House vacation rentals in Downtown Chicago
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Top-rated house rentals in Downtown 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 Downtown 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*
Nov 14 – 21
Home in Chicago
4.86 out of 5 average rating, 37 reviewsLuxury Cabin in Lakeview
Jul 7 – 14
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 19 – 26
Home in Glen Ellyn
4.94 out of 5 average rating, 16 reviewsGlen Ellyn Home
Jul 23 – 30
Home in Chicago
4.8 out of 5 average rating, 15 reviews2Bed+2Bath PentHouse in South Loop
Jan 22 – 29
Home in Plainfield
4.89 out of 5 average rating, 27 reviewsPool* King beds* Grill & Patio* 30mi to Chicago
Aug 7 – 14
Home in Carol Stream
4.55 out of 5 average rating, 20 reviewsAmazing Summer Pool Awaits You!
Nov 11 – 18
Weekly house rentals
Home in Whiting
4.8 out of 5 average rating, 227 reviewsWhiting Getaway
Nov 17 – 24
Home in Berwyn
5.0 out of 5 average rating, 78 reviewsRetro Modern Bungalow | free parking | fire pit
Nov 13 – 20
Home in Chicago
4.96 out of 5 average rating, 27 reviewsLakeview Condo
Feb 20 – 27
Home in Chicago
5.0 out of 5 average rating, 48 reviewsCharming 3-BED in Lincoln Park/ Old Town & Parking
Dec 11 – 18
Home in Chicago
4.91 out of 5 average rating, 88 reviewsBoho Chic Coach House 30Min to downtown W/ Parking
Mar 2 – 9
Home in Chicago
5.0 out of 5 average rating, 11 reviewsCubby Blue home - Wrigley ~Free Parking~
Jan 22 – 29
Home in Chicago
5.0 out of 5 average rating, 52 reviewsArchitect's Family Friendly Oasis | 4bd/3ba I Luxe
Nov 18 – 25
Home in Wilmette
4.98 out of 5 average rating, 92 reviewsUnique porcelain-enamel paneled "Lustron" home
Sep 23 – 30
Private house rentals
Home in Chicago
4.95 out of 5 average rating, 19 reviewsSpacius unit in historic gem
Nov 6 – 13
Home in Chicago
5.0 out of 5 average rating, 48 reviewsCozy, Quiet, Riverwalk Sanctuary
Jan 5 – 12
Home in Chicago
4.89 out of 5 average rating, 35 reviewsBrand New Spacious Duplex
Oct 22 – 29
Home in Chicago
5.0 out of 5 average rating, 12 reviewsHidden Gem on the CHI north side
Jun 30 – Jul 7
Home in Chicago
5.0 out of 5 average rating, 15 reviewsChicago Home by Midway near Downtown Attractions
Jan 8 – 15
Home in Chicago
5.0 out of 5 average rating, 5 reviews1-bedroom with full kitchen, washer/dryer inside
Jun 4 – 11
Home in Chicago Ridge
4.9 out of 5 average rating, 52 reviewsQuiet cul-de-sac with huge fenced in backyard
Oct 2 – 9
Home in Chicago
4.93 out of 5 average rating, 71 reviewsModern Lux Getaway w/ Hot Tub, Lrg Yard, Parking
Aug 15 – 22
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