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House holiday rentals in Downtown Chicago
Find and book unique houses on Airbnb
Top-rated house rentals in Downtown Chicago
Guests agree: these houses are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for house rentals in Downtown Chicago
House rentals with a pool
![](https://a0.muscache.com/im/pictures/69d3bb7c-54f2-4454-ae3a-c4d38c5c61fe.jpg?im_w=720)
Home in Schaumburg
4.92 out of 5 average rating, 13 reviewsParadise 4BR w/ Pool & Games
![](https://a0.muscache.com/im/pictures/hosting/Hosting-1152484478779189306/original/4a3b2311-84f1-4d00-b28a-a60b1182f5fe.jpeg?im_w=720)
Home in Bloomingdale
4.93 out of 5 average rating, 14 reviewsGiant Swimming Pool with Whole House!
![](https://a0.muscache.com/im/pictures/hosting/Hosting-868236911692412929/original/860125fb-662e-4cc7-ba73-7bf9a86831a2.jpeg?im_w=720)
Home in Schaumburg
4.95 out of 5 average rating, 20 reviewsSchaumburg Woodfield Pool House 4bedroom 2.5bath
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Home in Chicago
4.85 out of 5 average rating, 46 reviewsLuxury Cabin in Lakeview
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Home in Chicago
4.82 out of 5 average rating, 22 reviews2Bed+2Bath PentHouse in South Loop
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Home in Bensenville
5 out of 5 average rating, 3 reviewsNew! Bensenville home by OāHare-Arcade/Sauna/Slots
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Home in Riverwoods
Riverwoods Nature Retreat
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Home in Evanston
New place to stay1/2 mile to NU, 5min walk to Lake, Swim Spa pool
Weekly house rentals
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Home in Chicago
4.9 out of 5 average rating, 82 reviewsFamily friendly 2 bedroom w/ private office
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Home in Chicago
4.98 out of 5 average rating, 92 reviews3BD Home Mins from Airport | Free Wi-Fi + Parking
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Home in Chicago
4.97 out of 5 average rating, 31 reviewsCharming and Classic Brick Home in Bridgeport
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Home in Chicago
4.93 out of 5 average rating, 28 reviewsSpacius unit in historic gem
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Home in Chicago
4.96 out of 5 average rating, 56 reviewsCity Cottage in Logan Square-Avondale
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Home in Chicago
4.9 out of 5 average rating, 39 reviewsBrand New Spacious Duplex
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Home in Westmont
4.94 out of 5 average rating, 33 reviewsCharming Home in Westmont, Close to Chicago!
![](https://a0.muscache.com/im/pictures/hosting/Hosting-U3RheVN1cHBseUxpc3Rpbmc6OTYyMzQ5ODM5NzYwMDg1MDkx/original/9c03b2aa-a5b4-46a9-9155-6c507266dab4.jpeg?im_w=720)
Home in Chicago
4.96 out of 5 average rating, 27 reviewsChicago Home (1st floor) by Midway near Downtown
Private house rentals
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Home in Chicago
4.97 out of 5 average rating, 34 reviewsLakeview Condo
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Home in Chicago
4.92 out of 5 average rating, 36 reviewsNorthside Chicago Getaway
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Home in Chicago
4.91 out of 5 average rating, 22 reviewsSteel and Sky
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Home in Robbins
4.92 out of 5 average rating, 48 reviewsComfy Updated 3 Bdrm/2Bth -Near SXU & Midway
![](https://a0.muscache.com/im/pictures/airflow/Hosting-796866365414874330/original/3b7ff553-5fd4-424d-b37b-ba817bf6e78f.jpg?im_w=720)
Home in Chicago
4.88 out of 5 average rating, 17 reviewsHidden Gem on the CHI north side
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Home in Chicago
4.94 out of 5 average rating, 86 reviewsModern Lux Getaway w/ Hot Tub, Lrg Yard, Parking
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Home in Chicago
5 out of 5 average rating, 8 reviewsWicker Park Entire House, Private Yard and Parking
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Home in Chicago
5 out of 5 average rating, 13 reviewsBeautiful Lincoln Park House
Destinations to explore
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