5 of Chicago’s Most Charming Rooftops


Fig & Olive

This beautifully-chic restaurant brings nature to you, where a huge tree sits in the middle of the bar. Enjoy light Mediterranean cuisine and perfectly crafted cocktails as you look over one of the only rooftops in the entire Gold Coast area. While many rooftops in Chicago tend to boast their square footage or floor number, Fig & Olive does none of that. Instead, you get a unique Chicago experience with beautiful foliage surrounding you and the ability to look up at skyscrapers from a relaxed canopy setting. Some may consider this place a “hidden gem” in its neighborhood, but it’s not going to stay that way for long. 

Photo credit to Fig & Olive


Widely considered as one of the best views in the city, Cindy’s rooftop is a must-see for tourists and locals alike. As you exit the elevator onto the 13th floor of the Chicago Athletic Association, you are transported into a world with expertly-crafted cocktails and breathtaking scenery. Their rooftop overlooks the entirety of Millenium Park, with spectacular views of Cloud Gate (the Bean), The Art Institute of Chicago, and Lake Michigan. Whether it be standing by the fire on the outdoor deck or sitting at one of their community tables with friends, you are sure to find a great time at Cindy’s. 

Photo credit to Cindy’s

Homestead on the Roof

Most restaurants claim to be “organic” or “farm-to-table” but fail to detail where their food actually comes from. At Homestead on the Roof, they literally bring the farm to you. With a beautiful 1,000 square foot patio in the Ukrainian Village, Homestead on the Roof combines rustic American charm with innovative flair. Their organic garden is situated around every single table, so you get to see the ingredients for your tasty meals grow in real-time. Unlike other skyscraper settings, this second-story rooftop focuses on telling a story about the food and keeping you comfortable. This is the perfect place to enjoy an early happy hour or relax with your friends on a Sunday. 

Photo Credit to Homestead on the Roof


LondonHouse sits high above the Chicago River where the water flows, just like the drinks. Enjoy a cocktail or a glass of wine while you take in one-of-a-kind views at one of the city’s tallest rooftop restaurants. If you work up an appetite, try their crispy-skinned roasted duck or other classic American Fare. Sitting 22 stories above some of the most picturesque sites in the city, you can truly feel like royalty when dining at this swanky rooftop lounge. 

Photo Credit to LondonHouse


Situated on the 18th floor of the Rafaello Hotel, Drumbar still seems to not be on everybody’s radar. This is a good thing because it has allowed for this beautiful rooftop setting to be much less crowded than it should be. Grab a bite to eat or sip on a country-inspired drink as you look over the city. With a brag-worthy selection of whiskey, scotch, bourbon, and cognac, this is definitely a top cocktail destination in Chicago. Drumbar gives you the feeling that you have the entire city to yourself while you enjoy beautiful views and a charming setting. Get here before others find out because it won’t go unnoticed for long. 

Photo Credit to Drumbar

Author: Colin Jay

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