Chicago is a magical place all year round (despite how much I gripe about the winter weather!) but summertime is when the city really comes alive–it’s like it takes on a whole new personality!
And because Chicagoans have to soak up as much summer as they can while the weather is good–there’s certainly no shortage of rooftop bars and patios. Regardless of if you’re visiting for the weekend or you’re a local, putting a few alfresco spots on your must-visit list is pretty much a non-negotiable.
Below, I’ve rounded up my 25 favorites–from the well-known spots downtown, to some lesser-known, unsung hero’s off the beaten path. Whatever experience you’re seeking, I promise you’ll find something you’ll love on this list!
1. 90 Miles Cuban Cafe: Ridiculously delicious Cuban food, BYOB, and an even better patio make this a perfect, affordable date night option. This is one of my all time favorite spots in the summer! It was also featured on my favorite show, DDD. (Diners Drive-ins and Dives, obviously.)
2. Parlor Pizza: Not classic Chicago style, but perhaps my very favorite pizza place in the city. They also happen to have one of my favorite patios in the West Loop, perfect for a casual get-together with friends, strung with beautiful patio lights, and there are even some beer pong tables, too.
3. Homestead on the Roof: Above Roots Pizza in Ukrainian Village, this is a rooftop restaurant is the definition of “farm to table.” Yes, they actually have a farm on the roof. Everything they grow in the rooftop garden is served up in the form of some incredible gourmet dishes. The atmosphere is upscale casual and I truly can’t imagine a more perfect spot to be on a warm summer night.
4. Ada Street: One of the best restaurants in Chicago and one of my favorite meals. We went here for my birthday one year–there’s a big garage door that opens up onto an awesome patio surrounded by string lights and exposed brick.
5. Bridge House Tavern: Somewhat of a dark horse on this list, Bridge House isn’t the trendiest spot on the block–in fact, it’s even a little hard to find, but it’s one of the best restaurants that sits right on the edge of the river. They also offer a bottomless brunch on Sundays.
6. Kaiser Tiger: One of the coolest spots to be when it’s warm outside, this restaurant boasts a giant back patio with communal picnic tables, bocce ball, and live music.
7. Big Star: Probably the most beloved Mexican restaurant in all of Chicago, Big Star also happens to have a giant patio, delicious margaritas, and some of the best tacos north of Pilsen. Just make sure to bring cash–they don’t take cards!
9. Athena: You’ll truly feel at home at this Greektown eatery. I’ve never met a gyro I didn’t like, but Athena offers something truly unique. Not only do they make you feel like you’re pulling up a seat at the family table, but their huge outdoor patio makes this place ideal for group dinners, and the views of the skyline from this West Loop spot do not disappoint!
10. Frontier: This is where Neal and I went for our first “real” date. They have a pretty adventurous menu–alligator ribs, llama meatballs (plenty of normal stuff, too) but the patio is a great spot to grab a cocktail as well! It’s a little off the beaten path, but worth the trek. They also have a great brunch!
11. Zed451: The rooftop of this popular argentinian steakhouse is to die for. They make a mean Prosecco cocktail, and their “woodsy-chic” patio provides a cool escape from the concrete jungle. This place is not to be missed!
12. Piccolo Sogno: With their garden patio and incredible Italian fare, it’s no wonder this place is often referred to as the most romantic date spot in the city.
13. III Forks: Because it’s located in The Loop, this upscale steakhouse is an ideal spot for an after-work cocktail, plus, it’s never busy on the weekends! They also have fire pits and heat lamps when it gets chilly!
14. Troquet: Another dark horse on the list–this French bistro is little known spot in River North, but it’s a great one. This little place attached to Hotel Felix boasts awesome food and is a great place to grab some rosé. Never too crowded, it’s perfect for an impromptu meal, and is one of my favorites for brunch.
15. RM Champagne Salon: While we’re on the topic of romance, RM Champagne Salon probably has one of the most romantic, rustic-chic patios in the West Loop. If you haven’t been, you’re definitely missing out!
16. City Winery: Chicago’s first working winery located in the West Loop. Although one would think it would be jam packed with tourists and locals alike, I don’t think the masses have caught on to what a true experience this place is. Fantastic burrata and an amazing selections of wine (on tap!) In addition to their spacious patio, be sure to check out their concert hall for an ever-changing rotation of blues, country, comedy, and pretty much anything in between! They also just opened a second location in the Chicago Riverwalk!
17. Rock Bottom: Yes, this is a chain that is typically found in the suburbs, but it actually has one of the best rooftops downtown! It’s a fun, casual atmosphere, and they have great beer!
18. Drumbar: Not far from the Hancock is another swanky (perhaps, the swankiest of them all) rooftop cocktail lounge. If you’re looking for some of the best drinks in the city, this place should be at the top of your list. It’s a great way to end a day of shopping on Michigan Avenue.
19. Cindy’s Rooftop: This restaurant and bar at the top of the Chicago Athletic Association has one of the coolest views of the city and the lake. Cindy’s is a must-do for a cocktail or two (great for brunch as well!) After, head down to the game room to have some fun!
20. NoMi Garden: NoMi’s garden terrace in the Park Hyatt right off Michigan Avenue is an ideal spot if you’d like to be a “lady who lunches.” (There are a lot of those ladies there on a daily basis!) I’m a sucker for their lunch menu in particular, but they’ve also got great cocktails, and a delicious dinner menu, too! Fare is upscale casual, and they’re well-known for their sushi, too.
21. Parson’s Chicken and Fish: I just went here for the first time with Neal and fell in love! Insanely good fried chicken, ridiculous hush puppies, famous boozy slushies, and a giant, adorable back patio with ping pong tables. I mean…what else could you want?
22. Homeslice: Another pizza joint near and dear to my heart, Homeslice has a woodsy patio with plenty of heat lamps, complete with a refurbished air stream that you can dine in. Get the Radler–it’s one of my favorite summer drinks! Also, their ranch is SO DELICIOUS.
23. Howell’s and Hood: One of our favorite spots when Neal lived in the Loop, this place is absolutely massive, complete with a large patio, great menu, and a good list of cocktails.
24: Twisted Spoke: A quirky biker themed dive bar in West Town, one of my favorite neighborhoods. You’ll know it when you see it–there’s a motorcycle riding skeleton spinning on top of the bar. Twisted Spoke is known for some ridiculous burgers, and their rooftop deck is a great spot to grab a beer on a hot day.
25: G&O: Across the street from Twisted Spoke is G&O–a smaller, yet trendier bar serving up some amazing cocktails, foodie-approved small plates and the BEST EVER MAC AND CHEESE. Their patio is small, but charming and adorable. Go there now.