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A Guide to Chicago's Outdoor Hotspots

Updated: Oct 6, 2020

Whether you're a Chicago native or just visiting for the weekend, these

summer hot spots will be sure to spice up your weekend!

Wondering which locations are hot hot hot for some fun in the sun?! Here's a curated list, from downtown to the neighborhoods, of some of my favorite outdoor bars and restaurants that'll let you take full advantage of Chicago in the summer!

Cindy's Rooftop

Nestled across from Millennium Park with great views of the Cloud Gate sculpture (AKA The Bean) you'll find Cindy's Rooftop.

Located in the Chicago, Cindy's has breathtaking views of the skyline and the lake. You can head up here for dinner or just for a few drinks on the terrace, whatever the occasion it's definitely a must see!

Visiting in the evening? No problem! Grab a sweater and cozy up to one of the fire pits on the terrace and enjoy the views! ​

London House

One of Chicago's most coveted views is of the river. The London House rooftop bar has one of the best views in the city, overlooking the river and skyline! With a view like this, there's usually a line to get up but it's definitely worth the wait.

City Winery

You can find City Winery tucked away, only accessible from the riverwalk. This is one of my all time favorite places to be in the summer! It's affordable and easy to grab a drink at the walk up bar and you can grab a seat at a table or on the steps inches away from the glistening Chicago river.


If you've kept up with the local news you probably heard of the brand new bar as of summer 2019 that came to Navy Pier. You also probably heard that it's the nation's largest rooftop bar. Offshore is at the very end of the pier, overlooking Lake Michigan and the entire Chicago skyline. It's styled with indoor and outdoor seating along with fire pits scattered throughout. They even have a patch of turf perfectly suited for backyard games like corn hole.

The Robey

The Robey is a hotel located in Wicker Park with a fabulous wrap around rooftop bar and unique skyline views from the west. There's usually a wait to go upstairs and if that's the case, you can grab dinner and drinks at the downstairs restaurant.


If you're looking for an energetic atmosphere and an experience you won't find anywhere else, Federales is the place! Maybe it's the open concept, large patio, or great food/drinks. Or maybe it's the the shot bell, where you can order a shot of tequila and try your chances at hitting the bell!

Utopian Tailgate

Utopian Tailgate is a new rooftop bar as of 2019, located in Old Town overlooking Wells Street and the downtown sky scrapers! It's a vibrant spot with tons of backyard games to keep everyone entertained for hours! Perfectly suited for large groups and celebrations!

Happy Camper, Wrigleyville

Happy Camper is an eclectic bar that's set up well for big groups with large bar tops, booths, and picnic tables. With two different locations, the newest one on Wrigleyville's main strip is perfectly laid out to enjoy the summer weather. The indoor/outdoor concept along with an upper patio and bar makes it a definite summer hot spot.


If you enjoy the fresh air but not necessarily sitting in the sun all day, Gaslight has it all for you! With an adaptable patio open year round, you can enjoy the summer vibes and still have coverage over your head!

With unique drinks accompanying the delicious appetizers and entree's, it'll be hard for anyone to leave! If you're in the mood to drink and try something new, ask about their Fla-bong-o! Trust me!

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