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Upstairs At The Gwen Chicago

Photo credits: Upstairs At The Gwen Chicago

5+ Rooftops Open On Wednesday In Chicago (2024 Update)

Boost your Wednesday. Check out Chicago’s top rooftops. Perfect for relaxing.

Written by Michael Ford

Updated on March 2, 2024

Ready for a new Chicago thrill? Picture this: the city's buzz, now a quiet hum, as you’re up high, taking in the skyline. This isn't just any Wednesday; it's your ticket to a unique Chicago night out.

Our 2024 guide shows you the best rooftops open on Wednesdays. These spots offer luxury and a bit of adventure too. Perfect for unwinding after a long day or for a special treat in the heart of the city. Here, fancy drinks and stunning views go hand-in-hand. Join us on a journey to Chicago's top rooftops, where every detail spells luxury and every moment makes your midweek special. Ready to change how you see Wednesday nights? Let’s go up.

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Guide
Stylish rooftop bar with a glowing interior and panoramic city views at sunset, featuring a fully stocked bar and comfy seating.

Photo credits: Offshore

(4.5)

1. Offshore

What is it? Offshore is the biggest rooftop bar in the world, right on Navy Pier. It's not just a bar. It's a special place high above Lake Michigan with amazing views of the Chicago skyline. This cool spot has comfortable lounging areas, modern decor, and warm fire pits, all with a touch of glamour.

Why we love it: When night comes, Offshore lights up with music from live DJs, creating a top-notch vibe. You can enjoy creative drinks, tasty snacks, and stunning views here. Offshore turns a regular night into something amazing. It's a perfect choice for anyone looking to make their Chicago visit more exciting.

Sunday, Monday, Tuesday, Wednesday, Thursday, Friday, Saturday

1000 E Grand Ave, 60611 Chicago

Chic rooftop setting at Cindy's Chicago with cozy seating, vibrant yellow balloons, and a sleek wooden floor, offering an inviting space for relaxation and social gatherings.

Photo credits: Cindy's

(4.4)

2. Cindy's

What is it? Cindy's sits high above Chicago at 12 S Michigan Avenue. This rooftop spot offers amazing views of the city and Lake Michigan. The atmosphere is stylish and welcoming. Enjoy live music and a lively vibe, perfect for a magical night under the stars.

Why we love it: Cindy's is a charming spot. The views are incredible, but there's more to it. It's great for a romantic date or a fun night with friends. It feels special and different from other places. Cindy's is a peaceful and exciting escape in the bustling city, making you want to come back again and again.

Sunday, Monday, Tuesday, Wednesday, Thursday, Friday, Saturday

12 S Michigan Ave, 60603 Chicago

Vibrant party scene at VU Rooftop Bar in Chicago, with people dancing and enjoying drinks under colorful lights and modern decor.

Photo credits: VU Rooftop Bar

(4.3)

3. VU Rooftop Bar

What is it? Up high at 133 E Cermak Rd, VU Rooftop Bar is a cool escape. Here, great views meet cool vibes and every night is a party.

Why we love it: It’s more than just the pretty sights. VU Rooftop Bar comes alive as the sun sets, open to all. With live music in the air and a dreamy list of drinks, it’s the perfect spot for laughs, chats, and creating memories. Cheers to love or start a night out with friends - this place turns simple moments into something special, way above the city buzz.

Sunday, Monday, Tuesday, Wednesday, Thursday, Friday, Saturday

133 E Cermak Rd, 60616 Chicago

Inviting rooftop bar scene at The Gwen with modern furniture, a large umbrella, vibrant flowers, and city skyscrapers in the background.

Photo credits: Upstairs at The Gwen

(4.1)

4. Upstairs at The Gwen

What it is: Upstairs at The Gwen is a rooftop spot in Chicago's heart. It's not just any place; it's a cool vibe. You get awesome skyline views that make any night special. There's stylish seating, cool lights, and a modern feel that lifts you above the city buzz.

Why we love it: This place is all about fun times and cool music, with a live DJ that keeps things lively. It's where the trendy crowd hangs out - from city pros to hip young people, all fitting in together with the city lights shining bright. Upstairs at The Gwen is where to be for memorable nights in Chicago's nightlife.

Sunday, Monday, Tuesday, Wednesday, Thursday, Friday, Saturday

521 N Rush St 5th Floor, 60611 Chicago

Elegant interior of Z Bar Chicago with a glowing Christmas tree, chic bar seating, and stylish decor under ambient lighting.

Photo credits: Z Bar

(4.1)

5. Z Bar

What is it? Z Bar is a fancy rooftop spot in Chicago. It sits high up, giving you great views of the city. As the sun sets, Z Bar comes alive with cool music, special drinks, and a fun atmosphere.

Why we love it: Z Bar is more than a rooftop bar. It's the best place in Chicago for a fun night out. It's stylish and cool but also friendly. At night, it's where you can really feel the city's buzz, with both locals and tourists enjoying themselves. Going to Z Bar means enjoying good times and living it up in the city.

Sunday, Monday, Tuesday, Wednesday, Thursday, Friday, Saturday

108 E Superior St, 60611 Chicago

Panoramic view of LH Rooftop in Chicago, featuring chic outdoor seating areas with stylish furniture, surrounded by high-rise buildings and offering a clear view of the city skyline.

Photo credits: LH Rooftop

(4.1)

6. LH Rooftop

What is it? LH Rooftop is a cool spot in Chicago, right on the 22nd floor of 85 E Wacker Dr. It mixes awesome city views with style in a great rooftop place.

Why we love it: It's not just the views (and they're amazing) that make us love this place. It's the chill yet fancy feel that pulls you in. With its neat decor and the right music, everything about LH Rooftop feels like a trendy city getaway. It's where the city's energy meets a peaceful break, making each visit special. Whether you're here to relax, chat, or just enjoy Chicago from above, LH Rooftop is where you'll make memories you won't forget.

Sunday, Monday, Tuesday, Wednesday, Thursday, Friday, Saturday

85 E Wacker Dr 22nd Floor, 60601 Chicago

Lush rooftop dining area at Aba Chicago with twinkle lights, abundant green plants, and stylish, cozy seating.

Photo credits: Aba

(4.0)

7. Aba

What is it? Aba is a rooftop treasure at 302 N Green St, making the city shine. It mixes cool music and trendy feelings, taking your mood to new heights. Enjoy a Mediterranean feast that feels like a trip.

Why we love it: Aba is more than a place; it's a feeling. Here, the city's pulse meets live tunes and a mix of people - locals and travelers alike. It's great for any time - from fun brunches to romantic evenings under the stars. This rooftop spot offers not just food, but unforgettable moments in the city's buzz.

Sunday, Monday, Tuesday, Wednesday, Thursday, Friday, Saturday

302 N Green St 3rd Floor, 60607 Chicago

Final word

Dive into Chicago's nightlife with our guide to top rooftop spots, making Wednesdays amazing. From cool lounges with awesome views to lively bars full of Chicago's energy, we've picked the best just for you. Turn your midweek routine into something special, enjoying stunning views of the Windy City from above. You're choosing an experience that'll stick with you, not just a place to hang out. Ready to start? Our list is your guide to an amazing skyline adventure. And there's more on our blog for those who want to see the best of Chicago's luxury travel scene. Let's make a plan: Wednesdays in Chicago are about to get so much better. Are you in to find your new favorite rooftop spot?

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