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
Get the amount of space that is right for you
Popular amenities for house rentals in Downtown Chicago
House rentals with a pool
Home in Glen Ellyn
4.94 out of 5 average rating, 17 reviewsGlen Ellyn Home
Home in Schaumburg
5.0 out of 5 average rating, 3 reviewsParadise 4BR w/ Pool & Games
Home in Chicago
4.86 out of 5 average rating, 37 reviewsLuxury Cabin in Lakeview
Home in Schaumburg
4.93 out of 5 average rating, 14 reviewsSchaumburg Woodfield Pool House 4bedroom 2.5bath
Home in Chicago
4.8 out of 5 average rating, 15 reviews2Bed+2Bath PentHouse in South Loop
Home in Lisle
5.0 out of 5 average rating, 3 reviewsWelcoming, cozy, and a fur baby paradise.
Home in Niles
5.0 out of 5 average rating, 12 reviewsLuxury Modern House Epic Master Bath & Pool Table
Home in Lisle
Cozy Lisle Home w/ Fenced Backyard: Pets Welcome!
Weekly house rentals
Home in Chicago
4.95 out of 5 average rating, 264 reviewsThe Roscoe House near Wrigley Field
Home in Chicago
5.0 out of 5 average rating, 51 reviewsCharming 3-BED in Lincoln Park/ Old Town & Parking
Home in Berwyn
4.99 out of 5 average rating, 83 reviewsRetro Modern Bungalow | free parking | fire pit
Home in Chicago
4.98 out of 5 average rating, 57 reviews2BD/1 BA with summer patio in quiet Roscoe Village
Home in Chicago
4.91 out of 5 average rating, 89 reviewsBoho Chic Coach House 30Min to downtown W/ Parking
Home in Chicago
5.0 out of 5 average rating, 52 reviewsArchitect's Urban Oasis | 4bd/3ba I Luxe
Home in Chicago
4.97 out of 5 average rating, 29 reviewsLakeview Condo
Home in Chicago
4.86 out of 5 average rating, 66 reviewsChicago getaway for two!
Private house rentals
Home in Chicago
5.0 out of 5 average rating, 12 reviewsCubby Blue home - Wrigley ~Free Parking~
Home in Chicago
5.0 out of 5 average rating, 49 reviewsCozy, Quiet, Riverwalk Sanctuary
Home in Chicago
5.0 out of 5 average rating, 17 reviewsChicago Home by Midway near Downtown Attractions
Home in Chicago
4.93 out of 5 average rating, 73 reviewsModern Lux Getaway w/ Hot Tub, Lrg Yard, Parking
Home in Chicago
4.97 out of 5 average rating, 71 reviewsEntire first floor in Lincoln Square!
Home in Chicago
5.0 out of 5 average rating, 13 reviewsHidden Gem on the CHI north side
Home in Chicago
4.9 out of 5 average rating, 20 reviewsSpacius unit in historic gem
Home in Chicago
5.0 out of 5 average rating, 12 reviewsModern Family-Friendly Home in the Heart of Pilsen
Destinations to explore
- Milwaukee Holiday rentals
- Lake Geneva Holiday rentals
- Lake Michigan Beach Holiday rentals
- Saugatuck Holiday rentals
- Evanston Holiday rentals
- Holland Holiday rentals
- South Haven Holiday rentals
- Naperville Holiday rentals
- South Side Holiday rentals
- South Bend Holiday rentals
- New Buffalo Holiday rentals
- Chicago Holiday rentals
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- Rentals with an EV charger Downtown Chicago
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