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Vacation rentals in Chicago Loop
Book unique vacation rentals, houses, and more on Airbnb
Top-rated vacation rentals in Chicago Loop
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
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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
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Superhost
Rental unit in Lincoln Park
4.83 out of 5 average rating, 138 reviewsChicago Lincoln Park Getaway
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Guest favorite
Rental unit in Wicker Park
4.95 out of 5 average rating, 268 reviewsHeart of Bucktown
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Superhost
Rental unit in East Rogers Park
4.89 out of 5 average rating, 112 reviewsLAKESIDE PIED `A TERRE STEPS TO BEACH
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Superhost
Townhouse in West Town
4.85 out of 5 average rating, 153 reviews⭐️Cozy Garden Unit by Downtown & Blue Line Stop⭐️
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Guest favorite
Condo in Lake View
4.98 out of 5 average rating, 40 reviewsChic & Comfy • Close to Wrigley
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Guest favorite
Guest suite in West Loop
4.91 out of 5 average rating, 92 reviewsCozy one-bedroom suite in the heart of West Loop
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Guest favorite
Rental unit in Lincoln Park
4.97 out of 5 average rating, 59 reviewsRecently renovated 1 bedroom in the best location!
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Guest favorite
Condo in Avondale
4.94 out of 5 average rating, 70 reviewsLovely top floor 2BR/2BA, steps from everything!
Quick stats about vacation rentals in Chicago Loop
Total rentals
960 properties
Total number of reviews
31K reviews
Family-friendly rentals
270 properties are a good fit for families
Pet-friendly rentals
520 properties allow pets
Rentals with a pool
470 properties have a pool
Rentals with dedicated workspaces
620 properties have a dedicated workspace
Destinations to explore
- Rentals with an EV charger Chicago Loop
- Fitness-friendly rentals Chicago Loop
- Rentals with a sauna Chicago Loop
- Boutique hotel rentals Chicago Loop
- Monthly Rentals Chicago Loop
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- Family-friendly rentals Chicago Loop
- Rentals with a washer and dryer Chicago Loop
- Rentals with a fire pit Chicago Loop
- Rentals with pools Chicago Loop
- Rentals with lake access Chicago Loop
- Rentals with breakfast Chicago Loop
- Pet-friendly rentals Chicago Loop
- Rentals with a patio Chicago Loop
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- Kid-friendly rentals Chicago Loop
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- Condo rentals Chicago Loop
- Rentals with a hot tub Chicago Loop
- Apartment rentals Chicago Loop
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