Where to Eat and Drink Outdoors in Chicago This Summer

Waldorf Astoria Chicago is the only hotel in the city with its own private courtyard, which transforms into a Champagne-filled escape courtesy of Veuve Clicquot. The sun-drenched Peacock Garden feels like an elegant Parisian hideaway, bursting with blooms and bubbles. Book a 75-minute happy hour with free-flowing Yellow Label and a curated charcuterie and cheese board, or splurge on caviar service and unlimited pours of La Grande Dame.

Sifr’s year-round rooftop is one of the largest in River North, with space for 90 guests in both covered and open-air sections. Start with a mezze platter before moving on to toum- and harissa-marinated black tiger prawn kebabs, baharat-spiced hearth-roasted cauliflower, or lamb shank with Persian pilaf. Most dishes are cooked over a massive live-fire grill downstairs, with flavors inspired by chef Sahil Sethi’s years in Abu Dhabi.

This iconic steakhouse is prime for people-watching, with its red awning and front-row perch on the glitzy Gold Coast. The menu sticks to the classics—seafood towers, housemade pasta, double-baked potatoes, and USDA Prime steaks—backed by classic cocktails and a deep wine list.

The sprawling, tri-level rooftop on the 21st floor of LondonHouse Chicago offers unmatched views of the Chicago River and Magnificent Mile. The giant stone cupola sets the stage for countless proposals, while Luminescence dazzles after dark with cascading LED blooms and a floral-inspired lightscape. Bold cocktails are paired with globally inspired bites such as Jamaican jerk chicken wings, Argentine-style baked provolone, and Aleppo-roasted heirloom carrots. On weekends, executive chef Elizabeth Sweeney serves an indulgent brunch featuring oversized cinnamon rolls to share, tres leches French toast, country-fried A5 wagyu steak, and lobster biscuits and gravy.

Tucked away on the fifth floor of The Gwen, this rooftop retreat channels refined Art Deco style in the heart of the Gold Coast. Lounge by the fire pits and take advantage of happy hour specials Monday through Thursday from 4 to 5:30 p.m. Share hamachi tostadas and Publican Quality sourdough with colorful spreads, or opt for a hearty burger or pastrami sandwich paired with barrel-aged cocktails and local drafts. On Wine Wednesdays, bottles are half off, with exclusive glass pours and live jazz by the Cosmic Jaywalkers.

Perched eight floors above its full-service sibling avec, this playful River North rooftop delivers sweeping skyline views. Chef Dylan Patel blends Midwestern and Mediterranean influences in dishes like shawarma-fried chicken thighs with fermented chili sauce and grilled asparagus with crispy garbanzo beans. Visit on Mondays for $8 martinis or Tuesdays for half-priced wine by the glass.

This whimsical, kaleidoscopic 10,000-square-foot playground for adults is located above The Second City comedy club, with some of the best views of the city's famous skyline. Pause between playing super-sized versions of Jenga and Connect Four to appreciate the panorama whilst sipping on refreshing large-format cocktails. To eat, there's crave-able finger food like sliders, footlong hot dogs, mozzarella sticks and dessert tacos filled with creamy cheesecake. No matter your age, Utopian Tailgate will make you feel like a kid again. 

Family-friendly Roots Pizza specializes in Quad Cities-style malted-crust pizza, with a wide array of toppings, including homemade mozzarella. Their South Loop location is their newest and largest, with a fully-retractable glass rooftop on their second-floor atrium, which seats up to 100 guests. Everything from heaped bowl salads – a sleeper hit – to pizzas is totally customizable so you can build your own perfect meal whatever your preferences or dietary restrictions may be. There are always a few local chef collaboration specialty pizzas on the menu and a wide array of Midwestern beers on tap, while multiple flat-screen TVs and hearty food make this a favorite place for game day too. 

Whether you prefer your seafood raw or gently grilled over charcoal, the menu and Chicago River views from RPM Seafood's 112-seat patio are sure to impress. The expansive seafood-friendly wine list is among the best in the city, including more than two dozen by-the-glass pours, along with an exciting list of white and red Burgundy for wine connoisseurs, rounded out with Bordeaux, super Tuscans and great value wines from around the world. You'll be tempted to order a bottle to accompany crab cakes, fish tacos and grilled mixed seafood presented tableside with a flaming flourish. Lunch here can easily become a leisurely three-hour affair. 

The prettiest patio in the trendy Fulton Market district is this Italian-Croatian restaurant by Top Chef champion Joe Flamm. Rose Mary is named after his grandmothers, as well as the herb rosemary, native to the rocky regions of the Mediterranean and Adriatic from where Flamm draws inspiration. There's ample shade under Rose Mary’s striped umbrellas to keep diners cool on the 32-seat patio while they enjoy peka-style octopus, zucchini fritters and tuna crudo with a smattering of crispy capers. Flamm blends timeless Italian recipes with the bold, bright flavors found in Croatian cuisine, like gnocchi with beef cheek pašticada and Croatian paški sir sheep's milk cheese.