Where To Eat Outside When It Might Randomly Rain guide image


Where To Eat Outside When It Might Randomly Rain

You’ve angered the gods. Here’s where to go.

After a 17-month-long quarantine, Chicagoans are now able to sit outside and eat at a restaurant. But this is summer in Chicago - so while it might be 85 degrees and sunny when you order, by the time your check comes the patio might look like the set from White Squall.

So when it comes to finding a restaurant on a day when the forecast is iffy, use this guide. Each spot has outdoor dining with fully-covered tables so you and your food won’t turn into soggier, unhappier versions of yourselves.

The Spots

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Paradise Park


1913 W North Ave, Chicago
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This pizza spot in Wicker Park has a covered outdoor area that’s decorated like a retro trailer park (yes, really - with pink flamingos and swingsets). And the fact that it’s temperature-controlled and covered means you can enjoy the crowd-pleasing pizzas and it doesn’t even need to be nice out. Plus, this place is dog friendly.

Homeslice in Lincoln Park has spent a lot of time curating its outdoor space. There are big, comfortable couches with lots of space, and light-up signs that remind you, ”No Mask, No Pizza.” The patio goes to extreme lengths to make sure it’s still functional and comfortable even during the rain - it’s covered in plastic and temperature controlled. So that plus the masks makes it feel a little bit like eating in a tent from Outbreak, but with more swing sets.

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Truth Italian Restaurant

The large outdoor space at Black-owned Truth Italian is perfect for a date, and the covered patio means you can’t use the weather as an excuse to cancel. Also worth noting - this place serves a fantastic breakfast (with lots of french toast variations) seven days a week, and their long mimosa menu makes it ideal for a boozy weekend brunch.

Recess in the West Loop is a theme bar, and the theme is basically “City Hall,” which means menus are made to look like municipal forms, and cocktails have names like the “Alderman’s Choice.” The drinks and food are tasty (with bites like sliders and pigs in a blanket), and the outdoor space is huge (14,500 square feet), which includes tables situated inside repurposed shipping containers. It’s a great place for just hanging out, or talking about the second season of The Wire. You know the one.

Bernie’s is one of our favorite rooftops in the city, and they just expanded their awning. So they still take reservations even when it rains, and more importantly, your hair won’t get wet. Also important? They have one of our favorite burgers in Chicago.

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Roots Handmade Pizza- Printer's Row

This pizza place’s South Loop location is huge, with two patios and an incredibly high retractable roof. The pizza is Quad-Cities style, which means it’s cut into rectangles and the toppings are under the cheese. The menu is long with a surprisingly fantastic selection of salads and a rotating group of pizzas created by local chefs.

OK - so you’re probably not coming to this tasting-menu restaurant because it’s raining and you just want to eat outside. But if you want to plan a special occasion dinner, you can make reservations for Next’s covered patio without worrying about the weather. This place is known for its frequently changing menus, and right now the theme is “Mexico City” with prices ranging from $185-$205 per person.

This is the low-key rooftop restaurant on top of Pacific Standard Time in River North. The Laurel Room is from the same team, which means you’ll find the same California-inspired seasonal menu. As a bonus, since the rooftop is covered, you can sit outside even when it’s raining.

A lot of restaurants talk about serving “farm to table” food, but Homestead On The Roof takes it a few steps further - they grow their own vegetables and herbs in their rooftop garden. And during the summer, that garden doubles as a tented-outdoor seating area. Come here if your date really likes to know where their basil was sourced from, or if you’re the type of couple who gave out sunflower seeds as a wedding favor.

This Greek restaurant in Lincoln Park is one of a few locations of Avli, and it’s on a quiet side street that makes their covered sidewalk seating a nice outdoor option in the neighborhood. Also good to know: they have a long list of Greek wines and specialty cocktails made with Greek spirits.

The West Loop is full of brand new restaurants, so it’s not surprising if you forgot about Saint Lou’s Assembly’s enclosed (and slightly hidden) patio. The backyard has a large covered area with picnic benches, and an outdoor bar so you never have to go inside. Plus, the upscale cafeteria-style food (like meatloaf and sides) and small plates like foie gras with biscuits make Saint Lou’s someplace that should always be in your rotation - raining or not.

The partially-covered outdoor area at Frontier will protect you from the elements, which is more than we can say about the poor pioneers that lived on the actual frontier. And while you will find things like antelope and water buffalo on the menu, thankfully their commitment to the theme stops there since pioneers didn’t have hand sanitizer. Or air conditioning.

Right now Beatnik is allowing diners to eat in their garden room, which qualifies as “outdoor dining” because even though it’s inside, the windows fully open. It looks (and feels) like a hybrid of a ’90s metal ballad and a Wes Anderson film, which makes it a pretty interesting place to drink cocktails and share some small plates.

Summer House keeps a literal “countdown to summer” on their wall, so it’s not surprising they have a covered sunroom that’s open for dining. Coming here can feel depressing during our endless winter, but it’s perfect in the middle of July.

3 Arts Club Cafe is less of an outdoor space and more of a large-scale terrarium to prepare us for when we need to finally leave Earth. It’s a huge space with a glass ceiling and lots of full-size trees surrounding the tables. Come to the all-day cafe for breakfast or lunch (with dishes like soft-scrambled eggs and truffled grilled cheese) and discuss important things like what you’re going to pack for your new life on Mars.

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Your House


Sometimes it’s just too gross to leave the house, period. When this is the case, stay home. Close the windows, rewatch The Wire, and order something delicious for takeout.

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