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
Apartment in Chicago
4.98 out of 5 average rating, 134 reviewsModern Apt with style & comfort in Pilsen Chicago
Apartment in West Town
4.92 out of 5 average rating, 309 reviewsSpacious & private! Free parking! Great location!
Apartment in Pilsen Historic District
4.89 out of 5 average rating, 246 reviewsModern
Apartment in Logan Square
4.92 out of 5 average rating, 492 reviews2BR Bursting w/ Character in Hip Logan Square!
Apartment in West Town
4.92 out of 5 average rating, 329 reviewsBright, Modern Apartment in a Vintage Greystone
Guest suite in Lincoln Square
4.97 out of 5 average rating, 366 reviewsPrivate suite in Lincoln Square
Apartment in West Town
4.98 out of 5 average rating, 225 reviewsUkrainian Village Garden Retreat
Guesthouse in Lincoln Park
4.96 out of 5 average rating, 168 reviewsCoach House w/ Heated Garage & Pvt. Rooftop Deck
Other great vacation rentals in Chicago Loop
Guest suite in Lincoln Square
4.92 out of 5 average rating, 405 reviewsPrivate Lincoln Square Garden Apt
Guest suite in Bridgeport
4.95 out of 5 average rating, 191 reviewsAttic cozy guests suite near South Loop in Chicago
Guest suite in Lincoln Square
4.94 out of 5 average rating, 180 reviewsLincoln Square In-laws Suite: Private Entrance
Guesthouse in Andersonville
4.91 out of 5 average rating, 344 reviewsPrivate, Charming, Coach House Loft in Andersonville
Guest suite in Chicago
4.98 out of 5 average rating, 114 reviewsGorgeous Studio 15 Minutes From Ohare!
Apartment in Roscoe Village
4.95 out of 5 average rating, 243 reviewsRoscoe Village One Bed Lux Apartment Near Wrigley
Guest suite in Lake View
4.91 out of 5 average rating, 360 reviewsContemporary, private suite w fireplace
Apartment in Logan Square
4.96 out of 5 average rating, 380 reviewsKing Bed, Huge Spa Shower, Dining Destination
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
- Rentals with beach access Chicago Loop
- Family-friendly rentals Chicago Loop
- Rentals with a washer and dryer Chicago Loop
- Fitness-friendly rentals Chicago Loop
- Rentals with an EV charger Chicago Loop
- Loft rentals Chicago Loop
- Rentals with outdoor seating Chicago Loop
- Monthly Rentals Chicago Loop
- Kid-friendly rentals Chicago Loop
- Rentals with a sauna Chicago Loop
- Rentals with a patio Chicago Loop
- Rentals with breakfast Chicago Loop
- Boutique hotel rentals Chicago Loop
- Rentals with a hot tub Chicago Loop
- Hotel rentals Chicago Loop
- Pet-friendly rentals Chicago Loop
- Rentals with lake access Chicago Loop
- Rentals with pools Chicago Loop
- Condo rentals Chicago Loop
- Rentals with a fireplace Chicago Loop
- Apartment rentals Chicago Loop
- Rentals with a fire pit Chicago Loop
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