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The Outdoor Greatest Hits List

Our guide to Chicago’s classic summertime spots.

Written by
16 Spots
Launch Map
17 Spots
Launch Map

After a brutal winter and the “will it or won’t it” continual cliffhanger of spring, there is nothing like the reward of Chicago in the summertime. So naturally, every day it’s nice out, you’re going to want to be outside. Here’s our list of the quintessential places for you to do that.

Featured In

The Outdoor Spots

Saint Lou's Backyard

$$$$ 664 West lake Street

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. All this combined with a new menu for summer 2021, with dishes like schmaltzy biscuits, po’ boys, and tahini soft serve.

Kim Kovacik

Kaiser Tiger

$$$$ 1415 W Randolph St

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. If everyone is able to function after eating it, there’s a bocce court here, too.

Susie Lacocque

Park + Field

$$$$ 3509 W Fullerton Ave

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.

Susie Lacocque


$$$$ 6363 N. Milwaukee Ave.

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.

Kim Kovacik

Big Star

$$$$ 1531 N Damen Ave

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.

Parson's Chicken & Fish

$$$$ 2952 W Armitage Ave

Parson’s is another spot that has an outdoor area more memorable than its food. We’re not saying the food is bad - the fried chicken and fish here are pretty good. But as with Big Star, we’re mostly here for the patio, which is big and enclosed so you don’t feel like you’re sitting on the street. Plus, there’s an outdoor bar serving negroni slushies. The large picnic tables make it perfect for groups, and there are big umbrellas to shade you from the sun. Basically, if there is an inside to this restaurant, we don’t want to know about it.

Kim Kovacik

Bistro Campagne

$$$$ 4518 N Lincoln Ave

Bistro Campagne’s courtyard is charming, with brick walls, ivy, and lots of plants and trees. It’s one of our favorite summertime spots, and it happens to also be one of the best-kept secrets in Lincoln Square. This means the crowd (to the extent that there is one) seems to be filled with mostly regulars. Stick with French classics like escargot and boeuf bourguignon, and plan on ordering a second bottle of wine as an excuse to spend more time here. Who knows, maybe you’ll become a regular, too.

The Moonlighter

$$$$ 3204 W Armitage Ave

The Moonlighter in Logan Square is a fantastic spot, primarily because of its massive shaded front patio. Add in pitchers of cocktails and an extensive bar food menu full of things like burgers and wings, and coming here is an easy choice to make. Plus, their patio is dog-friendly.

The Duck Inn

$$$$ 2701 S. Eleanor St.

One of our favorite summertime spots is the enclosed backyard patio at The Duck Inn in Bridgeport - it’s easy to forget you’re in the city. Order anything involving duck (including the whole rotisserie duck, which needs to be arranged ahead of time), or the duck-inn dog (a hot dog cooked in duck fat). Just make sure you have enough time to hang out after dinner and have drinks. The space has fire pits and comfortable chairs that will make you want to stay a while.

Susie Lacocque


$$$$ 1072 N Milwaukee Ave

As the name suggests, this place has a theme - it’s decorated like a cabin from the 1800s, and there’s a lot of game on the menu. The partially-covered outdoor area at Frontier in Wicker Park 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.

Moody's Pub

$$$$ 5910 N Broadway St

This Edgewater classic has been around since 1959, and while we weren’t regulars back then, it feels like it probably hasn’t changed a lot. The menu is short, focusing on drinks and a small selection of sandwiches and burgers, all of which are solid. But what makes Moody’s particularly special is its outdoor area. The patio, surrounded by large trees and decorated with twinkly lights, is huge - so come with a group and camp out.

Piccolo Sogno

$$$$ 464 N Halsted St

For an easy romantic Italian meal outside, the answer is Piccolo Sogno every time. The patio here is covered with string-lit trees, sequestered from the street, and large enough to accommodate a lot of people without feeling too crowded. As mentioned, it’s great for dates, but it also works for dinner with just about anyone else - parents, colleagues, friends, time-share salespeople, etc.


$$$$ 12 S. Michigan Ave.

Cindy’s is an all-season player. The covered rooftop offers a fantastic view of the Chicago skyline, so even when it’s 15 degrees outside, you can show friends and family why living here is still a good idea (yes, you can see Pequod’s if you squint). When it’s nice out, you can also make use of the terrace. Come here with a group for brunch - their large-format dishes (like blueberry pancakes and lox and bagel platters) are meant to serve three to four.

Parlor Pizza

AmericanBar FoodPizza  in  West Loop
$$$$ 108 N Green St

Parlor is Big Star’s college freshman brother home for the weekend. This spot has two patios (guaranteeing you won’t have to wait too long to snag a seat) and plenty of shade, so basically, you can hang out here for as long as the beer and food last. While the pizza isn’t going to win any awards, it’s tasty, and the long menu of solid bar food makes this spot a crowd-pleaser. It works even if you’re not rushing a fraternity.

Susie Lacocque

Calumet Fisheries

$$$$ 3259 E 95th St

Do a few sets of tables and chairs outside a seafood shack count as outdoor dining? We vote yes. And those tables and chairs are the best place to enjoy the smoked fish at Calumet Fisheries on the 95th Street Bridge. Also valid: eating while leaning against your car, or sitting in the trunk with the back door open (don’t eat it with the windows closed unless you want your whole car to smell like fish). Get the smoked salmon and fried shrimp.

Sandy Noto

Mott St.

$$$$ 1401 N Ashland Ave

We like the Asian fusion food at Mott Street in Logan Square more and more every time we eat here. And we enjoy this place the most when we get to sit on the outdoor patio. It’s large enough for a group, but still calm enough for date night. Plus, if you come for brunch, you can eat the delicious burger outside (normally it’s reserved for those sitting at the bar).

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