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 Lincoln Square
4.94 out of 5 average rating, 190 reviewsSpacious, light-drenched studio-private entrance!
Jul 8 – 15
ﺩ.ﺇ411 per night
Guest favorite
Condo in Lincoln Park
4.95 out of 5 average rating, 436 reviewsUnique Lincoln Park Duplex Apt
Sep 28 – Oct 5
ﺩ.ﺇ676 per night
Superhost
Apartment in West Town
4.92 out of 5 average rating, 326 reviewsBright, Modern Apartment in a Vintage Greystone
Dec 19 – 26
ﺩ.ﺇ545 per night
Guest favorite
Apartment in Pilsen Historic District
4.89 out of 5 average rating, 242 reviewsModern
Aug 25 – 30
ﺩ.ﺇ433 per night
Guest favorite
Home in Bridgeport
4.95 out of 5 average rating, 119 reviewsCozy & Modern Chic Full House in Trendy Bridgeport
Feb 6 – 13
ﺩ.ﺇ435 per night
Guest favorite
Guest suite in East Pilsen
4.93 out of 5 average rating, 114 reviewsEntirely Private Suite - Urban Oasis - Pilsen/UIC
Jun 20 – 27
ﺩ.ﺇ438 per night
Guest favorite
Loft in Pilsen Historic District
4.91 out of 5 average rating, 305 reviewsPilsen Modernist, Creative, Lightfilled Loft
Sep 8 – 15
ﺩ.ﺇ631 per night
Guest favorite
Apartment in Chicago
4.98 out of 5 average rating, 127 reviewsModern Apt with style & comfort in Pilsen Chicago
Jul 9 – 16
ﺩ.ﺇ560 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
- Kid-friendly rentals Chicago Loop
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