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 Schaumburg
4.93 out of 5 average rating, 14 reviewsSchaumburg Woodfield Pool House 4bedroom 2.5bath
Jan 16 – 23
Home in Chicago
4.86 out of 5 average rating, 37 reviewsLuxury Cabin in Lakeview
Jul 7 – 14
Home in Chicago
4.8 out of 5 average rating, 15 reviews2Bed+2Bath PentHouse in South Loop
Mar 10 – 17
Home in Skokie
Skokie town home
Aug 11 – 18
Weekly house rentals
Home in Bolingbrook
4.92 out of 5 average rating, 99 reviewsThe Sunshine Spot
Nov 12 – 19
Home in Chicago
5.0 out of 5 average rating, 5 reviews1-bedroom with full kitchen, washer/dryer inside
Jan 25 – Feb 1
Home in Berwyn
5.0 out of 5 average rating, 79 reviewsRetro Modern Bungalow | free parking | fire pit
Dec 1 – 8
Home in Chicago
4.88 out of 5 average rating, 64 reviewsChicago getaway for two!
Apr 3 – 10
Home in Chicago
4.91 out of 5 average rating, 88 reviewsBoho Chic Coach House 30Min to downtown W/ Parking
Oct 24 – 31
Home in Chicago
4.98 out of 5 average rating, 56 reviews2BD/1 BA with summer patio in quiet Roscoe Village
Mar 31 – Apr 7
Home in Chicago
4.96 out of 5 average rating, 28 reviewsLakeview Condo
Jan 6 – 13
Home in Chicago
5.0 out of 5 average rating, 11 reviewsCubby Blue home - Wrigley ~Free Parking~
Jan 16 – 23
Private house rentals
Home in Chicago
4.89 out of 5 average rating, 36 reviewsBrand New Spacious Duplex
Aug 19 – 26
Home in Chicago
4.95 out of 5 average rating, 19 reviewsSpacius unit in historic gem
Nov 24 – Dec 1
Home in Chicago
5.0 out of 5 average rating, 49 reviewsCharming 3-BED in Lincoln Park/ Old Town & Parking
Dec 25 – Jan 1
Home in Chicago
5.0 out of 5 average rating, 16 reviewsChicago Home by Midway near Downtown Attractions
Nov 15 – 22
Home in Chicago
4.89 out of 5 average rating, 28 reviewsPrivate Condo in Chicago w/ Parking, Near Evanston
Sep 10 – 17
Home in Chicago Ridge
4.91 out of 5 average rating, 53 reviewsQuiet cul-de-sac with huge fenced in backyard
Feb 11 – 18
Home in Chicago
4.99 out of 5 average rating, 77 reviewsFlat in Lincoln Park 2-Flat Central to Everything
Oct 4 – 11
Home in Chicago
4.93 out of 5 average rating, 71 reviewsModern Lux Getaway w/ Hot Tub, Lrg Yard, Parking
Oct 31 – Nov 7
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