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The Outdoor Greatest Hits List

Our guide to Chicago’s classic summertime spots.

Written by
13 Spots
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13 Spots
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Summer Guide
See the full Summer Guide

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.

the spots

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.

Café Ba-Ba-Reeba!

$$$$ 2024 N Halsted St

Cafe Ba-Ba-Reeba has been in Lincoln Park for more than 30 years, and it’s still going strong. It’s a friendly, upbeat spot for tapas, and works for all sorts of groups, from a low-key girls’ night to dinner with the family. It’s even better when you’re in the large, open-air room, and you particularly want to come for brunch, when you can try a lot of different small bites, like waffle-battered chicken sticks or shrimp and grits. There’s a make-your-own Bloody Mary bar, too, and as far as we’re concerned, the garnishes count as tapas.


$$$$ 4539 N Lincoln Ave

Your Northside outdoor go-to for everything from dates to group meals. The American food at this Lincoln Square spot is tasty, and there’s a fantastic brunch with great pastries. The nicely-sized covered back patio is spacious and pretty, decorated with plants and flowers, and because it isn’t in a trendier neighborhood, you can typically get a seat. Order one of the charcuterie boards to share.

The Promontory

$$$$ 5311 S Lake Park West

This spot is from the same people who own Dusek’s/Thalia Hall in Pilsen, and is similar in that it also serves modern American food (like pierogi ravioli and a great cheeseburger) and has an upstairs music venue. But one big difference is that at Promontory, there’s a huge outdoor patio. So have dinner on it with your parents, or come before a show with friends.

Summer Guide
See the full Summer Guide

Saint Lou's Assembly

$$$$ 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 upscale cafeteria-style food (like meatloaf and sides) and small plates like foie gras with biscuits makes Saint Lou’s unique.

Spacca Napoli

Pizza  in  Ravenswood
$$$$ 1769 W Sunnyside Ave

Spacca Napoli, on a quiet corner in Ravenswood, is one of our favorite pizza places in all of Chicago. It has the most authentic Neapolitan pies in the city, and the non-central location keeps the patio peaceful and relaxed. You probably won’t leave without briefly considering buying a house with a yard in the charming tree-lined neighborhood, but honestly, just keep coming back for pizza instead. It doesn’t require as much maintenance.

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.

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.

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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