1 Avli River North

The River North location of this modern Greek restaurant features a Greek Isles–inspired patio lounge. Popular with a fashionable happy-hour crowd, it’s a chic spot for noshing on housemade spinach pies and phyllo shrimp. Avli keeps the space toasty with a fully enclosed and heated patio. 702 N. Wells St., River North

2 The Dandy Crown

With veggie-centric offerings like roasted cauliflower nachos, Dandy Crown is one of River West’s best-kept secrets for date night. Its sprawling patio feels like a cool neighborhood park — just with cocktails. Each seating area has two heavy-duty heaters, and if those don’t do the job, the winter-friendly beverages should. Order a round of Crockpot cocktails, made with rye, amaro, lemon, and cassis and served warm. 694 N. Milwaukee Ave., River West

3 Devereaux

The sleek hotel lounge atop the Viceroy channels a European vacation destination, even for those just passing through for the evening. Come winter, it has an après-ski vibe, with fire pits and custom-designed greenhouses to keep you warm while you take in views of the neighborhood. Indulge with special packages, like Champagne paired with caviar, and s’mores made with booze-laced marshmallows, which start at $90. Book on Tock. 1112 N. State St., Near North Side

4 The Duck Inn

With a large backyard patio, the Bridgeport favorite is a destination for outdoor dining any time of the year. In winter, a tent covers the space, which is left partially open for air, and heaters are spread throughout. Plus, you’ll find soul-warming fare like the signature rotisserie duck, shaved prime rib Italian beef sandwiches, and housemade buttermilk biscuits spread with duck fat whipped butter. 2701 S. Eleanor St., Bridgeport

5 Le Sud

This French-Mediterranean bistro has freshly revamped its outdoor seating options with two different areas this winter. The enclosed sidewalk café features a retractable roof (for those occasional not-so-cold nights) and heaters to keep things cozy. There’s also a new enclosed rooftop space. Both are ideal for winter dates — split house specialties, like herb-roasted chicken and honey-glazed duck. 2301 W. Roscoe St., Roscoe Village

6 Z Bar

The Peninsula’s rooftop bar overlooks the Mag Mile, and in the winter, its views are best enjoyed while snuggled under a faux fur blanket with a cocktail in hand. A canopy covers part of the terrace, and a roaring outdoor fireplace keeps things extra toasty. If you want to go big, this is the place: You can reserve an outdoor table that seats up to six for a $750 deposit. It’ll cover part of the $1,000 Manhattan Royale, made with 40-year Balvenie and gold-laced ice. Book on Tock. 108 E. Superior St., Near North Side