House vacation 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.
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
4.93 out of 5 average rating, 14 reviewsSchaumburg Woodfield Pool House 4bedroom 2.5bath
Home in Schaumburg
4.33 out of 5 average rating, 6 reviewsParadise 4BR w/ Pool & Games
Home in Chicago
4.87 out of 5 average rating, 39 reviewsLuxury Cabin in Lakeview
Home in Chicago
4.82 out of 5 average rating, 17 reviews2Bed+2Bath PentHouse in South Loop
Home in Riverwoods
Riverwoods Nature Retreat
Home in Lisle
Cozy Lisle Home w/ Fenced Backyard: Pets Welcome!
Home in Bloomingdale
5.0 out of 5 average rating, 3 reviewsWhole House in Bloomingdale, IL
Weekly house rentals
Home in Whiting
4.8 out of 5 average rating, 231 reviewsWhiting Getaway
Home in Chicago
4.98 out of 5 average rating, 176 reviewsThe Evergreen House
Home in Chicago
4.83 out of 5 average rating, 140 reviewsLincoln Park - DePaul House w/Patio Free Parking
Home in Chicago
4.92 out of 5 average rating, 237 reviewsCool Quiet Coach House W/ Private Access and Outdoor Space
Home in Chicago
4.91 out of 5 average rating, 92 reviewsBoho Chic Coach House 30Min to downtown W/ Parking
Home in Berwyn
4.99 out of 5 average rating, 84 reviewsRetro Modern Bungalow | free parking | fire pit
Home in Chicago
4.86 out of 5 average rating, 70 reviewsChicago getaway for two!
Home in Chicago
4.98 out of 5 average rating, 59 reviews2BD/1 BA with summer patio in quiet Roscoe Village
Private house rentals
Home in Wilmette
4.98 out of 5 average rating, 98 reviewsUnique porcelain-enamel paneled "Lustron" home
Home in Chicago
5.0 out of 5 average rating, 54 reviewsCharming 3-BED in Lincoln Park/ Old Town & Parking
Home in Chicago
4.9 out of 5 average rating, 30 reviewsPrivate Condo in Chicago w/ Parking, Near Evanston
Home in Chicago
5.0 out of 5 average rating, 12 reviewsCubby Blue home - Wrigley ~Free Parking~
Home in Chicago
5.0 out of 5 average rating, 13 reviewsHidden Gem on the CHI north side
Home in Chicago
4.98 out of 5 average rating, 52 reviewsCity Cottage in Logan Square-Avondale
Home in Chicago
5.0 out of 5 average rating, 54 reviewsCozy, Quiet, Riverwalk Sanctuary
Home in Chicago
4.99 out of 5 average rating, 77 reviewsFlat in Lincoln Park 2-Flat Central to Everything
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- Family travel hub Tips and inspiration
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