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 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 15 – 22
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
Dec 15 – 22
Home in Carol Stream
4.55 out of 5 average rating, 20 reviewsAmazing Summer Pool Awaits You!
Nov 6 – 13
Home in Tinley Park
4.8 out of 5 average rating, 5 reviewsPerfect safe stay
Mar 28 – Apr 4
Home in Lisle
Welcoming, cozy, and a fur baby paradise.
Oct 26 – Nov 2
Weekly house rentals
Home in Lake View
4.98 out of 5 average rating, 55 reviews2BD/1 BA with summer patio in quiet Roscoe Village
Feb 18 – 25
Home in Berwyn
5.0 out of 5 average rating, 78 reviewsRetro Modern Bungalow | free parking | fire pit
Dec 2 – 9
Home in Lake View
5.0 out of 5 average rating, 5 reviews1-bedroom with full kitchen, washer/dryer inside
Jan 19 – 26
Home in Chicago
4.97 out of 5 average rating, 75 reviewsCozy/Spacious WFH Family Friendly w Permit Parking
Feb 3 – 10
Home in Chicago
4.91 out of 5 average rating, 88 reviewsBoho Chic Coach House 30Min to downtown W/ Parking
Dec 5 – 12
Home in Chicago
5.0 out of 5 average rating, 52 reviewsArchitect's Family Friendly Oasis | 4bd/3ba I Luxe
Dec 31 – Jan 7
Home in Chicago
4.87 out of 5 average rating, 63 reviewsChicago getaway for two!
Mar 16 – 23
Home in Wilmette
4.98 out of 5 average rating, 92 reviewsUnique porcelain-enamel paneled "Lustron" home
Oct 22 – 29
Private house rentals
Home in Chicago
5.0 out of 5 average rating, 48 reviewsCharming 3-BED in Lincoln Park/ Old Town & Parking
Oct 26 – Nov 2
Home in Chicago
5.0 out of 5 average rating, 48 reviewsCozy, Quiet, Riverwalk Sanctuary
Jan 5 – 12
Home in Chicago
4.99 out of 5 average rating, 77 reviewsFlat in Lincoln Park 2-Flat Central to Everything
Dec 24 – 31
Home in Chicago
5.0 out of 5 average rating, 12 reviewsHidden Gem on the CHI north side
Jun 23 – 30
Home in Chicago
4.89 out of 5 average rating, 35 reviewsBrand New Spacious Duplex
Oct 5 – 12
Home in Chicago
4.98 out of 5 average rating, 87 reviews3BD Home Mins from Airport | Free Wi-Fi + Parking
Sep 11 – 18
Home in Chicago
4.93 out of 5 average rating, 71 reviewsModern Lux Getaway w/ Hot Tub, Lrg Yard, Parking
Aug 15 – 22
Home in Chicago
4.99 out of 5 average rating, 96 reviewsHuge Sunlit Gem, Free Parking, No Cleaning Fee
Apr 11 – 18
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