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, 62 reviewsSpanish style Home (w/heated pool)
Aug. 20 – 27
Home in Schaumburg
5.0 out of 5 average rating, 3 reviewsParadise 4BR w/ Pool & Games
Nov. 21 – 28
Home in Schaumburg
4.93 out of 5 average rating, 14 reviewsSchaumburg Woodfield Pool House 4bedroom 2.5bath
Nov. 14 – 21
Home in Chicago
4.86 out of 5 average rating, 37 reviewsLuxury Cabin in Lakeview
Jul. 7 – 14
Home in Glen Ellyn
4.94 out of 5 average rating, 16 reviewsGlen Ellyn Home
Jul. 23 – 30
Home in Lake Forest
4.91 out of 5 average rating, 58 reviewsBeautiful 137 Year Old Farm Home (3night min)
Apr. 8 – 15
Home in Chicago Heights
Olympia field -matteson IL- homewood, park forest
Sep. 1 – 8
Home in Gary
4.82 out of 5 average rating, 213 reviewsOasis , Near Beach, Hard Rock and Dunes
Jun. 6 – 13
Weekly house rentals
Home in Chicago
4.96 out of 5 average rating, 128 reviewsChicago Riverhouse summer on our patio!
Mar. 5 – 12
Home in Des Plaines
4.78 out of 5 average rating, 307 reviewsUrban Farmhouse near O'Hare
Aug. 11 – 18
Home in Chicago
4.88 out of 5 average rating, 372 reviewsPro Cleaned & Isolated West Loop Coach House
Mar. 4 – 11
Home in Chicago
4.98 out of 5 average rating, 175 reviewsThe Evergreen House
Jun. 22 – 29
Home in Chicago
5.0 out of 5 average rating, 5 reviews1-bedroom with full kitchen, washer/dryer inside
Dec. 10 – 17
Home in Berwyn
5.0 out of 5 average rating, 78 reviewsRetro Modern Bungalow | free parking | fire pit
Jan. 6 – 13
Home in Chicago
4.91 out of 5 average rating, 88 reviewsBoho Chic Coach House 30Min to downtown W/ Parking
Dec. 5 – 12
Home in Wilmette
4.98 out of 5 average rating, 92 reviewsUnique porcelain-enamel paneled "Lustron" home
Sep. 22 – 29
Private house rentals
Home in Chicago
5.0 out of 5 average rating, 12 reviewsHidden Gem on the CHI north side
Oct. 7 – 14
Home in Munster
4.97 out of 5 average rating, 35 reviewsEntire home: Private, Cozy Oasis in Quiet Locale
Dec. 30 – Jan. 6
Home in Chicago
5.0 out of 5 average rating, 15 reviewsChicago Home by Midway near Downtown Attractions
Jan. 8 – 15
Home in Chicago
4.98 out of 5 average rating, 87 reviews3BD Home Mins from Airport | Free Wi-Fi + Parking
Sep. 11 – 18
Home in Geneva
4.97 out of 5 average rating, 76 reviewsCozy Ranch duplex close to downtown Geneva
Mar. 14 – 21
Home in Lockport
5.0 out of 5 average rating, 36 reviewsPrivate Hideaway House Apartment
Oct. 22 – 29
Home in Munster
5.0 out of 5 average rating, 14 reviewsCozy Farmhouse in Munster
Jun. 13 – 20
Home in Chicago
5.0 out of 5 average rating, 48 reviewsCharming 3-BED in Lincoln Park/ Old Town & Parking
Dec. 11 – 18
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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