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.
NEW FOR 2023:
This Japanese restaurant is on the rooftop of the $700-a-night St. Regis Hotel in Lakeshore East. The view of the skyline is incredible, and the service is even better. Miru's food isn't amazing (the long menu ranges from just-OK sushi to not-very-good entrees like burnt miso cod), but great food isn't why you're here. It's to admire the view, have a bunch of drinks or dessert, and feel like you can afford to throw money off said rooftop.
Tetto is a rooftop from the Recess team, who’ve proven they know what’s required of a fun outdoor space: lots of places to sit, a great sound system, and strong drinks. That all applies here, including little cabanas with couches and the option to buy bottle service. But what makes this West Loop rooftop someplace we want to be is that it serves food from Professor Pizza. The (former) takeout-only spot is now operating out of Tetto, which means you can eat some of the best tavern and New York-style pizza in Chicago with an incredible view of the city and an $85 cocktail tower.
After a three-year hiatus, Best Intentions quietly reopened this year, simply writing “we back” on a teeny note posted outside their building. This also included this Logan Square bar's secluded back patio. And that cute outdoor space happens to be an ideal place to drink $10 cocktails (which are way better than they have a right to be) and eat $6 smashburgers—you can even get a baker’s dozen for $72.
If you’re familiar with Big Star, then you pretty much know what to expect from Big Star Mariscos in West Town: wooden booths, a large patio, and a menu full of margaritas and tacos. But as the name suggests, this iteration of Big Star is more seafood-focused, with a selection of ceviche, aguachile, and coctels. The food is about on par with the original (kind of average) but the service is good and it’s a lovely outdoor space to grab some cocktails and share lime-marinated corvina.
Pizza Lobo’s original Logan Square location has great pizza-by-the-slice, pitchers of beer, and a large outdoor patio. And their new Andersonville location is the same, including an enormous back patio that has firepits, astroturf, and (probably) a bunch of cute dogs. They serve thin crust (for Chicago at least) pies, and have solid red sauce options like the “amatrice yo-self” (roasted tomato, pancetta, and Calabrian chile), and white pies. Plus, they're open until midnight.
RPM Seafood checks all the boxes. It has great seafood, solid cocktails, a lively crowd, and a large riverfront patio with umbrellas to protect you from the elements. And because it’s at street level, it doesn’t suffer from the smell of sewage wafting from the underside of the Clark Street bridge. Instead, you’re treated to an elevated river view surrounded by beautiful architecture and high rises reflecting the water. Go for a golden hour dinner, and watch the sunset shining in the glassy buildings melt into a twinkly backdrop.
THE SPOTS
The inside of Middle Brow in Logan Square is decorated like a DIY wedding—with tea lights, reclaimed 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 of 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. Order anything that involves the housemade bread (like the toasts and spreads), plus the pepperoni pizza, and plenty of their light, hoppy beers.
This iconic Lincoln Park spot that’s famous for its take-no-shit staff and wild late-night atmosphere now has a spacious back patio, and it’s wonderful. The partially-covered backyard has tons of tables, a full bar, mini basketball court, ping pong table, TVs, and heaters. Just know that you can’t order food from the bar, so hit up the regular ol’ Wiener Circle line for a char dog and some good-natured verbal abuse—then head towards that great patio.
The Lardon is a salumeria, so the menu is full of salumi, cheese, and various meats they cure in-house. Basically a bunch of fun, snack foods that are perfect for a solo meal while getting some work done, or a casual date. Sit out on their patio, order a meat and cheese spread (which come with housemade accouterments like onion jam), some wine, and wave a cornichon around to emphasize a hilarious-yet-charmingly-relatable point you’re making.
Rose Mary is a great Croatian spot in the West Loop and reservations are hard to get. But now they’re a little bit easier thanks to extra seating on their outdoor patio. Those new outdoor tables are all covered with large umbrellas to protect you from the sun, and decorated with string lights to distract you from noticing all the construction cranes swinging around the neighborhood. The menu has dishes like a tomato, farro, and asparagus salad, delicious crni rizot topped with grilled squid, and incredible pastas. And the service here is great—both inside and outside..
Every summer we tell people to go hang out at the outdoor space at Green Street Smoked Meats. You should still do that, but now you should also check out Trivoli Tavern. It’s owned by the same team and they’re also a part of Gin Alley. This means they have a twinkly lit cobblestoned patio that’s very cute for a date. Trivoli serves upscale bar food like fish and chips (they have a very good steak frites) and dinner here just might take the sting out of your canceled European vacation.
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 thin-crust 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, and you’ll never need to worry about your breadsticks getting soggy because of rain.
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 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.
Parson’s Chicken & Fish
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.
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.
This Filipino restaurant in Wicker Park works well for date night, dinner with a friend, or even just having some chicken adobo by yourself. The charm factor increases even more when you can sit on their small, tree-lined back patio. It feels like the kind of tiny urban backyard you’re certain exists but have never experienced for yourself, like exact change or a runner’s high. Don’t skip out on dessert while you’re here—the pastries are fantastic and the halo halo is some of the best we’ve had in Chicago.
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.
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).
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 all-weather outdoor area at Frontier in West Town will protect you from the elements, which is more than we can say about the poor pioneers who lived on the actual frontier. And while you will find things like antelope and elk on the menu, thankfully their commitment to the theme stops there since pioneers didn’t have hand sanitizer. Or air conditioning.
Adalina can be a bit of a sh*tshow. This upscale Italian spot is busy and loud, walks the line between fancy and overly formal (you’ll find servers in jackets), and gets pretty chaotic after 9pm. But the vibe on the sidewalk patio is much calmer and you’ll still have friendly service. Plus, the food is good. The patio menu has dishes like gnocco fritto with prosciutto, whipped ricotta, and honey (a fantastic starter) salads, and a $165 shellfish tower. So if you’re looking for a celebratory meal but don’t want to make conversation with the drunk people at the table next to you, sit outside.
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.
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.
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.
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.
You go to Azul Mariscos when you’re in the mood for the kind of spot that has a live DJ, bottle service, a rooftop and patio on the water, and gives you the option to order cocktails for the table in a $150 clay pot. This seafood restaurant recently opened along the Chicago River in Goose Island, and the food is Latin-inspired. This means the menu is full of things like lobster empanadas, tacos, shrimp aguachile, and seafood towers. Is it Miami? No, but it doesn’t feel like Chicago either.
