House vacation rentals in Chicago
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Top-rated house rentals in 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 Chicago house rentals
House rentals with free parking
Home in Des Plaines
4.78 out of 5 average rating, 309 reviewsUrban Farmhouse near O'Hare
Home in West Chicago
4.92 out of 5 average rating, 107 reviewsThe Train Conductor's Cottage
Home in Bolingbrook
4.92 out of 5 average rating, 99 reviewsThe Sunshine Spot
Home in Joliet
4.9 out of 5 average rating, 144 reviewsThe Garden House - Murals and more
Home in Winfield
4.98 out of 5 average rating, 133 reviewsCozy, Clean & Well-Stocked Home!
Home in Chicago
4.91 out of 5 average rating, 89 reviewsBoho Chic Coach House 30Min to downtown W/ Parking
Home in Berwyn
5.0 out of 5 average rating, 81 reviewsRetro Modern Bungalow | free parking | fire pit
Home in Chicago
4.89 out of 5 average rating, 28 reviewsPrivate Condo in Chicago w/ Parking, Near Evanston
House rentals with a hot tub
Home in Homewood
4.91 out of 5 average rating, 106 reviewsPeaceful & Private Hot Tub Vacation Home Getaway
Home in Chicago
4.85 out of 5 average rating, 292 reviewsLux Urban 3BR/3BA Duplex + Parking!
Home in Chicago
4.93 out of 5 average rating, 71 reviewsModern Lux Getaway w/ Hot Tub, Lrg Yard, Parking
Home in Westchester
4.79 out of 5 average rating, 24 reviewsModern 2Bdrm Westchester/Chicago Home.With Hot tub
Home in Elmhurst
4.94 out of 5 average rating, 49 reviewsLuxe 3BR, 2BA + Hot Tub
Home in Gary
4.94 out of 5 average rating, 86 reviewsSunset beach house
Home in Palatine
4.85 out of 5 average rating, 40 reviewsPrivate Room with attach bath and personal kitchen
Home in Chicago
5.0 out of 5 average rating, 16 reviewsWrigley Penthouse w/Private Roof Deck and Parking
House rentals with a pool
Home in Plainfield
4.95 out of 5 average rating, 63 reviewsLarge Spanish style Home (w/heated pool)
Home in Schaumburg
4.93 out of 5 average rating, 14 reviewsSchaumburg Woodfield Pool House 4bedroom 2.5bath
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 Glen Ellyn
4.94 out of 5 average rating, 17 reviewsGlen Ellyn Home
Home in Lake Forest
4.91 out of 5 average rating, 58 reviewsBeautiful 137 Year Old Farm Home (3night min)
Home in Chicago Heights
Olympia field -matteson IL- homewood, park forest
Home in Gary
4.82 out of 5 average rating, 213 reviewsOasis , Near Beach, Hard Rock and Dunes
Quick stats about house rentals in Chicago
Total rentals
1.8K properties
Rentals with dedicated workspaces
1.2K properties have a dedicated workspace
Rentals with a pool
10 properties have a pool
Pet-friendly rentals
470 properties allow pets
Family-friendly rentals
950 properties are a good fit for families
Total number of reviews
69K reviews
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