beginning at the Chicago Theatre, work your way to the Chicago Pedway, an elaborate network of underground tunnels used by locals and commuters. Stroll the Chicago Riverwalk and the Magnificent Mile, then embark on a food tour to taste some of the city’s famous foods.

Explore Chicago's iconic landmarks on this sightseeing tour led by an expert guide. Board a comfortable, large-windowed minibus and explore downtown and Northside neighborhoods. You have a chance to get out and 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.

Learn about Chicago’s brewpub scene and taste different types of craft beer on this guided brewery tour. Visit unique breweries for craft beer samples plus an additional brewing production facility for an in-depth tour. Discover the science behind the brewing process, complete with step-by-step procedures, and enjoy plenty of beer samples throughout the tour. Round-trip transportation in a Prohibition-era-styled barrel bus is included.

Enjoy a performance of the legendary Blue Man Group, one of Chicago’s longest-running shows, at the Briar Street Theater. This worldwide performance troupe, whose hilarious and quirky show has earned them raves in cities around the world, has recently updated their performance with new technology. Experience the group’s gigantic tablet, the “GiPad,” as you enjoy the laugh-inducing antics, stunning visuals and high-tech stage show of this ever-changing, family friendly show. Your ticket purchase also includes a choice of seating options and show times.

Sample some of the Windy City’s tastiest donuts on this Underground Donut Tour, celebrating the magic of Chicago’s tastiest sugar-filled concoctions. Donut-lovers are sure to enjoy this visit to some of Chicago’s tastiest donut purveyors, offering a chance to savor all of your favorite varieties, on the city's only donut-themed excursion. All tastings are included, and vegan, gluten-, and nut-free options are also available.

Feel the rush of skydiving without going anywhere near a plane, with this indoor skydiving experience in Chicago. Start off with thorough training so you feel confident and know what to expect. Then, enjoy two 60-second ‘free fall’ experiences in a technologically advanced vertical wind tunnel, which feels much like real skydiving. No experience is necessary, and your instructor will give you hands-on assistance when you need.

Explore Chicago's Chinese food scene on this walking tour in the Chinatown district. With a guide, learn about the cuisine of different regions of China and how Chinese culture has influenced Chicago and other areas. Enjoy included tastings from restaurants and other food venues in Chinatown—a great way to start a night out in the city.

Have only a short stay planned in Chicago? Make the most of your time in the Windy City, and see more of the city in less time, when you book a private driving tour of Chicago. Pick between several convenient tour times, and meet your guide and driver directly at your hotel. Over the course of your excursion, you’ll make stops at highlight attractions like the Lincoln Park Conservatory, Millennium Park, and Museum Campus. You’ll also learn about Chicago’s history and can spy other remarkable sights as you go.

One of Chicago’s most popular and recognizable landmarks, the Field Museum of Natural History offers a wide array of treasures, from its Hall of Gems to Sue—one of the best-preserved Tyrannosaurus Rex fossils ever found. Guarantee your admission to this in-demand museum, and prevent any stress, by booking your tickets before you travel. Upon arrival, you can explore the museum at your own pace, and even embark on a complimentary, docent-led tour.

The easiest and most affordable way to explore some of Chicago's top attractions at your own pace, the Chicago Explorer Pass by Go City saves you up to 40 percent off compared to buying individual attraction tickets. Create your own sightseeing itinerary by choosing 2, 3, 4, 5, 6 or 7 attractions, tours, and activities from among more than 25 top sites, including SkyDeck, 360 Chicago, the Field Museum, a shoreline sightseeing cruise, a hop-on hop-off Big Bus tour, Lincoln Park Zoo, Navy Pier, and LEGOLAND® Discovery Center. Please note: Enjoy the extra flexibility in case your travel plans need to change: All passes are valid for two years from purchase date and only become activated with your first attraction visit. After activation your pass will be valid for 60 days and/or the remaining number of attraction choices purchased.

Discover the adrenaline rush of skydiving without setting foot on a plane at iFly Chicago-Rosemont. Offered 9am to 10pm, you can easily find a session that fits with your busy schedule. Feel confident after a small-group training session, then head into the tunnel for your solo floats.  An instructor is present for both 60-second sessions to give you personalized instruction. Afterwards, take home a flight certificate to commemorate your adventure.

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.

Located in River North, these adventures offer a one-of-a-kind premium experience. Follow clues and solve puzzles to complete your mission together. You might escape...You WILL have fun! Choose to play one of five uniquely immersive games: - Gold Rush: Find hidden gold in the California hills! - Prison Break: Complete a daring escape from the evil warden! - Special Ops: Mysterious Market: Uncover the truth as a secret agent! - The Heist: Recover a stolen masterpiece from an art thief! - Mission: Mars: Launch your spaceship from the Red Planet!

Enjoy Chicago’s only bus guided neighborhood pizza tour.  Eat like a local as you travel off the beaten path into Chicago neighborhoods to savor the best pizza.  Your local guide will teach you the science behind ingredient selection and baking as you sample slices from historic pizzerias.  In just a few hours, you’ll leave stuffed, and with an understanding of why pizza is such an important part of Chicago’s culture.