The Best Rooftop Bars In South Loop

Nothing beats a great view – well, possibly a great view with a great drink to enjoy it with – so to that end we decided to find out just what the best rooftop bars in South Loop are. Everyone loves a place to kick back, look out, and have eye candy as far as the eye can see and we’re happy to report that South Loop has quite a few places to enjoy.

First off, we headed out (and up) to Cindy’s. Overlooking Millenium Park, the Art Institute and Lake Michigan, Cindy’s is set within a vaulted glass and steel rooftop atrium. It might be a tourist trap but what a trap! Be sure to get there early as the work crowds quickly filled up. The drinks are a little pricy but you’re paying for the view – we sampled the Western Cape and Grey Garden and enjoyed both. We were most impressed with their innovative flavors, ingredients and flavor combinations. The food on hand is great and the portions huge. We sampled the Burrata which comes with grilled ciabatta, frisee, melon jam and candied vegans. Yum! There’s also a DJ although to be honest, we couldn’t find out how often he shows up.


Next up is the 52Eighty Rooftop Lounge based atop the Cambria Hotel. We sampled the Goat Cheese cheesecake, risotto balls, and fried oysters and enjoyed them all And the ambience is cool too; the architectural vision is modern, minimalistic, and inviting.
Finally we checked out the Plymouth Rooftop Bar & Grill. Along with a stunning view it comes with weekday drink specials and half-price appetizers from 3-6pm.  We sampled the Chicken Tenders Basket and Hummus Platter and enjoyed them both; it’s basically upscale bar food. There’s a very lively atmosphere here too; once you exit the elevator doors on the rooftop level you’re assaulted by the noise of music, people, and ice clinking – along with an amazing smell of food! We’d heard the Plymouth has the best pub burger in Chicago and once we sampled it, we have to agree.

Whichever rooftop bar in the South Loop that you hit, enjoy it and then hit a new one the next time you go! Hopefully we’ll see you there!