15 fun things you can only do in Chicago

One of the most beautiful things about Chicago is the ability to take in the stunning natural scenes the Midwest is known for, then turn around to immediately immerse yourself in big-city vibes. From a park dedicated to the Wizard of Oz to escape rooms and tales of former gangsters, Chicago has plenty of hidden attractions and cultural sites to explore. So whether you consider yourself a food-lover, a history buff, or an urban explorer, here are the activities and sights that will gain you a nod of approval from locals.

The Art Institute of Chicago is the only museum in the world to be top-ranked by Tripadvisor four years in a row, and upon visiting, it’s clear why. At the renowned museum in Grant Park, you can experience the greatest Impressionist collection outside Paris and view contemporary masterpieces in the spectacular Modern Wing. Stand before classics like Edward Hopper’s “Nighthawks” and travel the globe through galleries devoted to the art of ancient Greece, Japan, Africa, and the Americas. Allocate two or three hours to visit on your own or as a stop on city tours like the Big Bus Chicago Hop-On Hop-Off Tour.

For fans of The Wizard Of Oz, you’ll be delighted to know that Chicago is home to a park dedicated to the magical tale. Featuring Emerald Gardens, Dorothy’s Playlot, and plenty of statues of the main characters from the movie, Oz Park is the perfect family-friendly spot for a weekend picnic. Plus, guests are invited to enjoy and make use of its public basketball courts, ball fields, tennis courts, and community garden.

Chicago Favorite’s Ultimate Food & Walking Tour, a Travelers’ Choice Award Best of the Best winner, combines tastes of Chicago's most famous foods with stops at local must-see landmarks. The tour dives deep into Chicago's history, both architectural and culinary, through guided commentary over the course of a 1.5-mile walk. You’ll start with deep dish pizza at the famous Lou Malnati's (day tour) or Gino's East (evening tour), head to Millennium Park to learn about its role as a Chicago landmark, then walk along the Chicago River in pursuit of other signature bites, from hot dogs to sweets. Food's included, and a tasting of locally brewed beer can be added for an additional charge.

Escape the hustle of city life at the Morton Arboretum, located a 30-minute drive from downtown Chicago. Exhibits vary seasonally throughout the arboretum's 1,700 acres, and more than 16 miles of hiking trails means you can endlessly wander around this beautiful urban oasis.

There are many different ways to step back in time and uncover the history of a new place, and this Chicago gangster tour accomplishes that in the most unique way. Walk the streets on this guided tour, which combines supernatural tales with stories of the roaring '20s. Tours, which are offered daily at 11 a.m., 1 p.m., 4 p.m., and 8 p.m., depart from the Royal Sonesta Hotel.

A trip to Chicago wouldn’t be complete without a visit to the legendary Wrigley Field, home of the Chicago Cubs. Originally built in 1914, this must-see attraction is fun for baseball fans and history buffs alike. Visit during a Cubs home game to see it in full swing, or join a non-gameday Ivy Tour, which includes the opportunity to take a photo in front of the historic ivy wall. Carve out some extra time to stroll around Wrigleyville, the neighborhood surrounding the stadium, to experience the lively sports bars, baseball-themed gift shops, and Gallagher Way, a popular gathering place for neighbors, locals, and visitors.

At 6,000 square feet, the Medieval Torture Museum is home to hundreds of tools and devices used to inflict pain and secure confessions, offering a chilling look into one of the darkest chapters of human history. Fans of horror films will love it—just don’t blame us if you can’t sleep at night.

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

Originally built in 1893 and restored in the mid 1990s, this tranquil slice of green on Wooded Island in Jackson Park was designated the Osaka Garden in honor of Osaka, Chicago's Japanese sister city. As a Japanese strolling garden, or kyuush iki, the space is best enjoyed by meandering along the paths, which are lined with cherry trees and rock formations.

Explore the art of deception and stock up on gadgets and gizmos that may even impress James Bond at the Wicker Park Secret Agent Supply Co. The storefront and bookstore has its own not-so-secret mission: It’s run by 826CHI, a non-profit organization dedicated to supporting students aged 6-18 with their creative and expository writing skills, and helping their teachers inspire them students to write. There's plenty of kid-friendly programming, including interactive activities, author readings, and writing sessions.

The Garfield Park Conservatory is one of the largest and most stunning conservatories in the world—and entry is free, with reservation. Often referred to as “landscape art under glass,” the Conservatory showcases thousands of plant species from around the world throughout eight indoor display gardens. Year-round, visitors can enjoy the lush flora and tropical temperatures indoors through more than 10 acres of gardens. Be sure to check out the events calendar for information on the many cultural performances, hands-on classes, unique fundraisers, and educational demonstrations that take place throughout the year.

Wander through the rich exhibitions that display the history of American currency at this niche museum. The Money Museum at the Federal Bank Reserve has an interactive element, too, thanks to the dollar-shredding machine that rips up old bills to create "mon-fetti," which visitors can take home as a unique souvenir. You'll walk away with about $300 in cash—shredded, of course.

Perhaps the most famous Chicago brewery, Goose Island was founded in 1988 and is the longest continuously operating craft brewery in Chicago. The historic brewhouse at 1800 N. Clybourn brews limited, one-of-a-kind beers onsite and serves elevated pub fare. You can also visit the Goose Island production brewery on West Fulton Street; regular weekend tours cover all aspects of the beer-making process, from the Brew Deck (where you can watch brewers in action) through the fermentation cellar, packaging line, and beyond. And yes, you can sample the goods along the way.

Towering 94 stories above street level at the 360 Chicago Observation Deck, TILT is Chicago’s highest thrill ride that is—quite literally—changing the way visitors see the city; that is, from 1,030 feet up. The giant moving platform leans up to eight visitors at a time over the edge of the Magnificent Mile and Chicago's famous skyline. If you prefer to sit this one out—or perhaps want to quell your nerves after the adrenaline rush—hit BAR 94 next door.

If you’re not keen on heights, the Chicago River or Monroe Harbor offer new perspectives of the city, particularly on warm, clear days. Link up with Urban Kayaks for kayak rentals and guided tours. There’s also a membership option for a seasonal pass, which is a great way for regular visitors or locals who want to stay cool all summer long.