Vacation rentals in Chicago
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Top-rated vacation rentals in Chicago
Guests agree: these stays are highly rated for location, cleanliness, and more.
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Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Chicago vacation rentals
Other great vacation rentals in Chicago
Superhost
Home in Omaha
4.93 out of 5 average rating, 46 reviewsWest Omaha hot tub shuffleboard & foosball 1900 sq
Apr 23 – 30
$142 per night
Guest favorite
Home in Omaha
4.85 out of 5 average rating, 54 reviewsFamily Home/ No Cleaning Fee
Nov 28 – Dec 5
$124 per night
Guest favorite
Guest suite in Waterloo
4.99 out of 5 average rating, 83 reviewsLake Life (Something For All Ages & Seasons)
Sep 8 – 15
$189 per night
Guest favorite
Cabin in Waterloo
4.83 out of 5 average rating, 30 reviewsCharming riverfront house
Dec 25 – Jan 1
$350 per night
Superhost
Home in Omaha
4.79 out of 5 average rating, 43 reviewsBEST HOT TUB VIEWS; 7,000 sqft Masterpiece
Sep 8 – 15
$707 per night
Guest favorite
Home in Omaha
4.92 out of 5 average rating, 86 reviews2 bedroom villa with garage in quiet neighborhood
Mar 11 – 18
$106 per night
Guest favorite
Barn in Bennington
4.96 out of 5 average rating, 98 reviewsBarn Loft - Mueller Suite: Private Room
Aug 6 – 13
$82 per night
Guest favorite
Home in Omaha
4.97 out of 5 average rating, 98 reviewsBeautiful large home in Historic Downtown Elkhorn
May 20 – 27
$226 per night
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