Chicago Alfresco Dining

Summer is wrapping up, those long summer days are getting just a little shorter, and fall is just around the corner. So, before the kids go back to school and the leaves turn golden it is time to make the most of the remaining summer nights. What better way then to enjoy a good meal and cocktail outside?

Chicago has some great outdoor patios and rooftop bars that are not to be missed. Here are a few personal recommendations to plan into your final summer weekends with some quality alfresco dining.

ROOF

This rooftop lounge above the TheWit is certainly the hottest lounge in the city during the summer months. Long lines are a guarantee on the weekends, but the wait is worth it. Plush couches, huge cabanas, fresh cocktails, and breathtaking views of the city await you. The setting alone will make you feel like you are a Chicago VIP!

Big Star

Nothing beats a Paul Kahan (big time Chicago chef) dinner for under $10! This casual taco joint in the heart of Wicker Park serves up delicious tacos and a full bar with a highlight on the whiskey. The indoor setting is very simplistic and outdoor tables sprawl across the parking lot, but it definitely draws a fun crowd every weekend making it a place to see and be seen by both locals and tourists.

Volo

This is patio dining at its’ absolute best – beautiful, simple, and leisurely. The back patio of this little Roscoe Village wine bar offers adorable private booth seating, as well as basic tables across the patio. The wine menu is fantastic and paired with a nice menu of small plates, including a good selection of cheese flights.

Piccolo Sogno

If you can only try one alfresco dining locale by the end of this summer, Piccolo Sogno has to be it! The Italian food and wine selection are superb and the setting is gorgeous with warm light and ivy covered walls. It is is a little hidden gem of Chicago that will make you feel you escaped the hustle and bustle of the city for this lovely meal.

Halsted’s

This simple patio in the heart of Boystown will allow you to easily hang onto that nice summer feeling. The patio is surprisingly large that is shaded and private. The food is nothing amazing – pretty standard bar food, but it is a great place to bring a group of friends or family for a fun and relaxing dinner outside.

Photo Courtesy of Bobbi Bowers