The Best Things to Do in Downtown Chicago

Shop at notable boutiques, take in lunch by the river and enjoy Downtown Chicago.

In the '80s, "Ferris Bueller" blew off school to soak up downtown Chicago. While we don't encourage you to pretend to be Abe Froman, the sausage king of Chicago, we absolutely recommend taking in the city. Dare to step onto the glass ledge at Skydeck atop the Willis Tower, grab a chic lunch at a see-and-be-seen restaurant and catch a game at Wrigley Field. Chicago has more than to offer than the AWOL teen ever imagined. Here, our picks for a more grown up adventure in downtown Chicago. 


Chicago Sports Museum

Things to Do in Downtown Chicago

Chicago Sports Museum: Play and pay homage to the Chicago greats at this interactive sports museum. Measure your jump against Michael Jordan's and try to score a goal against the Hawks' Tony Esposito. Step into the replica of Wrigley Field's broadcast booth and channel your inner Harry Caray. The forensic sports exhibit explores how CSI-type technology has been used to solve some of Chicago's most infamous sports mysteries. 

The American Writers Museum: Jack Kerouac, Mark Twain, Maya Angelou—they are all here at the American Writers Museum. Maybe not physically, but their works are celebrated through interactive exhibits at this museum dedicated to American literature. See the word waterfall—a presentation that combines words, imagery and soundscapes to create a contemplative experience. Write your own story in the Mind of a Writer exhibit and post it on the museum's story wall. This isn't some museum full of dusty manuscripts, everything is designed to be interactive and engaging—a digital-age look at our literary history.  

The Art Institute of Chicago: The second largest art museum in the country is the Art Institute of Chicago includes iconic works by Georges Seurat, Pablo Picasso, Andy Warhol and Grant Wood. Collections range from Art of the Americas to architecture and design to textiles to arms and armor of the Renaissance. Don't miss the Thorne Miniature Rooms, scaled one inch to one foot featuring interior design from the late 13th century to the 1930s in Europe and the 17th century to the 1930s in America.

Maggie Daley Park: Maggie Daley Park takes the neighborhood playground to a whole new level. This recreation center features a climbing wall, a roller skating path, play gardens tailored to specific age groups, tennis courts and mini golf. A snack bar offers soup, sandwiches, nonalcoholic drinks and treats for purchase. Stroll through the cancer survivor's garden and explore the three stages of healing: acceptance, support and celebration.  


Bridge House Tavern

Where to Eat in Downtown Chicago

Bridge House Tavern: Spend the day out on the Chicago River, then dock at Bridge House Tavern for dinner and a drink. It's one of the only restaurant in Chicago where you can do so, and it offers some of the best views in the city. The "Industrial Tavern" atmosphere features wood panel and flagstone walls. The menu is packed with exciting flavor combinations like duck tacos with curry ranch slaw, Porchetta—pork roast stuffed with Italian sausage— and buffalo fried oysters. Pair it with a selection from the robust wine and specialty cocktail list and you've got a perfect sun-soaked afternoon.

Mariposa: Shopping on the Mag Mile? Break for lunch at Mariposa, inside Neiman Marcus. This elegant fine-dining restaurant located inside the store offers a touch of something special during a shopping excursion. Dishes are locally sourced whenever possible and support a health-conscious lifestyle. Enjoy shrimp and grits, sautèed salmon or a mahi-mahi taco. 

Ramen-San: Choose your broth, seasonings, meat, and toppings to create your perfect bowl of ramen at this local ramen shop and wash it down with Japanese whiskey, Asian-inspired cocktails or craft beer. The atmosphere is comfortable and casual, warmed by exposed brick and reclaimed wood. 


Cocktails at Otto Mezzo

Where to Get a Cocktail

Apogee: Twenty-six stories above the heart of Chicago stands Apogee, whose moniker literally means "the point in orbit at which an object is the furthest from earth." The rooftop bar is on top of the Dana Hotel and Spa. Cocktails are served in unique, hand-blown glassware and custom ceramic vessels designed to be shared by groups of friends. All of the produce, herbs and flowers are carefully sourced daily. Look for unusual garnishes such as dehydrated starfruit in a rum, cognac and absinthe drink called Panda Party; or burnt marshmallows and coconut ash in a Fifth Char, featuring Jim Beam Rye Whiskey, Flaernum and Demerara. 

Otto Mezzo: This Italian-inspired cocktail bar is taking a different direction by creating food to complement its cocktails. It caters to the late-night crowd, opening at 8:30 pm. Start with marinated and roasted olives, savor a different pasta each night—or try a panini—and finish it off with an amaro-flavored gelato. The bar is helmed by Brandon Phillips, who was named Bartender of the Year by the Chicago Tribune in 2016. 


Ikram boutique in Chicago

Where to Shop

Ikram: This ultra luxe boutique makes an unmistakable statement from the street. Its bold red exterior and circular doors and windows sets it apart from the sand-colored, brick and black square buildings around it. Inside is a beautiful selection of clothing, shoes, jewelry, bags and other accessories chosen by one of fashion's elite, Ikram Goldman (she's helped launch the careers of designers like Thakoon, Prabal Gurung and Proenza Schouler). Designer brands include Lanvin, Alexander McQueen, Narciso Rodriguez and Viktor & Rolf. 

Azeeza: Chicagoan Azeeza Khan may have become a global phenom (her designs are carried in Barney's and she's a favorite of publications like Vogue India), but she kept her flagship store in her home city. The chic white style oasis on the Magnificent Mile is a top destination according to Forbes List. Her designs are worn by notable women like Sarah Jessica Parker, Sophia Bush and Gabrielle Union. The eponymous brand is known for its feminine silhouettes, silk gowns, crystal collars, and rich jewel tones. The store also offers consultations, custom fittings and global shipping. 

Restoration Hardware: Restoration Hardware chose Chicago to build something extra special. It's Gold Coast flagship isn't just a furniture store, it is a dazzlingly well-appointed decor mecca, stuffed with high-end, luxury furniture lighting, textiles, accessories and outdoor furnishings. It's also home to the 3 Arts Club Cafè, a beautiful restaurant located in the store's indoor garden where diners brunch under the opulent chandelier. 

Lisa Kaylor
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