Top 5 Chicago rooftop lounges

Chicago Skyline

Chicago Skyline

Summer is here! Well maybe not officially, but it’s Memorial Day and it’s hot out, so let the roof top shenanigans begin!

This year, I’m celebrating Memorial Day in Chicago and I’m learning that people here, really know how to do summer right. Not just with the rooftops, but with the pools, terraces, beaches and patios. It’s starting to seem like Chicagoans spend all eight weeks of summer (summer is so short here…lol) outdoors, and while I’m in the city, I’ll be joining in the fun.

So this weekend with this great weather, I’m going to be stopping by my favorite five bars in the sky. See below for my list.

1. Vertigo Sky Lounge  As I mentioned, it’s Memorial Day and although the days are pretty warm, the evenings can be chilly. So it only makes sense to head to a rooftop imagethat not only has fantastic panoramic views of the city, but also a cozy fire pit. At Vertigo bar & lounge, there are fire features and intimate seating zones lining the perimeter of the terrace. If you’re looking for good music, and a young YOLO-ish crowd then be sure to check out this club in the sky.

2. Roof on the Wit  If you’re looking for fun during the day, definitely check out the Ladies-at-The-Wit-Rooftop-Bar-ChicagoRoof on the Wit. This reminds me of a Vegas style spot. I recommend going for Sunday brunch, the food is decent, the music is loud and the dancers are on tables. There is a retractable glass roof- a nice architectural feature, although one has to wonder if they ran out of money and weren’t able to make it automatic. Two men literally pull and push the roof open and closed. Get there early to score a cozy booth and enjoy the year round scenery in the bar, it rivals that of the outdoors.

Terrace-at-Trump-6 3. Terrace at Trump This glass structure is hard to miss along the river front. It really is a beautiful building; the lobby is nice, the scent is heavenly and the staircase leads to the tucked away Rebar. This dimly lit, lavishly decorated space is only made better by the upstairs Terrace. This outdoor space has one of the best views of the Loop’s architecture and the River (insider’s tip- go on Wed or Sat in the summer for great views of the Navy Pier fireworks). There are so many buildings to admire as you sip cocktails from the center of the city, in this bar in the sky.

4. NoMI Garden This sky high gem is great for cocktails and food. This terrace is stepsNoMI garden away from the indoor dining area, which is warm and rich with leather and wood and fantastic floor to ceiling windows. The terrace is equally inviting, relaxing and casual with teak furniture and greenery. This terrace can get very busy, a sign of how popular it is to unwind in this city Garden.

5. Urban Roofscape The Godfrey Hotel is definitely one of Chicago’s secrets, hidden in plain sight just off of Michigan Ave. It has one of my favorite rooftops and it’s brand nRetractable_Roof_At_IO_Urban_Roofscapeew (opened this Spring). The staff is great and the terrace is even better. The only thing lacking is a pool, aside from that the views are good- it’s a different perspective of the city and the cocktails, are delicious. There are a variety of seating options, sun shields and multiple bars which helps make the service even faster. In addition to the terrace are stylish interiors on the lounge floor. This open concept floor with an indoor/outdoor bar, lounge, conference area are perfect for when the sun gets too hot on the terrace.

So that’s it, my list of favorite bars in the sky. Check back at the end of summer for an updated list, as I explore more of the Windy City.


  1. Eric

    Great list! I visited NoMI twice, for a friend’s engagement and a birthday party. It was a fun experience both times. The service is always so impeccable, the food was delicious, and the scenery was amazing. I highly recommend it too!

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