Chicago Loop vacation rentals
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Top-rated vacation rentals in Chicago Loop
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
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 suite in Lincoln Square
4.95 out of 5 average rating, 244 reviewsGreat location, private entry and patio!
Guest suite in Lincoln Square
4.94 out of 5 average rating, 180 reviewsLincoln Square In-laws Suite: Private Entrance
Apartment in Near North Side
4.89 out of 5 average rating, 379 reviewsGreat Location Studio in the Gold Coast!!
Apartment in West Town
4.92 out of 5 average rating, 331 reviewsBright, Modern Apartment in a Vintage Greystone
Apartment in West Town
4.96 out of 5 average rating, 266 reviewsTurquoise Wonder - Clean, Cozy & Stylish Apt
Loft in Pilsen Historic District
4.91 out of 5 average rating, 315 reviewsPilsen Modernist, Creative, Lightfilled Loft
Apartment in Chicago
4.84 out of 5 average rating, 177 reviewsThe Cottage
Apartment in Avondale
4.97 out of 5 average rating, 122 reviewsDesigner Avondale Attic
Other great vacation rentals in Chicago Loop
Guest suite in Chicago
4.93 out of 5 average rating, 176 reviewsBike the Lakefront from a Sleek Urban Retreat
Guesthouse in Andersonville
4.91 out of 5 average rating, 345 reviewsPrivate, Charming, Coach House Loft in Andersonville
Apartment in Logan Square
4.96 out of 5 average rating, 382 reviewsKing Bed, Huge Spa Shower, Dining Destination
Home in Lake View
4.98 out of 5 average rating, 208 reviewsWrigleyville Southport Studio
Guest suite in East Pilsen
4.92 out of 5 average rating, 117 reviewsEntirely Private Suite - Urban Oasis - Pilsen/UIC
Apartment in Chicago
4.96 out of 5 average rating, 102 reviewsCute, Clean, Cozy Apartment in Pilsen
Apartment in The Loop
4.9 out of 5 average rating, 114 reviewsBright 2BR-2BA steps from The Bean & Michigan Ave
Guest suite in West Loop
4.92 out of 5 average rating, 85 reviewsCozy one-bedroom suite in the heart of West Loop
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
- Apartment rentals Chicago Loop
- Fitness-friendly rentals Chicago Loop
- Rentals with a hot tub Chicago Loop
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- Hotel rentals Chicago Loop
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- Family-friendly rentals Chicago Loop
- Rentals with a washer and dryer Chicago Loop
- Rentals with lake access Chicago Loop
- Rentals with a sauna Chicago Loop
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- Kid-friendly rentals Chicago Loop
- Monthly Rentals Chicago Loop
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- Rentals with pools Chicago Loop
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- Rentals with an EV charger Chicago Loop
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- Boutique hotel rentals Chicago Loop
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