AL FRESCO BLISS: Outdoor Dining in Chicago



Located on Michigan Ave. across from Millennium Park, Acanto offers a perfect spot for outdoor dining. Known for its incredible pasta, pizzas and Italian classics, Acanto is also iconic for its award-winning wine bar.


Courtesy of DineAmic Hospitality

This phenomenal farm-to-table restaurant has more to offer than their delectable dishes. One of the West Loop’s best kept secrets is the Bandit’s back patio, a perfect place to dine and sip. Relax in the secluded, airy atmosphere with classic comfort foods and cold cocktails! This spot is a model choice when it comes to dining fresco. Did we mention that there’s an outdoor bar?


Inspired by the beauty found on the Mediterranean, Greektown’s Athena throws a festive party on its patio, which includes a waterfall. Athena’s take on authentic Greek fare possesses a local twist with saganaki, a pan-fried cheese that was first served in Chicago. Make sure to also check out Athena’s innovative cocktail menu.

Big Star

Big Star’s outdoor patio has been a staple in hip Wicker Park for more than 10 years. The menu, inspired by Mexican street food, contains an extensive single-barrel whiskey and craft beer program. Big Star has a second location across from Wrigley Field.


Known for its gluten-free options, Aba serves twists on Mediterranean cuisine in an undeniably upscale atmosphere. Aba creates a comfortable vibe within the trendy Fulton Market neighborhood, especially during weekend brunch on its gorgeous and vast rooftop patio.

Pizzeria Portofino

With its downtown setting overlooking the Chicago River, Pizzeria Portofino’s outdoor terrace makes the act of eating pizza feel extravagant. The menu of hand-crafted pies is enhanced by pastas, seafood dishes, and decadent desserts.

The Duck Inn

If you’re heading to the South Side to catch a White Sox game, consider the garden at Bridgeport’s The Duck Inn as an alternative to traditional stadium fare. True to its name, variations on duck dot the menu, but there’s much more on display at the award-winning gastropub, whose interior boasts a retro design.

Bar Siena

Courtesy of DineAmic Hospitality

Perfectly centralized in West Loop’s ‘Restaurant Row,’ Bar Siena is a prime place to dine al fresco. Taking after its sibling, Siena Tavern, this establishment offers a menu with endless Italian street food and pizza. However, it does not end here. Whether its lunch, dinner, a late night, or weekend brunch, Bar Siena has you covered. The streets of both West Loop Fulton Market and Skokie Old Orchard both host this indoor/outdoor restaurant. The West Loop location offers a quaint 20 seats, while The Old Orchard location offers 100. Both locations are  blazing candidates for the perfect day al fresco.


Tzuco is the creation of Carlos Gaytán, the first Mexican-born chef to win a Michelin star. Gaytán brings a unique twist to Mexican cuisine, fusing it with French techniques. Tzuco’s street-side seating puts you in the heart of River North at the corner of State St. and Superior St.

The Hampton Social

The Hampton Social’s relaxed, coastal vibe pairs perfectly with al fresco dining. Proudly advertising the “Rosé All Day” lifestyle, this establishment prides itself in its cuisine and hand-crafted cocktails. The social atmosphere is unmatched, regardless of the meal you’re going for. The Hampton Social serves brunch, lunch, and dinner, so go and dine at any time!


Courtesy of DineAmic Hospitality

LÝRA brings fresh, authentic Greek cuisine to the city in a seamless way. Their dishes are carefully created with island cooking techniques, leading to simple dishes with bold flavors. The indoor-outdoor space is both welcoming and striking, with rustic elements of rural Greek landscapes. Their inviting street-side patio seats 80, across the tables and lounge area. 

BLVD Steakhouse

This upscale establishment opens up patio doors for the first time on May 6th! To celebrate, Chef Joe Flamm has curated an elegant spring menu for returning patrons. Indulge in seasonal flavors while breathing in the fresh, seasonal air. The 120-seat patio is also hosting a Derby Day party on this date, so be sure to attend! The event includes a four-course lunch experience with Derby-themed cocktails; reserve your bar spot here, or your patio spot here!


Much like its sister restaurant, LYRA, VIOLI delivers outstanding cuisine to all visitors within its grand walls. The menu, as well as the establishment’s aesthetic, are authentically Mykonian. It is easily one of the hottest dinner tickets in Oakbrook, so consider making your spring and summer plans here! The fabulous 2,000 square foot all-season pergola patio featuring retractable guillotine windows, infrared heat lamps, and olive trees is perfect for any al fresco outing. 

Siena Tavern

Courtesy of DineAmic Hospitality

This River North staple is known for its modern Italian flare and comfortable establishment. The well respected Chef Fabio Viviani has perfected dishes from pizza and crudo to housemade pastas, impressing all patrons. The polished interior of Siena Tavern has an approachability like none other, creating a dining experience that is socially kind. The spacious corner patio and outdoor lounge seats 112 guests, making it a perfect place for large crowds who enjoy an evening al fresco.

Sweetwater Tavern & Grille

This inviting bar and restaurant sits right upon Michigan Avenue, offering an authentic view of the city’s most iconic area. Their modern American food menu can be enjoyed inside or on the patio. Either environment pairs well with the extensive craft beer and seasonal cocktail list. Whether it is lunch, dinner, or drinks that you’re having at Sweetwater, it is perfect al fresco.

South Branch Chicago  

This contemporary restaurant can be found along the Chicago River. Known as a Chicago Loop staple, you can expect to be impressed by the establishment’s individuality and fantastic cocktails. With its large outdoor patio and open-air bar, it can seem as though this place was made to be experienced al fresco.

Notify of
Inline Feedbacks
View all comments
Would love your thoughts, please comment.x

Discover more from Concierge Preferred

Subscribe now to keep reading and get access to the full archive.

Continue reading