No one enjoys summer more than Chicagoites—after all, it’s their reward for surviving up to six months of tundra-like climates. So it’s no wonder that those few months are filled with locals out in the streets and parks, on rooftop bars, and crowding the lakeshore for beach volleyball, bike rides, and swimming. Here’s how you should experience the city in summertime like a true local.
DAY 1: The Beach
STAY
Voted the top Chicago hotel by Travelerreaders this year, The Langham delivers on location and luxury, occupying 13 floors of an iconic Mies van der Rohe skyscraper in the heart of downtown. Many of the suites come with views of the Chicago River.
For a different experience, Longman & Eagle in Logan Square (whose six rooms come with in-room cassette players and complimentary mix tapes) is a Chicago riff on the classic bed and breakfast—it’s the rare inn with a Michelin-starred restaurant and a Sunday doughnut shop…all steps from your bed.
PLAY
Pack a towel and swimsuit and find a spot along Chicago’s 27 miles of beaches. We recommend North Avenue Beach, a great (albeit crowded) spot in Lincoln Park. Join a pick-up game of volleyball before grabbing a post-game bite at the beachside bar and grill Castaways (don't miss its burger or the shrimp ceviche). And try not to let the beach’s free Wi-Fi distract you from taking a dip—true, the water temperature is usually pretty brisk, but on a humid summer day, there’s nothing better.
It’s also smart to plan a trip around one of the city’s summer festivals—there’s a never-ending lineup of events, though we love The Blues Festival (the biggest free blues fest in the world, drawing the likes of Ray Charles and B.B. King over the years), the Jazz Festival (a Labor Day weekend tradition in the city), and Venetian Night in early September. Grab a spot along the lakefront to watch the decorated, brightly lit boats parade by.
DRINK
Chicagoans split their summer bar time between two spots: rooftop patios and brewpubs. Wind permitting, head to Drumbar, which is perched atop the Gold Coast–located Raffaello Hotel, 18 floors up; it’s a buzzy spot serving single-cask scotches along with views of Lake Michigan. Meanwhile, the cozy West Loop rooftop at Little Goat Diner is a favorite among residents for its rotating beer menu.
Day 2: Go Shopping
SHOP
Chicago has a wealth of trendy boutiques, luxury lines, and art shops from River North to Lincoln Square, but Wicker Park/Bucktown has one of the best mixes of shops and wares (more on that in a minute). For luxury shopping, skip Michigan Avenue in favor of nearby Oak Street in the Gold Coast. Emporio Armani, Tom Ford, Jimmy Choo, Kate Spade, Carolina Herrera, Dolce & Gabbana, Christian Louboutin, and Hermès are just a few of the labels with addresses there.
EAT
If all you do on a visit to Chicago is eat, no one will blame you. The city’s food scene includes 24 Michelin-starred restaurants and hundreds more catering exclusively to Chicago’s famous staples of Italian beef, pizza, and hot dogs. The Publican won’t disappoint meat lovers (order the charcuterie plate and the suckling pig), nor will Big Star with its chorizo or pork belly tacos. GT Fish & Oyster has an inventive menu perfect for sharing (don’t miss the oyster po’boy sliders with kimchi). If you’re really looking to splurge and don’t want to be disappointed, book tickets to three-star Alinea for a foray into chef Grant Achatz’s inimitable take on molecular gastronomy.
DRINK
Time for a local beer: The big names in the Chicago microbrewery scene are Revolution Brewing, whose converted Logan Square warehouse is always packed (and deservingly so), and North Center–based Half Acre, where locals gather in the exposed-brick tap room to sample from the ever-changing lineup of suds; order the Daisy Cutter pale ale if you can.
Day 3: Get Cultured
EXPLORE
Since the 1960s, when the Chicago Imagists (painters Ed Paschke, Jim Nutt, and Roger Brown among them) attracted international attention with their shows at the Hyde Park Art Center, the city has been a breeding ground for emerging artists and innovative art dealers. Today the primary art gallery district is concentrated in River North—the area west of the Magnificent Mile and north of the Chicago River— where century-old redbrick warehouses have been converted into lofty exhibition spaces. More recently, a new generation of gallery owners has set up shop in the West Loop neighborhood, where you'll tend to find more cutting-edge work. Be sure to check out the Chicago Artists Coalition, featuring more than 120 local artists, and Kavi Gupta Gallery, who (until very recently) was repping Theaster Gates, considered by many one of the most influential creators in the city.
Meanwhile, the gentrification of the Wicker Park/Bucktown area has led to a crop of new restaurants and bars, as well as new retailers that reflect the neighborhood's bohemian spirit. Mixed in with old neighborhood businesses (discount furniture stores, religious icon purveyors) is a range of galleries, clothing boutiques, and antique furniture shops like Salvage One on Hubbard Street. Despite the hefty price tags in many of them, the neighborhood still has its charms.
SHOP
To browse the best of Wicker Park/Bucktown, start at the Damen El stop on the Blue Line, and walk north along Damen Avenue to Armitage Avenue to scope out the trendiest shops: Futurgarb (men and women's clothing), Reckless Records (music), and Myopic Books (used books). If you have time, some stores are also scattered along Milwaukee Avenue south of North Avenue.
PLAY
No visit to Chicago, especially in the summer, would be complete without an architecture boat tour along the Chicago River. Book Chicago Architecture Foundation’s 7:30 twilight cruise aboard Chicago’s First Lady to catch more than 50 of the city's architectural icons—Raymond Hood’s Gothic Revival Tribune Tower among them—as the sun sets. It’s a perfect post-dinner activity.