Holiday rentals in Chicago Loop
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Top-rated holiday rentals in Chicago Loop
Guests agree: these stays are highly rated for location, cleanliness and more.
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Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Chicago Loop holiday rentals
Other great holiday rentals in Chicago Loop
Guest favourite
Guest suite in East Pilsen
4.92 out of 5 average rating, 115 reviewsEntirely Private Suite - Urban Oasis - Pilsen/UIC
Guest favourite
Apartment in Lincoln Park
4.95 out of 5 average rating, 441 reviewsUnique Lincoln Park Duplex Apt
Guest favourite
Flat in Chicago
4.98 out of 5 average rating, 132 reviewsModern Apt with style & comfort in Pilsen Chicago
Superhost
Flat in Pilsen Historic District
4.86 out of 5 average rating, 235 reviewsTeeny Tiny Bohemian Lodge - Clean & Affordable
Guest favourite
Flat in Logan Square
4.92 out of 5 average rating, 492 reviews2BR Bursting w/ Character in Hip Logan Square!
Guest favourite
Townhouse in Near West Side
4.85 out of 5 average rating, 278 reviewsCITY CONDO with GARAGE 7 min Walk to Train
Guest favourite
Flat in West Town
4.89 out of 5 average rating, 473 reviewsiKlektik House Chicago / Robin
Guest favourite
Flat in Bridgeport
4.98 out of 5 average rating, 171 reviewsBridgeport Garden Apartment
Quick stats about holiday 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 washing machine and dryer Chicago Loop
- Monthly Rentals Chicago Loop
- Fitness-friendly rentals Chicago Loop
- Loft rentals Chicago Loop
- Apartment 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 firepit Chicago Loop
- Rentals with an EV charger Chicago Loop
- Flat rentals Chicago Loop
- Family-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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