Chicago skyline as seen from the Willis Tower Skydeck

Chicago’s Most Unique Travel Activities

Chicago’s Most Unique Travel Activities

By Lola Mendez

Get off-the-beaten-path in Chicago for an authentic take on the Midwestern city. Fat Tire Tours offers several in-depth cultural cycle and Segway tours that will introduce you to the Windy City. After you’ve spun around town, head off on one of these unique-to-Chicago experiential travel activities.

Take a quirky museum tour. 

Go on a museum tour of the Art Institute of Chicago with Museum Hack led by local Chicago Drag Queen, Wanda Screw, that’s sure to be anything but boring. Museum Hack’s best-selling museum tour is the feminist Badass Bitches. If you’d prefer to spend your daylight hours outside then go on the newly launched Thursday Night Tour. Museum Hack tours always run Mondays, Thursdays (free museum admission for IL residents), and Saturdays for $59-$69 per tour. The Badass Bitches and Drag Tour are sometimes available on Saturdays.

Snap the perfect photo.

Try out your photography skills on a guided tour around Chicago to find the best spots for pictures with professional photographer and city expert on Tour Through a Lens. The tour is customizable based on what sort of places you’d like to capture and your camera equipment. As you’ll build your own tour, you can book the photo walk whenever suits your schedule during your trip to Chicago.

See the whole city in tiny form.

Visit the Chicago City Model Experience to check out over 4,000 miniature buildings with interactive elements that’ll introduce you to the fascinating history of the city of Chicago. At the Drake Family Skyscraper Gallery’s Building Tall exhibit there are scale models of famous skyscrapers from Chicago and around the world. Continue your immersive education at the Chicago Gallery, which features the City of Architecture and From Me to We: Imagining the City of 2050 timeline where several local architects offer insights and predictions for the future of Chicago. The Chicago City Model Experience offers complimentary general admission and is open daily from 9 AM to 5 PM.

Eat your way through Chicago’s classic foods.

Hungry? Jump on the Chicago Food Planet Tour—the longest-running and most celebrated food tour in Chicago. Experience the city by taste-testing the culinary scene while learning about Chicago’s historic neighborhoods and delicious foods. Choose from the 2 or 3-hour walking food tour experiences which are suitable for all ages and fitness levels. Tours range from $50-$75 and are led by Chicagoans who know the most savory spots in their city including unique specialty food stores, locally-owned restaurants, and ethnic eateries. Don’t forget to grab a bag of the world-famous Garrett’s popcorn to gorge on once you’ve finished digesting Chicago’s famous deep-dish pizza.

Hike at a unique urban green space.

The 606 is one of Chicago’s newest green spaces. The elevated linear trail used to be a railroad line. The park system runs along the Bloomingdale Trail for 2.7 miles between Ashland Avenue and Ridgeway Street. There are access points every quarter-mile or so and 17 accessible ramps.

Get playful and ignite your sense of wonder.

Stop by the wndr museum, Chicago’s experiential art museum that encourages folks to enjoy discovering the sixth sense of wonder. All ages will enjoy exploring the Yayoi Kusama’s ‘Let’s Survive Forever’ Infinity Mirror Room, seeing the sequin tunnel, riding down the rainbow slide, and chilling out in the zen room. Other rooms are dedicated to language, music, color, and more. Tickets must be purchased in advance online for $32 and visiting hours are from Wednesday — Sunday at various times.

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Walk on air, if you dare.

The Willis (formerly known as Sears) Tower is the second tallest building in the Western Hemisphere. Head to the 1,353 feet tall Skydeck, the highest observation deck in the U.S. To walk on air visit the 103rd-floor glass viewing platform, The Ledge. More than 1.7 million visitors visit the glass balcony viewing boxes that extend 4-feet out of the Willis Tower every year. Offering a spectacular view that spans 50-miles and offer vistas of four states, the Skydeck is a must-do uniquely Chicago experience. If you’re looking for a more daring experience, go to The Tilt instead. 

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It’s wine O’Clock.

Tucked away in the Chicago suburb of Roselle is the urban family-owned Lynfred Winery. Take a rideshare to reach the 40 year-old winery which is a 25-minute drive west of O’Hare Airport or hop on the Metra for 45-minutes from Union Station! Don’t drive yourself as you’ll want to taste all the amazing wines. Lynfred wines are created by Chilean-born winemakers Andres Basso and Rodrigo Gonzalez. Lynfred Winery produces over 70 varietals and 30,000 cases of fine wine per year. Daily wine tastings are open to the public from 10 AM to 7 PM—for $11 you can try 7 wines. Check their calendar to see if your visit coordinates with many other weekly events such as the Winemaker Roundtable and Tasty Tuesday events.  

Be dazzled by a light show. 

At night, head to Art on theMART to witness the long-term public art installation that illuminates the facade of Chicago’s Merchandise Mart with spectacular digital projections from 7 days a week through September 29th and begin around 8:30 PM or 15 minutes after sunset. The current projections were created by renowned lighting designer John Boesche and reflect the 2019 Year of Chicago Theatre theme. 

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Get to know the Gangs of Chicago.

Airbnb experiences offer a 2-hour Gangsters and Ghosts Tours led by a local historian for $27. Hit the streets and hear the haunting stories of past the violent past that formed the city. Learn about the crimes, deals, and busts of the Chicago Loop Vice District. Be sure to bring some ghost repellent!