10 Best Things to Do in Chicago During the Summertime

When I was in Mexico City, I met four different people who told me they’d been to Chicago – but visited during the winter. What. A. Waste. I’ve done a lot of traveling, and the experience of summer in Chicago is legitimately one of the best in the world.

Summer in Chicago is magical. The food, the people, the free activities, the festivals, the lake, the biking … it never ends. And best of all: You can actually afford to do these fun things because living in Chicago is super affordable compared to living in other major cities, and many of these activities are completely free.

Spring is taking forever. I want it to be summertime, like yesterday. As both an ode to my city and an impassioned cry for warmer weather, I thought I’d share my favorite things to do in Chicago during the summertime. If you’re visiting, take note!

Go to Street Festivals

When you’re in Chicago in the summer, it’s hard not to stumble upon a street festival or two, as long as you’re staying in a residential neighborhood (I would never recommend staying downtown). You’ll know you’ve found a street festival because you’ll be greeted by food trucks, live music, art vendors, and beer tents galore.

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These festivals take place throughout the city all summer long. Many are free, but donations are requested. The food and drinks, obviously, are not free.

Street festivals are often themed – there’s a Ribfest, a Green Music Fest, a Food Truck Fest, a Greek Fest, a Mayfest, an Oyster Fest, a Midsommar Fest, a Columbian Fest, a Burger Fest, an Art Fest, etc. – and they are put on by the various neighborhoods in order to raise money for the local community. Though they’re themed, they all offer live music, drinks and great food.

My favorite festivals are Do Division and Wicker Park Fest, mainly because I lived in the Wicker Park area and am most familiar with those events. They tend to be big yuppie/hipster parties because of the young age of residents in those areas.

Eat and Drink on Patios

Is there anything more enjoyable than drinking a cold beer on a sunny, warm patio in the summertime? I honestly can’t think of anything better. Throw in some oysters, fries, or a burger, and you’ve pretty much got me hunkering down and refusing to leave.

Day drinking is my fave. I love the relaxed vibe of sitting around with friends, getting a little boozy, and feeling nice and warm in the sun. Chicago offers hundreds of different patio options for your drinking and dining pleasure.

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I know there are lots of al fresco spots in Lakeview, Lincoln Square, Lincoln Park and River North, but as most of you know, I’m a Blue Line girl. Here are a few of my favorite spots to sit and chill in the Wicker Park, Ukrainian Village and Logan Square areas:

  •  Big Star (Wicker Park): To warn, there’s always a super long line to get a table at Big Star. The place is pretty renowned for its tacos (try the tacos al pastor if you’re a meat-eater), and the outdoor seating is really perfect: views of the El, Wicker Park, hip passersby and cute dogs.
  • Happy Village (Ukrainian Village): Not exactly known for its food, but Happy Village is a super-pleasant neighborhood bar with a large patio, games, cheap beer and a jukebox. Definitely more of a dive-y vibe but with access to the outdoors. What more could you want?
  •  Northside Bar and Grill (Wicker Park): Kind of a yuppie vibe, but this place has a phenomenal falafel wrap. Yes, I just said “phenomenal falafel wrap.” I know that sounds weird, but it is actually really great. I’m always on the lookout for yummy vegetarian fare.
  • Tuman’s Tap and Grill: This may be my favorite place in the area. The food at Tuman’s is delicious, and it’s off the beaten path (which means you don’t usually have to wait for an outdoor table). They have a nice beer selection, friendly waiters and bartenders, and TVs for sports-watching, if you’re into that kind of thing.

Bike Along the Lake

Lake Michigan might not be the most delightful place to swim, but it sure is delightful to look at. Biking alongside it is even better. During the summer, Chicagoans head to toward the miles of green park space that lines the waterfront to play frisbee, walk their dogs, dock their boats, picnic, lie in the sun, and generally enjoy the warm weather.

You can see it all by biking the Lakefront Trail, which extends from the southern edge of the downtown area all the way up through Lakeview. The trail is paved and perfect for biking. Chicago also offers a bike-share system called Divvy, which allows you to rent bikes from kiosks around the city for an hourly rate. Trust me, they’re everywhere.

I’d recommend getting on the trail near Millennium Park downtown, as there are Divvy bikes for rent all over the place, and then heading north along the trail. You’ll wind through Lincoln Park and Lakeview, enjoying views of the city skyline, Lake Michigan, marinas, beach areas, parks and flower gardens.

Do Yoga in the Park

During the summer, the City of Chicago offers free yoga (and tai chi, Pilates and Zumba) classes on Saturday mornings in Millennium park. You have to force yourself to wake up kind of early – yoga begins at 8 a.m. – but it’s a peaceful, fun experience.

You get to practice yoga as the people of the city wake up around you, and you always leave feeling refreshed and energized for the weekend to come. Best of all, the classes are completely free, which means a lot. Yoga classes can be pretty expensive in Chicago!

… or Listen to Music in the Park

Chicago’s Summer Music Series is legit. I know that a lot of concerts in the park tend to be questionable, but some of the bands that play in Millennium Park are actually pretty good! Not only that, a lot of my friends and peers really enjoy going. So if you’re looking to meet cool, interesting new friends, head to Millennium Park on Tuesday and Thursday evenings.

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The concerts begin at 6:30, and people tend to set up camp on blankets and lawn chairs. You can buy beer and wine near the Jay Pritzker Pavilion, though I’ve been known to just pour a little vino into a water bottle and call it a day.

Catch a Flick, Outside

Similar to the Summer Music Series, Movies in the Parks brings Chicagoans together for some free summer evening socializing. I’m most acquainted with Logan Square, which I think has the best setup in the city (though I may be biased). You basically park yourself on a blanket along one of the neighborhood’s fragrant, green boulevards and catch a movie on a hot summer evening, beer in hand.

Run the 606

The 606 is my favorite feature in all of Chicago. I love it. When I lived in Logan Square, the 606 was my running spot. It’s a really well-done public space that opened up just last year and is already beloved by locals.

The 606 is an elevated train track that was renovated into a walking/biking/running path, similar to New York’s High Line. It runs through Humboldt Park, Logan Square, Bucktown and Wicker Park (all of my favorite neighborhoods) connecting them via a pedestrian-and-cyclists-only pathway dotted with greenery, trees and flowers. There are benches for stopping to read or catch your breath, a special line of padded track specifically for runners, and exits on almost every block, making it a really convenient way to get around.

If you’re into fitness, I’d totally recommend running the 606. Really any entry point is fine – once you get up there, you’ll see lots of other Chicagoans zipping along, walking their dogs, pushing strollers and getting their sweat on.

Go to the Beach

Don’t forget that Chicago has a beach scene! I personally prefer not to swim in Lake Michigan – it’s kind of cold, and the water near Chicago tends to be pretty gross – but there’s nothing bad about lying in the sun, people watching, playing volleyball and showing off your tan.

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If you want a party, head to North Avenue Beach. Located in Lincoln Park, the beach is close to the city’s big singles scene and has the crowd to prove it. There’s also an egregiously overpriced bar and restaurant that has a rooftop deck and DJs, if that’s to your liking.

For a more relaxing vibe, check out Montrose Beach. It’s further north, still fun, not as crowded, and a lot less bro-y.

Read a Book in the Park

Chicago has some seriously amazing parks. I know it sounds simple, but one of my biggest pleasures in life is sitting under a tree in one of Chicago’s parks, book in hand. Lincoln Park is gigantic, spanning an entire neighborhood’s worth of lakeside real estate, giving you plenty of choices for trees.

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On the near West side of things, I love Palmer Square, a shaded, green, family-oriented spot right near my last apartment. A walking trail circles around the the park, attracting runners, dog walkers and stroller pushers. The trees in Palmer are pretty old, so it’s a nicely shaded spot. It’s authentically LS and beloved by the people who live there.

Outside of that, Wicker Park is tiny but fun for people-watching, especially if you like hobos and skateboarders. Hamlin Park, located in family-friendly Roscoe Village, is tiny and cute, with lots of dogs and babies around to add to the tininess and cuteness. And of course, if you’re staying downtown, you can always check out Millennium and Grant parks to see what’s going on in that neck of the woods.

Creep on Cute Puppies at the Dog Beach

Last but certainly not least, go to Montrose Dog Beach! Remember when I said that Montrose Beach has a chill, relaxed vibe? Maybe that’s because everyone just got done playing with the dogs in the vicinity. The dog beach is a small stretch of land that’s designated specifically for pups, and dog-lover than I am, it’s one of my favorite spots in the city.

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I used to take Amber (my beagle, for those who don’t know) there during the summer – but she never wanted anything to do with it. For her, it was all about running up to the water, sniffing, getting scared, and running back.

Man, after writing this, I am even more pumped for summer to start! I hope to get into the city as much as I can this year, depending on how my freelancing career goes. Not many patio-dining options here in Twin Lakes!

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