PLAY
Museum of Contemporary Chicago
See some of the finest contemporary art in all of Chicago, including “David Bowie Is…,” an upcoming exhibition of all things David Bowie that opens next month.
The Great Chicago Fire Festival
On October 4 the Red Moon Theater will present a spectacle along the Chicago River that will incorporate special effects, dance and fire! The city’s answer to Mardi Gras in New Orleans and the Running of the Bulls in Pamplona, this festival celebrates the city’s grit and strength.
SHOP
Apartment Number 9
For the best menswear in Chicago, pay a visit to Apartment Number 9, where you’ll find labels like A.P.C., Warby Parker and Jack Spade, as well as homegrown favorite Astor + Banks.
EAT & DRINK
Art of Pizza
Head to Art of Pizza for some of the deep dish that the Windy City has to offer. The tomato sauce is a little spicy, the crust is nice and flakey, and they dot the ooey gooey cheese with dots of oregano. How could you go wrong here?
Fulton Market Kitchen
Located in one of the city’s most up-and-coming neighborhoods, the Fulton Market Kitchen is decorated with street art by local Chicago artists, and you can even purchase some of the creations on the wall. Oh yeah, the microbrew selection is superb, as are the dishes, which include ravioli and foie as well as a suckling pig for two.
Nightwood
If farm-to-table cuisine is what you’re after, then head to Nightwood. Based in Pilsen, this charming restaurant offers a delicious wood-grilled chicken breast and an awesome salad made with City Farm head lettuce, shallot aigre-doux, hard boiled egg, radish, bacon, croutons, parmesan and a green goddess dressing.
Punch House
Housed in the basement of a former public house from the 19th century, this bar feels like a dive bar and ‘70s rec room combined into one. The punches range from a classic Pimm’s Cup to the sinful Dusek Punch #2 — a mix of bourbon, rum, hefeweizen, pineapple, lime, ango and absinthe. Don’t forget to check out the rest of the multi-use space, which also includes a restaurant and a concert hall.
STAY
The Chicago Athletic Association
Once you get here you’ll never want to leave. Between the cool Roman & Williams decor, the games and the food — there’s a Shake Shack on the ground floor! — and the roof top bar, there’s plenty to do at this hotel.
The Langham
If you want sheer luxury, this is the place to stay. Situated in a building designed by the great architect Ludwig Mies van der Rohe, The Langham is just steps away from Grant Park and the famed Magnificent Mile.
PUBLIC
For those in need of affordable cool, Ian Schrager’s (one of the owners of the famed Studio 54) Chicago boutique hotel PUBLIC is the place to stay. For an extra-added bonus, the hotel is also home to the legendary Pump Room, an eatery now helmed by chef Jean-Georges Vongerichten, used to be the hot spot of choice for countless celebrities, including Frank Sinatra and Marilyn Monroe.
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