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
Rental unit in West Town
4.96 out of 5 average rating, 267 reviewsTurquoise Wonder - Clean, Cozy & Stylish Apt
Guest suite in Lincoln Square
4.92 out of 5 average rating, 406 reviewsPrivate Lincoln Square Garden Apt
Condo in Lincoln Square
4.97 out of 5 average rating, 339 reviewsLincoln Square Gem!
Condo in Lincoln Park
4.96 out of 5 average rating, 448 reviewsUnique Lincoln Park Duplex Apt
Rental unit in Gold Coast
4.88 out of 5 average rating, 146 reviewsCharming Gold Coast One-Bedroom Near Downtown!
Rental unit in Chicago
4.98 out of 5 average rating, 142 reviewsModern Apt with style & comfort in Pilsen Chicago
Rental unit in West Town
4.98 out of 5 average rating, 227 reviewsUkrainian Village Garden Retreat
Rental unit in East Rogers Park
4.89 out of 5 average rating, 108 reviewsLAKESIDE PIED `A TERRE STEPS TO BEACH
Other great vacation rentals in Chicago Loop
Rental unit in Wicker Park
4.97 out of 5 average rating, 240 reviewsStylish First Flr. Studio. Best Location Division+Hermitage.
Rental unit in West Town
4.92 out of 5 average rating, 336 reviewsBright, Modern Apartment in a Vintage Greystone
Rental unit in Humboldt Park
4.98 out of 5 average rating, 111 reviewsHumboldt Park Loft
Rental unit in West Town
4.89 out of 5 average rating, 482 reviewsiKlektik House Chicago / Robin
Guest suite in Lincoln Square
4.95 out of 5 average rating, 246 reviewsGreat location, private entry and patio!
Guest suite in Chicago
4.93 out of 5 average rating, 177 reviewsBike the Lakefront from a Sleek Urban Retreat
Rental unit in Chicago
4.96 out of 5 average rating, 104 reviewsCute, Clean, Cozy Apartment in Pilsen
Townhouse in Near West Side
4.86 out of 5 average rating, 284 reviewsCITY CONDO with GARAGE 7 min Walk to Train
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
- Family-friendly rentals Chicago Loop
- Rentals with a washer and dryer Chicago Loop
- Rentals with an EV charger Chicago Loop
- Rentals with pools Chicago Loop
- Pet-friendly rentals Chicago Loop
- Rentals with a patio Chicago Loop
- Boutique hotel rentals Chicago Loop
- Loft rentals Chicago Loop
- Fitness-friendly rentals Chicago Loop
- Rentals with beach access Chicago Loop
- Condo rentals Chicago Loop
- Hotel rentals Chicago Loop
- Rentals with lake access Chicago Loop
- Apartment rentals Chicago Loop
- Rentals with a sauna Chicago Loop
- Monthly Rentals Chicago Loop
- Rentals with breakfast Chicago Loop
- Rentals with outdoor seating Chicago Loop
- Rentals with a hot tub Chicago Loop
- Rentals with a fireplace Chicago Loop
- Rentals with a fire pit Chicago Loop
- Kid-friendly rentals Chicago Loop
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