10 Spots for Romantic Outdoor Dining in Chicago

Chicago’s outdoor dining scene is dotted with gardens, patios, and rooftops that make for a romantic summer evening with your sweetie. Check out 10 of our favorite al fresco venues from River West to Hyde Park to Lincoln Park.

If you’ve lived in the Chicago area for any amount of time, you know that even before we brush the last of the late-spring snow off our cars, we’re already thinking about enjoying outdoor dining. One reason is the cuisine itself. Chicago’s downtown, lakefront and bevy of neighborhoods offer countless opportunities for unforgettable al fresco meals – breakfast, lunch and dinner.

But there’s something else about eating outdoors in Chicago in the summertime: It can be an almost magical experience, one that seemingly transports us in place and time, lending it a certain romantic quality.

In this post, we’re exploring 10 of the city’s most romantic outdoor dining spots, dotted all over the map. Whether you prefer a secluded garden retreat or a buzzy rooftop scene, you’ll find the perfect spot to create lasting memories with your loved one. So, get ready to rediscover iconic spots and uncover hidden gems among Chicago’s best outdoor dining venues.

Piccolo Sogno:

Piccolo Sogno’s outdoor patio is often the first name on Chicagoans’ lips when they talk about romantic meals al fresco. And there’s no wonder why: Who doesn’t want to sip prosecco and nibble truffled stracci di farro between ivy-covered trees in the heart of rocking River West? Reservations aren’t available for their patio seating, though, so you’ll need to reserve a regular table and wait for one to open up outdoors. 464 N. Halsted St. (312) 421-0077.

Virtue:

Outdoors at Hyde Park gem Virtue restaurant , there’s a sidewalk café ambiance that’s both urbane and warm – like sitting on the porch at your coolest friend’s house. Maybe you’ll start with biscuits with pimento cheese and local honey, go on to blackened red drum with stone-ground grits and crawfish etouffee, and end your meal with carrot cake with cream cheese frosting, candied walnut and butterscotch. Now that’s romance for the heart and the stomach. 1462 E 53rd St. (773) 947-8831.

The Duck Inn:

This Bridgeport restaurant features a summer backyard-style patio with café lights, overhanging trees and cedar-slat fencing, giving the space an intimate feel that’s uniquely Chicago. On the menu, the signature whole rotisserie duck – with or without fois gras and black summer truffles – is perfect for sharing. But the special dish takes three hours to make, so if you’re hankering for one, don’t forget to order it ahead. 2701 S. Eleanor St. (312) 724-8811.

Homestead on the Roof:

Every summer, Homestead on the Roof tackles a different menu, pop-up style, and, this year, it’s all about Portugal. Situated above Roots Handmade Pizza in West Town, the rooftop garden also plays home to innumerable weddings and other events, so the leafy, flowered space is primed for romantic interludes. 1924 W. Chicago Ave. (773) 904-1149.

North Pond:

From the charm of its Arts and Crafts design-inspired building to the relaxing sounds of the lapping waters of North Pond, this Lincoln Park gold standard offers one of the best locales for romantic outdoor dining in the city. The 112-year-old structure boasts a long history, from its early days as a warming house for North Pond ice-skaters, to the 1998 opening of the restaurant, which was awarded a Michelin star in 2022. It’s the ideal background for a “Pink Drink” (Uruapan rum, Diplomático Planas aged rum, strawberry, grapefruit and sparkling rosé) and duck fat-poached scallops and peas. Reservations are required. 2610 North Cannon Drive. (773) 477-5845.

Antico:

Just off Armitage Avenue, on one of Bucktown’s quiet residential streets, you can take a trip to Northern Italy at Antico , where they’re serving classics like gnocchi with browned butter and crispy sage under winding grapevines and gauze ceilings. The outdoor seating is nestled inside their patio garden, where they’re growing their own ingredients, giving it a vacation B&B flavor. Request the “Quatro Portale” for special pricing on a four-course meal. 1946 N Leavitt St. (773) 489-4895.

Shanghai Terrace:

This swanky Cantonese restaurant inside the Peninsula Hotel in the Loop offers an ultra-chic outdoor garden, with the gorgeous city skyline providing the backdrop for fine-dining dim sum. You and your sweetie can try the turnip cake with XO sauce, cayenne pepper and dried shrimp while you canoodle amid the luxury environs. You’ll pay top dollar for the experience, but it’s worth it. 108 E Superior St. (312) 573-6744.

Gibsons Italia:

The al-fresco game is strong at this Italian-inspired West Loop addition to the Gibsons steak franchise . It’s all sleek chrome and white linens inside, and glittering views of the city’s architectural triumphs from the patio overlooking the Chicago River outside. You can, of course, rely on the prime Angus, Wagyu beef or grassfed Australian steaks, but the menu also features luxury seafood and homemade gold-extruded pasta for those seeking to branch out. 233 N Canal St. (312) 414-1100.

Summer House Santa Monica:

This Lincoln Park spot lets you and your snuggle bunny get plenty of rays along with your cocktails and dinner at the end of a Chicago summer day. The California menu explores global beach vibes, with cuisine inspired by sunny locales like Italy and Mexico, and the restaurant also offers a “Martini Hour” and a Summer Nights Supper Club series for different types of dining experiences. 1954 N Halsted St. (773) 634-4100.

Chant:

Hip Asian fusion leads the way in this Hyde Park restaurant that calls its menu “inspired global cuisine.” There’s also top-notch people-watching from the European café-style outdoor seating. And make sure to check the restaurant’s events calendar in case you want to add a musical element to your upcoming romantic interlude. 1509 E 53rd St. (773) 324-1999.

The long and short of the situation is this: If you’re getting hungry for some alone time with your significant other, choices abound for al fresco dining in Chicago. So, make this a summer to remember and eat up the gorgeous weather (along with some truly stellar cuisine) while you can. Soon enough, we’ll be back in our heavy coats, only dreaming of living it up outdoors.