Activities & Tours: Illinois

Chicago in a Day: Food, History and Architecture Walking Tour

Ready to discover some of the best Chicago has to offer with a local by your side? Join us on an epic tour of some of the city’s greatest hits: incredible architecture both old and new, delicious local treats and iconic Chicago dishes, a uniquely Chicago transit ride, stunning river views and much more!

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based on 751 reviews

See Details → Duration :5 hours
From $131.54

2-Hour Guided Segway Tour of Chicago

2 hours of being a kid again!!! Take a Segway tour with us and discover how beautiful Chicago truly is. Ride through some of Chicago's most popular destinations with an experienced guide. We will glide through scenic and historic downtown Chicago and explore the beautiful Grant Park, around the Buckingham Fountain, near the Museum Campus and near the lakefront. Or take our Riverwalk tour to explore the Chicago River to view Navy Pier and famous Chicago bridges, traveling up historic Michigan Avenue and passing by Millennium Park. No matter which tour you choose, it will be a memory lasting a lifetime!

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based on 340 reviews

See Details → Duration :2 hours
From $65

BYOB Spray Paint 'n' Sip at Studio W.I.P. Chicago

Studio W.I.P. by Native 312 Events offers a unique spin on BYOB paint night! Join us as we host an intimate look into the world of Street 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 workshop you will be able to go home with your own piece of art!

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based on 303 reviews

See Details → Duration :1 hours 30 minutes
From $45

Chicago Lincoln Park Indoor Skydiving with Two Flights

When you arrive at the Chicago Lincoln Park indoor skydiving location, get started by putting on your provided gear and going through a specialized training session from a flight instructor. Learn how to safely float in a 1,400-horsepower vertical wind tunnel that generates a wall-to-wall cushion of air, commonly used by professional skydivers. Experience the thrill of skydiving without having to hurl yourself from an airplane, and no experience is necessary. Once inside the enclosed space of the flight chamber, a tunnel operator slowly increases the wind speed until you and your instructor are airborne. Feel your adrenaline pumping as you 'free fall' at wind speeds reaching 180 mph (290 kph). The stable wind flow keeps you from falling off the column of air, and your instructor is on hand at all times to guide you. The first-time flyer experience takes about 75min. Each session includes up to 12 people, but fly one-on-one with your instructor in the wind tunnel twice for 60 seconds.

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based on 57 reviews

See Details → Duration :1 hours 15 minutes
From $98.09

Lake Michigan 30-Minute Speedboat Ride

Enjoy Chicago’s iconic skyline with an exciting speedboat Tour on Lake Michigan. Departing from Navy Pier, the Lakefront Speedboat Tour is the best way to view Chicago from the water. Seadog offers fun for the whole family (and the dog, too!) combining an exciting speedboat ride along the shoreline with informative and amusing descriptions of the world-famous Chicago skyline!

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based on 263 reviews

See Details → Duration :30 minutes
From $37.44

Chicago City Minibus Tour

Enjoy Chicago’s famous sights and fabulous skyline views on this award-winning small-group sightseeing tour of the city. Travel through Chicago with an expert guide on a comfortable minibus, stopping at iconic locations like early skyscraper "The Rookery" (Frank Lloyd Wright architecture), Museum Campus (for the BEST skyline view in town) and The Buckingham Fountain. You'll also see The Magnificent Mile, Lincoln Park, The Chicago River, Millennium Park, The Gold Coast, Lake Shore Drive and more! Along the way, your guide will provide historical and informational and at times humorous commentary about the area and its many attractions. The small-group atmosphere with maximum of 10 people ensures a more personal experience.

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based on 254 reviews

See Details → Duration :2 hours
From $47.95

Chicago Walking Food Tour With Secret Food Tours

On our Secret Food Tour: Chicago, you'll enjoy a variety of foods with culinary influences from the people who built this city. You'll experience all the city's biggest food hits, many dishes with roots dating back over 150 years. This moving feast incorporates a walk through some of the city's world renowned architecture and public art in the famed Chicago Loop District. Experience our famous deep dish pizza, taste the amazing Italian beef sandwich, enjoy gourmet popcorn, and lots of other treats. Plus, there is our mouth-watering secret dish that you can only find out about on the day of the tour!

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based on 505 reviews

See Details → Duration :3 hours
From $89

Bikes, Bites, and Brews: Chicago's Signature Dishes Bike Tour

Taste all of Chicago’s classic eats on this 4 1/2 hour guided bicycle tour! Join the expert tour guides of Bobby’s Bike Hike, America’s longest-running city bike tour company, on this exciting and informative adventure which recently ranked Top 20 in the World by TripAdvisor. The journey is 13 miles (at a leisurely pace) and includes deep dish pizza, a gourmet brownie, a Chicago-style hot dog, and samples of local craft beer! On the daytime version of the tour, you’ll drink in the sights of Chicago’s beautiful northside neighborhoods, including the Lakefront and Wrigleyville, home to our Chicago Cubs baseball team. On the nighttime version, you'll ride through the party districts of downtown and see the lights of Buckingham Fountain, Millennium Park and the glorious skyline. Cruise the Lakefront Trail, one of the most popular waterfront bike paths in the country. Don’t miss out on this fun tour! You’ll leave with a profound understanding of our town, even if you only came for the beer.

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based on 535 reviews

See Details → Duration :4 hours 30 minutes
From $89.99

Chicago's Ultimate City Bike Tour

Get acquainted with Chicago’s most iconic landmarks on this riotous guided bicycle tour! Join the expert guides of Bobby’s Bike Hike, America’s longest-running city bicycle tour company, on this exciting and informative adventure. Over the course of a 3-hour bike ride (traversed at a nice leisurely pace), you’ll get up close and personal with Chicago’s legendary Museum Campus, Grant Park, and Millennium Park. You’ll become intimately familiar with Soldier Field, The Adler Planetarium, Buckingham Fountain, The Pritzker Pavilion, and Cloud Gate (the formal name of Chicago’s dearly-beloved “Bean”). This tour is perfect for first time visitors looking to see all of the classic hotspots, and for returning guests looking to understand more about the landmarks they know and love. Hop on two wheels, and come make memories that are sure to last a lifetime!

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based on 139 reviews

See Details → Duration :3 hours
From $54.99

Chicago Private Sunset Sail on Lake Michigan

Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefront. Kick back, relax, and let the US Coast Guard licensed captain treat you to stunning views of Chicago’s spectacular skyline. Make the experience your own. The flexibility of a private charter allows customization of virtually any aspect of the sailing adventure from guest list to music selection to sailing route. All charters are NON-SMOKING experiences.

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based on 21 reviews

See Details → Duration :2 hours
From $483.96

Chicago's Navy Pier Firework Sail Aboard a Tall Ship

A Truly Special Event Sail! During the summer, every Wed & Saturday night, Tall Ship Windy sails from Navy Pier for our guests to enjoy the spectacular night fireworks from the best seat in town. Enjoy the amenities of the 148 foot, four masted Schooner that is the official ship of the City of Chicago. Sail from Navy Pier and see the picturesque Chicago Skyline. Enjoy one of the best summer fireworks displays in the nation aboard a world-class tall ship. Then, get your history fix with a rousing rendition of traditional shipboard working songs against the backdrop of the brilliantly lit Chicago skyline. This is a one of a kind uniquely Chicago experience. The Wednesday Fireworks Boat Tour departs promptly at 8:45pm. The Saturday tour departs promptly at 9:15pm.

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based on 37 reviews

See Details → Duration :1 hours 30 minutes
From $99

Chicago Lakefront and Museum Campus Small-Group Segway Tour

Looking for fun things to do in Chicago? Look no further - Explore Chicago with one of our professional guides on this scenic 7 or 8 mile Chicago Segway tour. Begin these guided Chicago Segway tours traveling through the fragrant garden paths of Grant Park to view Buckingham Fountain. Enjoy the breeze as you glide effortlessly to the most popular Chicago tourist attractions along the Chicago lakefront: the Museum Campus, the Shedd Aquarium, the Field Museum, and of course Soldier Field, home of the Chicago Bears. You can't go wrong with this perfect sightseeing tour.

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based on 202 reviews

See Details → Duration :2 hours
From $75.65

Bike Tour of Chicago's Lakefront Neighborhoods

This is the tour that made Bobby famous! Bobby’s Bike Hike is America’s longest-running city bicycle tour company, and has been repeatedly recognized for excellence by National Geographic, USA Today, The Associated Press, Conde Nast Traveler, and more! Bobby’s now offers over a dozen specialized tours, but The Lakefront Neighborhoods ride is what started it all. Join one of Bobby’s expert guides on this 3-hour romp through Chicago’s beautiful North Side neighborhoods. See the ever-rising skyscrapers of Streeterville, the luxe residential property of the Gold Coast, the cozy artists’ village of Old Town, and the rolling greenery of Lincoln Park. You’ll finish off with a cruise down the Lakefront Trail, one of the most popular waterfront bike paths in the nation. This leisure-paced journey is sure to make memories that’ll last a lifetime! Tour departs from 540 N. Lake Shore Drive, Chicago.

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based on 198 reviews

See Details → Duration :3 hours
From $54.99

Chicago: Architecture, History & Highlights Small Group Tour

Chicago has it all – amazing architecture, great food, and iconic sights both old and new. This walking tour takes you to some of the city’s best spots alongside a local guide where you’ll get the inside scoop on what makes Chicago so special. Not only that, we’ll throw in a couple of sweet, local treats to keep you going as we explore on foot.

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based on 66 reviews

See Details → Duration :2 hours 30 minutes
From $59

Chicago Private Custom City Tour with Hotel Pick Up

PRICE IS PER VEHICLE AND YOU MAY BRING UP TO 5 PASSENGERS. Thank you for contacting Chicago Private Tours! We would love to help your group discover Chicago. Our services include pick up from your downtown Chicago hotel, a 3-4 hour private City Tour in a chauffeured vehicle, and the services of one of our knowledgeable guides. This means you will have two people working with you the entire time, allowing you to get out of the vehicle with your guide at several stops. These stops include, but are not limited to Millennium Park, Lincoln Park Conservatory, Museum Campus, and more. The tour will be interactive and entertaining, covering history, architecture and culture. We share stories to bring Chicago's rich history to life. Once the tour concludes, we will drop your group off at your preferred, downtown Chicago location.

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based on 181 reviews

See Details → Duration :3 to 4 hours
From $489

Activities & Tours: Illinois

Chicago in a Day: Food, History and Architecture Walking Tour

2-Hour Guided Segway Tour of Chicago

BYOB Spray Paint 'n' Sip at Studio W.I.P. Chicago

Chicago Lincoln Park Indoor Skydiving with Two Flights

Lake Michigan 30-Minute Speedboat Ride

Chicago City Minibus Tour

Chicago Walking Food Tour With Secret Food Tours

Bikes, Bites, and Brews: Chicago's Signature Dishes Bike Tour

Chicago's Ultimate City Bike Tour

Chicago Private Sunset Sail on Lake Michigan

Chicago's Navy Pier Firework Sail Aboard a Tall Ship

Chicago Lakefront and Museum Campus Small-Group Segway Tour

Bike Tour of Chicago's Lakefront Neighborhoods

Chicago: Architecture, History & Highlights Small Group Tour

Chicago Private Custom City Tour with Hotel Pick Up

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