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
Home in Bridgeport
4.95 out of 5 average rating, 120 reviewsCozy & Modern Chic Full House in Trendy Bridgeport
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
Guest suite in Lake View
4.95 out of 5 average rating, 175 reviews1 mile from Wrigley Field
Apartment in Edgewater
4.99 out of 5 average rating, 103 reviewsNewly Renovated, Spacious 2BR in Andersonville
Apartment in Little Italy
4.98 out of 5 average rating, 198 reviewsSpacious 2BR on Quiet St - Free Park/Late Checkout
Apartment in Pilsen Historic District
4.85 out of 5 average rating, 233 reviewsTeeny Tiny Bohemian Lodge - Clean & Affordable
Loft in Wicker Park
4.78 out of 5 average rating, 482 reviewsWicker Park Loft - Walk To Everything!
Condo in Lincoln Park
4.95 out of 5 average rating, 438 reviewsUnique Lincoln Park Duplex Apt
Other great vacation rentals in Chicago Loop
Guesthouse in Edgewater
4.95 out of 5 average rating, 366 reviewsCozy Coach House
Apartment in Wicker Park
4.97 out of 5 average rating, 236 reviewsStylish First Flr. Studio. Best Location Division+Hermitage.
Apartment in Roscoe Village
4.96 out of 5 average rating, 237 reviewsRoscoe Village One Bed Lux Apartment Near Wrigley
Apartment in Uptown
4.96 out of 5 average rating, 265 reviewsCozy loft in Chicago's Uptown
Guest suite in Chicago
4.98 out of 5 average rating, 111 reviewsGorgeous Studio 15 Minutes From Ohare!
Apartment in Pilsen Historic District
4.89 out of 5 average rating, 242 reviewsModern
Apartment in Lincoln Park
4.99 out of 5 average rating, 193 reviewsExplore Lincoln Park from a Polished Apartment
Apartment in Chicago
4.81 out of 5 average rating, 86 reviewsMcCormick Pl 420 friendly 1br/1ba parking/sleeps 4
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 lake access Chicago Loop
- Rentals with beach access Chicago Loop
- Loft rentals Chicago Loop
- Kid-friendly rentals Chicago Loop
- Rentals with outdoor seating Chicago Loop
- Hotel rentals Chicago Loop
- Pet-friendly rentals Chicago Loop
- Fitness-friendly rentals Chicago Loop
- Monthly Rentals Chicago Loop
- Rentals with a washer and dryer Chicago Loop
- Rentals with pools Chicago Loop
- Waterfront rentals Chicago Loop
- Rentals with a sauna Chicago Loop
- Boutique hotel rentals Chicago Loop
- Rentals with a patio Chicago Loop
- Rentals with an EV charger Chicago Loop
- Rentals with a fire pit Chicago Loop
- Family-friendly rentals Chicago Loop
- Apartment rentals Chicago Loop
- Rentals with a fireplace Chicago Loop
- Rentals with a hot tub Chicago Loop
- Condo rentals Chicago Loop
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