The patio at Chicago Cut Steakhouse
Chicago Cut Steakhouse
300 N. La Salle St. 312-329-1800
This luxe steakhouse stands out from the others not just because of its iPad wine menu and double-cut steaks that are dry-aged on site, but also because of its riverside patio, warmed with heat lamps on chilly nights.
The Motel Bar
600 W. Chicago Ave. 312-822-2900
This throwback bar was one of the early embracers of classic cocktails such as the sidecar, gimlet and sazerac before the trend blew up citywide. The spacious front patio features retro orange-and-white lawn chairs and umbrellas for shade.
151 W. Erie St. 312-274-1111
In addition to a candlelit dining room and secluded lounge, this Spanish-inspired restaurant features a bustling bar called Barcito, with windows that open out to sidewalk seating on the corner of Erie and La Salle.
Bridge House Tavern
321 N. Clark St. 312-644-0283
Descend the elevator on the north side of the Clark Street Bridge to find this bar and restaurant hidden below street level. No question, the best feature is the killer riverside patio with a prime view of boats floating by.
661 N. Clark St. 312-335-8121
Prefer your Guinness with a side of sunshine? Head to this Irish corner pub, where umbrella-covered tables crowd a plant-lined sidewalk cafe packed with business lunchers and people kicking off the weekend early.
Clark Street Ale House
742 N. Clark St. 312-642-9253
Hidden away behind this wood-trimmed tavern, you’ll find a small, wall-bound beer garden perfect for sipping a beer or whiskey under the stars.
Bull & Bear
431 N. Wells St. 312-527-5973
Other bargoers may clamor for the table-tap booths inside, but the umbrella-shaded sidewalk tables along both Wells and Hubbard Streets make for prime post-work people-watching.