Supper With Sylvia – Rooftop Roundup

By September 3, 2015On Sylvia's Mind

Summer is almost over so I wanted to get my final list out and I’m calling it my “Rooftop Roundup.”

It is part of my Summer 2015 quest to find the perfect rooftop bar. I’ve been trying to hit one of these places twice a month. Here’s what I’ve learned. When it comes to outdoor bars, you are paying for the view, signature cocktails and a social scene. The food is an also-ran in some cases.

IMG_7967Godfrey Hotel I/O-Really nice setting in the Godfrey Hotel with a beautiful city backdrop. Of all the rooftops I’ve tried, this one seems to offer the biggest food and beverage options. I thought the food was  good especially the sliders and truffle fries. There was a variety of cocktails to choose from. When the sun went down, we were surrounded by sparkling city lights.  The staff was a little odd, almost appearing snobby at times. I’m not sure why.

Streeterville Social-This one is billed as Chicago’s largest rooftop bar.


It’s 9,000 square feet at the new Loews Chicago Hotel located in Streeterville. This terrace is separated into two bar areas. Again, limited menu but our favorites were the kimchi chicken wings and the bucket o’ fries. Not healthy but fun finger picking food with the girls. There’s even a grassy lawn for games. It’s pretty over the top. Very relaxing because it’s so large and does not feel crowded.


J Parker–We did a girlfriends’ birthday party here and it was standing room only. Fortunately we had a beautiful sectional reserved just for us. The view is spectacular, overlooking Lincoln Park and Lake Michigan.


Once again a limited menu but a big selection of signature cocktails and wine, liquor and beer.  We loved the pork sliders and  the salumi platter from West Loop Salumi.  J Parker is where the young and hip hang out, which I am not and if you’re not, I still think it’s definitely worth going at least once. Service was good and the workers were very, very friendly.


Cindy’s-The hottest rooftop in Chicago these days seems to be Cindy’s at the new Chicago Athletic Association hotel.

Rooftops-Cindy_sIt’s very pretty but know there is almost always a line to get in.  The food is top notch and so is the view.  If you go, just note that the actual rooftop that has you seated outside is very small. Most of the restaurant is enclosed with a glass ceiling. But if you get a chance to sit or walk outside you will love the view. It overlooks Millennium Park and the Chicago Lakefront. It’s stunning. The seating in the enclosed area is picnic style which after a while can wear on your other end.  The food was good. I went with several girlfriends and we shared the burrata, meatballs and grilled cauliflower.

Finally, you can’t do a rooftop roundup without mentioning Trump. No matter your political affiliation, this by far is the most beautiful view. Lake Michigan, Chicago River, and surrounded by city high rises, you can’t lose. The problem is it’s way over priced and the service can definitely be on the snooty side and very slow. I leave this up to you but if you go, you will be in awe of the surroundings.

This is my list for now. Are there any you want to recommend to me? Hurry up and let me know, time is running out. To quote a line from a favorite TV series, “Winter is Coming.”

Sylvia Perez

About Sylvia Perez

Sylvia Perez is an Emmy Award winning broadcast journalist, news and health reporter, and major market anchor. Her expertise in revealing the personal side of headline stories and drawing their impact into “news you can use” viewership is now the foundation of Sylvia Perez Productions, a multi-faceted company specializing in video production and event planning for non-profits.

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