House holiday 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.
Holiday rentals for every style
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Popular amenities for house rentals in Downtown Chicago
House rentals with a pool
Home in Glen Ellyn
4.94 out of 5 average rating, 16 reviewsGlen Ellyn Home
23–30 Jul
Home in Schaumburg
4.93 out of 5 average rating, 14 reviewsSchaumburg Woodfield Pool House 4bedroom 2.5bath
17–24 Aug
Home in Chicago
4.86 out of 5 average rating, 37 reviewsLuxury Cabin in Lakeview
7–14 Jul
Home in Chicago
4.8 out of 5 average rating, 15 reviews2Bed+2Bath PentHouse in South Loop
2–9 Feb
Home in Lisle
Cozy Lisle Home w/ Fenced Backyard: Pets Welcome!
26 Jul – 2 Aug
Home in Riverwoods
Riverwoods Nature Retreat
5–12 May
Home in Lisle
Welcoming, cozy, and a fur baby paradise.
27 Sep – 4 Oct
Home in Skokie
Skokie town home
6–13 Aug
Weekly house rentals
Home in Chicago
5.0 out of 5 average rating, 5 reviews1-bedroom with full kitchen, washer/dryer inside
4–11 Dec
Home in Berwyn
5.0 out of 5 average rating, 77 reviewsRetro Modern Bungalow | free parking | fire pit
3–10 Nov
Home in Chicago
4.91 out of 5 average rating, 88 reviewsBoho Chic Coach House 30Min to downtown W/ Parking
30 Nov – 7 Dec
Home in Chicago
4.87 out of 5 average rating, 63 reviewsChicago getaway for two!
9–16 Jan
Home in Chicago
4.98 out of 5 average rating, 54 reviews2BD/1 BA with summer patio in quiet Roscoe Village
3–10 Apr
Home in Wilmette
4.98 out of 5 average rating, 92 reviewsUnique porcelain-enamel paneled "Lustron" home
11–18 Sep
Home in Chicago
4.98 out of 5 average rating, 50 reviewsCity Cottage in Logan Square-Avondale
1–8 Oct
Home in Chicago
4.96 out of 5 average rating, 27 reviewsLakeview Condo
6–13 Dec
Private house rentals
Home in Chicago
5.0 out of 5 average rating, 15 reviewsChicago Home by Midway near Downtown Attractions
19–26 Oct
Home in Chicago
4.89 out of 5 average rating, 35 reviewsBrand New Spacious Duplex
14–21 Sep
Home in Chicago
5.0 out of 5 average rating, 11 reviewsCubby Blue home - Wrigley ~Free Parking~
4–11 Dec
Home in Chicago Ridge
4.9 out of 5 average rating, 52 reviewsQuiet cul-de-sac with huge fenced in backyard
7–14 Mar
Home in Chicago
4.98 out of 5 average rating, 87 reviews3BD Home Mins from Airport | Free Wi-Fi + Parking
11–18 Sep
Home in Chicago
4.8 out of 5 average rating, 15 reviewsCozy 2 bed Condo in Bronzeville!
5–12 Jun
Home in Chicago
5.0 out of 5 average rating, 15 reviewsCozy Haven
16–23 Oct
Home in Chicago
4.95 out of 5 average rating, 19 reviewsSpacius unit in historic gem
20–27 Aug
Destinations to explore
- Milwaukee Holiday rentals
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