The Best Airbnbs in Chicago, From Midcentury Townhouses to a Sprawling Sunlit Loft


Bed & bath: 6 bedrooms, 2.5 baths
Top amenities: 26-foot-tall timber-beamed ceilings, multiple skylights, private garden patio and rooftop deck, commercial-grade kitchen
Nearby attractions: Wicker Park, Logan Square Theatre, Humboldt Park

A former factory turned sprawling apartment and event venue, Loft606 is a destination in itself. With a fully equipped, commercial-grade kitchen, exposed brick, 26-foot timber ceilings, and large skylights, the entire unit is bathed in bright, natural light. Built, essentially, for large groups and parties, there’s even a built-in bar, rooftop patio, and private garden walk-out. The six large bedrooms can sleep up to 16. Our favorite design features? The brick-enclosed smoke staircase that leads to the primary bedroom, or the ‘70s-inspired glass-paneling in the primary bath around the shower and toilet. If you’re feeling bougie, you can book a private chef, bartender, or even spa appointment right to your room (for an extra fee).



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