Summer in Chicago: How to Experience the City's Favorite Season

April 24, 2024

It’s hard to understate just how dramatically the mood changes in Chicago when the city finally begins to thaw out for summer. Even mild winters in the Midwest can be bleak—endlessly gray, damp, and socially subdued, especially after the December holidays. At worst, winter can be a monthslong slog of frigid lake-effect wind, snowy whiteouts, and absentee sunshine. 

But on that first really nice summer day? Hoo boy. Meetings get canceled. Grills get scraped. Bike tires get pumped. The Lakefront Trail gets crowded with joggers, in-line skaters, and dogs basking in the first opportunity to absorb outdoor warmth in half a year.  

Summer in Chicago is more than a vibe—it’s a real life Brigadoon. And unlike many destinations this time of year, Chicago doesn’t become so overcrowded with tourists that residents feel compelled to escape; in fact, residents will be right there celebrating the season alongside you.   

From leafy parks and lakefront beaches to outdoor dining and a packed calendar of street festivals, there are a multitude of ways to enjoy a Chicago summer. Here are some faves to fill a weekend—or the whole season. 

Despite what you may have heard, Chicagoans don’t actually care if you put ketchup on a hot dog. That may be a perversely sweet, flavor-deadening addition to a bright and briny, dragged-through-the-garden Chicago-style wiener. But hey, you’re free to make your own mistakes. 

Something that really will annoy a Chicagoan, though, is the suggestion that you need an ocean to have beaches. 

The mighty Lake Michigan will do just fine, thank you. The Great Lake gives Chicago 26 miles of shoreline and about two dozen public, accessible, free, and close-to-transit beaches. With sand and everything. And an opposite shore you can’t see, just like with the ocean. Minus the sharks. So there.  

North Avenue Beach and Oak Street Beach are summer go-tos, and for good reason—downtown’s nearby skyscrapers make for a striking urban backdrop. Those spots can get crowded, however, so for a more relaxed alternative head north for the queer-friendly Osterman (aka Hollywood) Beach, where you’ll get an even more gorgeous panorama of the skyline as well as the high-rises of the Far North Side.

Or there’s 12th Street Beach on Northerly Island, located a stone’s throw from the busy Museum Campus in Grant Park—but feeling like a world away, thanks to the dunes and greenery. Foster Beach and Montrose Beach are popular with families and set near an active harbor (pictured above). That's where scores of folks gather for Friday Morning Swim Club, a weekly meetup anybody can participate in. (Seems like an especially fun idea for solo travelers.)

On the South Side, the 57th Street Beach is adjacent to the Museum of Science and Industry and just south of the Promontory Point rocks, which provide readers and sunbathers a tucked-away respite. 

Don’t forget about the Chicago River, either. Architecture boat tours along the downtown waterway are highly regarded, but there’s a cheaper option: Hop on the Chicago Water Taxi for a quick ride that shows off many of the same iconic buildings for a single-digit fare. 

To see the lake- or riverfront by paddle, take an excursion with Urban Kayaks or Kayak Chicago to get up close to bridges, commercial ships, and skyscrapers. 

Chicago is a city of neighborhoods, and downtown, for all its attractions and grandeur, is more of a meeting point than a neighborhood. To really experience the city, you need to go south, west, or north (to go east you’ll need swimwear) to where most residents actually live. A great way to get to know different parts of town is to partake in one (or several) of the gazillion street festivals held throughout the summer. 

You’ve got the kid-friendly, carnival-ride-filled Fiesta Back of the Yards, Lincoln Square’s Oktoberfest-esque Maifest, the historic Chinatown Summer Fair, Pilsen’s Tacos y Tamales, Humboldt Park’s Puerto Rican Festival and People’s Parade (the 2018 edition is pictured above), the charred-chicken-scented Taste of Greektown, Andersonville’s Midsommarfest, Lakeview’s (arguably) better-than-Pride Northalsted Market Days, Jefferson Park’s rockin’ Jeff Fest, the small-but-lively Argyle Night Market in Uptown, and dozens more.

Choose Chicago maintains a well-updated list.  

Chicago’s live music and performing arts scenes are easily among the best in the country. The passion of the audiences, the quality of the talent (both homegrown and touring), the ticket prices and accessibility of the venues—it’s a town that treats artists and fans well. 

Beyond the massive summer music festivals like Pitchfork and the Chicago Blues Festival, visitors shouldn’t miss the city’s intimate-to-midsized venues. Shows at Thalia Hall in Pilsen, The Empty Bottle in Ukrainian Village, and (on the larger side) the indoor/outdoor Salt Shed just outside of Goose Island offer incredible experiences that you just can’t get at a behemoth like Lollapalooza (though that annual 4-day fest in Grant Park can be fun, too, as shown in the above photo of Chicago-born rapper Saba's set in 2019).  

Similarly, certain comedy institutions may have strong name recognition outside the Second City (ahem), but travelers looking for laughs will also want to check the lineup at Lincoln Lodge near Bucktown or The Den in Wicker Park for great standup, and, for improv and sketch comedy, The Annoyance in Lakeview and The iO Theater in Lincoln Park.    

Thanks to Chicago’s extensive network of alleys and utilization of dumpsters, enjoying a long stroll along the city’s sidewalks requires no maneuvering around mountainous piles of garbage. For an even more pleasant walking/jogging/biking experience, residents and visitors alike take to networks of paved trails, like the popular Riverwalk along the Chicago River, the Lakefront Trail next to Lake Michigan, or The 606 (pictured above), an elevated trail along a repurposed industrial rail line over four west side neighborhoods. 

Paths like the North Branch Trail and the Major Taylor Trail are hits with cyclists, and, while not technically a hiking trail (or all that functional), the Loop’s underground Pedway, a roughly 5-mile-long warren of tunnels, transit entrances, and shops, can be fun to explore, especially that stretch Batman sped through on his Batpod in The Dark Knight. 

No shade (other than what’s thrown by the trees) to the sprawling and lovingly manicured Chicago Botanic Garden and Morton Arboretum, but those require day trips to the suburbs. For visitors staying in the city, an easier stroll through serene and tree-canopied paths can be found in Chicago’s historic final resting places. 

It may seem paradoxical, but in summertime these graveyards abound with life: lush foliage, wildlife (birds, foxes, coyotes, deer), joggers, and people out for a stroll. On the North Side, the city’s largest cemetery, Rosehill, is full of winding paths (a nice break from the city’s rigid grid), and the chapel has even served as a live performance venue for comedians and theater troupes. Graceland Cemetery is a certified arboretum that actively encourages people to visit (respectfully) and wander through, whether mourning or not. (Pictured above is the baseball-themed monument of William Hulbert, one of the founders of the sport's National League and a onetime president of the Chicago White Stockings.)

If you’re up for venturing farther afield, Bachelor's Grove Cemetery in Midlothian is popular among paranormal enthusiasts and folks who enjoy a spookier mood on their nature walks. 

The quickest way to run up a tab while eating out is ordering booze—unless you’re at a BYOB establishment. The concept of allowing diners to drink alcohol they brought for a small corkage fee (usually around the price of one or two drinks) isn’t unique to Chicago, but there’s an unusually rich BYOB culture here. 

Even diners who don’t imbibe may want to seek out BYOB restaurants. Chains or eateries owned by big culinary groups rarely offer the service, so those four letters in a window are more often than not a sign of uniqueness and owner-operated quality.

There’s nothing better than chasing the buttery, salty, umami-rich Asian escargot at Tanuki Sushi & Grill with a corner store Sapporo (there’s a well-stocked South Loop Market kitty-corner to the restaurant), or uncorking a Malbec at South American steakhouse Tango Sur along the Southport Corridor.  

BYOB or not, summer is also a great (okay, the only) time to enjoy Chicago’s outdoor dining-and-drinking scene. Just about every swanky downtown hotel boasts a chic rooftop bar perfect for taking selfies, socializing, and sipping overpriced cocktails. 

To take in the fresh air while bringing things down to earth in all senses of the phrase, join the locals at Moody’s Pub, Edgewater’s pretense-free neighborhood tavern with an inviting brick patio and faux-medieval interior straight out of The Elder Scrolls. Similar vibes, albeit with an Irish brogue, can be found in the beer garden at Chief O'Neill's Pub. 

There’s nothing like the caramelized crust on a hearty Pequod's pie, but most Chicagoans rarely choose deep dish as their go-to slice (don't even think about suggesting Jon Stewart’s infamous roast of the delicacy has nothing to do with that). Delicious though they may be, deep-dish pizzas take forever to cook, they tend to get soppy during delivery, and their heaviness feels better-suited to a cold winter night out.  

The more accessible summertime option is the crispy, thin-crust, square-slice tavern-style pizza you’ll find at Pat’s or Vito & Nick’s or Italian Fiesta or Kim’s Uncle. And don’t overlook the humble Pizza Puff, a ubiquitous and affordable lunchtime staple originated by Iltaco and sold at casual hot dog/gyro/chicken shacks such as Harold’s Chicken and Byron’s Hot Dogs. Flaky, buttery, and tender, the deep-fried puff is loaded with a Bolognese meat sauce and cheese, the whole thing wrapped in wax paper so you can eat on the go. Is it technically pizza? Next question!

Little ones will enjoy a visit to downtown’s Maggie Daley Park, where a 3-acre play garden features a pyramid slide, a refreshing water-spraying playground, and other climbable structures, open during the summer starting in May.

Catching a Cubs baseball game at Wrigley Field is a classic summer outing for families, though the blocks around the "Friendly Confines" look more like an outdoor mall these days. Fans of spectator sports can also watch a Chicago Fire soccer match at Soldier Field or the annual skyline-backdropped summer NASCAR race.

For even more octane, consider traveling an hour outside the city and 20,000 feet up to Skydive Chicago, which offers tandem jumps for first-timers with certified professionals. A more kid-friendly aerial adventure can be found on the zip lines and ropes courses at The Forge: Lemont Quarries, located southwest of the city. To the north stand the roller coasters of Six Flags Great America in Gurnee.