Chicago Outdoor Dining Guide – Rooftops, Patios And Sidewalk Cafes

III Forks

Rooftops with a City View

ZED451’s stunning rooftop lounge, set in the heart of River North, boasts incredible city skyline views.  The outdoor space features three cabanas, multiple couches, a fireplace, a serene grassy area and beautiful walnut bar.  The a la carte, lounge “Cravings” menu and seasonally-inspired liquid market cocktail menu are offered from 4:30 p.m. to midnight Monday-Friday, and from 10 a.m. to midnight on Saturday and Sunday.

III Forks
III Forks’ impressive rooftop lounge offers semi-private, cabana-style seating complete with built-in heaters, large knotty pine and granite bar, flat panel televisions, stone fireplaces and serene, city and park views.  Chef Clark Grant’s small plates menu is available exclusively on the rooftop, along with creative cocktails and hand-selected wines. The rooftop is open from 4 p.m. to midnight.

Palatial Patios

Park Grill / The Plaza at Park Grill 
This enormous alfresco dining location, set in Millennium Park, offers two areas and two menus to choose from.  Park Grill’s sophisticated lunch and dinner fare may be enjoyed in the enclosed outdoor area adjacent to the dining room.  The Plaza at Park Grill is the City’s largest alfresco dining venue, the ultimate room with a view. The Plaza at Park Grill offers more casual fare, with seating in the middle of the park, just beneath the “bean.” Having cocktails? Head to the lounge-like tents on the North side of the plaza where drinks, appetizers and live music may be enjoyed. Park Cafe offers easy, grab-n-go selections as well as picnic baskets for pavilion performances.

Kit Kat Lounge & Supper Club
This Lakeview mainstay has recently redesigned their large alfresco area, located on Waveland Avenue. The stylish, South Beach-inspired, patio lounge features low-top tables and couch seating, colorful LED lighting, oversized umbrellas, sleek furniture and heaters, all set amongst gorgeous florals.  Dinner and cocktails are offered nightly from 5:30 p.m. to midnight and brunch is served on Sunday from 11 a.m. to 3 p.m.

The Red Canary
The Red Canary offers “Real. American. Comfort.” fare in Chicago’s River West neighborhood. The lush, 2,000 square foot, enclosed garden patio is complete with ivy-clad walls, imported olive trees, lounge furniture and table seating.  Relax and dine alfresco while sipping custom-made cocktails, local craft beer or a chilled glass of summer white from the approachable American wine list. Weekend brunch is served Saturdays and Sundays from 10 a.m. to 3 p.m. Dinner and drinks are available on the patio every night from 5 p.m. to midnight.

Hidden Gem (Enclosed Backyard Patio)

Due Lire Vino & Cucina
Due Lire in Lincoln Square,  has a secret garden patio in the located  rear of the building, reminiscent of a backyard in an Italian home. Sip a beatiful glass of wine while enjoying a platter of Chef Kevin Abshire’s formaggi e salumi, followed by tagliatelle (fava beans, rocket rucola, heirloom tomatoes) and torta semolina (semolina custard, rhubarb, saba).There are 36 seats available in the backyard. Dinner and drinks are offered Tuesday through Sunday evenings (Tuesday-Thursday 5-10 p.m., Friday-Saturday 5-11 p.m. and Sunday 5-9 p.m.). 


Sidewalk Cafes

Nacional 27 
Nacional 27’s lush “mojito garden” is the perfect setting for a sipping a freshly muddled mojito on a hot summer night. The sidewalk patio, located on Huron Street, can seat up to 24 guests. The weeknight “5-7 at N27” promotion is a great time to enjoy half-price tapas and ceviche while sipping creative cocktails after work. Nacional 27 is open Monday-Saturday starting at 5 p.m.

ZOCALO Restaurant and Tequila Bar
With alfresco seating on Ontario Street, Zocalo offers an updated version of authentic Mexican cuisine. They offer over 130 tequilas made with 100-percent blue agave, and have one of the city’s largest mezcal menus. Zocalo offers monthly tequila distillery tasting events and daily dining deals. Lunch, dinner and drinks may be enjoyed outdoors. Zocalo opens Monday-Friday at 11:30 a.m. and on Saturday-Sunday at 5 p.m.

Timothy O’Toole’s Pub
Shopped out? Enjoy cocktails, appetizers or a meal at a classic Irish Chicago pub, located 
in Streeterville just steps from Michigan Avenue. The sidewalk cafe on Ontario street is open for brunch, lunch and dinner service. O’Toole’s opens at 11 a.m. Monday-Friday, and at 9 a.m. Saturday-Sunday.

Cactus Bar and Grill

At Cactus, you’ll feel like you’re on vacation (while actually in the heart of the Financial District). Their motto: “Don’t Drink and Trade.” Lunch, dinner and drinks are offered outdoors on the Wells Street, enclosed patio. Enjoy hand-shaken margaritas, great burgers, interesting brews and a host of specialty events. Cactus opens Monday-Saturday at 11 a.m.

Cantina Laredo
Cantina Laredo, featuring modern Mexican cuisine in River North, offers lunch, dinner and weekend brunch. Both lounge areas (first and second floors) feature accordion fold, floor-to-ceiling glass walls that open to the outdoors. The element of fire is utilized in four locations throughout Cantina Laredo, including the street-side, outdoor stone fire pit area with white mesh metal, over-sized seating for eight. Cantina Laredo opens everyday at 11 a.m.

La Madia
Although the outdoor patio is closed due to nearby construction, La Madia’s European, floor-to-ceiling doors will be open. This season, guests will still feel the breeze and sit amongst the sights and sounds of the city. “Almost Alfresco” dining (lunch, dinner and late night) is offered Monday through Thursday from 11:15 a.m. to 11:15 p.m., Friday and Saturday 11:15 a.m. to 12 a.m. and Sunday 12 p.m. to 10 p.m.

Pleasant Porches


Quince, located at The Homestead in Evanston, offers contemporary American cuisine, craft cocktails and diverse wines on the charming veranda. Located on the front porch of the building, dining guests will enjoy the sleek silver furniture, white tablecloth linens and comfy taupe pillows. The veranda seats approximately 20.
 Executive Chef Andy Motto’s menu is available Tuesday through Sunday evenings (Tuesday-Thursday 5:30-9:30 p.m.; 
Saturday 5-10 p.m. and Sunday 5-9 p.m.).


739 North Clark Street
Chicago, Illinois 60611

III Forks
Upper Randolph and Field
333 East Benton Place
Chicago, Illinois 60601

Park Grill / The Plaza at Park Grill
11 North Michigan Avenue
Chicago, Illinois 60602

La Madia
59 West Grand Avenue
Chicago, Illinois 60654

Kit Kat
3700 North Halsted Street
Chicago, Illinois 60657

The Red Canary
695 North Milwaukee Avenue
Chicago, Illinois 60642

Due Lire Vino & Cucina
4520 North Lincoln Avenue
Chicago, Illinois 60625

Nacional 27
325 West Huron
Chicago, Illinois 60610


ZOCALO Restaurant and Tequila Bar
358 West Ontario
Chicago, Illinois 60610

Timothy O’Toole’s Pub Chicago
622 North Fairbanks Court
Chicago, Illinois 60611

Timothy O’Toole’s Pub Gurnee
5572 Grand Avenue
Gurnee, Illinois 60031

Cactus Bar & Grill

404 South Wells
Chicago, Illinois 60607

Cantina Laredo
508 North State Street
Chicago, Illinois 60654


358 West Ontario
Chicago, Illinois 60610

1625 Hinman Avenue
Evanston, Illinois 60201

18 thoughts on “Chicago Outdoor Dining Guide – Rooftops, Patios And Sidewalk Cafes

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