Our guide to Chicago’s all-time best summertime spots.Less
The inside of Middle Brow in Logan Square is decorated like a DIY wedding—with tea lights, wooden tables, and decorative plants in birdcages. And this brewpub/pizza spot’s huge patio has the same charming instead-of-wedding-cake-let’s-make-s’mores aesthetic. It’s a partially covered mish mash picnic tables and rustic outdoor furniture with a cute wooden bar and fire pits. It’s perfect for small groups of friends, or anytime you feel sad that you don’t have a giant backyard of your own.
If you just want to sit with friends outside, drink some cocktails, and eat delicious pizza, Pizzeria Lobo in Logan Square is where you can do this. They serve Neapolitan pies, and you’ll find excellent red sauce options like the “amatrice yo-self” (roasted tomato, pancetta, and Calabrian chile), and white pies like the castello bianco - with meatballs, ramps, and parm. Plus, their large patio is heated and partially covered.
The West Loop is full of brand new restaurants, so it’s not surprising if you’re inclined to choose one of those over St Lou’s Assembly. But during the summer, this place needs to be in your rotation, primarily because of its backyard, which is perfect for a number of situations. In addition to a covered area with picnic benches, you’ll find round tables on mulch, some stadium seating benches, bocce ball, and an outdoor bar so you never have to go inside.
When it comes to a big group hang outside, Kaiser Tiger in the West Loop is indispensable. This place has giant picnic tables that can easily fit you and 18 of your closest friends, and its sausage-and-beer-focused menu includes something called The Bomb - five pounds of beef and pork sausage stuffed with bacon and wrapped in a brown sugar bacon weave. It’s served with buns and fries, and in case this wasn’t painfully clear, it’s a good thing to share.
Park + Field in Logan Square is less of an outdoor patio and more of an outdoor empire. The space is gigantic, with tables, bocce courts, Adirondack chairs, multiple firepits (where you can make s’mores), and a camper-turned-bar. If you’re forced to go inside for some reason, you’ll find that it’s decorated like an old-timey gymnasium. But unless you’re curious about what the Olympics looked like during WWII, just plan on enjoying the patio instead.
Brew Yards is four taprooms in one. There’s beer from Burnt City, Around The Bend, Bold Dog, and Casa Humilde, as well as Lillie’s Q Barbeque—all on a 90 person patio with fire pits. Plus, you pour your own beer here, so you can control your drinking destiny.
Superdawg has definitely put the time in to qualify as an outdoor greatest hit: it’s an old-fashioned drive-in that’s been around since 1948. You can order your hot dogs, cheeseburgers, and milkshakes from a speaker, and a carhop will bring them out to you. They’ll even hook a tray to your window so you can eat without getting mustard on your dashboard. Afterwards, go to a drive-in movie, if you can find one. If you do, let us know.
Back in 1776 when America was founded and we did our first Summer Guide, we pledged that as long as The Infatuation had a Summer Guide, Big Star in Wicker Park would always be on it. This is because it has one of the most likeable patios in the city. It’s lively, perfect for day drinking, and dog-friendly, too. The tacos are perfectly fine, but you’re here for the space. So unless a meteor destroys it, it’s staying on here.
Fiya in Andersonville is a wonderful Israeli restaurant. From the pillowy pita to the tahini-rich hummus that’s slick with olive oil to a khachapuri filled with shakshuka—it’s all delicious. And you can’t see it from the street, but they have a large, quiet, courtyard behind the restaurant that’s filled with strings lights and trees. It’s exactly the kind of relaxing spot that’s perfect in for a low-key summer dinner.
Recess in the West Loop is a theme bar, and the theme is basically “adult playground." The outdoor space is huge (14,500 square feet), and includes tables situated inside repurposed shipping containers, giant games of things like Connect Four, and it even has an outpost of Bob’s Pizza. In conclusion, come here, get drunk, order pizza, and repeat all summer long.