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Chicago in the Summer

My Kind of Town

By Kelsey Ogletree

Chicago is known for its striking skyline, world-class restaurants, magnificent shopping, efficient public transportation, and, of course, less-than-gentle winters. But when May finally arrives, baseball season begins, the trees start to bloom, and the parkas get put away. Chicagoans forget all about the snow and ice and revel in those sun-soaked days, strolling down tree-lined streets, trading treadmill slogs for lakefront runs, and dining on patios wherever possible. Sure, Midwestern hospitality is present year-round, but during glorious summer, it’s out in full force—people are just happier—and for visitors, there’s no better time to enjoy the city.


Every city has two sides—the one the tourists see and the one the locals see—and Chicago is no different. However, one activity that’s a perennial favorite of both is the Chicago Architecture Foundation River Cruise. Held aboard Chicago’s First Lady Cruises, it’s rated the number one tour in the city on TripAdvisor for a reason. What better way to spend ninety minutes on a beautiful day than cruising down the Chicago River in an open-air vessel complete with a full-service bar while getting an exciting history lesson from a knowledgeable guide? The cruise departs from Chicago’s Riverwalk at Michigan Avenue and Wacker Drive (look for the blue awnings). Plan to arrive early to get the best seats up front.

Building buffs can learn more about the city’s architectural legacy at the expanded Chicago Architecture Center, a twenty-thousand-square-foot facility opening this summer above the dock where the river cruise begins. The main attraction of the center will be the twenty-six-foot Skyscape Gallery, along with a gallery exploring Chicago’s neighborhoods, a hands-on design studio, and a retail shop.

Another way to see the city from the river, rain or shine, is aboard the glass-enclosed Odyssey Chicago River Experience. The boat, which will debut this summer, will be available for brunch, lunch, dinner, and cocktail cruises.


Chicago offers hundreds of free events year-round, but perhaps the best variety occurs in summer. Millennium Park serves as a hub for many of them, such as the Millennium Park Summer Music Series at the Jay Pritzker Pavilion. Pack a picnic (or stop at nearby Pastoral Artisan Cheese, Bread & Wine on East Lake Street to pick up supplies or have them put together a basket for you) and choose a spot on the lawn to catch one of the free concerts taking place June through August. Before or after the music, pop into The Blackstone hotel on South Michigan Avenue for a cocktail in the 1960s-inspired lobby bar, Timothy’s Hutch.


Every July, the free five-day Taste of Chicago in Grant Park is packed with people enjoying live music, family activities, and chef demonstrations in addition to the main attraction: Chicago-famous food. Sample the iconic dishes of the city (like deep-dish pizza, hot dogs, and Eli’s Cheesecake) in one stop and also try a lot of other tasty bites (think bread pudding, fried shrimp, dumplings, baked potato frites, and peach cobbler). When you’re ready to escape the crowds, head to the lakefront path and walk north to work off the indulgences while taking in peaceful views of the lake.

The Chicago Air and Water Show, held each August, is the longest-running free show of its kind in the United States. This year’s sixtieth annual event will include the US Air Force Thunderbirds, the US Army Golden Knights, the US Navy Leap Frogs, and other military and civilian demonstration teams. People gather in droves, spreading out beach towels and picnic blankets along the lakefront between Lincoln Park and downtown to take in the dips, twists, and barrel rolls, but the best views (as well as the densest crowds) are at North Avenue. Even if you’re not an aerophile, the people watching, the sunshine, and the frozen lemonades make this a can’t-miss event.


With twenty-six miles of shoreline, Chicago has a surprising number of beaches—most of which are free to visit. Perhaps the best known is Oak Street Beach, located off the Magnificent Mile, Chicago’s famous shopping district on Michigan Avenue. This beach is an easy walk from many downtown hotels and superb for people watching—it’s a magnet for the see-and-be-seen crowd. Oak Street Beach Food + Drink serves casual fare like chips and guacamole and margaritas.

North Avenue Beach at North Avenue and Lake Shore Drive in Lincoln Park is another favorite hangout. It boasts the always-buzzing Castaways Bar & Grill that looks like a massive ship yet takes itself seriously as host for international volleyball tournaments like Volleywood (July) and AVP Pro Beach Volleyball Championships (August). Lesser-known beaches like Loyola, Lane, Foster, Oakwood, and Osterman are more laid back and provide water activities like stand-up paddleboarding and kayaking. June visitors can catch one of Chicago’s newest music festivals, Mamby on the Beach, which takes place on Oakwood Beach.


Traveling with a dog (or just love them)? Montrose Beach is one of only two public dog beaches in Chicago. A fenced-off section at one end lets pups run free without their leashes, while owners can kick back and relax with burgers and electric lemonades at The Dock at Montrose Beach.

Not keen on swimming in the lake? Several pools around Chicago are great spots to dive right in. A well-kept secret is the one atop Viceroy Chicago, a hotel that opened in the Gold Coast neighborhood last year. On the eighteenth floor is Devereaux, a 1970s-themed rooftop bar with views of Lake Michigan, a tasty menu of snacks and cocktails, and, of course, a pool—open to the public as well as hotel guests.


Another way to take advantage of the river views—especially at sunset—without being on a boat is to find a perch at one of the city’s trendiest rooftop bars, many of which are at the finest hotels. Fantastic views can be had on the twenty-second-floor LH Rooftop at LondonHouse Chicago, as evidenced by the frequent lines out the door. Brunch at LH means bottomless mimosas, Nutella crepes, and a variety of hearty, savory dishes. For dinner, LH will pack an American picnic basket for two with crave-worthy snacks like jamón serrano, potato salad, and fresh-baked bread.

Fantastic views can be had on the twenty-second-floor LH Rooftop at LondonHouse Chicago, as evidenced by the frequent lines out the door.

A new menu debuted in May at The Terrace (formerly known as Sixteen), the rooftop restaurant and bar on the east-facing sixteenth floor of Trump International Hotel & Tower Chicago. Both light bites and full-course meals (including ingredients sourced from the terrace garden on the same level) are available here from award-winning chef Nick Dostal. The hotel will debut its newly redesigned indoor dining room later this year.

This June, the Peninsula Chicago added Z Bar, a rooftop space where mixologist Vlad Novikov creates chemistry-centric concoctions that incorporate luxe ingredients like gold leaf and caviar. While it doesn’t have river views, Z Bar is an ideal spot to grab an upscale cocktail on the Magnificent Mile. Another good option is Noyane, the seasonal rooftop at Conrad Chicago, which offers elevated izakaya pub-style cuisine and cocktails, plus lunch and weekend brunch.

Further south, on Michigan Avenue, Cindy’s—first opened in 2016 on the thirteenth floor of Chicago Athletic Association Hotel—became an overnight sensation when guests discovered the allure of its unparalleled views of Lake Michigan and Millennium Park, not to mention its apothecary-style “evening potions.” Try the Friesling (frozen Riesling) or a selection of interesting mocktails, such as the Reanimator (made with activated charcoal, blueberry, and ginger), this summer.


Unlike other great American cities like San Antonio and Savannah, Chicago didn’t develop its riverfront into a true attraction until recent years. In 2016, construction was completed on the Chicago Riverwalk, which stretches one and a quarter miles between Wacker Drive/Franklin Street and Lake Shore Drive. (This spring, Mayor Rahm Emanuel announced vague plans to extend the Riverwalk all the way to Lake Michigan.) In addition to serving as a convenient, scenic walkway for commuters who want to avoid traffic, the Riverwalk is a destination in itself, with a variety of spots to dine and imbibe.


City Winery, a well-known concert venue and restaurant in the West Loop, opened an outpost offering cocktails and light bites on the Riverwalk last year. (The Schmear Plate, with spreads like romesco, tapenade, and tzatziki, is an optimal order with a round of bubbles.) Also try Tiny Tapp & Cafe (on the Riverwalk between the Clark and Dearborn Street bridges), which began operations last summer and this year will introduce an expanded wine program. The café portion also serves locally roasted coffee, ice cream, and pastries. For an afternoon pick-me-up, grab a cone from Frost Gelato as you walk the Riverwalk end to end.

On the opposite side of the river is River Roast, an upscale restaurant serving contemporary American tavern fare from James Beard Award–winning chef Tony Mantuano and executive chef John Hogan alongside inventive cold-brew cocktails and a wide selection of Midwestern beers. Share the Adult Sundae Fundae, a dessert with Guinness ice cream, whiskey cherries, rum pineapple whipped cream, and bourbon butterscotch.

For an upscale dinner on the water, try Chicago Cut Steakhouse, which also has views of the river, owing to its prime location on LaSalle Street. Order a nice bottle from the iPad wine list and Lobsterscargot as an appetizer, then consider splitting an entrée, as you’ll want to save room for the dessert cart. An insider tip: Chicago Cut is also open for breakfast.


Face it: you’re going to do a lot of eating on a trip to Chicago. But as widespread as the city’s incredible restaurants are, so are its options for invigorating workouts. On Saturday mornings from June through August, Millennium Park offers four free workouts on the Great Lawn, including Pilates, yoga, strength training, and Zumba, plus weekday yoga on Tuesdays and Thursdays. Equinox holds Tuesday and Saturday morning sweat sessions at Shore Club on North Avenue Beach ($10 for Equinox members, $20 for nonmembers) that range from cardio kickboxing to HIIT. At the Field Museum, anyone can join the free hour-long, family-friendly classes in Fitness at the Field, taught by Fitness Formula Club instructors on Sundays in July and August. The Park at Wrigley, which opened last year in front of Wrigley Field, offers free classes on the grass on select mornings throughout the summer, and various hotels offer fitness programs as well, including yoga sessions on the rooftop at Loews Chicago and HIIT-style classes at Chicago Athletic Association Hotel.

If you’re craving something sweet, doughnuts are the way to go in Chicago! Stan’s Donuts has three locations to help you get your fix.
If you’re craving something sweet, doughnuts are the way to go in Chicago! Stan’s Donuts has three locations to help you get your fix. | Photo courtesy of Stan’s Donuts


When it comes to starting your morning on the right note, Chicago’s coffee scene does not disappoint. Local brands like Intelligentsia (six locations) and Dollop (eleven locations) are both solid choices for a strong, quality cup of joe. But venture beyond downtown to find memorable handcrafted drinks that are as Instagrammable as they are delicious.

Get the incredible glitter latte and a pastry by Bittersweet bakery at Passion House Coffee Roasters in Logan Square, or try the not-too-sweet toasted marshmallow iced latte at Coffee Joint in Irving Park. If you need to get some work done, both are great spots for setting up shop at a table for a few hours. In the West Loop, Japanese barista Hiroshi Sawada is world renowned for his coffee art, and his matcha lattes are somewhat of a legend in the city. Wisconsin import Colectivo opened its first Chicago café in Lincoln Park last year. You can’t beat a sunny morning spent on its expansive patio with an iced latte and a fresh-baked raspberry scone, and the gorgeous historic homes around the neighborhood are fun to explore on foot too.

You can’t beat a sunny morning spent on its expansive patio with an iced latte and a fresh-baked raspberry scone, and the gorgeous historic homes around the neighborhood are fun to explore on foot too.

Of course, any Chicagoan knows a cup of coffee is only as good as the local doughnut it’s paired with. Stan’s Donuts, Firecakes, Dinkel’s, and Doughnut Vault are all worthy choices, but the buttermilk old-fashioned and Michigan apple fritter from Do-Rite Donuts & Coffee truly take the cake.

— V —

Learn more and plan your trip at ChooseChicago.com.

Where to Stay

Looking for a shiny new hotel room? Consider one of these recently opened (or coming soon) properties:

Hotel Zachary Opened this spring across the street from Wrigley Field, this boutique property has a brilliant lobby/restaurant/bar level that pays homage to Zachary Taylor Davis, the architect of Wrigley Field. HotelZachary.com

The Wheelhouse Hotel Baseball fans can also get a front-row seat to the Chicago Cubs by staying at this twenty-one-room hotel, which opened in late spring right in the middle of the action on Clark Street. WheelhouseHotel.com

Moxy Chicago New this summer, Moxy is as much a social scene as it is a hotel, with a buzzing lobby that’s an urban coffeehouse by day and a craft cocktail bar by night—and a complimentary signature cocktail for each guest. Moxy-Hotels.Marriott.com

Cindy’s on Michigan Avenue is another great stop for drinks on the terrace—try their unique apothecary-style “evening potions.”
Cindy’s on Michigan Avenue is another great stop for drinks on the terrace—try their unique apothecary-style “evening potions.” | Photo courtesy of Cindy’s Rooftop

St. Jane Replacing the former Hard Rock Hotel on Michigan Avenue this summer, this arts-and-culture-focused hotel will have an eclectic style and multiple drinking and dining outlets. StJaneHotel.com

Sophy By late summer, the neighborhood of Hyde Park (near the site of the future Barack Obama Presidential Center) will get a luxury lifestyle hotel and restaurant, the first of its kind for the area. SophyHotel.com

You also can’t go wrong with some of the city’s classic, classy hotels:

The Peninsula Chicago One of ten Peninsulas in the world, this hotel off the Magnificent Mile has impeccable style, high-tech guest rooms, lovely afternoon tea service, and a luxury spa. Chicago.Peninsula.com

The impressive lobby of The Langham, Chicago hotel. Check out more on this historic building in “The Rebirth of a Landmark” in this issue of VIE.
The impressive lobby of The Langham, Chicago hotel. Check out more on this historic building in “The Rebirth of a Landmark” in this issue of VIE. | Photo courtesy of Choose Chicago

The Langham, Chicago Don’t let the office-building facade fool you: this luxury property (which has its lobby on the second floor) is one of the city’s best, from the service to the elegant touches of Langham pink and the elevated cuisine at Travelle Kitchen + Bar. LanghamHotels.com/Chicago

Sofitel Chicago Magnificent Mile Francophiles will appreciate this European brand’s subtle nods to French culture, including the seasonal tasting menus at Café des Architectes and the Paris-born bartenders at Le Bar. Sofitel-Chicago.com

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