House vacation rentals in Chicago
Find and book unique houses on Airbnb
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 Des Plaines
4.78 out of 5 average rating, 307 reviewsUrban Farmhouse near O'Hare
Aug 11 – 18
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
Home in Chicago
4.96 out of 5 average rating, 27 reviewsLakeview Condo
Feb 26 – Mar 5
Home in Chicago
5.0 out of 5 average rating, 47 reviewsCharming 3-BED in Lincoln Park/ Old Town & Parking
Dec 11 – 18
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 Highland Park
4.98 out of 5 average rating, 59 reviewsCharming Ranch-Style Cottage
Sep 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
Jun 5 – 12
Home in Chicago
4.85 out of 5 average rating, 292 reviewsLux Urban 3BR/3BA Duplex + Parking!
Apr 14 – 21
Home in Palatine
4.85 out of 5 average rating, 39 reviewsPrivate Room with attach bath and personal kitchen
Oct 5 – 12
Home in Chicago
4.93 out of 5 average rating, 71 reviewsModern Lux Getaway w/ Hot Tub, Lrg Yard, Parking
Aug 15 – 22
Home in Chicago
4.88 out of 5 average rating, 16 reviewsHot Tub Logan Family Designer Home
May 20 – 27
Home in Westchester
4.76 out of 5 average rating, 21 reviewsModern 2Bdrm Westchester/Chicago Home.With Hot tub
Feb 8 – 15
Home in Chicago
5.0 out of 5 average rating, 16 reviewsWrigley Penthouse w/Private Roof Deck and Parking
Nov 6 – 13
Home in Gary
4.94 out of 5 average rating, 85 reviewsSunset beach house
Dec 16 – 23
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*
Nov 14 – 21
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
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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