With Lollapalooza right around the corner, creative types and festival-goers alike will be descending upon the Windy City all week long. Whether you’re booking a trip to enjoy the music or to find the best slice of pizza money can buy, the charms of Chicago—from jaw-dropping architecture and inspiring concept stores to farm-fresh restaurants and juiceries—are sure to capture your heart for years to come.
What to See
Greetings from Chicago Mural—Whether you’re an amateur or an Instagram pro, like blogger Jess Keys, a pit stop at this mural is a must for anyone visiting the Windy City for the first time. After all, picture or it didn’t happen, right?
Cloud Gate—British artist Anish Kapoor’s reflective bean is one of the most recognizable public sculptures on earth, with a stunning backdrop to boot, so it’s hard not to take a great snap of it. Make like photographer Paul Octavious and stop by Millennium Park to bask in its reflective beauty (and take the selfie of a lifetime!).
Gather Home + Lifestyle—If minimalist, modern, or organic are words you’d include when describing your personal style, then this dream of a store was made for you. Stop by to swoon over the handmade ceramics, just as Maryland-based creative Luke Wright does whenever he’s in town, and find yourself wondering how they keep all those plants looking perfect.
Logan Square—Go for a wander in Logan Square, like blogger Alex Zouaghi, and you’re bound to be delighted and surprised at every turn, with cute coffee shops and cafés opening up in this neighborhood every day.
Where to Eat
Parson’s Chicken & Fish—For the best fried chicken in the city, a stop to one of Rosie Clayton’s favorite casual haunts, Parson’s, is an absolute must. Come with a big appetite and time to spare—you’ll want to relax on the sunny patio for hours.
Jeni’s Southport—Hot summer days and ice cream go together like peanut butter and jelly, and in Chicago, nobody does it better than Jeni’s Splendid Ice Creams. Stop by either of its two Chi-Town locations for an all-natural scoop (or two!), and stay for the darling diner-inspired design, as travel photographer Andrea Tamburrini does.
La Sirena Clandestina—Chicago-based photographer Nathan Michael knows a thing or two about finding the most photogenic local haunts, so trust when he says that this is the place to be. Serving both authentic and deconstructed Brazilian cuisine and cocktails in a design-driven space, La Sirena is guaranteed to be a memorable meal.
Pomp & Circumstance—Whether you had a little too much fun the night before and need some carbs ASAP or are looking to have a little too much fun tonight, pop by Taylor Wolfe’s go-to brunch and cocktail spot, Pomp & Circumstance, to let loose. After all, its motto is “Where food is food and drinks are stiff.” Cheers!
Where to Drink
Bernie’s Lunch & Supper—With the perfect mix of old-timey charm (exposed brick, bistro-style lighting) and modern blogger appeal (brass accents, herringbone tiles), Bernie’s is both a local standby and a tourist destination. Follow the lead of The Everygirl cofounder Danielle Moss and belly on up to the bar for great snaps and cocktails alike.
The Hampton Social—“Rosé all day” is our summer mantra, and no place embodies that spirit more than The Hampton Social. It’s basically a blogger’s dream come true, and it’s open seven days a week. Stop by for a glass as Jessica Sturdy does, and make sure to snap its signature neon sign before the sun goes down.
Hopewell Brewing Co.—If “unpretentious, fresh, good beer” is your thing, you’ve come to the right place. With a minimalist diner vibe, great natural light, and even better brews, Hopewell Brewing is the place to go for predinner drinks without the fuss.
Left Coast Food + Juice—With an interior that was practically made to be double-tapped, Left Coast is as ’grammable as they come. Another bonus? Lifestyle blogger Jill Green recommends it for on-the-go goodies that fit a variety of dietary needs, such as the Whole 30 diet or gluten- and dairy-free.
Where to Stay
The Peninsula Chicago—One of the most beautiful luxury hotels in the Windy City, The Peninsula also happens to be one of the most convenient; it’s only a 3-minute walk to the Museum of Contemporary Art and another 15 to Lollapalooza locale Grant Park. We recommend taking a dip in the stunning lap pool, à la Jenny Cipoletti.
Soho House—Even if you’re not a club member, you can still reap all the benefits of Soho House’s Chicago outpost as a hotel guest. That means exclusive access to the club’s bars, restaurant, spa, and rooftop pool can be yours—even if only for the weekend. Pro tip: Cozy up to the bar at The Allis early, as Blair Staky did, for the best seats and people-watching.
Public Chicago—Formerly the famed Ambassador East, Public Chicago has undergone a complete transformation to become a modern hotel steeped in history (with the good bones to prove it!). In addition to the sleek, minimalist design, snapped here by fashion blogger Naty Michele, the hotel boasts both a pet-friendly policy and a new food concept by world-famous chef Jean-Georges Vongerichten. Bon appétit!