The It-Girl’s Guide To Chicago

This weekend began the Pitchfork music festival in Chicago—featuring PJ Harvey, Dirty Projectors, LCD Soundsystem, A Tribe Called Quest, Solange and more—which will be followed closely by the ever-epic Lollapalooza at the beginning of August. If you’re using one or both of these events as an excuse to enjoy Chicago in one of its rare warm (if, too warm) months, we’re here to help you optimize your time outside of the festival gates. Here, where to go, eat, sleep, shop and more in one of our favorite cities in the U.S.


Everything You'll Want To Do In Chi-Town

The Robey

Where To Stay

Vogue recently named the Hotel Robey one of the "coolest hotels in Chicago," and we couldn't agree more. The historic art deco building is located in hip Wicker Park and offers a rooftop cocktail bar for imbibing with a view and shares the Cabana Club—a pool—with its sister property next door, The Hollander.

Other Chi-town hotels we love include Freehand, Hotel Palomar, Longman & Eagle, The James and Soho House. We always love an Ace Hotel as well, and Chicago's is brand new and in preview mode—book a room now and a portion of the proceeds go to benefit community partners.


Where To Eat

The real question here is where not to eat. Chicago is definitely a foodie's dream and then some, so this was an incredibly difficult-to-curate list that is far from comprehensive and yet probably overwhelming all the same.

Proxi is currently one of Eater Chicago's hottest restaurants of the summer. Only a month old, it boasts meat-heavy, street-food influences. Split-Rail, on the other hand, draws more from traditional American cuisine (think chicken nuggets), for those wanting comfort foods after (or before) festival-ing. Cajun and creole spot Big Jones is currently listed as one of Eater's essential brunch destinations in the city—don't miss the Biscuits and Debris Gravy, particularly if you're fighting a hangover. Parachute is one of the most critically-acclaimed restaurants in America, and while it's a difficult table to get, it's well worth the effort if you manage to snag a seat. Monteverde is a similarly-difficult reservation to get—try the pastas if you manage to make it happen.

As our list is too long to go on, we'll simply list the rest of our favorites and let you explore on your own: Leña Brava and Cruz Blanca (both Rick Bayless); Au Cheval (eggs are everything here); Girl & The Goat (many a chef's favorite); Fat Rice (Portugal & China meet here, in inventive fusion); Dove's Luncheonette ("Mex-Tex"); Pequod Pizza (for a real deep-dish experience); Bang Bang Pie & Biscuits (just read the menu!); The Purple Pig (for breakfast); Mott Street (for Asian street food); Mindy's Hot Chocolate (for brunch); Piccolo Sogno (the best patio in town); Portillo's (Chicago street food); The Publican (one of Eater's best restaurants in America); Grace (recent James Beard-award winner), Calumet Fisheries (Anthony Bourdain-beloved); and Alinea (of course!)


Where To Drink

If you want to pre- or post-party around festival set times, here are a few ideas: Maude’s Liquor Bar (try a smash); Lost Lake (tiki!); The Violet Hour (pre-Prohibition-style cocktails); The Robey (rooftop!); Apogee (rooftop!); Noyane (rooftop!) Otto Mezzo (late-night drinks); The Lunatic, The Lover & The Poet (the name alone!); Quiote (speakeasy-style mezcal bar); Tapster (pour-your-own-beer bar); and Parson's Chicken & Fish (dangerous Negroni slushies).


Where To Shop

For upscale shopping—think Gucci—make Magnificent Mile your move. For more of a local boutique shopping experience, try North Damen Avenue and the Bucktown and Wicker Park neighborhoods.

Specific shops to check out include Merz Apothecary (beauty from all over the world), P.O.S.H. (curated antiques); Blake (Gwyneth Paltrow's favorite shop for high-end designer wares); Chalk Boutique (big lables, think The Row); Ikram (with an owner who styled Michelle Obama); Penelope's (mens and women's, think A.P.C.); Asrai Garden (jewelry and home decor); Salvage One (salvaged furniture); Space 519 (a modern general store, boasting everything from stationary to designer clothing); Luxury Garage Sale (high-end consignment); Dovetail (contemporary and vintage); Azeeza (Sophia Bush is a fan); Moon Voyage (quirky curation of an eclectic mix of designers); and Gather Home + Lifestyle (go for the Insta opps).