After visiting over 20 rooftop restaurants in Chicago this year, we've could narrow it down to 10 that deserves a visit in 2025! From upscale downtown venues to charming rooftop gardens, the best rooftop restaurants you can find in Chicago offers something for everyone.
Update: This article was updated on April 22, 2025, with new information, new restaurants, updated photos, booking links and insider tips.
Most restaurants on this list demands a reservation. Use the booking links provoded to secure your spot! Also check out for rooftop brunches, as some of these venues offer bottomless brunches with a view.
Our complete and up-to date guide to the 10 Best Rooftop Restaurants in Chicago - 2025 feature all info you need about each rooftop, all at the same place, so you don’t have to scroll around on several different sources finding it.
For each rooftop, this guide presents:
We are full-time rooftop reviewers and content creators. Since launching The Rooftop Guide in 2015, we’ve visited over 1 200 rooftop venues worldwide.
Except from our own experiences and insights, we also work closely with thousands of rooftops and local reviewers, so we can secure correct and updated content for all our guides & articles.
With our vast experience and exclusive focus, we can present you with the most complete and up-to date guides about rooftop venues. And with our insider tips and knowledge, we can guide you to the best and most suitable rooftops for your own needs.
Whether you’re looking for an upscale rooftop dinner, a laid-back rooftop brunch, a vibrant rooftop party or a luxurious hotel rooftop pool, we’ve got you covered.
In short: Perched 13 floors up at the Chicago Athletic Association hotel, this vibrant rooftop restaurant and bar is open for both lunch, dinner and rooftop weekend brunch.
Food & Drinks: Here you can enjoy an inspired menu featuring local wild and seasonal produce and fresh seafood, created by Executive Chef Kaleena Bliss. The menu ranges from 'Chilled King Crab & Lobster Sallad' and 'Salmon Carpaccio', to 'Lamb Ragu Mafaldine' and 'Whole Fried Branzino'. To go with the food, Cindy's Rooftop also offers perfectly crafted cocktails, local brews and an impressive selection of wines.
What we think: If you're looking for a Chicago rooftop meal with the very best views over Millenium Park and Lake Michigan, Cindy's Rooftop is undoubtedly the place to visit. With a stylish and spacious glass atrium lounge, complemented with an open-air rooftop terrace, Cindy's is at your service year round.
Dress code: The Cindy's Rooftop dress code is smart casual.
Also featured in:
30 Best Rooftop Bars in Chicago
9 Best Rooftop Brunches in Chicago
5 Hyped Rooftop Bars in Chicago
8 Best Party Rooftops in Chicago
In short: Named for a move from Argentine tango, Boleo is found on the top floor of the Kimpton Gray Hotel Chicago, bringing a large slice of Latin vibes to the Chicago Loop.
Food & Drinks: Made to evoke the dynamic energy of South America, here you can indulge in Peruvian and Argentinian street food-inspired small plates with a modern twist. Munch on some ceviche, anticuchos or empanadas. Over at the rooftop bar, you'll find mainstays like Fernet & Cola, Chilcanos, seasonal Pisco creations, and other delicious cocktails that transport you to South America.
What we think: The reason we like this rooftop so much and also why we always come back when in Chicago, is the fun and vibrant atmosphere. Boleo is an elevated gathering place where the music is always playing, the food is good and the drinks are strong. Industrial-chic in design, the stylish, sleek and lush rooftop restaurant and bar is set under a retractable glass roof, keeping the weather warm no matter the season.
Dress code: The Boleo dress code is casual.
In short: Perched on the 11th floor, right in the heart of West Loop, the rooftop blends a stylish interior lounge with a sleek, lush and airy outdoor terrace, surrounded with some of the best panoramics the city has to offer.
Food & Drinks: Aiming to provide a more relaxed, cocktail driven lounge experience, you can visit for a stylish after work, sipping specialty cocktails and other fine drinks. But, the Rooftop at Nobu Hotel also caters to the more hungry ones. Famous sushi chef Nobu Matsuhisa has created a selection of hot and cold plates, ranging from Yellowtail Jalapeno and Tuna Ginger Tosazu, to Wagyu Sliders, Lamb Chop Anticucho and a tasty array of nigiri and maki.
What we think: Filled with the vibes of Chicago’s famous Restaurant Row and the views of the stunning city skyline, the Rooftop at Nobu Hotel is a prime spot for an upscale and elevated experience. We love the trendy vibe and delicious food. Not many rooftops in Chicage serves Japanese food.
Dress code: The Nobu Hotel Chicago dress code is smart casual.
Also featured in:
30 Best Rooftop Bars in Chicago
In short: Located on the 16th floor of the Trump International Hotel & Tower, along the Chicago River, Terrace 16 offers vibrant, new American flavors, complemented with breathtaking views of Chicago.
Food & Drinks: From breakfast and weekend brunch to dinner, Terrace 16 serves vibrant menu's that features new American flavors, allowing ingredients to speak simply and powerfully for themselves. There are fresh options for a variety of tastes and preferences, and the expert culinary team can accommodate any dietary needs. The food is complemented with a thoughtful wine list and an extensive craft cocktail program that really enhance the experience of this downtown Chicago restaurant.
What we think: We visited Terrace 16 both in 2018 and in 2025, and we still love this rooftop. The sweeping city views are of course the most amazing thing up here. A great spot from some evening cocktails and bar bites. Or why not do the full weekend brunch. It’s both luxurious and tasty!
Dress code: The Terrace 16 dress code is business casual.
Also featured in:
30 Best Rooftop Bars in Chicago
6 Best Rooftop Bars in River North
In short: Located in Chicago's historic Fulton Market District, Aba (which means father in Hebrew) is the sister restaurant to the River North located Ēma (which means mother in Hebrew).
Food & Drinks: Aba is a collaboration between chef CJ Jacobson and Lettuce Entertain You, serving both bites and more filling options of steaks and seafood, all with influences from the Mediterranean, including Israel, Lebanon, Turkey and Greece. As dinner or weekend brunch you can indulge in signature dishes like Crispy Short Rib Hummus, Char-Grilled Lamb Chops and Jerusalem Bagel with Labneh, as well as a bar program by mixologist Liz Pearce, focusing on rare Mediterranean-inspired wines and spirits.
What we think: With a lush, unique and beautiful decoration, the restaurant has both an indoor dining room and seating out on the spacious rooftop terrace. The rooftop is partially enclosed and heated during the colder season, so it can stay open as long as the weather is not to bad. There are also some cosy rooftop greenhouses.
Dress code: The Aba dress code is smart casual.
Also featured in:
9 Best Rooftop Brunches in Chicago
In short: Homestead On The Roof is 'a literal farm-to-table restaurant', set on top of Roots Handmade Pizza in the heart of West Town Chicago.
Food & Drinks: Open for dinner Wednesday to Saturday, Homestead on the Roof serves a seasonal menu based around the planting schedule. The menu includes dishes to share, as well as smaller and larger selections. Like a Rooftop Garden Salad or a Grass-Fed Steak Frites.
What we think: Truly an urban rooftop garden oasis, this charming and rustic rooftop restaurant might not offer the most dazzling skyline views, but instead comes with a 3,000 square foot organic rooftop garden and two massive, vertical hanging gardens. With a lovely and intimate setting, Homestead on the Roof is pretty much the perfect venue for a romantic rooftop dinner in Chicago.
Dress code: The Homestead On The Roof dress code is casual.
Also featured in:
30 Best Rooftop Bars in Chicago
In short: Set 4 floors up at the five star hotel The Peninsula Chicago, Shanghai Terrace is a offers both a lovely rooftop terrace and a great Chinese restaurant.
Food & Drinks: A visit at Shanghai Terrace is really something for the taste buds. Voted "The Best Chinese Restaurant in Chicago", you can enjoy a wide range of fantastic dishes, from Dim Sum and Asian Salad to Peking Duck and Dong Po Pork Belly. Apart from the Cantonese and Shanghainese goodies, the rooftop offers a drink list just as impressing, with Asian beers, premium sake and beautiful specialty cocktails.
What we think: Here you find an indoor restaurant with a 1930s supper club décor, and a stylish decorated terrace with dining tables, cabanas and comfy lounge sofas along with cool views of the downtown sky scrapers. With great service and a pleasant, upscale atmosphere, it is not surprising that the price tag is quite high. But, it is well worth it.
Dress code: The Shanghai Terrace dress code is smart casual.
In short: Located by the waterfront in West Loop, Gibsons Italia is one of several smaller siblings to the iconic Gibsons Bar & Steakhouse, which has been one of Chicago’s leading restaurants since 1989.
Food & Drinks: True to both its name and its roots, Gibsons Italia serves modern steakhouse dishes as well as authentic Italian creations. Run by Chef Jose Sosa, the kitchen offers everything from risotto and gold-extruded pasta to a world-class tour of beef featuring Gibsons USDA Prime Angus, grass-fed Australian and Japanese Kobe.
What we think: Well worth a visit if you ask us! Bright, modern and quite swanky in decoration, Gibsons Italia is set over three levels, with both an outdoor terrace and a rooftop with retractable roof. And, best of all, fantastic views over Chicago River and the skyline.
Dress code: The Gibsons Italia dress code is smart casual.
In short: Tanta brings a large slice of the flavors and culture of Peru to the heart of Chicago and River North. And best of all, they do so with a second floor rooftop terrace, where summer alfresco food and drinks can be combined with cool skyline views.
Food & Drinks: Open daily for dinner, and during weekends for a brunch special, the menu includes everything from ceviches, skewers and beef empanadas, with many dishes made perfect to share. As with the food, drinks also walks side-by-side with the Latin American influnces, and the Pisco inspired Peruvian cocktails are a 'must try'.
What we think: Tanta is a great rooftop restaurant Chicago for everything from charming weekday dinners to vibrant weekend fun. Run by acclaimed South American Chef Gastón Acurio, Tanta Chicago is filled with a lively, fun and friendly atmosphere.
Dress code: The Tanta dress code is smart casual.
Also featured in:
9 Best Rooftop Brunches in Chicago
In short: Situated steps from Navy Pier, the luxurious Loews Chicago Downtown Hotel comes with one of the most impressive rooftop terraces Chi-Town has to offer, called Streeterville Social.
Food & Drinks: Taking the rooftop restaurant and bar experience to the next level, the Streeterville Social menu includes plenty of Gourmet grub. Divided into sections of 'Snack Shack' and 'Keep It Social', here you find everything from Chorizo Popcorn, Burrata and Spicy Tuna Tacos, to Grilled Beef Short Rib, Sous Vide New York Strip and Avocado Toast.
What we think: Open during the warmer season, this summer airy hot-spot is both spacious and stylish, mixing plenty of comfy lounge spots with dining tables. Overlooking the downtown skyline, this is an elevated place to meet, eat, drink and celebrate all things summer.
Dress code: The elNico Rooftop dress code is smart casual.
Also featured in:
30 Best Rooftop Bars in Chicago
9 Best Rooftop Brunches in Chicago
Rikard has spent the last 10 years exploring, enjoying, researching and working with rooftop venues. During these years he has visited more than 700 rooftops across the globe. The experience he has gained is used to create helpful, in-depth and accessible content, and to share his knowledge and rooftop expertise with fellow rooftop-lovers.
Browse all the cities & articles at The Rooftop Guide
Follow The Rooftop Guide