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30 ways to still have an amazing summer in Chicago

Summer isn't canceled. Here's how to make the most of Chicago's best season in 2020.

Morgan Olsen
Zach Long
Written by
Morgan Olsen
&
Zach Long
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Affectionately known as Summertime Chi, the warmest months in Chicago are incomparable. It's not just a season—it's a state of mind. But there's no denying that summer 2020 offers a very different landscape. The city is still cautiously reopening, social distancing remains in place and all of the annual events we're used to attending have been canceled. Instead of dwelling on all the stuff we can't do, let's take a look at what we can do to make the most of summer in Chicago. This seasonal bucket list highlights only the activities that are allowed, acknowledging that not everyone is comfortable heading to a Chicago rooftop bar just yet. Whether you're still ordering delivery and checking out ebooks or you're comfortable venturing outside, this list has something for everyone. Take a look at 30 ways you can still make the most of summer in Chicago.

The best things to do this summer in Chicago

  • Things to do

If you haven't already heard, it's the summer of the drive-in theater in Chicago. Lucky for us, plenty of options have popped up all over the city (and just outside of city limits), offering a chance to see throwback films from the safety of your car. Stock up on popcorn and Junior Mints and hit the road.

  • Restaurants

One thing that's not canceled this summer? The city's best ice cream shops. Whether you like fancy-ass popsicles, sky-high cones of soft-serve or hand-spun custard, there's an ice cream parlor on this list for you. Click through to see some of our favorites.

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  • Things to do

While the city boasts plenty of great restaurants with outdoor seating, there's something wonderfully old school about going on a picnic. The best part? You don't need a reservation—just grab a blanket, pack up some food or order takeout and find your way to one of the most peaceful picnic spots in Chicago.

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  • Restaurants

The best rooftop restaurants in Chicago offer a two-for-one special: Excellent food and breathtaking views. Come summertime, these sky-high kitchens fling open their doors to Chicagoans emerging from hibernation—and this year is no exception. Check out some of our favorite rooftop eateries for alfresco dining.

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  • Restaurants
  • Drinking

Still making cocktails at home? No sweat! Lost Lake co-owner Paul McGee hooked us up with the recipe for the bar's frosty Daiquiri Frappe. You'll need just three ingredients: rum, a lime and sugar. Dust off your blender and push aside that stack of frozen pizzas to dig some ice out of your freezer.

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  • Bars

If there's one thing Chicagoans love more than drinking in the sun, it's drinking in the sun high above the city streets. This year, some of the best Chicago bars and restaurants are reopening their rooftops to vitamin D-deprived residents, who can expect new safety measures, capacity restrictions and masked servers. These Chicago rooftop bars are officially open for the season, and there's no shortage of rosé, frozen cocktails and craft beer to go around.

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  • Attractions
  • Parks and gardens
  • Humboldt Park

Looking for a new walking route? The 2.7-mile elevated path that runs through Logan Square, Humboldt Park, Wicker Park and Bucktown has reopened to the public. It's worth noting that the Park District is working with social-distancing ambassadors, who will be present to keep people from congregating. If you do plan on hitting the 606, be sure to pack a mask, steer clear of crowds and avoid lounging around.

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  • Music
  • Music

With in-person concerts postponed indefinitely and giant summer music festivals like Lollapalooza canceled, artists and venues are increasingly turning to streaming platforms to provide fans with live music. But if you're tired of watching sets performed via screens, Evanston venue SPACE is willing to bring a socially distanced concert to your doorstep... as long as you're willing to foot the bill.

  • Things to do

All located within city limits, these beautiful roadways will take you through Chicago parks, along the lakefront and into the heart of the city. Just be sure to bring you mask along for the ride if you plan on getting out of the car and checking out some local shops and restaurants along the way.

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  • Bars

If you prefer brews to cocktails, the city's best beer gardens are your playground this summer. Many of these outdoor drinking locales are known for their scenic patios, with some hiding behind Chicago dive bars, set up in taproom parking lots or on rooftops. Once you've snagged a table (you may need to make a reservation), you can order burgers, barbecue or frites to enjoy while you sip beer from local breweries.

  • Things to do

Get some exercise while you admire the views from the Chicago River or Lake Michigan by renting a kayak and paddling your way through the city. While the Chicago Park District's rental facilities are currently closed, many other local businesses are still offering rentals throughout the summer.

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  • Things to do
  • City Life

If you're searching for ways to support and uplift Black-owned businesses in Chicago right now, you don't have to look far. Organizations like Chicago Black Restaurant Week, Black Owned Chicago and Black People Eats have made it their mission to connect locals with these resources for years. And organizers say that they need the community's backing now more than ever before.

  • Things to do

The Chicago Riverwalk has been one of the city's top attractions since it was expanded in 2015, making way for restaurants, bars and stellar views of architectural marvels. Here's a quick rundown of what's changed this year: From 5 to 10am, guests are welcome to run, jog, walk and bike along the path between Lake Shore Drive and Lake Street. The Riverwalk briefly closes at 10am for cleaning and then reopens from 11am to 9pm to allow access to businesses and select recreation areas along the path. While some Riverwalk restaurants and businesses allow walk-up customers, some require a reservation, so call ahead if you're unsure. Don't forget to bring along a face covering (they're required), maintain 6 feet of distance from other visitors and stay home if you're feeling sick.

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  • Things to do

Sometimes it's necessary to make a quick escape and spend a few nights amidst nature. Thankfully, if you're looking for places to go camping near Chicago, there's no shortage of great options within a two-hour drive, from lakeside retreats in Michigan and Wisconsin to densely forested areas in Illinois. Book your site in advance and don't forget s'mores supplies!

  • Restaurants

If you're not ready to dine out just yet but you're sick of cooking, consider supporting a Chicago restaurant and ordering delivery or takeout. We've outlined dozens of our favorite options here, including a handful of restaurants that didn't previously offer to-go menus.

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  • Things to do

Offering acres upon acres of green space throughout the city, Chicago's 600 park facilities are the ultimate post-quarantine hangout spot if you want to get some fresh air, have a picnic or workout outside. Because of that reason, you should always wear a mask, as there's a good chance you'll run into other humans looking to do the same.

  • Things to do
  • Walks and tours

Boats have returned to the Chicago River and Lake Michigan at 50 percent capacity (with a maximum of 100 people), allowing you to take a tour of the city's architectural achievements or simply admire the skyline from afar. Don't forget to bring a face mask along—many companies are requiring that passengers and staff cover their faces while on the water.

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  • Theater
  • Theater & Performance

You can text your friends, send them a postcard or show up on their doorstep for a socially-distanced hangout, but if you really want to tell them how much you care, you might want to say it with puppets. The Chicago International Puppet Theater Festival will begin booking "Pop-Up Puppet-Grams"—the marionette equivalent of a singing telegram, performed live (from at least 6 feet away) for its recipient. That's so much better than FaceTime.

  • Things to do
  • Literary events
  • Suburbs
  • price 2 of 4

For now, guests will only be able to traverse a 2.3-mile trail that loops around the perimeter of the Chicago Botanic Garden, offering views of the North Lake, Malott Japanese Garden, Dixon Prairie and McDonald Woods. All other areas in the garden will be closed to guests, including the visitor center, which houses several exhibitions and a collection of bonsai trees. Visitors will need to maintain six feet of distance from other parties and wear a face covering when they come within 6 feet of others.

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  • Things to do
  • City Life

If you're craving a change of scenery from your daily neighborhood walk, consider heading to a nearby state park, all of which are now open to the public. These wide-open green spaces are working hand in hand with state officials, which means there are new guidelines and regulations that visitors must follow. Pack a mask, keep your distance from other groups and leave if things get too crowded. Don't forget water and snacks, as most visitors' centers are still closed.

  • Travel

Caught with a bad case of wanderlust and a short supply of vacation time? Look around the Midwest and you'll discover that Chicago is a launching spot for a host of fun, fast escapes—especially if you're not ready to spend the night elsewhere just yet. Before you hit the road, make sure to check for COVID-19 updates and guidelines for the state and city that you're heading to. It's not advised to travel to places that are seeing a rise in cases.

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  • Things to do
  • City Life

Chicago artist Jim Bachor has been filling potholes with colorful mosaic masterpieces that depict everything from ice cream cones and Chicago-style hot dogs to bunches of flowers. This year, he created four works depicting toilet paper, hand sanitizer, a can of Old Style and a star from the Chicago flag—each surrounded by white rays that hint at religious iconography. Find them in Uptown on Gunnison Street just west of Broadway.

  • Things to do
  • City Life

Determined to spend the summer reading a slate of new releases? We don't blame you. Your Chicago Public Library eCard functions a lot like a regular, physical library card, allowing you to check out and download e-books, audiobooks and digital magazines directly to your tablet or device, pending availability. Stock up on start bookwormin'!

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