The 15 most stunning outdoor dining spaces in Chicago

The Peninsula's impressive rooftop lounge has it all: sweeping city views, globally inspired cocktails and a roster of delicious, shareable snacks. But it's the terrace's thoughtful design elements that really tie everything together. Plush loungers invite you to stay a while, fresh florals adorn the planters and a gold-accented overhang shields your eyes from the sun and casts a spiderweb-like pattern on the floor.

Want to feel alive again? Utopian Tailgate, a rooftop deck perched atop the Second City in Old Town, does the trick with its wildly playful space. The 10,000-square-foot deck is accessorized with neon-colored tables and chairs, plants and string lights hanging from above and vibrant graffiti artwork. Between sips, play mini-golf, foosball, bocce and giant board games.

In a city full of sweeping views, everyone wants to be on top. But this tri-level venue is the tippy top of all rooftop bars. Located on the 21st floor of LondonHouse Chicago, LH Rooftop affords guests stunning vistas of the architecture along the Chicago River and Michigan Avenue. The posh, loungey couches and verdant planters only heighten the feeling that you're having a very special experience.

Looking for something a bit more lowkey? Make a dinner reservation at Homestead on the Roof, situated just above Roots Handmade Pizza in West Town. The literal farm-to-table restaurant is surrounded by a lush garden that's packed with summer produce and fresh herbs. Expect to see those same ingredients on your table as soon as your meal arrives.

When the Chicago River is in your backyard, you don't have to do much to make your restaurant look impressive. But the folks at River Roast have gone the extra mile to ensure their waterfront terrace really shines. Adorned with twinkling lights and sun-shielding canopies, the alfresco space offers a front-row seat to the busy waterway.

You wouldn't know it from the street, but chef-owner Kevin Hickey's Bridgeport restaurant has a sunken garden patio out back that doubles as an enchanted garden when the sun goes down. Nosh on succulent rotisserie duck and fried cheese curds between sips of your frozen cocktail.

Upon entering this breathtaking riverfront oasis, you might catch yourself wondering if you've been transported to a faraway destination. An offshoot of the popular West Town dining destination by the same name, Beatnik On the River draws inspiration from the ’50s and ’60s, offering dishes and drinks from around the globe. The best tables in the house are on the patio, which sits along the Chicago River and is outfitted with colorful tile, Indonesian daybeds and fringe-lined umbrellas. Order a glass of bubbly and stay awhile. 

Arguably one of the more unique dining experiences to surface this summer, the Darling's Rose Garden offers 10 private greenhouses that each seat two to four guests. String lights and potted roses dress up the space, and the menu is filled with cocktails that beg to be photographed. And yes, each greenhouse is fully sanitized between parties.

One of the Loop's best-kept secrets, this U-shaped rooftop bar is located on the third floor of the Renaissance Hotel on the Chicago River. What the bar lacks in height it makes up for in unobstructed views of some of Chicago's best architecture. The space itself is a designer's dream, with a jewel-shaped skylight jutting out from the middle of the terrace.

Occupying what was once a Gold Coast home, La Storia exudes warmth and comfort. When the weather cooperates, the dining room overflows into a secluded backyard patio that's adorned with string lights and lush ivy, creating the perfect backdrop for date night. An order of tiramisu to share is a must—if only to make the evening last a few minutes longer.

Situated on one of the city's busiest intersections, Piccolo Sogno manages to transport guests to the quiet Italian countryside with the help of a rather tall fence, plenty of lush greenery and cheerful yellow umbrellas. Of course, the food doesn't hurt either: Antipasti, house-made pastas and flame-kissed pizzas pair perfectly with a lengthy wine list that's rife with hits.

Come summertime, the Promontory nearly doubles its footprint with a bi-level outdoor setup. Here's your game plan: Spend the day exploring nearby Promontory Point before heading inland for cocktail carafes and eats from a local food truck.

Tucked away from the hustle and bustle of Randolph Street, Elske's sweet courtyard patio looks like it was torn straight from the pages of a design magazine. The serene, Scandinavian-skewing space has just a few tables, making it the perfect place to really savor David and Anna Posey's seasonal tasting menu, which is always priced under $100.

True to its name, the views at VU are epic from 22 stories above street level. Once you've secured a seat, order from a selection of classic cocktails (like the gin-based Last Word or the refreshing cherry mule) before ordering a few bites for the table. With three bars and two patios spread across 13,000 square feet, there's plenty of room to spread out and relax in the sun.

The loungey, greenery-lined setup at this West Loop restaurant makes it easy to sit back and relax. The summer-ready cocktails don't hurt either—including Day One favorite Aloe? It's Me with mezcal, aloe, green juice, lime and jalapeño. Break for refreshing bites, like the spicy hummus, whipped feta dip or the big eye tuna carpaccio.