House vacation rentals in Downtown Chicago
Find and book unique houses on Airbnb
Top-rated house rentals in Downtown Chicago
Guests agree: these houses are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Downtown Chicago house rentals
House rentals with a pool
Home in Schaumburg
4.93 out of 5 average rating, 14 reviewsSchaumburg Woodfield Pool House 4bedroom 2.5bath
Home in Chicago
4.87 out of 5 average rating, 39 reviewsLuxury Cabin in Lakeview
Home in Chicago
4.84 out of 5 average rating, 19 reviews2Bed+2Bath PentHouse in South Loop
Home in Riverwoods
Riverwoods Nature Retreat
Home in Skokie
Skokie town home
Weekly house rentals
Home in Chicago
4.98 out of 5 average rating, 179 reviewsThe Evergreen House
Home in Berwyn
4.99 out of 5 average rating, 85 reviewsRetro Modern Bungalow | fire pit | pet friendly
Home in Chicago
4.97 out of 5 average rating, 31 reviewsLakeview Condo
Home in Chicago
4.86 out of 5 average rating, 73 reviewsChicago getaway for two!
Home in Chicago
4.98 out of 5 average rating, 62 reviews2BD/1 BA with summer patio in quiet Roscoe Village
Home in Chicago
5.0 out of 5 average rating, 55 reviewsCharming 3-BED in Lincoln Park/ Old Town & Parking
Home in Chicago
4.91 out of 5 average rating, 93 reviewsBoho Chic Coach House 30Min to downtown W/ Parking
Home in Chicago
5.0 out of 5 average rating, 56 reviewsCozy, Quiet, Riverwalk Sanctuary
Private house rentals
Home in Chicago
4.99 out of 5 average rating, 77 reviewsWhole apartment! 2 Bed/2 bath steps from Wrigley!!
Home in Lincoln Park
4.99 out of 5 average rating, 78 reviewsFlat in Lincoln Park 2-Flat Central to Everything
Home in Chicago
4.85 out of 5 average rating, 94 reviews503LOFT | Top Floor 5 BED, 2 BA Downtown Loft
Home in Chicago
4.93 out of 5 average rating, 14 reviewsHidden Gem on the CHI north side
Home in Chicago
4.93 out of 5 average rating, 76 reviewsModern Lux Getaway w/ Hot Tub, Lrg Yard, Parking
Home in Chicago
4.99 out of 5 average rating, 99 reviewsHuge Sunlit Gem, Free Parking, No Cleaning Fee
Home in Chicago
4.98 out of 5 average rating, 57 reviewsUP-SCALE Wicker Park 4BD/3.5BA HOME (+garage)
Home in Chicago
5.0 out of 5 average rating, 17 reviewsCozy Haven
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