1 Ina’s Beachwood Inn
at Ina Mae Tavern & Packaged Goods
Best for:Faux camping
Nightcap:The Hurricane, a classic New Orleans sip
If kitschy Minnesota Northwoods cabin is your ideal vacation vibe, you can head to Wicker Park for an escape without the drive. Ina Mae’s Airbnb is named for the Beachwood Inn, the former bar at this address, and the old sign hangs in the living room. There’s a balcony overlooking the tavern’s dining area, oversize bunk beds, and a retro kitchen (which is more for garnering likes than for cooking). You’ll get a 15 percent discount downstairs and at sister spots Lottie’s Pub and Frontier, but if you don’t want to venture out, don’t worry: The staff will bring your plate to you. $120–$250 per night. 1415 N. Wood St.
2 Bluebird Inn
at the Long Room
Best for:Staying with visiting friends in apartments bigger and better than your own
Sleeps:Eight in three-bed units; five in loft
Nightcap:Any Begyle beer— it’s brewed just down the street
There’s a long history of bars renting rooms to travelers, which inspired Long Room co-owner Jason Burrell to turn the top three floors into apartments. The two three-bed units and the two-bed loft are huge, with double beds and pullout sofas, so find some friends to join you. It shouldn’t be hard — Erin Boone, who designed Elske and the Dawson, gave the Lake View digs a midcentury feel with vintage furniture and incorporated Chicago touches, like books from Rebecca Makkai and other local authors. In the morning, cash in a token for coffee and a biscuit down at the bar. Loft: $100–$150 per night; three-bed: $200–$250 per night. 1614 W. Irving Park Rd.
3 Spilt Milk
Best for:Your home base for a weekend of eating and drinking your way through Logan Square
Nightcap:The Baller old-fashioned, made with Jack Daniel’s Single Barrel Rye
There are comparatively few frills (and nothing to Instagram) in Spilt Milk’s two-bedroom apartment, but the sunny space provides revelers an affordable landing pad with exposed brick and a well-stocked kitchen. Keep the party going after last call — you can buy nearly anything on Spilt Milk’s back bar, plus beer, wine, and bags of ice, to take upstairs. $100–$300 per night. 2758 W. Fullerton Ave.