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
Mar 13 – 20
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
Mar 14 – 21
Guest suite in Lake View
4.95 out of 5 average rating, 175 reviews1 mile from Wrigley Field
Sep 5 – 12
Apartment in Edgewater
4.99 out of 5 average rating, 103 reviewsNewly Renovated, Spacious 2BR in Andersonville
Jan 22 – 29
Apartment in Little Italy
4.98 out of 5 average rating, 198 reviewsSpacious 2BR on Quiet St - Free Park/Late Checkout
Dec 31 – Jan 7
Apartment in Pilsen Historic District
4.85 out of 5 average rating, 233 reviewsTeeny Tiny Bohemian Lodge - Clean & Affordable
Aug 15 – 22
Loft in Wicker Park
4.78 out of 5 average rating, 482 reviewsWicker Park Loft - Walk To Everything!
Nov 4 – 11
Condo in Lincoln Park
4.95 out of 5 average rating, 437 reviewsUnique Lincoln Park Duplex Apt
Sep 26 – Oct 3
Other great vacation rentals in Chicago Loop
Guesthouse in Edgewater
4.95 out of 5 average rating, 366 reviewsCozy Coach House
May 5 – 12
Apartment in Wicker Park
4.97 out of 5 average rating, 236 reviewsStylish First Flr. Studio. Best Location Division+Hermitage.
Nov 13 – 20
Apartment in Roscoe Village
4.96 out of 5 average rating, 237 reviewsRoscoe Village One Bed Lux Apartment Near Wrigley
Dec 19 – 26
Apartment in Uptown
4.96 out of 5 average rating, 265 reviewsCozy loft in Chicago's Uptown
Oct 14 – 21
Guest suite in Chicago
4.98 out of 5 average rating, 111 reviewsGorgeous Studio 15 Minutes From Ohare!
Sep 13 – 20
Apartment in Pilsen Historic District
4.89 out of 5 average rating, 242 reviewsModern
Oct 1 – 6
Apartment in Lincoln Park
4.99 out of 5 average rating, 193 reviewsExplore Lincoln Park from a Polished Apartment
Nov 30 – Dec 7
Apartment in Chicago
4.81 out of 5 average rating, 86 reviewsMcCormick Pl 420 friendly 1br/1ba parking/sleeps 4
Jan 16 – 23
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 pools Chicago Loop
- Rentals with an EV charger Chicago Loop
- Hotel rentals Chicago Loop
- Rentals with beach access Chicago Loop
- Loft rentals Chicago Loop
- Family-friendly rentals Chicago Loop
- Waterfront rentals Chicago Loop
- Rentals with a hot tub Chicago Loop
- Monthly Rentals Chicago Loop
- Boutique hotel rentals Chicago Loop
- Rentals with a fire pit Chicago Loop
- Condo rentals Chicago Loop
- Rentals with a fireplace Chicago Loop
- Rentals with a patio Chicago Loop
- Rentals with lake access Chicago Loop
- Wheelchair accessible rentals Chicago Loop
- Apartment rentals Chicago Loop
- Rentals with outdoor seating Chicago Loop
- Kid-friendly rentals Chicago Loop
- Fitness-friendly rentals Chicago Loop
- Pet-friendly rentals Chicago Loop
- Rentals with a washer and dryer Chicago Loop
- Rentals with a sauna Chicago Loop
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