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 a pool
Home in Highland Park
4.9 out of 5 average rating, 125 reviews2-Acre Highland Park Retreat with Heated Pool ~ 5*
Feb. 17 – 24
Home in Schaumburg
4.93 out of 5 average rating, 14 reviewsSchaumburg Woodfield Pool House 4bedroom 2.5bath
Dec. 8 – 15
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 Schaumburg
New place to stayParadise 4BR w/ Pool & Games
Nov. 30 – Dec. 7
Home in Chicago
4.8 out of 5 average rating, 15 reviews2Bed+2Bath PentHouse in South Loop
Jan. 19 – 26
Home in Olympia Fields
4.58 out of 5 average rating, 31 reviewsLuxurious South Suburban Villa
Sep. 30 – Oct. 7
Home in Plainfield
4.89 out of 5 average rating, 27 reviewsPool* King beds* Grill & Patio* 30mi to Chicago
Aug. 21 – 28
Weekly house rentals
Home in Chicago
4.98 out of 5 average rating, 175 reviewsThe Evergreen House
Jun. 26 – Jul. 3
Home in Chicago
4.91 out of 5 average rating, 87 reviewsBoho Chic Coach House 30Min to downtown W/ Parking
Feb. 25 – Mar. 4
Home in Chicago
4.87 out of 5 average rating, 63 reviewsChicago getaway for two!
Mar. 3 – 10
Home in Chicago
4.98 out of 5 average rating, 54 reviews2BD/1 BA with summer patio in quiet Roscoe Village
Apr. 2 – 9
Home in Chicago
5.0 out of 5 average rating, 5 reviews1-bedroom with full kitchen, washer/dryer inside
Oct. 27 – Nov. 3
Home in Chicago
5.0 out of 5 average rating, 12 reviewsHidden Gem on the CHI north side
Jun. 29 – Jul. 6
Home in Chicago
4.98 out of 5 average rating, 50 reviewsCity Cottage in Logan Square-Avondale
Oct. 1 – 8
Home in Highland Park
4.98 out of 5 average rating, 59 reviewsCharming Ranch-Style Cottage
Apr. 17 – 24
Private house rentals
Home in Chicago
4.99 out of 5 average rating, 71 reviewsWhole apartment! 2 Bed/2 bath steps from Wrigley!!
Jan. 18 – 25
Home in Palatine
4.85 out of 5 average rating, 39 reviewsPrivate Room with attach bath and personal kitchen
Sep. 28 – Oct. 5
Home in Chicago
5.0 out of 5 average rating, 29 reviewsLight and bright 3BD duplex in Avondale, Chicago
Jan. 12 – 19
Home in Oak Park
4.96 out of 5 average rating, 73 reviewsClean, Cozy Duplex with Kitchen & Free Parking
Aug. 25 – Sep. 1
Home in Chicago
4.98 out of 5 average rating, 87 reviews3BD Home Mins from Airport | Free Wi-Fi + Parking
Sep. 29 – Oct. 6
Home in Chicago
5.0 out of 5 average rating, 46 reviewsCharming 3-BED in Lincoln Park/ Old Town & Parking
Jan. 1 – 8
Home in Maywood
4.83 out of 5 average rating, 60 reviewsMaywood Relaxation
Apr. 9 – 16
Home in Lockport
5.0 out of 5 average rating, 36 reviewsPrivate Hideaway House Apartment
Jun. 15 – 22
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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