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 house rentals in Chicago
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*
16–23 Apr
Home in Schaumburg
4.93 out of 5 average rating, 14 reviewsSchaumburg Woodfield Pool House 4bedroom 2.5bath
25 May – 1 Jun
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
23–30 Jul
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
5–12 Aug
Home in Chicago Heights
Olympia field -matteson IL- homewood, park forest
14–21 Jul
Home in Chicago
4.8 out of 5 average rating, 15 reviews2Bed+2Bath PentHouse in South Loop
23–30 Nov
Weekly house rentals
Home in Chicago
4.83 out of 5 average rating, 113 reviewsExclusive and Spacious Pilsen Guest House
30 Oct – 6 Nov
Home in Homewood
4.91 out of 5 average rating, 106 reviewsPeaceful & Private Hot Tub Vacation Home Getaway
17–24 Sep
Home in Chicago
4.98 out of 5 average rating, 175 reviewsThe Evergreen House
20–27 Jun
Home in Chicago
4.91 out of 5 average rating, 87 reviewsBoho Chic Coach House 30Min to downtown W/ Parking
11–18 Sep
Home in Chicago
4.96 out of 5 average rating, 27 reviewsLakeview Condo
7–14 Feb
Home in Chicago
4.87 out of 5 average rating, 62 reviewsChicago getaway for two!
19–26 Mar
Home in Chicago
4.98 out of 5 average rating, 54 reviews2BD/1 BA with summer patio in quiet Roscoe Village
16–23 Dec
Home in Chicago
5.0 out of 5 average rating, 4 reviews1-bedroom with full kitchen, washer/dryer inside
26 Oct – 2 Nov
Private house rentals
Home in Chicago
5.0 out of 5 average rating, 11 reviewsCubby Blue home - Wrigley ~Free Parking~
12–19 Jan
Home in Munster
4.97 out of 5 average rating, 34 reviewsEntire home: Private, Cozy Oasis in Quiet Locale
16–23 Mar
Home in Chicago
5.0 out of 5 average rating, 15 reviewsChicago Home by Midway near Downtown Attractions
28 Oct – 4 Nov
Home in Chicago
4.97 out of 5 average rating, 70 reviewsEntire first floor in Lincoln Square!
10–17 Dec
Home in Highland Park
4.98 out of 5 average rating, 59 reviewsCharming Ranch-Style Cottage
2–9 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 Chicago
4.88 out of 5 average rating, 26 reviewsPrivate Condo in Chicago w/ Parking, Near Evanston
15–22 Oct
Home in Lansing
4.85 out of 5 average rating, 65 reviewsThe Walter Experience(2bd 1ba) April special
13–20 Aug
Quick stats about house rentals in Chicago
Total rentals
1.8T properties
Rentals with dedicated workspaces
1.2T 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
69T reviews
Destinations to explore
- Downtown Chicago Holiday rentals
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