I love Chicago. Rooftops.


I thought I should review some of my favorite Chicago spots. There is so much to do in this city.  I arrived on August 1, just in time to enjoy some gorgeous weather. For me, the end of summer was all about the rooftop bars. So let’s start there.

The Chicago bar.
Citizen is one of my favorite rooftops. A small, neighborhood
feel with the friendliest people in all of Chciago. I recommend calling ahead to
reserve a table on the rooftop. Great drinks, great food, great people. The black bean quesadilla, fries + black bean veggie burger are all amazing. The tater tots are dangerously good.

364 W Erie St.
(312) 640-1156

The scene.
Epic. Not your typical laid back Chicago rooftop. If you are looking to get all dressed up for a night out on the town, this would be a fun place to go. I feel like I want to throw the words “hip” and “swanky” out there, but that wouldn’t be very hip or swanky of me, so I won’t do that.



112 W. Hubbard St.



The sports bar.
I have been to Benchmark many times. It is in the heart of Old Town — a great area to spend a summer day. During the day it’s a fun, laid back {but still nice} sports bar. Good drinks & great scene. This place is packed both day & night. During the summer the roof comes off the second story. I’ll let the photos speak for themselves. Rumor has it that this is where the taller Chicago guys hang out. I didn’t start the rumor

With & without the roof.

1510 North Wells Street
(312) 649-9640

The city.
Zed451. If you want to sit on a rooftop surrounded by buildings, this is the place to go. A nice stop for drinks and apps before heading out for a night with the girls.


739 N Clark St
(312) 266-6691

The views.
The rooftop at The Wit is exceptional. Definitely has that “hot spot” city feel, so if that’s your scene, you should check it out. Flames burn down the center table and it all feels very urban & chic. As my friends and I would say, it is very Chicago. And the views…to die for.


The Wit
201 N. State St.
(312) 467-0200

  • amber

    i've never been to chicago and never been on a cool rooftop. i think i am missing out…

  • suburban prep

    Boy you have had some wonderful adventures and views in Chicago since your arrival. I hope it always as great for you.

  • dubious

    you missed the creme de la creme – sixteen @ the trump and what about citizen?

  • Veggies, Cake & Cocktails

    I've been to The Wit a couple times and you are right, the views are very impressive. However, the service has not been all that great.

  • Lauren

    Ummmmm, when I come to visit you, and oh I will come to visit you…Pretty please take me to ALL those places, haha!!! 🙂

  • Danielle Moss

    I'll have to revise this post. Completely forgot trump & citizen, although Trump isn't technically a rooftop. It's a terrace.

  • {Selma} Crazy Little World Of Mine

    Love these…I'm definitely missing the big city life and its endless restaurant/bar opportunities!!! 🙂

    Happy Friday.

  • Amanda @ Bits & Pieces

    Great rooftop round-up!

  • Connie

    Love this post! Really makes me miss Chicago 🙂 I love our visits there in the Summer and Fall to see family…I would move in a heartbeat if it weren't for Uncle Sam telling our family where to live, ha!!

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