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15 interesting and unusual things you can only do in Chicago

15 interesting and unusual things you can only do in Chicago

15 interesting and unusual things you can only do in Chicago


One of the most wonderful things about Chicago is the opportunity to soak in the breathtaking natural views the Midwest is renowned for, yet turn around to quickly immerse oneself in big-city sensations. From a park devoted to the Wizard of Oz to escape rooms and stories of former gangsters, Chicago offers lots of hidden attractions and cultural venues to discover. So whether you consider yourself a food-lover, a history buff, or an urban adventurer, these are the activities and places that will garner you a nod of approval from residents.

1. Experience a world-class Impressionist collection

The Art Institute of Chicago is the first museum in the world to be top-ranked by Tripadvisor four years in a row, and upon visiting, it’s evident why. At the famous museum in Grant Park, you can discover the biggest Impressionist collection outside Paris and witness modern masterpieces in the magnificent Modern Wing. Stand before masterpieces like Edward Hopper’s “Nighthawks” and tour the world via galleries dedicated to the art of ancient Greece, Japan, Africa, and the Americas. Allocate two or three hours to explore on your own or as a stop on city excursions like the Big Bus Chicago Hop-On Hop-Off Tour.

2. Stroll a park inspired by The Wizard of Oz

For lovers of The Wizard Of Oz, you’ll be happy to discover that Chicago is home to a park devoted to the fantastic story. Featuring Emerald Gardens, Dorothy’s Playlot, and dozens of sculptures of the key characters from the movie, Oz Park is the ideal family-friendly destination for a weekend picnic. Plus, people are encouraged to explore and make use of its public basketball courts, ball fields, tennis courts, and community garden.

3. Eat your way through the city

Chicago Favorite’s Ultimate Food & Walking Tour, a Travelers’ Choice Award Best of the Best winner, mixes tastings of Chicago's most renowned cuisines with visits at local must-see locations. The trip goes deep into Chicago's history, both architectural and gastronomic, via guided discussion over the course of a 1.5-mile walk. You’ll start with deep

dish pizza at the famed Lou Malnati's (day tour) or Gino's East (evening tour), proceed to Millennium Park to learn about its position as a Chicago icon, then stroll down the Chicago River in quest of various distinctive meals, from hot dogs to desserts. Food's provided, and a taste of locally made beer may be added for an extra price.

4. Visit Morton Arboretum

Escape the buzz of city life at the Morton Arboretum, just a 30-minute drive from downtown Chicago. Exhibits rotate periodically across the arboretum's 1,700 acres, and more than 16 miles of hiking paths means you may eternally meander around this lovely urban paradise.

5. Embark on a mobster tour

There are many various ways to journey back in time and learn the history of a new area, and this Chicago gangster tour does that in the most unusual manner. Walk the streets on this guided tour, which blends ghostly tales with legends of the booming '20s. Tours, which are available daily at 11 a.m., 1 p.m., 4 p.m., and 8 p.m., leave from the Royal Sonesta Hotel.

6. Catch a game (or tour) at Wrigley Field

A journey to Chicago wouldn’t be complete without a visit to the renowned Wrigley Field, home of the Chicago Cubs. Originally erected in 1914, this must-see sight is exciting for baseball enthusiasts and history lovers alike. Visit during a Cubs home game to see it in full swing, or join a non-gameday Ivy Tour, which includes the chance to snap a picture in front of the iconic ivy wall. Carve out some extra time to meander around Wrigleyville, the area around the stadium, to see the bustling sports bars, baseball-themed souvenir stores, and Gallagher Way, a favorite meeting spot for neighbors, residents, and tourists.

7. Take in a horrific history lecture (not for the faint of heart) (not for the faint of heart)

At 6,000 square feet, the Medieval Torture Museum is home to hundreds of instruments and techniques used to inflict torture and obtain confessions, giving a disturbing view into one of the darkest chapters of human history. Fans of horror flicks will adore it—just don’t blame us if you can’t sleep at night.

8. Make a visit at the French Market

This European-inspired market offers more than 30 high-quality vendors, making it a one-stop shop for the panoply of the Chicago eating scene, from seafood and French pastries to empanadas and dim cuisine. The French Market is open Monday through Saturday; get goods to or enjoy the in-house dining area, which is reminiscent of a Parisian café.

9. Flaneur in the Osaka Japanese Garden

Originally established in 1893 and rebuilt in the mid 1990s, this serene patch of green on Wooded Island in Jackson Park was dubbed the Osaka Garden in honor of Osaka, Chicago's Japanese sister city. As a Japanese walking garden, or kyuush iki, the place is best experienced by wandering around the trails, which are dotted with cherry trees and rock formations.

10. Stock up on spy materials

Explore the art of deceit and stock up on gadgets and gizmos that may even amaze James Bond at the Wicker Park Secret Agent Supply Co. The shop and bookstore has its own not-so-secret mission: It’s administered by 826CHI, a non-profit organization devoted to aiding kids ages 6-18 with their creative and expository writing abilities, and helping their instructors motivate them pupils to write. There's lots of kid-friendly programming, including interactive games, author readings, and writing workshops.

11. Surround yourself with flora at the Garfield Park Conservatory

The Garfield Park Conservatory is one of the biggest and most gorgeous conservatories in the world—and admittance is free, with reservation. Often referred to as “landscape art behind glass,” the Conservatory shows hundreds of plant species from across the globe within eight indoor display gardens. Year-round, guests may experience the lush vegetation and warm temperatures inside via more than 10 acres of gardens. Be sure to check out the events calendar for information on the various cultural performances, hands-on seminars, unusual fundraisers, and educational demos that take place throughout the year.

12. Cash in at the Money Museum

Wander through the extensive galleries that show the history of American cash at this specialty museum. The Money Museum at the Federal Bank Reserve has an interactive aspect, too, due to the dollar-shredding machine that shreds up old notes to form "mon-fetti," which visitors may take home as a unique gift. You'll walk away with roughly $300 in cash—shredded, of course.

13. Tour a renowned Chicago brewery

Perhaps the most renowned Chicago brewery, Goose Island was established in 1988 and is the oldest continually running craft brewery in Chicago. The historic brewhouse at 1800 N. Clybourn makes limited, one-of-a-kind beers onsite and offers upscale pub cuisine. You can also visit the Goose Island production brewery on West Fulton Street; frequent weekend tours cover all stages of the beer-making process, from the Brew Deck (where you can see brewers at work) to the fermentation cellar, bottling line, and beyond. And sure, you may taste the products along the way.

14. Take to the skies at TILT

Towering 94 storeys above street level at the 360 Chicago Observation Deck, TILT is Chicago’s biggest thrill coaster that is—quite literally—changing the way people perceive the city; that is, from 1,030 feet above. The gigantic movable platform leans up to eight people at a time over the edge of the Magnificent Mile and Chicago's famed skyline. If you choose to sit this one out—or maybe want to settle your nerves after the adrenaline rush—hit BAR 94 next door.

15. See the city from a new aspect

If you’re not keen on heights, the Chicago River or Monroe Harbor provide different viewpoints of the city, especially on warm, clear days. Link up with Urban Kayaks for kayak rentals and guided trips. There’s also a membership option for a seasonal pass, which is a terrific method for frequent tourists or residents who want to remain cool all summer long.


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