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 Chicago
4.83 out of 5 average rating, 135 reviewsLincoln Park - DePaul House w/Patio Free Parking
Jul 20 – 27
Home in Joliet
4.9 out of 5 average rating, 140 reviewsThe Garden House - Murals and more
Dec 17 – 24
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
4.88 out of 5 average rating, 26 reviewsPrivate Condo in Chicago w/ Parking, Near Evanston
Oct 5 – 12
Home in Wilmette
4.98 out of 5 average rating, 92 reviewsUnique porcelain-enamel paneled "Lustron" home
Sep 23 – 30
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
Home in Chicago
4.99 out of 5 average rating, 70 reviewsWhole apartment! 2 Bed/2 bath steps from Wrigley!!
Feb 15 – 22
House rentals with a hot tub
Home in Homewood
4.91 out of 5 average rating, 106 reviewsPeaceful & Private Hot Tub Vacation Home Getaway
Oct 8 – 15
Home in Chicago
4.85 out of 5 average rating, 292 reviewsLux Urban 3BR/3BA Duplex + Parking!
Aug 31 – Sep 7
Home in Chicago
4.87 out of 5 average rating, 15 reviewsHot Tub Logan Family Designer Home
May 20 – 27
Home in Chicago
4.93 out of 5 average rating, 70 reviewsModern Lux Getaway w/ Hot Tub, Lrg Yard, Parking
Nov 8 – 15
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 Westchester
4.76 out of 5 average rating, 21 reviewsModern 2Bdrm Westchester/Chicago Home.With Hot tub
Sep 2 – 9
Home in Chicago
4.73 out of 5 average rating, 26 reviews1501HOME | West Town Single Family Home + Garage
Jan 16 – 23
Home in Carol Stream
4.9 out of 5 average rating, 89 reviewsLAKE HOUSE HotTub/Kayak/Billiards/Pets/Fenced Yard
Apr 2 – 9
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
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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