Illinois 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).

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.

Tower above the Windy City’s world-famous skyline with admission to 360 Chicago (John Hancock Observatory). Ascend 94 stories to the observation deck of one of the tallest buildings in North America aboard its lightning-fast elevator. Then check out bird’s-eye views of landmarks like the famous Willis (Sears) Tower and the lakefront shoreline, and enjoy a variety of educational exhibits on site. Upgrade your ticket to include TILT, a thrill ride that offers visitors unique, downward facing views from 1,030 feet. Or, choose the Sun and Stars package for two visits to the observation deck within 48 hours. With mobile tickets, simply scan your phone for direct entry into 360 Chicago.

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 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.

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, and the Field Museum as well as a choice of the Art Institute of Chicago or Adler Planetarium, and Museum of Science and Industry or 360 Chicago (John Hancock Observatory). Plus enjoy a wealth of useful Chicago tips and savings at a variety of other venues and retailers.

Get off the beaten path to experience some of Chicago's best street art on this immersive tour. With a guide in the lead, you can leave the navigation to them and simply take in the scenery. Listen to in-depth commentary focused on the street-art community, the artists, and the history and meaning behind the art.

Step into the heart of Chicago with this 2-hour walking tour of the Loop. You’ll meet your local guide at the Chicago Cultural Center and make your way through the city’s downtown. Stop to check out the elevated “L” train, buildings by Burnham and Sullivan, busy commercial centers and lesser-known quiet corners of this vibrant area. You’ll come away with a deeper sense of Chicago’s rich history and architecture.

Transport yourself back in time to Chicago’s roaring twenties at Tommy Gun’s Garage, a unique speakeasy dinner show in the Windy City. Say the password at the front door and then step into an era of mob guys and flappers, Broadway tunes by Cole Porter and George Gershwin and lively dances like the Charleston. This gut-busting show, full of song, dance and audience participation, is sure to please.

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.

Discover Chicago from 1,500 feet (457.2 m) above the ground at the 360 Chicago Observation Deck. Open between 9am to 10:30pm, you can visit at a time that fits with your schedule. It’s a great experience for adults and children alike. Your ticket also includes admission to TILT, a thrill ride that gives you a hair-raising view over The Magnificent Mile.

Rather than taking selfies everywhere you go or trusting a stranger to take a picture for you, leave capturing the special moments to us. You will be escorted by a local professional photographer who will guide you through your chosen route and will take pictures of your experience so you can return home with the ultimate souvenir. Your photo tour includes: -1 or 2-hour private session with a professional, local photographer -High-resolution edited images delivered via a private online gallery within 24-48 hours

Explore Chicago by Segway with the benefit of a scenic 7- or 8-mile tour led by your guide. Start with an orientation to operating the Segway and a few minutes to practice. Then roll through the paths of Grant Park to Buckingham Fountain and glide along the Chicago lakefront to view attractions such as Museum Campus, Shedd Aquarium, The Field Museum, and Soldier Field, homefield for the Chicago Bears.

Delve deep into the world of natural history with this Field Museum admission ticket in Chicago. Spend as long as you like exploring the museum's collection of more than 26 million artifacts. Get to know SUE, the world's largest T. Rex, or stroll through the sparkling Hall of Gems. Time travel through 13,000 years of history in the Americas, from the Ice Age to Inca and Aztec temples. Take advantage of the free daily tours, led by Field Museum docents.

The easiest and most affordable way to explore some of Chicago's top attractions at your own pace, the Go Chicago Explorer Pass saves you up to 45 percent on regular ticket prices. Create your own sightseeing itinerary by choosing 2, 3, 4, or 5 attractions, tours, and activities from among more than 30 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 (purchased by December 31) are valid for two year 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.

Rather than taking selfies everywhere you go or trusting a stranger to take a picture for you, leave capturing the special moments to us. You will be escorted by a local professional photographer who will guide you through your chosen route and will take pictures of your experience so you can return home with the ultimate souvenir.

Tour the historic Chicago Theater, a must-see city landmark, with a guide providing in-depth commentary. You'll get the most out of your visit by traveling with a guide and get access to some areas of the theater that the public never sees. Learn about its architecture, history, and famous performers throughout the years.

On this two-in-one tour, you won’t just discover Chicago’s highlight public park: you’ll also do so in the company of a professional photographer, who will capture portrait shots as you explore. Pick from multiple daily tour times, and meet your private guide at Millennium Park. You can look forward to seeing park highlights like Anish Kapoor’s "Cloud Gate" sculpture (better known as “The Bean”), Lurie Garden, Maggie Daley Park, Buckingham Fountain, and more. Following the tour, receive high-quality digital photos of your experience.

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.

Enjoy a private and authentic cooking class in a local Chicago home with your hosts Nancy and Don. This is a perfect experience for anyone looking to connect with local culture over food. After enjoying charcuterie and cheese on the terrace, head down to their home kitchen for your cooking class. Nancy and Don will teach you to prepare a fresh salad and how to construct deep-dish pizza with a variety of fillings! After cooking, you will enjoy your meal together. Friends for many years, Don and Nancy love meeting new people, sharing interesting stories, and good food and wine. Don has lived in downtown Chicago for 34 years and is a wealth of information about the city and its history. Nancy has been cooking for as long as she can remember. She loves cooking for friends and entertaining and is excited to share her cuisine and culture with guests from around the world. These two Chicago friends have teamed up to give you a fun and delicious food experience in the windy city!

Native 312 offers a unique spin on paint night! Join us as we host an intimate look into the world of Urban Art as we learn about some different styles and techniques with guest artists. Then you get your hands dirty as you walk around our gallery setting and test out your skills in different mediums like aerosol spray and stencil. At the end of your private workshop you will be able to go home with your own piece of art!

Enjoy a private portrait session with your own professional photographer during this VIP shoot in Chicago. Discover top landmarks in the city as you follow a photogenic, pre-planned route, with backdrops such as the Adler Planetarium, the Field Museum, and the Shedd Aquarium. Then, receive a digital portrait gallery of edited images within just one to two days.

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.

Get the perfect introduction to the wealth of sights in the Windy City during this 4-hour Chicago day tour. Discover the many landmarks spanning both the city's North Side and South Side, enjoying a scenic ride along Lake Michigan on Chicago's Outer Drive along the way. You'll also have the chance to admire the city's Washington and Grant Parks, explore inside the Lincoln Park Conservatory, see Adler Planetarium and visit the iconic Wrigley Building. This Chicago in a half day tour also includes transport between all sites and tour narration.