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
4.95 out of 5 average rating, 101 reviewsModern, Fully Renovated Logan Square Coach House
Dec 1 – 8
Home in Chicago
4.83 out of 5 average rating, 135 reviewsLincoln Park - DePaul House w/Patio Free Parking
Sep 8 – 15
Home in Berwyn
5.0 out of 5 average rating, 75 reviewsRetro Modern Bungalow | free parking | pets ok
Dec 28 – Jan 4
Home in Chicago
4.91 out of 5 average rating, 87 reviewsBoho Chic Coach House 30Min to downtown W/ Parking
Oct 3 – 10
Home in Chicago
4.88 out of 5 average rating, 26 reviewsPrivate Condo in Chicago w/ Parking, Near Evanston
Oct 4 – 11
Home in Wilmette
4.98 out of 5 average rating, 92 reviewsUnique porcelain-enamel paneled "Lustron" home
Sep 23 – 30
Home in Chicago
5.0 out of 5 average rating, 11 reviewsCubby Blue home - Wrigley ~Free Parking~
Jan 7 – 14
Home in Chicago
4.99 out of 5 average rating, 70 reviewsWhole apartment! 2 Bed/2 bath steps from Wrigley!!
Feb 14 – 21
House rentals with a hot tub
Home in Homewood
4.91 out of 5 average rating, 106 reviewsPeaceful & Private Hot Tub Vacation Home Getaway
Nov 19 – 26
Home in Chicago
4.85 out of 5 average rating, 292 reviewsLux Urban 3BR/3BA Duplex + Parking!
Nov 26 – Dec 3
Home in Chicago
4.93 out of 5 average rating, 70 reviewsModern Lux Getaway w/ Hot Tub, Lrg Yard, Parking
Oct 1 – 8
Home in Chicago
4.87 out of 5 average rating, 15 reviewsHot Tub Logan Family Designer Home
May 20 – 27
Home in Palatine
4.85 out of 5 average rating, 39 reviewsPrivate Room with attach bath and personal kitchen
Sep 26 – Oct 3
Home in Westchester
4.76 out of 5 average rating, 21 reviewsModern 2Bdrm Westchester/Chicago Home.With Hot tub
Jul 23 – 30
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
Oct 24 – 31
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 21 – 28
Home in Schaumburg
4.93 out of 5 average rating, 14 reviewsSchaumburg Woodfield Pool House 4bedroom 2.5bath
Jan 9 – 16
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 5 – 12
Home in Schaumburg
New place to stayParadise 4BR w/ Pool & Games
Jun 25 – Jul 2
Home in Chicago Heights
Olympia field -matteson IL- homewood, park forest
Jul 5 – 12
Home in Chicago
4.8 out of 5 average rating, 15 reviews2Bed+2Bath PentHouse in South Loop
Nov 6 – 13
Home in New Lenox
4.74 out of 5 average rating, 34 reviewsCheerful home. Heated pool, Hot tub!
Jun 21 – 28
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
Destinations to explore
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