Best Rooftop Bars and Restaurants to Go to in The Windy City

We all know how thrilling it can be to go to the roof of a tall building in a city to be able to see the beautiful lights in a city that are lighting up the dark night sky. One of the best ways to be able to see Chicago’s pretty skyline is by going to a rooftop bar or restaurant in the city to be able to experience the magnificent view while also being able to enjoy a delicious meal, or have a couple drinks with some friends. With the weather warming up, we know that people are eager to get out there and take advantage of it, so why not do this by going to one of Chicago’s finest rooftops bars or restaurants?

Interested in going to a fun rooftop bar or restaurant tonight? Well, consider paying for your drinks or meal by using a GiftYa electronic gift card! With purchasing a GiftYa electronic gift card, it will help set you up to easily pay for your night out with the gift card being right on your phone. GiftYa is a website that is a great website that is easy to redeem gift cards, and also to keep them organized as well. These gift cards can easily be accessed and redeemed straight onto your debit card. With your newly purchased GiftYa electronic gift card, you are ready to have an enjoyable night out at Chicago’s exciting rooftop bars or restaurants!

Castaways Bar & Grill

1603N Lake Shore Drive | Lincoln Park |

Enjoy this beachside rooftop bar and restaurant that features great food and live music on the weekends!

Want to sit by the beach while having a drink and some good bar food with friends? Stop by Castaways Bar & Grill, a popular rooftop bar located right in Chicago! Image courtesy of Chicago Bar Project

When you think of Chicago, do you think of sitting by the lake and enjoying a nice cold drink along with having delicious bar food? Well, get ready for one of the most popular spots located in Lincoln Park in Chicago called Castaways Bar & Grill! Castaways Bar & Grill is a hot spot for people to come for their famous ice cold drinks and delicious bar food. Castaways is known for their daily drink specials, along with offering live entertainment every weekend.

Castaways Bar & Grill offers some delicious bar food favorites. Some of the hot items on their menu are hot or BBQ style wings, chicken quesadillas, popcorn shrimp, a Mahi Mahi sandwich, and their famous Castaways signature burger that includes a half pound char burger, soft egg, grilled bacon, ham, and a cheddar and Castaways sauce served on a brioche bun. Castaways also has an extensive bar drink menu including vodka and Red Bull, vodka lemonades, their own version of a Long Island iced tea, while also featuring their signature frozen drinks and their beer menu. Check out Castaways Bar & Grill for a beautiful rooftop experience right by the lake!

Buy a GiftYa to Castaways Bar & Grill >

“For what this place is - primo beach location with a fantastic view and fun-loving vibe - this place is amazing!” - Yelp Review 

The J. Parker

1816 N Clark Street | Lincoln Park |

Enjoy Chicago’s gorgeous skyline with handcrafted cocktails in Hotel Lincoln’s own rooftop restaurant!

Want to be able to experience Chicago’s beautiful skyline while having a good meal? Look no further than The J. Parker right in the Hotel Lincoln! Image courtesy of RATIO Architects

Want to check out a swanky rooftop restaurant while checking out the Chicago skyline? Well, then we recommend that you check out The J. Parker located in Hotel Lincoln right in Lincoln Park. This restaurant sits right on top of the hotel and features 140 outside seats and 55 inside seats. The J. Parker is the perfect spot for a night out on the town, a pre-dinner cocktail, and it is the perfect spot for private events.

Along with having an amazing view, The J. Parker features many unique foods on their menu, including buffalo cauliflower, sweet potato waffle fries, soy ginger chicken wings, and even their signature J. Parker burger. The J. Parker also has a breakfast menu that has lots of flavorful foods for a delicious brunch out with friends. The J. Parker also handmakes their own signature cocktails that are named after famous celebrities or fictional characters. If you are feeling a fun night out on the town with friends, or a breakfast or brunch with your family, we highly recommend The J. Parker with their delicious menu with this unique rooftop restaurant.

Buy a GiftYa to The J. Parker >

“Such a great rooftop bar!! Located near Lincoln Park zoo, this is a great place to get a drink after hanging out in the area! It has great views of the skyline, the lake, and the park.” - Yelp Review


12 S Michigan Avenue | The Loop |

Enjoy the environment of a stylish rooftop bar and restaurant with Cindy’s while viewing the Chicago lights!

Want to see the Chicago lights while having a delicious meal in a hip and stylish rooftop restaurant? Well, then we think that Cindy’s is perfect for you! Image courtesy of Cindy’s.

Located right in the Chicago Athletic Association Hotel is Cindy’s a hip rooftop bar and restaurant with a breathtaking view of the Chicago skyline. This restaurant offers panoramic views of Millennium Park, Lake Michigan, The Art Institute of Chicago, and many more iconic spots within the city. This rooftop restaurant is open all year round for people who not only want to have a delightful meal, but a beautiful view no matter what time of the year. 

Cindy’s has lots of delicious food for every hungry mouth and for every season. With an ever changing menu, Cindy’s has a lot of different flavors and spices to offer. Cindy’s offers meals such as octopus a la plancha, burrata, salmon aguachile, and even a shellfish platter. This unique restaurant also offers a weekend brunch menu, along with a sweet dessert menu featuring dutch apple pie, spiced winter mousse, and many more! If you are looking for a night out on the town, a thirst quenching drink menu is also available for any occasion. Go out and enjoy a lovely time with a tasty meal at Cindy’s while taking in the view of the Chicago lights and buildings.

Buy a GiftYa to Cindy >

“Very good cocktail bar located in a unique setting. Came in based on recommendations by a few people and we weren't disappointed.” - Yelp Review


1 West Upper Wacker Drive | The Loop | 

Check out this fun indoor/outdoor rooftop bar that features craft cocktails, good food, and a place to enjoy the Chicago lights.

Take part in having a handmade cocktail while enjoying the Chicago skyline by going to RAISED, an urban rooftop bar located in The Loop. Image courtesy of Raised: An Urban Rooftop Bar.

Want to sit on a deck right in the middle of the gorgeous city of Chicago? We have found the perfect place for you to be able to accomplish this goal of yours! Raised is an urban rooftop bar that is located in The Loop. Raised features and indoor and outdoor seating areas featuring an open rooftop deck to see the breathtaking view of the Windy City. This exclusive rooftop bar has a snack, dinner, and a drink menu with many great options to choose from.

Raised is different (in a good way) because of their option to purchase shareable snacks featuring a local cheese selection, lobster rolls, and grilled skirt steak. This urban bar is also known for its many options when it comes to the drink menu featuring many different kinds of wine, cocktails, and even hot alcoholic beverages. If you’re looking to plant yourself on a deck with a jaw dropping view and good food and drinks, then Raised is the right place for you!

Buy a GiftYa to Raised >

“If you haven't gone yet, plan to go with your friends and you will instantly be in charge of finding the places to go from then on. Summer or Winter- they are always open.   The vibe is awesome, the staff are phenomenal, eager to make drinks for you that make your day.” - Yelp Review

VU Rooftop Bar

133 E Cermak Road | Near Southside | 

What’s better than three bars and two patios with a striking view of the Windy City? The one and only VU Rooftop Bar is the spot for you!

Want a gorgeous view of the city lights at night while lounging and having a drink with friends? The solution is to give VU rooftop bar in Chicago a try! Image courtesy of Chicago Food Magazine.

Being 22 stories high can be alarming, but when you’re looking at the beautiful Chicago skyline while enjoying a drink and a nice meal at VU rooftop bar, it’s all worth it. VU is known for its unparalleled views of the lake and downtown within a modern setting of the restaurant. Not only does this restaurant have a dinner and drink menu, but it also includes a brunch menu for all of your hunger needs. This is a unique restaurant to go to that is most well known for the city views and good food.

Some of Vu rooftop bar’s most famous dishes are the VU burger, Nashville hot chicken sandwich, shrimp spring roll, and spicy sausage flatbread. If you’re interested in the brunch menu, it includes buttermilk fried chicken and belgian waffles, salmon lox and every bagel, and even lobster chilaquiles. Vu also offers classic cocktails such as, bloody mary’s, mimosas, and the signature Vu sunrise drink. Check out VU rooftop bar today to be seated in a spot of the breathtaking Windy City while having a meal that you will surely remember!

“Very friendly vibe, customers were laughing and enjoying themselves, and the view was beautiful at sunset.” - Yelp Review

There are so many different ways to enjoy Chicago’s magnificent skyline and a great way of doing this is by going to a rooftop bar or restaurant. There are so many different ones to choose from, but we really hope that we were able to make your decision a little bit easier with the list we provided! Is there a rooftop bar or restaurant that you enjoy that we didn’t mention? Let us know in the comments!

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Trae Bodge

Trae Bodge is the shopping expert here at GiftYa. Trae helps people find the best deals and ideas on popular new items to purchase.

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