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
Guest suite in Lincoln Square
5.0 out of 5 average rating, 295 reviewsPrivate Lincoln Square one bed+bath studio apt.
Apartment in Chicago
4.97 out of 5 average rating, 236 reviewsStylish First Flr. Studio. Best Location Division+Hermitage.
Home in Chicago
4.95 out of 5 average rating, 121 reviewsCozy & Modern Chic Full House in Trendy Bridgeport
Apartment in Chicago
4.97 out of 5 average rating, 117 reviewsDesigner Avondale Attic
Apartment in Chicago
4.85 out of 5 average rating, 234 reviewsTeeny Tiny Bohemian Lodge - Clean & Affordable
Apartment in Lincoln Square
4.94 out of 5 average rating, 191 reviewsSpacious, light-drenched studio-private entrance!
Guest suite in East Pilsen
4.93 out of 5 average rating, 114 reviewsEntirely Private Suite - Urban Oasis - Pilsen/UIC
Apartment in The Loop
4.9 out of 5 average rating, 111 reviewsBright 2BR-2BA steps from The Bean & Michigan Ave
Other great vacation rentals in Chicago Loop
Townhouse in Near West Side
4.85 out of 5 average rating, 275 reviewsCITY CONDO with GARAGE 7 min Walk to Train
Guest suite in Bridgeport
4.96 out of 5 average rating, 183 reviewsClean, Cozy, Comfortable Studio Near Downtown
Guest suite in Lincoln Square
4.95 out of 5 average rating, 242 reviewsGreat location, private entry and patio!
Apartment in Little Italy
4.98 out of 5 average rating, 198 reviewsSpacious 2BR on Quiet St - Free Park/Late Checkout
Guest suite in Lincoln Square
4.91 out of 5 average rating, 420 reviewsCozy, Quiet, Garden Getaway!
Apartment in Cicero
4.98 out of 5 average rating, 202 reviewsCOZY 2Bdr Apt near MDW, Dwtn, United Ctr, Sox, Hwy
Guest suite in West Town
4.96 out of 5 average rating, 306 reviewsAugusta's Garden | Noble Square | Wicker Park
Apartment in Chicago
4.84 out of 5 average rating, 175 reviewsThe Cottage
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 outdoor seating Chicago Loop
- Rentals with a washer and dryer Chicago Loop
- Hotel rentals Chicago Loop
- Rentals with a sauna Chicago Loop
- Family-friendly rentals Chicago Loop
- Apartment rentals Chicago Loop
- Rentals with a hot tub Chicago Loop
- Rentals with pools Chicago Loop
- Rentals with a patio Chicago Loop
- Rentals with a fire pit Chicago Loop
- Kid-friendly rentals Chicago Loop
- Boutique hotel rentals Chicago Loop
- Rentals with beach access Chicago Loop
- Loft rentals Chicago Loop
- Waterfront rentals Chicago Loop
- Rentals with a fireplace Chicago Loop
- Fitness-friendly rentals Chicago Loop
- Pet-friendly rentals Chicago Loop
- Rentals with lake access Chicago Loop
- Condo rentals Chicago Loop
- Rentals with an EV charger Chicago Loop
- Monthly Rentals Chicago Loop
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