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 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
Weekly house rentals
Home in West Chicago
4.92 out of 5 average rating, 107 reviewsThe Train Conductor's Cottage
Home in Chicago
4.86 out of 5 average rating, 215 reviewsThe Avondale Guesthouse
Home in Chicago
4.89 out of 5 average rating, 375 reviewsPro Cleaned & Isolated West Loop Coach House
Home in Bolingbrook
4.92 out of 5 average rating, 100 reviewsThe Sunshine Spot
Home in Chicago
4.82 out of 5 average rating, 115 reviewsExclusive and Spacious Pilsen Guest House
Home in Chicago
4.98 out of 5 average rating, 175 reviewsThe Evergreen House
Home in Chicago
4.91 out of 5 average rating, 89 reviewsBoho Chic Coach House 30Min to downtown W/ Parking
Home in Chicago
5.0 out of 5 average rating, 5 reviews1-bedroom with full kitchen, washer/dryer inside
Private house rentals
Home in Chicago
4.97 out of 5 average rating, 29 reviewsLakeview Condo
Home in Chicago
4.98 out of 5 average rating, 51 reviewsCity Cottage in Logan Square-Avondale
Home in Chicago
4.99 out of 5 average rating, 73 reviewsWhole apartment! 2 Bed/2 bath steps from Wrigley!!
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 Munster
4.95 out of 5 average rating, 38 reviewsEntire home: Private, Cozy Oasis in Quiet Locale
Home in Munster
5.0 out of 5 average rating, 17 reviewsCozy Farmhouse in Munster
Home in Chicago
4.98 out of 5 average rating, 87 reviews3BD Home Mins from Airport | Free Wi-Fi + Parking
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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