Holiday rentals in Downtown Chicago
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Top-rated holiday rentals in Downtown Chicago
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 Downtown Chicago holiday rentals
Other great holiday rentals in Downtown Chicago
Guest favourite
Loft in Lake View
4.96 out of 5 average rating, 424 reviewsLakeview Loft-Vintage Chicago, Modern Amenities
Guest favourite
Apartment in Lincoln Park
4.96 out of 5 average rating, 446 reviewsUnique Lincoln Park Duplex Apt
Guest favourite
Guest suite in Lincoln Square
4.97 out of 5 average rating, 369 reviewsPrivate suite in Lincoln Square
Guest favourite
Flat in Little Italy
4.98 out of 5 average rating, 201 reviewsSpacious 2BR on Quiet St - Free Park/Late Checkout
Superhost
Flat in Pilsen Historic District
4.87 out of 5 average rating, 207 reviewsSpectacular Pilsen Studio for 2!
Superhost
Flat in East Rogers Park
4.89 out of 5 average rating, 107 reviewsLAKESIDE PIED `A TERRE STEPS TO BEACH
Guest favourite
Flat in Humboldt Park
4.98 out of 5 average rating, 111 reviewsHumboldt Park Loft
Superhost
Flat in Near South Side
4.8 out of 5 average rating, 70 reviewsMcCormick Place Studio/parking/sleeps up to 4
Destinations to explore
- Milwaukee Holiday rentals
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- Lake Michigan Beach Holiday rentals
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- South Haven Holiday rentals
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- South Bend Holiday rentals
- New Buffalo Holiday rentals
- Chicago Holiday rentals
- Flat rentals Downtown Chicago
- Family-friendly rentals Downtown Chicago
- Loft rentals Downtown Chicago
- Rentals with a sauna Downtown Chicago
- Beachfront rentals Downtown Chicago
- Townhouse rentals Downtown Chicago
- House rentals Downtown Chicago
- Smoking-friendly rentals Downtown Chicago
- Family-friendly rentals Downtown Chicago
- Rentals with breakfast Downtown Chicago
- Fitness-friendly rentals Downtown Chicago
- Rentals with a washing machine and dryer Downtown Chicago
- Rentals with an EV charger Downtown Chicago
- Rentals with a patio Downtown Chicago
- Apartment rentals Downtown Chicago
- Rentals with a fireplace Downtown Chicago
- Hotel rentals Downtown Chicago
- Rentals with outdoor seating Downtown Chicago
- Monthly Rentals Downtown Chicago
- Rentals with a firepit Downtown Chicago
- Rentals with lake access Downtown Chicago
- Waterfront rentals Downtown Chicago
- Rentals with a hot tub Downtown Chicago
- Rentals with beach access Downtown Chicago
- Rentals with a cinema Downtown Chicago
- Pet-friendly rentals Downtown Chicago
- Boutique hotel rentals Downtown Chicago
- Rentals with pools Downtown Chicago
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