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Holiday rentals in Downtown Chicago
Find and book unique accommodation on Airbnb
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
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Guest favourite
Loft in Chicago
4.91 out of 5 average rating, 328 reviewsPilsen Modernist, Creative, Lightfilled Loft
![](https://a0.muscache.com/im/pictures/hosting/Hosting-U3RheVN1cHBseUxpc3Rpbmc6NjI2Mjk0NTA4NDg2MzU5NjM1/original/3c79c547-8699-4299-9f91-c3cbb50655a5.jpeg?im_w=720)
Superhost
Rental unit in Chicago
4.83 out of 5 average rating, 93 reviewsMcCormick Pl 420 friendly 1br/1ba parking/sleeps 4
![](https://a0.muscache.com/im/pictures/miso/Hosting-958176890537691747/original/9263a134-cd15-48f9-a9c4-7ae123af8f54.jpeg?im_w=720)
Guest favourite
Apartment in Chicago
4.98 out of 5 average rating, 40 reviewsChic & Comfy • Close to Wrigley
![](https://a0.muscache.com/im/pictures/miso/Hosting-917294757690602460/original/b310ecc5-f2bc-4b5e-a77e-baa352b50d21.jpeg?im_w=720)
Guest favourite
Rental unit in Chicago
4.94 out of 5 average rating, 47 reviewsSerene Escape with King Sleep Number Bed, No Fees!
![](https://a0.muscache.com/im/pictures/hosting/Hosting-U3RheVN1cHBseUxpc3Rpbmc6MzI4MjExMDc%3D/original/6e75e7a2-04ae-4e34-b4ee-be0c55345313.jpeg?im_w=720)
Guest favourite
Apartment in Chicago
4.89 out of 5 average rating, 9 reviewsCozy, sunny, boho condo in Uptown/Sheridan Park
![](https://a0.muscache.com/im/pictures/hosting/Hosting-1118198200466838593/original/c0734f62-d9f8-43df-88ea-42703364f042.jpeg?im_w=720)
Guest favourite
Rental unit in Chicago
5 out of 5 average rating, 11 reviewsBright Apartment
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Guest favourite
Guest house in Chicago
4.89 out of 5 average rating, 37 reviewsLuxe Loft Guest House Great location!
![](https://a0.muscache.com/im/pictures/miso/Hosting-49093623/original/9f4b2fa5-522c-4e2b-ba11-3d8b8ac2c0e5.jpeg?im_w=720)
Guest favourite
Rental unit in Chicago
4.97 out of 5 average rating, 59 reviewsRecently renovated 1 bedroom in the best location!
Destinations to explore
- Milwaukee Holiday rentals
- Lake Geneva Holiday rentals
- Lake Michigan Beach Holiday rentals
- Saugatuck Holiday rentals
- Evanston Holiday rentals
- Holland Holiday rentals
- South Haven Holiday rentals
- Naperville Holiday rentals
- South Side Holiday rentals
- South Bend Holiday rentals
- Schaumburg Holiday rentals
- Chicago Holiday rentals
- Family-friendly rentals Downtown Chicago
- Rentals with a patio Downtown Chicago
- Rentals with an EV charger Downtown Chicago
- Rentals with breakfast Downtown Chicago
- Waterfront rentals Downtown Chicago
- Rentals with lake access Downtown Chicago
- House rentals Downtown Chicago
- Flat rentals Downtown Chicago
- Pet-friendly rentals Downtown Chicago
- Smoking-friendly rentals Downtown Chicago
- Rentals with a cinema Downtown Chicago
- Rentals with a hot tub Downtown Chicago
- Beachfront rentals Downtown Chicago
- Apartment rentals Downtown Chicago
- Townhouse rentals Downtown Chicago
- Rentals with a firepit Downtown Chicago
- Hotel rentals Downtown Chicago
- Rentals with beach access Downtown Chicago
- Rentals with a sauna Downtown Chicago
- Rentals with a fireplace Downtown Chicago
- Loft rentals Downtown Chicago
- Rentals with a washing machine and dryer Downtown Chicago
- Boutique hotel rentals Downtown Chicago
- Rentals with outdoor seating Downtown Chicago
- Rentals with pools Downtown Chicago
- Family-friendly rentals Downtown Chicago
- Monthly Rentals Downtown Chicago
- Fitness-friendly rentals Downtown Chicago
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