Analogue | Logan Square
Last summer Analogue, the craft cocktail bar that's gotten as much love for its Cajun menu as its drinks, opened a 30-seat back patio that will be back in action as of May 31. Hanging planters and lights soften the stark concrete with metal tables a bit, and the seafoam-green chairs are a nice touch. 2523 N. Milwaukee, 773-904-8567, analoguechicago.com.
- Danielle A. Scruggs
Barcocina | Lakeview
The 4,000-square-foot sidewalk patio seats 122, and retractable garage doors on two sides of the corner bar open so wide that even indoors it's like sitting on a covered patio. Cocktails and food are Mexican inspired, and there's wine on tap as well as a wide selection of beer. 2901 N. Sheffield, 773-687-9949, barcocinachicago.com.
Best Intentions | Logan Square
A cabana bar in the enclosed back patio serves a limited menu of cocktails, beer, and wine, but if you've really got your heart set on a boozy milk shake, anything ordered inside can be taken outside. Flower-filled planters around the perimeter of the fence enhance the tropical feel. 3281 W. Armitage, 312-818-1254, bestintentionschicago.com.
Burnt City Brewing | Lincoln Park
The 28-seat patio on Lincoln Avenue next to bowling alley the Seven Ten Lounge has been around for a few years now, but the brewpub behind it just went through an unexpected change. Atlas Brewing, forced to change its name in early May following a trademark dispute, decided to "burn it all down," changing up its beer and food recipes to take a less conservative approach than before (the brewpub is also absorbing the bowling alley next door). The beers now include Facemelter Hibiscus IPA and Retrofit Radler, a low-alcohol summer seasonal. 2747 N. Lincoln, 773-295-1270, burntcitybrewing.com.
Cindy's | Loop
The view of the lake from Cindy's, the restaurant and bar on top of the Chicago Athletic Association Hotel, is hard to beat. As with many downtown rooftops, you'll pay a premium for it—but the $9 draft beers and $15 glasses of wine just make bartender Nandini Khaund's seriously creative cocktails seem like a deal by comparison (most are about $15). Bring a crowd; the food comes on large platters meant for sharing. 12 S. Michigan, 312-792-3502, cindysrooftop.com.
Corridor Brewery & Provisions | Lakeview
This brewpub from the owners of Dryhop is currently rotating summery beers like a watermelon-hibiscus farmhouse ale, a blueberry blond, and a smoked chile pepper saison into its lineup. The 25-seat sidewalk patio on Southport is set off by planters and features bench seating made from old railroad boxcars, sky-blue vintage metal armchairs, and reclaimed wood tables. 3446 N. Southport, 773-270-4272, corridorchicago.com.
- Peter Ravenstel
- City Winery's pop-up on the Riverwalk
Island Party Hut | Loop
The Riverwalk's first and only tiki bar has returned for a second year and is planning to double in size and offer games—including tetherball, bocce ball, and a giant Connect Four set—in addition to tiki drinks and grilled meat. There's also live music from Thursday to Sunday. Other Riverwalk options include City Winery's pop-up location (11 Chicago Riverwalk, 312-229-5593) and O'Brien's (41 Chicago Riverwalk, 312-346-3131). 355 E. Riverwalk South, 312-600-0488, islandpartyhut.com.
J. Parker | Lincoln Park
Thanks to a retractable glass roof, patrons have been able to experience the J. Parker's rooftop deck since February, but now that the weather is warmer those 140 seats will be in the open air (there's still a 55-seat indoor area). The summer cocktail menu for this lounge atop the Lincoln hotel is inspired by David Bowie and includes the Ziggy Stardust, Moonage Daydream, and Suffragette City; Paul Virant created the menu of small plates. 1816 N. Clark, 312-254-4747, jparkerchicago.com.
Joy District | River North
The 3,000-square-foot rooftop patio in the former Epic space has an updated look, with new furniture, awnings, and string lights. There's a frozen drinks program that includes strawberry daiquiris and piña coladas, plus a menu of small bites. 112 W. Hubbard, 312-955-0339, joychicago.com.
- Jay Schroeder/Courtesy H2 PR
- Mexcal for the aficionado at Mezcaleria las Flores
Mezcaleria la Flores | Logan Square
The new mescal bar (formerly the Flower Shop) adjoining Johnny's Grill is getting a renovated patio inspired by Mexican street markets. The vibrantly colored space will be decorated with buckets of cut flowers (which are for sale) and seat 80-100 people; the menus from both the bar and the grill will be available. 3149 W. Logan, 773-278-2215, mezcalerialasflores.com.
Raised | Loop
The full name of this bar atop the Renaissance Chicago Downtown Hotel is Raised, an Urban Rooftop Bar—which pretty much sums it up. The third-floor lounge overlooks the river and offers several beers and wines on tap as well as many more by the bottle; cocktails are available by the glass and by the decanter. The food menu will focus on locally sourced small plates. 1 W. Wacker, 312-372-7200, marriott.com.
Whiskey Business | Wicker Park
Themed around the 80s movie Risky Business, Whiskey Business offers more than 100 whiskeys by the glass, though the cocktail menu runs the gamut from vodka to mescal to—well, whiskey (there's a full food menu as well). The 120-seat rooftop deck (which is shared with the Cheesie's Pub & Grub next door) includes three flat-screen TVs for sports fans and couches for lounging. 1367 N. Milwaukee, 773-698-7362, whiskeybusinesschicago.com.