Posted June 20, 2020

Chicago’s Best Neighborhoods for Summer Fun


There’s no place like Chicago in the summer. As soon as Buckingham Fountain flips the switch in May, it’s all systems go. Bring on the street festivals, free concerts, fireworks, family events…and, oh, those outdoor patios.

Find your ideal scene in Chicago’s most animated neighborhoods. Here’s where to head, what to do, and where to stay while you’re in town.

Chicago Riverwalk

riverwalk image credit joncrenshaw via twenty

Equal parts relaxing and entertaining, gaze at Chicago’s famed skyline from the Riverwalk. Image Credit: @jon.crenshaw via Twenty20

The scene: This beautifully developed 1.25-mile stretch along the south bank of the Chicago River, from Lake Shore Drive to Lake Street, is packed with places to eat, drink and watch the boats drift by. You’ll find yourself at the feet of some of the city’s most impressive architecture, like Wrigley Building and Tribune Tower.

The stops: Sip housemade wine at City Winery Chicago at The Riverwalk, eat like the Irish at O’Brien’s Riverwalk Café, get your barbecue fix at Tiny Tapp, or drink from a coconut at Island Party Hut Tiki Bar. From Riverwalk you can also set out on an open-air sightseeing cruise with Chicago Architecture Center River Cruise, Wendella Sightseeing or Mercury Chicago’s Skyline Cruiseline. Chicago Water Taxi excursions skim you to various points along the river; from Riverwalk you can travel all the way to Chinatown. Cool down inside McCormick Bridgehouse & Chicago River Museum, featuring exhibits on the river’s history, particularly its storied moveable bridges. Riverwalk is a great spot from which to watch Navy Pier’s fireworks, which go off every Wednesday and Saturday night throughout summer.

city winery exterior image credit john zomot

14 wines on tap, world-class live music, and a spacious outdoor patio? Count us in for an evening sipping vino at City Winery. Image Credit: John Zomot

The stay: The Kimpton Hotel Monaco Chicago, located just south of Riverwalk on Wabash Street, is a piece of city history. Constructed in 1912, the building was the headquarters of D.B. Fisk & Co., the country’s largest wholesale millinery. Today, enjoy the newly renovated property and don’t forget to request a guestroom or suite featuring its large signature bay windows overlooking the Chicago River.

Theater District 

The scene: This is Chicago’s answer to Broadway. With lit-up marquees on nearly every block of this area, located near the Loop around Michigan Avenue, live entertainment is always the answer to “What should we do?” 

The stops: See what shows are offering last-minute tickets by stopping at the Hot Tix booth at 72 E. Randolph St. It releases a certain number of half-price seats each day for some of the city’s most popular shows. Want a behind-the-scenes look? Broadway in Chicago offers tours of three historic theaters every Saturday at 11 a.m. (tours depart from James M. Nederlander Theatre, CIBC Theatre or Cadillac Palace Theatre). If you’re strolling around by day, you can usually find live entertainment in front of Daley Center as part of its “Under the Picasso” cultural series. A few blocks east of Michigan Avenue will find you at Millennium Park, where you can take a selfie in the reflection of Anish Kapoor’s Cloud Gate sculpture or splash in the shallow water of Plensa Fountain.

the bean image credit keivnfoley via twenty

Inspired by liquid mercury, Anish Kapoor’s Cloud Gate delightfully warps the city skyline. Image Credit: @kevinfoley13 via Twenty20

The stay: The Kimpton Hotel Allegro rests right next door to Cadillac Palace Theatre, and has stage presence all its own. It’s just launched a rotating Artist Window Series; each quarter a new installation in the ground floor entrance window will be unveiled, curated by a local artist.

River North

The scene: River North has long had an interesting dichotomy, drawing people to boisterous bars and restaurants, and quiet, contemplative galleries in equal doses. Recent months have put it on the wellness map due to an uptick in yoga studios, juice bars and spas.

sculpture image credit carl hammer

Discover exhibitions such as Neil Goodman’s cast bronze sculpture installation at Carl Hammer Gallery. Image courtesy of Carl Hammer Gallery

The stops: Chicago Gallery News offers tours of the art scene every Saturday at 11 a.m., leaving from Fabcakes bakery. We love Carl Hammer Gallery for its showing of contemporary, self-taught and outsider artists from Europe and America. Shopping break? The Shops at North Bridge is a multi-level mall anchored by Nordstrom and featuring everything from the cheeky and glam (Winky Lux cosmetics) to sleek and sophisticated (Hugo Boss). Moving on, you’ll find that good food is everywhere: Taste a real Chicago hot dog at Portillo’s, eat steak under crystal chandeliers at Prosecco, or head to the dim and music-filled Sunda for some of the city’s best Asian fusion. And when you’re ready for your moment of Zen, head to Freeze & Float for cryotherapy facials and meditative experiences in private floatation tanks. The street festival Taste of River North runs July 19-21 and gets Kingsbury and Erie streets popping with live bands and family fun.

freeze and float suite

Escape the urban hustle with rejuvenating treatments at Freeze & Float. Image courtesy of Freeze & Float.

The stay: The Kimpton Hotel Palomar Chicago, just west of Michigan Avenue on State Street, is all about the finer things, without being fussy. It has spacious guestrooms and suites, a hosted evening wine hour, and 17th-floor pool and terrace offer welcome refreshment after a day kicking around town.

Financial District

The scene: Chicago’s business heart beats here, and there’s palpable energy among the soaring office buildings and government institutions. Still, it’s not all work in the Financial District. The neighborhood has cultural attractions and, of course, plenty of sports worthy of a happy hour—whether you’re getting off work or just touring around.

skydeck view looking down image credit cavasottiphoto via twenty

Explore new heights (103 floors) at the vertigo-inducing glass floor of The Ledge at Willis Tower. Image Credit: @cavasottiphoto via Twenty20

The stops: Look up: The tallest skyscraper of them all is Willis Tower, and you can visit Skydeck Chicago for the best views of the city (if you dare: venture out on The Ledge, a glass box which juts out 1,353 feet into the air). At the south end of the LaSalle Street Financial Corridor, find the Chicago Board of Trade, a 1930s Art Deco building on which sits a steel sculpture of Ceres, goddess of grain. Tours of the inside, including the massive traders’ vault, are offered via Chicago Architecture Center. Along the river, the Civic Opera House is another Art Deco masterpiece and home to Lyric Opera of Chicago. Since 1954 the company has staged both core classics and new works. Last stop: Union Station, which is worth a look even if you’re not catching one of its 300 trains that come in and out each day. Originally designed by Daniel Burnham, it has shops, dining spots and photo ops in its recently restored Grand Hall.

The stay: The Kimpton Gray Hotel, centrally located at Monroe and LaSalle streets, has given stylish new life to the 1894 New York Life Insurance Building. Named for the Georgia Gray marble that enrobes much of the building, the hotel’s sophistication extends to its contemporary, clean-lined guestrooms. Clink champagne glasses at onsite Vol. 39, a lobby bar with bubbly and caviar; or have dinner under the retractable roof at Boleo on the top floor.

Kelly Aiglon


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