How to Do Summer Right in Chicago

EAT:

All five flavors in one lick. The opening of Original Rainbow Cone each year signals the start of the season for locals, when they can finally enjoy orange sherbet, pistachio, Palmer House (vanilla with cherries and walnuts), strawberry, and chocolate in one fell swoop of the tongue. The Beverly ice cream shop is a neighborhood institution, but for sweet cravings downtown, just head to their Navy Pier location. A few more summer-only staples: Mario’s Italian Lemonade, Miko’s Italian Ice, and The Freeze.

DO:

A baseball game. North Side or South Side — a summer afternoon spent rooting either of the home teams is a winner. Snag a bleacher seat and catch the Cubs play at their historic ballpark. Wander around all the new Wrigleyville developments like Brickhouse Tavern and Mordecai or do “old Wrigley” and stop at favorites like Murphy’s Bleachers. The Sox host some of the best deals in baseball with great promos like Family Sundays with tickets starting at just $5, Free T-shirt Thursdays, and $1 Hot Dog Wednesdays.

DO:

Check the calendar for the week’s festivals. Imagine a block party. Then invite the whole city. That’s basically the scene all summer long. Everyone becomes your neighbor at fun street fests like Do Division and Maifest. Mega events take food, drinks and live music to the next level—Taste of Chicago and Lollapalooza for example.

DRINK:

Outdoors in a beer garden. Yes we have sooo many craft breweries in Chicago but come summer, take your brew outside with places like Kaiser Tiger which has a 200-seat beer garden.

EAT:

Alfresco on a rooftop. The moniker “Windy City” may not mean what you think, but our rooftops do make a great place to catch that summer breeze. Or better yet, capture a beautiful skyline view. There’s a lot to choose from here (particularly if you just want to imbibe) but for rooftop dining some good options include Cabana Club atop The Robey Hall and The J. Parker, 13 floors above Hotel Lincoln.

DO:

Watch downtown summer fireworks. Big, bold displays of color fill our skies and reflect off beautiful Lake Michigan each season. These spectacular — and free — displays can be seen up close at Navy Pier on Wednesday and Saturday nights (Memorial Day to Labor Day), though anywhere along the downtown lakefront makes a good viewing spot.

EAT:

Ribs, pulled pork, smoked brisket, and every other type of BBQ. Such a definitive summer food, barbecue is best when enjoyed outdoors. Chicago does this in a big way with a lineup of meaty summer fests: Windy City Smokout, Ribfest Chicago in North Center and Windy City Ribfest in Uptown, and Chicago Bourbon & Barbecue Fest.

DO:

Plan a play day at the beach. On a beautiful summer day, it seems like everyone is out along the water. All free and open to the public from Memorial Day to Labor Day, the 26 Chicago beaches on Lake Michigan are soft, sandy stretches to take in the sun. Build sandcastles under the shadows of skyscrapers at Oak Street Beach or play volleyball at North Avenue Beach. Hit the lakefront trail to take it all in and refresh at waterside cafes like Castaways. Chicago Park District runs its free public pools following the same schedule so consider checking out these neighborhood gems, too, for an open swim session.

EAT:

The original Maxwell Street Polish. Yes you can get this all year round at Jim’s Original, but given the lack of indoor seating, coming in the summer makes sense so you can stand on the sidewalk like everyone else and have at it: a juicy Polish sausage, piled high with grilled onions, spicy sport peppers, and mustard.

EAT:

Even more encased meats aka the hot dog. It’s a similar operation at local hot dog stands — order and go. The indoor seating situation is little to none, so head to these colorful little shacks in the summer. Jr’s Red Hots and Red Hot Ranch in the Bucktown neighborhood are two prime examples, and both have picnic tables set up outside for when the weather is nice.

DO:

A picnic in Millennium Park. Bring a blanket and spread out under the stars for free classical performances during Grant Park Music Festival, free movies on the 40-foot LED screen for the Millennium Park Film Series, and free concerts for the Millennium Park Summer Music Series.

DO:

The Chicago Riverwalk. At lunch, at happy hour, at dusk… locals and visitors alike converge along the scenic waterfront promenade for a stroll, casual eats, and great outdoor drinks.

DO:

Splash around a fountain. Crown Fountain in Millennium Park and Polk Bros. Fountain at Navy Pier become delightful playgrounds each summer. The cool mist blowing off Buckingham Fountain is another refresher. Turned on just for the summer season (usually May to October), these iconic landmarks are great spots to people watch.

DO:

Scale the climbing wall. Tackle massive 40-foot-tall rock climbing walls in Maggie Daley Park. You can test your skills when the season opens, generally in April depending on the weather.

DO:

The foxtrot, tango, and bachata in the Spirit of Music Garden. This very seasonal event — hence the name Chicago SummerDance — is all about embracing the outdoors and dancing to live music. Grant Park hosts the popular dance party, which starts off with free lessons, every week from June to August.

DRINK:

Down an icy cool milkshake. The doughnut-topped treats from the walk-up window at BomboBar scream summer, though we’ll admit Portillo’s Chocolate Cake Shake is a year-round guilty pleasure.

EAT:

The freshest of the fresh. Colorful berries and crisp apples fill the stalls at our neighborhood farmers markets. Enjoy the harvests of the Midwest and snack on pastries, empanadas, and other ready-to-eat items while you check out chef demos and enjoy live music. Green City Market in Lincoln Park and Logan Square Farmers Market take place weekly in beautiful outdoor settings starting in May.

DO:

Your shopping outside. The West Loop bazaar known as Randolph Street Market sells antiques, vintage clothes, collectibles, and more from a sprawling outdoor space each month in the summer from May to September. Even better bargains can be had at Maxwell Street Market, a Sunday flea market known for its street food.

DO:

Take to the water. There’s nothing like being on a boat and we have a whole fleet to choose from each summer. Zip out on Lake Michigan with a Seadog Extreme Thrill Ride; for a leisurely option go with Entertainment Cruises. The Chicago River carves out a perfect path amid the Loop to snap pics of our amazing architecture. The top tour is Chicago’s First Lady Cruises, though Wendella Sightseeing Boats and Shoreline Sightseeing have the most fun with their themed events like wine tastings and craft beer nights. Or man your own vessel with Urban Kayaks.

EAT:

A smorgasbord of food truck fare. Head to where the food trucks gather for a mix-and-match lunch that you can take to the park or nearest bench. Chicago Food Truck Fest, kicking off for regular meetups starting in March, is a reliable option downtown.

DO:

Live music at a museum. MCA Chicago hosts Tuesdays on the Terrace featuring free concerts in their artful sculptural garden (June-September) and our lakefront aquarium draws crowds every Wednesday for Jazzin at the Shedd (June-October).

Finally, another way Chicago does summer is, funny enough, by sometimes leaving the city all together. Music concerts at Ravinia, roller coasters at Six Flags Great America, and acres of lush greenery at Chicago Botanic Garden are a few good reasons to travel out to the suburbs. There’s also the call of the “Mother Road.” Make Chicago your starting point for that epic summer road trip down Route 66.