BY SAMANTHA LEAL
Everyone in the Midwest knows summer is a truly fleeting season. Sure, Chicago has four seasons like the rest of the region, but instead of fall, winter, spring, and summer, it’s more like almost winter, definitely winter, still winter, and summer. Which only means one thing: you gotta enjoy it while you can. So what are some of the best things to do in the Windy City come summer? Here's our tried-and-true guide.
Visitor's Guide to Summer in Chicago
Head to Lollapalooza
Yes, it can make the city feel a little crazy (even if you're not attending, try to avoid going downtown when this music festival is happening), but Lollapalooza is a quintessential “summer is here” benchmark in Chicago, and you need to experience it at least once in your lifetime. If the Lollapalooza lineup isn't your thing (you can only see Tame Impala, Twenty One Pilots and The Chainsmokers so many times, let's be honest), there’s also the Pitchfork Music Festival, which specializes in more obscure and underground indie music (Robyn, Stereolab, Amen Dunes and Black Midi are highlights) and Spring Awakening, where you can get your EDM fix with Zedd, DJ Snake and Martin Garrix.
Walk the 606
Similar to the High Line in NYC, this 2.7-mile elevated pathway along an old rail line is an easy way to get some steps in while also seeing some of Chicago’s best neighborhoods: Bucktown, Logan Square, and Wicker Park. Not only will you have access to some quality parks and outdoor spaces, you can also take the occasional break from the path and grab a bite (Small Cheval for burgers in Wicker Park; Irazu's for authentic Costa Rican cuisine in Bucktown) or a drink (Scofflaw in Logan Square is always a great pick, but if you're looking for a uniquely Chicago experience, the nearby Go Tavern and Liquors is one of the city's few remaining "slashies," the local term for a bar that's also a liquor store) before resuming your walk. It’s a great way to see the city, interact with locals, and enjoy the outdoors.
Hit the Beach
Sorry, coastal natives and transplants, but Lake Michigan beaches are just some of the best. And in Chicago, you have a wide array of them at your disposal, each one with a unique vibe and setting. Foster Beach is a good pick for a north side option (especially because it's also dog-friendly), or you can head to the bustling North Avenue Beach (definitely the most popular Chicago beach). There, you can spend your time at the Shore Club and reserve lounges or even a signature cabana. Oak Street Beach is another popular spot, and it's close to downtown, providing an easy transition from beach to city. Pro tip: beaches on the south side are more scenic and much less crowded. 57th Street Beach, Margaret T. Burroughs Beach, and Rainbow Beach and Park make for a relaxing day at the lake.
Catch a Flick
The Summer Film Series in Millennium Park is a must-do. Running every Tuesday from June through August, catch a free film (on a state-of-the-art, 40-foot LED screen) while the sun sets. Take a seat at the Jay Pritzker Pavilion or bring a blanket (or some folding chairs) to join the masses on the Great Lawn. Outdoor screenings not your thing? Chicago is home to some incredible cinemas, most notably the Music Box Theatre, located in the beautiful Lakeview neighborhood and smack dab in the middle of the Southport corridor. This summer, the Music Box hosts a retrospective of films directed by the late, great John Singleton (Boyz in the Hood).
See a Game
You can’t be in Chicago during the summer and not catch a baseball game. It's basically sacrilegious. Whether you're on the south side for the White Sox or on the north side for the Cubs, make sure to snag some primo seats and grab a hotdog (or five) while you’re at it. Just make sure not to put any ketchup on it, unless you want to out yourself as a tourist and face ridicule from the locals during the game. If the Cubs are your pick, you'll find yourself in Wrigleyville, one of the city's classic neighborhoods whose recent developments have made it even more more of a Chicago must-visit.
Imbibe on a Rooftop
It's summertime, and the living is easy. Especially when you can have a great cocktail on a gorgeous rooftop high above the city. Popular options include Cindy’s (perched above the Chicago Athletic Association Hotel, with views of Millennium Park and Lake Michigan), Waydown (above the Ace Hotel in the buzzy West Loop, usually with DJs), and the NYC-born Royal Palms Shuffleboard Club (yes, of course there’s a shuffleboard on the roof, too). But there are plenty more rooftops where those come from—ask a local for even more recommendations.
Or Imbibe at a Beer Festival
Looking for some craft brews? Chicago boasts a myriad of microbreweries, and in the summer, you can find them at any number of the city's popular street festivals, many of which are totally beer-centric. Ravenswood on Tap, named after the beautiful north side neighborhood where it takes place, has become one of the permiere beer events in Chicago in just three short years; meanwhile, in Oak Park, the venerable Microbrew Review is twelve years strong. (Bonus: Oak Park is the location of MedMen's Illinois store.) There’s also the Chicago Ale Fest, which features 150 craft beers, live music, and more. (Pssst…they also do a fest in the winter, too.)
Get on a Boat
Last, but by no means least, is the The Chicago Architecture Boat Tour, a must for local and out-of-towners alike. Downtown Chicago features some of the country's most stunning and unique architecture, and you're guaranteed to see the city in a new light as you cruise along the river. Beyond just the tour, getting out on Lake Michigan in the summer is a must. You can have dinner on the Spirit of Chicago; charter a sailboat; rent kayaks; and, of course, there's always the infamous booze cruise. The lake is your oyster.
MedMen has a medical dispensary in Oak Park.