House holiday rentals in Downtown Chicago
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Top-rated house rentals in Downtown Chicago
Guests agree: these houses are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for house rentals in Downtown Chicago
House rentals with a pool
Home in Glen Ellyn
Glen Ellyn Home
Home in Schaumburg
Schaumburg Woodfield Pool House 4bedroom 2.5bath
Home in Chicago
Luxury Cabin in Lakeview
Home in Chicago
2Bed+2Bath PentHouse in South Loop
Home in Riverwoods
Riverwoods Nature Retreat
Home in Skokie
Skokie town home
Weekly house rentals
Home in Bolingbrook
The Sunshine Spot
Home in Chicago
The Evergreen House
Home in Berwyn
Retro Modern Bungalow | free parking | fire pit
Home in Chicago
2BD/1 BA with summer patio in quiet Roscoe Village
Home in Chicago
Boho Chic Coach House 30Min to downtown W/ Parking
Home in Chicago
Lakeview Condo
Home in Chicago
Chicago getaway for two!
Home in Chicago
Cozy, Quiet, Riverwalk Sanctuary
Private house rentals
Home in Wilmette
Unique porcelain-enamel paneled "Lustron" home
Home in Chicago
Chicago Home by Midway near Downtown Attractions
Home in Chicago
City Cottage in Logan Square-Avondale
Home in Chicago
Private Condo in Chicago w/ Parking, Near Evanston
Home in Chicago
Brand New Spacious Duplex
Home in Chicago
Cozy space in Wicker Park
Home in Chicago
Cozy Haven
Home in Chicago
1-bedroom with full kitchen, washer/dryer inside
Destinations to explore
- Milwaukee Holiday rentals
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- Lake Michigan Beach Holiday rentals
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