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
4.91 out of 5 average rating, 87 reviewsBoho Chic Coach House 30Min to downtown W/ Parking
Home in Maywood
4.83 out of 5 average rating, 60 reviewsMaywood Relaxation
Home in Highland Park
4.98 out of 5 average rating, 59 reviewsCharming Ranch-Style Cottage
Home in Wilmette
4.98 out of 5 average rating, 92 reviewsUnique porcelain-enamel paneled "Lustron" home
Home in Chicago
4.96 out of 5 average rating, 27 reviewsLakeview Condo
Home in Chicago
4.99 out of 5 average rating, 71 reviewsWhole apartment! 2 Bed/2 bath steps from Wrigley!!
Home in Chicago
5.0 out of 5 average rating, 46 reviewsCharming 3-BED in Lincoln Park/ Old Town & Parking
Home in Chicago
5.0 out of 5 average rating, 15 reviewsChicago Home by Midway near Downtown Attractions
House rentals with a hot tub
Home in Homewood
4.91 out of 5 average rating, 106 reviewsPeaceful & Private Hot Tub Vacation Home Getaway
Home in Chicago
4.85 out of 5 average rating, 292 reviewsLux Urban 3BR/3BA Duplex + Parking!
Home in Chicago
4.88 out of 5 average rating, 16 reviewsHot Tub Logan Family Designer Home
Home in Chicago
4.93 out of 5 average rating, 71 reviewsModern Lux Getaway w/ Hot Tub, Lrg Yard, Parking
Home in Palatine
4.85 out of 5 average rating, 39 reviewsPrivate Room with attach bath and personal kitchen
Home in Westchester
4.76 out of 5 average rating, 21 reviewsModern 2Bdrm Westchester/Chicago Home.With Hot tub
Home in Chicago
4.74 out of 5 average rating, 27 reviews1501HOME | West Town Single Family Home + Garage
Home in Elmhurst
4.93 out of 5 average rating, 46 reviewsLuxe 3BR, 2BA + Hot Tub
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*
Home in Schaumburg
4.93 out of 5 average rating, 14 reviewsSchaumburg Woodfield Pool House 4bedroom 2.5bath
Home in Chicago
4.86 out of 5 average rating, 37 reviewsLuxury Cabin in Lakeview
Home in Glen Ellyn
4.94 out of 5 average rating, 16 reviewsGlen Ellyn Home
Home in Schaumburg
New place to stayParadise 4BR w/ Pool & Games
Home in Chicago
4.8 out of 5 average rating, 15 reviews2Bed+2Bath PentHouse in South Loop
Home in Olympia Fields
4.58 out of 5 average rating, 31 reviewsLuxurious South Suburban Villa
Home in Plainfield
4.89 out of 5 average rating, 27 reviewsPool* King beds* Grill & Patio* 30mi to Chicago
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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