A Different Kind of Party: The Best Rooftops and Day parties for an LA and Chicago Summer!

Updated: Jul 8, 2019

I love to be outside during the summer time! I especially love hanging out during the warm evenings- no jacket required. It makes me happy to no longer be bundled up and huddled inside. Summers mean cookouts, visiting the beach, swimming in the lake, and so much fun. Summer can also mean gathering up your friends, after a long day or work week, to catch the sunset on a rooftop - talking until it’s past your bedtime. Today we discuss some of the best rooftop bars in LA and Chicago to catch a vibe, have a drink, and enjoy your summer a little closer to the sky. Chicago, you’re up first!


I | O Lounge at Godfrey Hotel

I | O Lounge

With 15,000 square feet of indoor/outdoor space, you are bound to find the perfect space to lounge with friends under the summer sun.

Located River North, I | O Lounge provides multiple ways to catch a vibe. There are fire pits, a retractable roof, sparkling water elements, a video wall and uninterrupted views of the Chicago skyline. It’s the perfect way to enjoy the weekend. “Happy Hour” is Monday through Thursday from 3 p.m. until 6 p.m. and Friday at 12p.m. until 3p.m.


Located in the Athletic Association Hotel, Cindy's offers views of Millennium Park, the Art Institute, Lake Michigan and more!

Gotta love a place with overhead string lights and brunch. This summer they are having a Chicago bartender series with featured mixologists, debuting curated menus between 7p.m. and 10p.m. on select days.

ROOF at theWit

Travel and Leisure crowned ROOF at theWit the third rooftop bar in the world! ROOF at theWit is a must. ROOF provides something for all the senses. Amazing views, tasty cocktails, and delicious food. To secure your spot, be sure to make a reservation before heading over.


LH Rooftop gives you options, options, options! LH on 21 is an indoor bar and restaurant. If your melanin is craving some sunlight, head up to the 22nd floor and enjoy amazing views of the Magnificent Mile, Lake Michigan and the Chicago River.

Want to try something new? Bridge Lounge offers its take on afternoon tea. Pinkies up sis!

I, for one, cannot wait to try out at least 2 of these locations when I travel to Chicago this summer!

Now for a little hometown love. Los Angeles, it’s your turn!


Perch has one of the best views of downtown LA hands down. During the week, you can catch a local jazz band on the 14th floor. Come back on the weekends and grab a seat on the 15th floor, as music pipes through the speakers and scatters across the rooftop. The drinks are delicious and not to mention, there is even a late night menu.


Ascend to new heights at the tallest open-air bar in the western hemisphere. Spire73 sits on the 73rd floor of the Intercontinental Hotel in Downtown LA. Enjoy DJs, food, and drinks while basking in an unrivaled view. It's $10 before 8 p.m. for non-hotel guests every day.


Get those front and back facing cameras ready. Pearl’s in West Hollywood offers up Instagram worthy content on top of great happy hour options - $1 oysters on Tuesdays with $8 chilled vodka shots.

For brunch, you can purchase a mimosa kit. The kit features fresh orange juice, strawberry puree and white peach puree with fresh fruit and flowers. All of it is yours when you purchase a bottle of champagne. It sounds like a good deal to me!


Tuck away for a secret rendezvous, or bring your next client here for an unpretentious, but well-curated rooftop experience. You will experience 360 views of West Hollywood. Let me be the first to tell you, the Hollywood Hills will put stars in anyone’s eyes. Good food and drinks without the crowd. You may have found your new ‘private’ summer escape.

If you are lucky to live in a place with great summer weather, take full advantage! Do you have a favorite rooftop bar? Did we leave off THE BEST bar? Tell us in the comments below. We want to know where to go from our Janes when we come to your city!