In Italian Piccolo Sogno means ‘little dream.’ True to its name, the enchanting outdoor dining at Piccolo Sogno is surrounded by lush green trees and ivy as well as white umbrellas and tables in the sun. The seasonal menu of rustic Italian fare compliments the romantic outdoor feeling. Try house favorites gnocchi or the spaghetti neri. They also have a fantastic wine list from different regions of Italy.
Piccolo Sogno, 464 N Halsted St Chicago, IL 60642 312-421-0077
With an amazing outdoor patio looking over the Chicago River and its bridges, dining at River Roast is an unforgettable experience. River Roast serves a hearty menu of finely roasted vegetables, beef and fish that are carved table side. Brunch is particularly popular, with their Brews & Blues Brunch featuring live blues performances and specialty cocktails, some infused with local Leatherbee gin. As you enjoy the likes of rabbit and waffles and sip the cocktails, watch the scenic river as barges go by.
River Roast, 315 N La Salle St Chicago, IL 60654 312-822-0100
This gastropub and wine bar has a great rustic, outdoor dining area. With overhead lights strung up and urban-chic walls surrounding the bricked courtyard, outside is the perfect place to drink on summer nights. Favorites here include the quail egg ravioli or any of the samplings from their beautiful, French-inspired desserts menu to go with the romantic ambiance. A great place to celebrate, you can also choose from the extensive champagne and wine menu ranges from or enjoy one of their creative cocktails.
RM Champagne Salon, 116 N Green St Chicago, IL 60607 312-243-1199
Gather’s small, modern patio with hanging lights and their wonderful cuisine make it a relaxing, intimate experience. Their New American cuisine is refined with creative ingredients and spices to keep things interesting. While you may find many New American cuisines in Chicago, Gather is one of the most peacefully refined atmospheres with a homey feeling—both inside and out.
Gather, 4539 N Lincoln Ave Chicago, IL 60625 773-506-9300
This elegant Chinese bistro takes you on an upscale, modern showcase of China. Their outdoor terrace, open May through September, is fitted with red drapes and canopies as well as chic They also have great food, including the authentic crispy duck and the kung pao chicken with seasonal vegetables. They offer terrace appetizers and while menu items are somewhat pricey, they are worth it for the atmosphere and quality.
Shanghai Terrace, 108 E Superior St Chicago, IL 60611 312-573-6695
This Lincoln Square French bistro is the perfect date night location. While the name translates to ‘countryside bistro,’ their charming outdoor patio is shaded with large and small trees and is considered romantic by anyone who dines here. The menu boasts traditional French food like mussels with frites or the onion soup, making it an authentic getaway right in the middle of Chicago.
Bistro Campagne, 4518 N Lincoln Ave Chicago, IL 60625 773-271-6100
The Dawson excels in outdoor dining. From the hanging lights to the sofa seats for large groups in front of the fireplace, Dawson has an assortment of seating arrangements to accommodate customers. The chic wooden dining area is the perfect for innovative, fun cocktails and brunches that range from oysters to chicken fried lobster. Conveniently, this large space has trees tucked away and a high fence to block out noise from traffic, making it a laid back experience.
The Dawson, 730 W Grand Ave Chicago, IL 60654 312-243-8955
Wicker Park’s Enoteca Roma has two outdoor dining options. The first is the quiet and spacious rear courtyard that includes a fountain and leafy plants, or sit in their sidewalk seating and view the lively street from the front. The staff provides blankets on cold nights. The thoughtful staff and excellent rustic Italian fare, like the pear ravioli and bruschetta flights, are perfect for sharing against the sounds of live music. Look out for their weekly specials that include half off pizzas or $5 wines.
Enoteca Roma Ristorante, 2146 W Division St Chicago, IL 60622 773-772-7700
Bridge House Tavern’s patio sits right on the bank of the Chicago River. The patio boasts umbrellas and small trees that add an elegant ambience to the extensive space. They offer traditional American cuisine like burgers and popcorn, and other appetizers with some unique twists. You’ll find filling meals like the bacon pancakes to duck tacos and pig wings. Those with boats are invited to pull their boat up next to the restaurant and climb onto the patio if they please. On weekdays they have $5 mimosas and bloody Marys, and they also have daily drink specials.
Bridge House Tavern, 321 N Clark St Chicago, IL 60654 312-644-0283