Chicago: Our Favorite Patios


Go on, pat yourself on the back—you made it through the hellish Chicago winter OR you’re smarter than the rest of us and decided to visit Chicago during the greatest time of the year, SUMMER. As anyone who has visited Chicago or lived in Chicago will tell you, this city comes to life in the summer. There is nothing better than hitting up a Chicago patio and basking in the happiness that all the locals exude. Thus, drinking on patios is one of our favorite hobbies. Here are our favorite spots (in no particular order) that never fail to remind us why we live here!

Our Favorite Chicago Patios

1.  Jack and Ginger’s, Bucktown


This is our go-to neighborhood bar for the following reasons: their food and drink deals are some of the best (did I hear $2.50 retro beer cans and $1 sliders on SATURDAY?), you can play darts and Big Buck Hunter, the patio is legit, dog-friendly, and if you get to know the waitresses they might let you set up a few games of beer pong. On the patio.  Done and done.

2048 W. Armitage Ave. Chicago, IL 60647

2. Raised Chicago, The Loop


New hotel rooftop openings can come with a “see and be seen” crowd that makes for a so-so atmosphere, but Raised is an exception. This playful and friendly rooftop has a down to earth vibe with a gorg view down the river. Order the frites and “watered flowers” cocktail and bask in the greatness that is patio season in Chicago.

1 West Upper Wacker Drive, Chicago, IL 60601

3. Mahalo, Wicker Park

mahaloÅ’kålè ma’luna! Cheers! Mahalo brings Hawaiian vibes, food, and libations to the Midwest. If you can’t tell by the name of this blog, I love pineapples and Mahalo has a little (big) something called “The Big Kahuna”, which is a cocktail for two served in a real pineapple #sold. Their fried rice, tropical décor, and fun cocktails make it a great spot for happy hour or a dinner with your family.

1501 N Milwaukee Ave, Chicago, IL 60622

4. Cindy’s Chicago, The Loop


Cindy’s made our list because it has one of the most unique views of Chicago in the city. As you enjoy dinner or drinks you get to take in views of the lake and Millennium Park, including “The Bean”. Now, remember when I said some rooftops are full of see and be seen people? This can be one of them. If you don’t snag a reservation for dinner you will have to wait in a line in the lobby of the Chicago Athletic Association Hotel. The prices are steep (especially the food), but that’s standard in The Loop. In my humble opinion, Cindy’s is worth a one-time stop for happy hour before you descend back down the elevators to the land of normalcy and cheap beers.

12 S. Michigan Avenue, Chicago, IL 60603

5. Big Star, Wicker Park


Welcome back to our neighborhood (the land of normalcy, if you will)! The wait for a table on Big Star’s patio can be 2+ hours for good reason: $6 craft beers on tap or $3 cans of Tecate for the budget-minded, $9 margs, and $4 kick ass tacos. This patio is always full and always fun, oh and it’s dog friendly! Drink on, Fido.

1531 N Damen Ave., Chicago, IL 60622

6. Parson’s Chicken and Fish, Logan Square


(photo cred to our great friend, Jill Groh @jillegroh)

Parson’s takes you into the “hipster” neighborhood of Logan Square, which is full of unique bars and restaurants. No doubt, you’ll feel on trend camping out at a picnic table on this patio. My go-to is one (or many) of their frozen cocktails, pimento toast, hush puppies, and fried chicken. If it’s frozen or fried, I’m in! If you’re punishing yourself by going outside during the Chicago winter, Parson’s also puts a smile on your face by turning their patio into an ice rink. So, it’s year round awesome.

2952 W. Armitage Ave. Chicago, IL 60647

7. Chop Shop, Wicker Park


Call us bias towards our neighborhood, but here’s another one in Wicker Park….Butcher shop  + bar + restaurant + music venue + patio = Chop Shop. This one stop shop has it all. You’ll get seasonal food and cocktails in a laid back atmosphere. The eclectic furniture, mural-ed walls, and peekaboo view of Wicker Park’s iconic Northwest Tower set it apart from other patios in the neighborhood. They have a legit cocktail, beer, and wine menu, but don’t forget about their punch bowls because, you know, sometimes bigger is better! #foreveryoung

2033 W North Ave, Chicago, IL 60647

8. River Roast, River North


Vegetarians be warned, this riverside joint has a serious meat focused menu. Their patio is unique because it’s right on the river and if you go for one of their roasts, they’ll carve it tableside. So, go on, grab a Moscow Mule, a slab of meat, and watch ambitious kayakers navigate the river, commuters rock the water taxi home, and boaters cocktailing with friends.

315 N LaSalle St, Chicago, IL 60654

9. Jazz at the Shedd Aquarium, South Loop

Shedd 2

All my dreams can true when I learned about Jazzin’ at the Shedd. Every Wednesday at 5pm the doors of the Shedd open for the world’s greatest adult field trip. You get all the great animals sans screaming children AND wine, live music, and, wait for it, fireworks! After walking through all of your favorite exhibits (and taking a selfie with a sea turtle), go out to the patio for unreal skyline views and a fireworks show around 9pm. Take a hint from a pro and skip frequent trips to the bar by ordering bottles of wine to share #efficiency.

1200 S Lake Shore Dr, Chicago, IL 60605

10. Weeds Tavern, West Town


Weeds Tavern is the hidden gem to end all hidden gems. This patio takes it the next level with super casual vibe and patio games. The only thing better than drinking outside, is drinking outside while playing games! Weeds has big Jenga, huge Connect Four, and bags for all to enjoy, which is asking for a day of beer olympics. The icing on this patio cake is the beautiful flower boxes, great drink deals, and the fact you won’t be waiting hours to get in. They don’t serve food, but there are plenty of places in the area that will deliver right to the bar.

1555 N Dayton St, Chicago, IL 60642



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