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