Best Outdoor Bars and Restaurants In Chicago

24 May J Parker
III Forks Rooftop

III Forks Rooftop

The time to enjoy rooftops, sidewalk cafes, patios, beer gardens and any chair you can find outdoors is here. In A-Z order, here are a few to check out this summer. Neighborhood and the type of outdoor space is noted in parenthesis.


III Forks (Lake Shore East / Rooftop)
180 N. Field Blvd.
Chicago, IL 60601
(312) 938.4303


10 Urban Roofscape (River North / Godfrey Hotel Rooftop, Retractable Roop)
127 W. Huron
Chicago, IL


Big Star (Bucktown / Patio)
1531 N. Damen Avenue
Chicago, IL


Cactus Bar & Grill (Loop / Sidewalk Patio)
404 South Wells
Chicago, IL 60607


Cantina Loredo

Cantina Loredo

Cantina Laredo (River North / Sidewalk Patio, Rooftop)
508 North State Street
Chicago, IL 60654


City Winery (West Loop / Patio)
1200 W Randolph St
Chicago, IL 60607 (312) 733-9463


Del Frisco’s (Gold Coast / Patio)
58 E. Oak Street
Chicago, IL


Drumbar (Gold Coast / Raffaello Hotel Rooftop)
201 E. Delaware Pl
Chicago, IL
(312) 933-4805




Dryhop Brewers (Lakeview / Patio)
3155 N. Broadway
Chicago, IL


Frontier (West Town-Wicker Park / 3 Season Patio)
1072 North Milwaukee
Chicago, IL 60642
(773) 772.4322


High Noon Saloon (Wicker Park / Sidewalk Patio)
1560 N Milwaukee Ave
Chicago, IL 60622
(773) 227-9339


Homestead On The Roof (Ukrainian Village / Rooftop)
1924 W. Chicago Avenue
Chicago, IL


Howells & Hood

Howells & Hood

Howell’s & Hood (Streeterville / Patio)
435 N Michigan Ave
Chicago, IL 60611
(312) 262-5310


Joe’s Bar Trackside (Clybourn Corridor / Rooftop)
940 W. Weed Street
Chicago IL 60642-2540
(312) 787-9600


Hopleaf (Andersonville / Patio)
5148 N. Clark Steet
Chicago, IL


Kit Kat (Lakeview / Patio)
3700 North Halsted Street
Chicago, IL 60657


La Madia (River North / Sidewalk Patio)
59 West Grand Avenue
Chicago, IL 60654


Little Goat Diner (West Loop / Patio)
820 W. Randolph Street
Chicago, IL 60607


Logman & Eagle (Logan Square / Patio)
2657 N. Kedzie
Chicago, IL


Mott Street (Wicker Park / Patio)
1401 N Ashland Ave
Chicago, IL 60622


RM Champagne

RM Champagne

Moody’s Pub (Edgewater / Patio)
5910 N. Broadway
Chicago, IL


Nacional 27 (River North / Sidewalk Patio)
325 West Huron
Chicago, IL 60610


RM Champagne (West Loop / Patio)
116 N. Green Street
Chicago, IL


Rock Bottom (River North / Rooftop)
1 W. Grand
Chicago, IL


ROOF on theWit (Loop / Rooftop)
201 N. State
Chicago, IL


Twisted Spoke (West Town / Rooftop)
501 N. Ogden Ave
Chicago, IL


Sheffield’s (Lakeview / Patio)
3258 N. Sheffield Ave
Chicago, IL


J Parker

J Parker

Small Bar (Logan Square / Patio)
2956 N. Albany
Chicago, IL


The Dawson (River West, Patio)
730 W. Grand
Chicago, IL


The J Parker (Lincoln Park / Hotel Lincoln Rooftop)
1816 N. Clark Street
Chicago, IL


The Southern (Bucktown / Patio)
1840 W. North Ave.
Chicago, IL


Timothy O’Toole’s Pub Chicago (Streeterville / Sidewalk Cafe)
622 North Fairbanks Court
Chicago, IL 60611


The Dec

The Dec

The Dec (Gold Coast / Ritz Hotel Rooftop)
160 E Pearson
Chicago, IL


Park Grill / The Plaza at Park Grill (Loop/ Sidewalk Cafe)
11 North Michigan Avenue
Chicago, IL 60602


West Town Cafe (Ukrainian Village / Sidewalk Patio)
1916 W. Chicago Avenue
Chicago, IL 60622


ZED451 (River North / Rooftop)
739 North Clark Street
Chicago, IL 60611


ZOCALO Restaurant and Tequila Bar (River North / Patio)
358 West Ontario
Chicago, IL 60610


Black Wednesday Specials & Black Friday Benefit at Flagship 11.25+11.27

16 Nov IMG_9437-1
  • Wednesday, November 25 and Friday, November 27

  • $3 to $4 specials
Guests who visit Flagship on Black Wednesday will enjoy Trivia Night from 7 p.m. to 9 p.m. as well as specials including $3 Blue Moon drafts, $3 Blue Moon seasonal bottles
and $4 Fireball shots.


On Black Friday, November 27, Flagship will offer their Friday Happy Hour package from 6 p.m. to 9 p.m. Options include a $25 package (well drinks and domestic drafts plus one food item) or a $30 package (call drinks, domestic drafts and bottles and one food item).


Additionally, patrons who bring a non-perishable food item anytime during the month of November will receive $5 off the happy hour package price. Donations will benefit the Lakeview Food Pantry.

Silversmith Hotel Black Friday + Cyber Monday Deals

13 Nov adamus-restaurant-at-the-silversmith-hotel

Silversmith Hotel {10 S Wabash Avenue} will be offering money saving specials over the Thanksgiving holiday weekend.

The hotel’s vibrant lounge and restaurant, Adamus, will be offering a Black Friday dining special for those who will be out shopping. Holiday shoppers can enjoy 20% off all lunch menu items on Friday, November 27. Lunch is served from 11:00 a.m. – 2:00 p.m.

Silversmith Hotel will also offer a Cyber Monday Hotel Deal {24 Hour Sale} of a special room rate of $99.00 per night, valid for stays between Dec. 3 – Feb. 28, 2016. Black out dates apply and New Years Eve is excluded. Request rate code CYBR when booking online here:

Compass Bar Black Wednesday & Black Friday Specials 11.25 +11.27

10 Nov Compass Bar_Interior 1

Compass Bar_Interior 1

  • Wednesday, November 25 and Friday, November 27
  • $5 specials
Guests who visit Compass Bar in Lincoln Park on Black Wednesday will enjoy specials including $5 Stout and Black IPA’s and $5 Jager shots. On Black Friday, Compass Bar will open at 3 p.m. and show the Blackhawks vs. Ducks game at 4 p.m. Specials will include Happy Hour from 4 p.m. to 6 p.m. featuring $5 well drinks.
433 W. Diversey
Chicago, IL 60614
Phone: 773-248-3230

Free Movember Lunch At South Water Kitchen 11.30

9 Nov IMG_6981

Join the “movember movement” this month at South Water Kitchen! On Monday, November 30th Chef Roger and his legendary moustache will be hosting a complimentary “Sliders, Staches & Suds” patio party at this Loop restaurant from 11am-3pm. Rain, snow or shine, the free lunch will be hosted on the patio and include Pulled Pork Sliders, a draft beer and mustache shenanigans, and just $3 for each additional draft beer. A suggested donation of $10 will go to the Movember Foundation. 

When: Monday, November 30 from 11am-3pm

Where: Patio at South Water Kitchen, 225 N Wabash

What: Complimentary sliders, draft beer + mustache shenanigans; $3 each additional draft beer

Cost: Complimentary; $10 suggested donation to the Movember Foundation

Reservations: Required by phone: 312-236-9300


*To be eligible for the complimentary lunch, guests must make a reservation by phone to dine outside. Guests who dine inside will not be eligible for a complimentary lunch but can still donate and take advantage of beer, wine and cocktail specials.


Vintage Garage Chicago Holiday Edition 11.15

6 Nov holiday-pic-for-website
Vintage Garage Chicago
Holiday Edition –  November 15
10a.m. till 5 p.m.
5051 N. Broadway
Chicago, IL 60040
Take the Redline to Argyle or the #36 Broadway bus
$5 at the gate

“Tom Skilling says it’s going to be an El Nina year, which hopefully means a mild fall/winter in Chicago. ” says Melissa Sands of Vintage Promotions, LLC, producer of the event. “We’ll be dry, dress warm and have hot chocolate.  Vintage holiday shopping at the Garage won’t be a problem.”

The market will be held at the parking garage venue at 5051 N. Broadway, November 15. The Garage dealers will be saving their best vintage holiday and Christmas merchandise for the occasion.   Vintage holiday trees, ornaments, blow molds, decorations, figurines, toys, lighting and more.  Expect to see 75 to 100 vendors and note that you can still expect to see your favorite vintage represented from all categories.  If you are interested in selling at the Vintage Garage Holiday Market, Click on the photo above or click HERE.

The Vintage Garage Holiday Market will provide enough clothing, jewelry, furniture, advertising memorabilia, games, appliances, glassware and electronics to get you through the winter.

VIG’s (Very Important Garagers) Your season pass will get you into this event, bonus!

To check out all Vintage Garage dates for this season, click HERE


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