Vacation rentals in Chicago Loop
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Top-rated vacation rentals in Chicago Loop
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 Loop vacation rentals
Other great vacation rentals in Chicago Loop
Guest favorite
Apartment in West Town
4.92 out of 5 average rating, 326 reviewsBright, Modern Apartment in a Vintage Greystone
Jan 16 – 23
$124 per night
Guest favorite
Apartment in Wrigleyville
4.92 out of 5 average rating, 185 reviewsTaj Ma-small at Wrigley
Feb 10 – 17
$104 per night
Guest favorite
Home in Bridgeport
4.95 out of 5 average rating, 120 reviewsCozy & Modern Chic Full House in Trendy Bridgeport
Jan 9 – 16
$102 per night
Guest favorite
Apartment in Pilsen Historic District
4.86 out of 5 average rating, 232 reviewsTeeny Tiny Bohemian Lodge - Clean & Affordable
Aug 15 – 22
$65 per night
Guest favorite
Home in Pilsen Historic District
4.96 out of 5 average rating, 316 reviewsGet Cozy at a Powder-Blue Residence in the Heart of Pilsen
Jan 28 – Feb 4
$121 per night
Guest favorite
Guest suite in Lake View
4.95 out of 5 average rating, 175 reviews1 mile from Wrigley Field
Sep 5 – 12
$132 per night
Guest favorite
Condo in Lincoln Park
4.95 out of 5 average rating, 437 reviewsUnique Lincoln Park Duplex Apt
Sep 26 – Oct 3
$160 per night
Guest favorite
Apartment in Portage Park
4.96 out of 5 average rating, 50 reviewsComfy & Private Chicago Studio
Jan 22 – 29
$77 per night
Quick stats about vacation rentals in Chicago Loop
Total rentals
890 properties
Rentals with dedicated workspaces
600 properties have a dedicated workspace
Rentals with a pool
480 properties have a pool
Pet-friendly rentals
460 properties allow pets
Family-friendly rentals
270 properties are a good fit for families
Total number of reviews
31K reviews
Destinations to explore
- Pet-friendly rentals Chicago Loop
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