Ambiance Matchmaking Meet Attractive Singles
Ambiance Matchmaking Meet Attractive Singles

Chicago's Best Patio Bars & Restaurants

Chicagoans swarm patios, rooftops, and beer gardens to soak up the sun in the short summers. However, choosing among the abundance of options can be overwhelming, especially when you want to make a good impression on your date. Each spot is picked for unique reasons and no two places are the same. Want a cabana-style lounge? An urban-chic escape? A dive beer garden? We have you covered!



This Lincoln Square charmer features a 40-seat outdoor terrace offering a special outdoor menu every day starting at 5 pm. In this renovated space, you can find lush garden seating, an oversized mural by a local artist, and custom benches and chairs. The food menu will focus on seasonality and fresh ingredients from local farmers alongside a changing lineup of craft cocktails and summer wine coolers. Start with a "gathering board" of charcuterie and cheese, and go from there. Sources: Chicago Tribune & Chicago Eater
Address: 4539 N Lincoln Ave, Chicago, IL 60625



The space, lighting, and overall atmosphere are excellent inside this Mexican-inspired restaurant right in the heart of Lakeview. Choose from the abundance of margarita varieties, categorized by "Sweet," "Spicy," and "Smoky" – my personal favorite is the spicy Margarita El Fuego topped with jalapeno foam. The interior is beautiful – the walls are lined with open-air garage doors among rustic reclaimed wood and sensual fireplaces. It will feel like you're relaxing on a sunny beach and the coziness of a mountain cabin all in the comfort of Chicago.
Address: 2901 N Sheffield Ave, Chicago, IL 60657


The massive outdoor beer garden was an institution even before they added a BBQ-minded kitchen. Thanks to the exhaustive beer selection and the enormous shade-providing tree, you will momentarily be taken to a whimsical forest, which is also a possible result of sampling enough of the beer. Source: Thrillist
Address: 3258 N Sheffield Ave, Chicago, IL 60657



Summer House Santa Monica embodies such an amazing atmosphere: bright, white decor, glimmering lights, driftwood walls, a high glass ceiling, and a front outdoor patio. It definitely has a Californian vibe here, yet people aren't walking around in shorts and flip-flops. Think business casual when dressing for your date. It features an artisanal bread program, an extensive wine list, fresh-squeezed juices, and Californian-influenced American cuisine with locally-sourced ingredients. I personally love the menu due to its abundance of seafood (I order the salmon every time). Tip: make a reservation ahead of time as there is usually a long wait list if you just show up.
Address: 1954 N Halsted St, Chicago, IL 60614


Homeslice gets an overall grade of an A+ for atmosphere, food, and drinks. The rustic inside makes you feel like you're in a log cabin nestled in a ski resort. The outdoor back patio has hanging Christmas lights spelling "AWESOME", heat lamps, cozy patio seating, and a gutted silver bullet trailer available for seating. They have the best gluten-free pizza I've personally ever had. And they serve their Moscow Mule just right and necessarily out of a copper mug (which you can buy for $10). 
Address: 938 W Webster Ave, Chicago, IL 60614


If you're looking for great al fresco seating that makes you forget that you're in Chicago, look no further. Las Fuentes' courtyard is one of the biggest outdoor seating spaces in the city. Murals, fountains, and string lights really make the ambiance of this place. 
Address: 2558 N Halsted St, Chicago, IL 60614



Chop Shop is a hybrid eatery consisting of a bar, restaurant, butcher shop, and event space called the 1st Ward for special events, like Dose Market. The meat-centric menu offers an overwhelming variety of meats and cheeses from around the world and local farms. But if you're going just for the drinks, you will not be disappointed. Select from the extensive beer, cider, and wine list or try a delicious cocktail – perhaps the Limoncello – a house-made secret recipe "aged up to 60 days."
Address: 2033 W North Ave, Chicago, IL 60647


Located right next to Wicker Park itself, Big Star is one of my favorite outdoor patios in the area. The people-watching is top-notch, and the fish tacos are even better – almost too good, as scoring a table can be rough. However, you can sip an amazing margarita at the indoor bar while you wait. This spot definitely exuberates a more friendly, laid-back atmosphere which makes it that much easier to enjoy sipping your cocktail under the sun.
Address: 1531 N Damen Ave, Chicago, IL 60622



The multiple bike racks out back are packed with every kind of two-wheeler imaginable, no matter the time of year at this biker bar (and by biker, we mean bicycle-r). Eco-minded folks chat over tasty vegan fare (the barbecue seitan is great), check out each other’s rides, and sample from the ample list of diverse drafts. Source: TimeOut Chicago
Address: 2311 W North Ave, Chicago, IL 60647



My recent dinner at Ada Street was long overdue. Only accepting reservations between the short window of 5:30-6:30 pm, I made a 6:30 pm reservation. We entered through the heavy, red velvet curtains which led us down a long, narrow hallway opening up to a well-lit dining area filled with just enough people to create a lively atmosphere. The food and cocktails exceeded my expectations. As a lover of small plates (probably stemming from my time in Spain), I got overly excited for the six dishes of smaller proportions to share. I was also impressed by their cocktails. We both ordered tequila concoctions, one sweet and the other bitter, which we shared because they complimented each other so well. Walk into the back where you will find the artificial-turf, brick-walled courtyard, complete with ping-pong tables and a grill.
Address: 1664 N Ada St, Chicago, IL 60642


The four-season, 2,500-square-foot beer garden adjacent to Frontier has a retractable roof that lets up to 100 people dine in open-sky splendor. Fitted with several fireplaces, the one in the beer garden is the most scenic. Drop in for brunch or your fix of gamey meats with a selection of house charcuterie and plates like gator ribs and antelope meatballs. For seafood lovers, enjoy $1 oysters on Wednesdays from 4-6pm. They have 16 seasonal and traditional beers on tap, including craft microbrews. The bar is one of the few in Chicago to extensively employ state-of-the-art ice taps, which keep the beer colder, fresher and cleaner for a perfect pour. Sources: Chicago Tribune & Chicago Eater
Address: 1072 N Milwaukee Ave, Chicago, IL 60642



If you're looking for a more laid-back and quirky environment, this is a good choice. Green Street Meats is not your normal restaurant. The interior is filled with tin, concrete, and faded picnic tables that wrap around the large, rectangular bar centered in the middle of the joint, while the exterior patio settles in underneath the warming, dangling Italian lights. Personally, one of my favorite spots in the city in terms of liveliness and atmosphere. Make your way to the cue and order from the chalkboard menu of meats and salmon that are served fresh off the 12,000 pound smoker. The bar has 16 beers on tap plus a dozen more in cans. 
Address: 112 North Green Street, Chicago, IL 60607


This industrial-chic pizzeria offers Neapolitan-inspired pizzas prepared in imported Italian Pavesi wood-burning ovens, but I heard the Craziest Bread is the secret star of the menu. Stuffed with garlic, mozzarella, cherry peppers and pepperoni, you’ll need some help finishing just one serving of this gooey beer bread. Their massive outdoor beer garden has a 145-seat patio and a 176-seat rooftop deck, made from an old freight container. The pizzeria serves American craft beers, artisan wines and inventive cocktails. Also on tap: weekend brunch with an impressive Bloody Mary Bar.
Address: 108 N Green St, Chicago, IL 60607


The addition of a retractable roof a few years back has made heading to this Greektown mainstay's outdoor patio a low-risk proposition, whatever the forecast. The food is solid and the east-facing city views are very pretty.
Address: 212 S Halsted St #1, Chicago, IL 60661


Another small-plates spot featuring dishes such as the smoked oysters, deviled eggs, duck liver mousse, and the chicken-friend lobster. The huge brick-paved patio with greenery and high walls makes you feel like you’re far away from the busy corner next to the Grand Blue Line stop. Other characteristics include the rough wood siding, barrel bar tables and a steel-and-wood pergola. Half the space is set with tables for full-menu dining; if you're in the bar area, grab a charcuterie plate and a cocktail and enjoy the people-watching. 
Address: 730 W Grand Ave, Chicago, IL 60654



The Hampton Social strives to bring the laid back and coastal atmosphere of the Hamptons to Chicago with bright, airy spaces, allowing a pseudo sea-breeze to flow in from Chicago's streets, fresh seafood–try the diver scallops with creole pan sauce, cheddar grits and bacon or an oyster belly o' boy – beach-themed cocktails, and even a swinging hammock for lounging. Every Tuesday through Friday from 3 to 6pm enjoy half-priced pizza and bottles of rose.
Address: 353 W Hubbard St, Chicago, IL 60654


I came to Celeste for Made In Brazil – a Brazilian samba party located on the rooftop garden. I was instantly mesmerized by the stringing Italian lights, ivy-covered walls, and swarming of people in lively chatter. They use the word whimsical to describe the "The Garden" and I couldn't agree more. Remember to try their delicious caipirinha!
Address: 111 W Hubbard St, Chicago, IL 60654


The new Asian hotspot should get even hotter with the arrival of a 20-seat, multi-level Zen garden patio, featuring cabanas, tiered wooden decks and evergreens. The traditional Japanese Zen garden will provide a tranquil environment for relaxation amidst the hustle and bustle of the city while Sumi’s bottled cocktails will help guests cool off. Source: Chicago Eater
Address: 702 N Wells St, Chicago, IL 60654



The neighborhood bar attracts a crowd from far beyond Humboldt Park borders, thanks to a funky, taxidermy-filled interior; large backyard patio with a summer bar and string lights; and cheap beer and shots. The lowlife, a shot of whiskey or a pull from the amaro machine, (like the old Jäger machines), plus a High Life is just $5, and is more consistent than the ever-rotating list of cocktails. It's cash only, and you can also bring your own food in, though the Tamale Guy will also likely make an appearance for late-night snacking. Source: TimeOut Chicago
Address: 948 N Western Ave, Chicago, IL 60622

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