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 Glen Ellyn
4.94 out of 5 average rating, 17 reviewsGlen Ellyn Home
Home in Schaumburg
5.0 out of 5 average rating, 3 reviewsParadise 4BR w/ Pool & Games
Home in Chicago
4.86 out of 5 average rating, 37 reviewsLuxury Cabin in Lakeview
Home in Schaumburg
4.93 out of 5 average rating, 14 reviewsSchaumburg Woodfield Pool House 4bedroom 2.5bath
Home in Chicago
4.8 out of 5 average rating, 15 reviews2Bed+2Bath PentHouse in South Loop
Home in Lisle
5.0 out of 5 average rating, 3 reviewsWelcoming, cozy, and a fur baby paradise.
Home in Niles
5.0 out of 5 average rating, 12 reviewsLuxury Modern House Epic Master Bath & Pool Table
Home in Riverwoods
Riverwoods Nature Retreat
Weekly house rentals
Home in Chicago
4.84 out of 5 average rating, 83 reviewsFree parking, close to public transit, dining
Home in Chicago
4.91 out of 5 average rating, 89 reviewsBoho Chic Coach House 30Min to downtown W/ Parking
Home in Chicago
4.86 out of 5 average rating, 66 reviewsChicago getaway for two!
Home in Chicago
5.0 out of 5 average rating, 5 reviews1-bedroom with full kitchen, washer/dryer inside
Home in Berwyn
4.99 out of 5 average rating, 83 reviewsRetro Modern Bungalow | free parking | fire pit
Home in Chicago
5.0 out of 5 average rating, 51 reviewsCharming 3-BED in Lincoln Park/ Old Town & Parking
Home in Chicago
4.98 out of 5 average rating, 57 reviews2BD/1 BA with summer patio in quiet Roscoe Village
Home in Chicago
4.98 out of 5 average rating, 51 reviewsCity Cottage in Logan Square-Avondale
Private house rentals
Home in Chicago
5.0 out of 5 average rating, 52 reviewsArchitect's Urban Oasis | 4bd/3ba I Luxe
Home in Chicago
5.0 out of 5 average rating, 12 reviewsHidden Gem on the CHI north side
Home in Wilmette
4.98 out of 5 average rating, 94 reviewsUnique porcelain-enamel paneled "Lustron" home
Home in Chicago
5.0 out of 5 average rating, 17 reviewsChicago Home by Midway near Downtown Attractions
Home in Chicago
4.99 out of 5 average rating, 77 reviewsFlat in Lincoln Park 2-Flat Central to Everything
Home in Chicago
4.97 out of 5 average rating, 32 reviewsLight and bright 3BD duplex in Avondale, Chicago
Home in Chicago
4.93 out of 5 average rating, 72 reviewsModern Lux Getaway w/ Hot Tub, Lrg Yard, Parking
Home in Munster
5.0 out of 5 average rating, 17 reviewsCozy Farmhouse in Munster
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