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 West Town
4.89 out of 5 average rating, 473 reviewsiKlektik House Chicago / Robin
Condo in Lincoln Park
4.95 out of 5 average rating, 441 reviewsUnique Lincoln Park Duplex Apt
Apartment in Chicago
4.98 out of 5 average rating, 132 reviewsModern Apt with style & comfort in Pilsen Chicago
Guest suite in East Pilsen
4.92 out of 5 average rating, 115 reviewsEntirely Private Suite - Urban Oasis - Pilsen/UIC
Guest suite in Lincoln Square
5.0 out of 5 average rating, 297 reviewsPrivate Lincoln Square one bed+bath studio apt.
Apartment in Lincoln Square
4.94 out of 5 average rating, 192 reviewsSpacious, light-drenched studio-private entrance!
Apartment in The Loop
4.9 out of 5 average rating, 112 reviewsBright 2BR-2BA steps from The Bean & Michigan Ave
Guest suite in Lincoln Square
4.97 out of 5 average rating, 364 reviewsPrivate suite in Lincoln Square
Other great vacation rentals in Chicago Loop
Townhouse in Near West Side
4.85 out of 5 average rating, 278 reviewsCITY CONDO with GARAGE 7 min Walk to Train
Apartment in Pilsen Historic District
4.89 out of 5 average rating, 243 reviewsModern
Apartment in Uptown
4.96 out of 5 average rating, 267 reviewsCozy loft in Chicago's Uptown
Guest suite in Bronzeville
4.94 out of 5 average rating, 155 reviewsBronzeville Beauty: Modern Style + Historic Charm
Apartment in Logan Square
4.96 out of 5 average rating, 376 reviewsKing Bed, Huge Spa Shower, Dining Destination
Guesthouse in Andersonville
4.91 out of 5 average rating, 342 reviewsPrivate, Charming, Coach House Loft in Andersonville
Apartment in Portage Park
4.96 out of 5 average rating, 54 reviewsComfy & Private Chicago Studio
Apartment in Chicago
4.97 out of 5 average rating, 63 reviewsLocation! Location! Location!
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 a patio Chicago Loop
- Family-friendly rentals Chicago Loop
- Rentals with a washer and dryer Chicago Loop
- Monthly Rentals Chicago Loop
- Fitness-friendly rentals Chicago Loop
- Loft rentals Chicago Loop
- Condo rentals Chicago Loop
- Rentals with outdoor seating Chicago Loop
- Rentals with a sauna Chicago Loop
- Rentals with lake access Chicago Loop
- Hotel rentals Chicago Loop
- Boutique hotel rentals Chicago Loop
- Rentals with pools Chicago Loop
- Rentals with a fire pit Chicago Loop
- Rentals with an EV charger Chicago Loop
- Apartment rentals Chicago Loop
- Kid-friendly rentals Chicago Loop
- Rentals with breakfast Chicago Loop
- Rentals with a fireplace Chicago Loop
- Pet-friendly rentals Chicago Loop
- Rentals with beach access Chicago Loop
- Rentals with a hot tub Chicago Loop
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