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 Highland Park
4.9 out of 5 average rating, 125 reviews2-Acre Highland Park Retreat with Heated Pool ~ 5*
Jan. 22 – 29
Home in Plainfield
4.95 out of 5 average rating, 62 reviewsLarge Spanish style Home (w/heated pool)
Aug. 7 – 14
Home in Schaumburg
4.93 out of 5 average rating, 14 reviewsSchaumburg Woodfield Pool House 4bedroom 2.5bath
Apr. 18 – 25
Home in Chicago
4.86 out of 5 average rating, 36 reviewsLuxury Cabin in Lakeview
Jul. 7 – 12
Home in Glen Ellyn
4.94 out of 5 average rating, 16 reviewsGlen Ellyn Home
May 6 – 13
Home in Lake Forest
4.91 out of 5 average rating, 58 reviewsBeautiful 137 Year Old Farm Home (3night min)
Jan. 12 – 19
Home in Schaumburg
New place to stayParadise 4BR w/ Pool & Games
Aug. 31 – Sep. 7
Home in Chicago Heights
Olympia field -matteson IL- homewood, park forest
Aug. 24 – 31
Weekly house rentals
Home in Homewood
4.91 out of 5 average rating, 106 reviewsPeaceful & Private Hot Tub Vacation Home Getaway
Oct. 8 – 15
Home in Chicago
4.83 out of 5 average rating, 113 reviewsExclusive and Spacious Pilsen Guest House
Jan. 14 – 21
Home in Berwyn
5.0 out of 5 average rating, 75 reviewsRetro Modern Bungalow | free parking | pets ok
Dec. 12 – 19
Home in Chicago
4.91 out of 5 average rating, 87 reviewsBoho Chic Coach House 30Min to downtown W/ Parking
Jan. 9 – 16
Home in Chicago
5.0 out of 5 average rating, 3 reviews1-bedroom with full kitchen, washer/dryer inside
May 7 – 14
Home in Chicago
4.87 out of 5 average rating, 62 reviewsChicago getaway for two!
Jan. 18 – 25
Home in Chicago
4.98 out of 5 average rating, 54 reviews2BD/1 BA with summer patio in quiet Roscoe Village
Oct. 19 – 26
Home in Chicago
4.98 out of 5 average rating, 49 reviewsCity Cottage in Logan Square-Avondale
Sep. 3 – 10
Private house rentals
Home in Chicago
5.0 out of 5 average rating, 15 reviewsChicago Home by Midway near Downtown Attractions
Jan. 27 – Feb. 3
Home in Munster
4.97 out of 5 average rating, 34 reviewsEntire home: Private, Cozy Oasis in Quiet Locale
Apr. 6 – 13
Home in Palatine
4.85 out of 5 average rating, 39 reviewsPrivate Room with attach bath and personal kitchen
Sep. 29 – Oct. 6
Home in Highland Park
4.98 out of 5 average rating, 58 reviewsCharming Ranch-Style Cottage
Apr. 1 – 8
Home in Lansing
4.85 out of 5 average rating, 65 reviewsThe Walter Experience(2bd 1ba) April special
Sep. 5 – 12
Home in Chicago
5.0 out of 5 average rating, 45 reviewsCharming 3-BED in Lincoln Park/ Old Town & Parking
Dec. 1 – 8
Home in Chicago
4.88 out of 5 average rating, 26 reviewsPrivate Condo in Chicago w/ Parking, Near Evanston
Oct. 5 – 12
Home in Chicago Ridge
4.9 out of 5 average rating, 50 reviewsQuiet cul-de-sac with huge fenced in backyard
Nov. 24 – Dec. 1
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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