Holiday houses in Old Town, Chicago
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Old Town, 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 Old Town, Chicago holiday rentals
Other great holiday rentals in Old Town, Chicago
Guest favourite
Home in Lake View
4.98 out of 5 average rating, 205 reviewsWrigleyville Southport Studio
15–22 Dec
$347 NZD per night
Guest favourite
Guest suite in Lake View
4.91 out of 5 average rating, 358 reviewsContemporary, private suite w fireplace
22–29 Oct
$171 NZD per night
Guest favourite
Guesthouse in Little Italy
4.99 out of 5 average rating, 784 reviewsPolk Street Coach House Apartment, Little Italy/Medical Dist
15–22 Feb
$295 NZD per night
Guest favourite
Apartment in West Town
4.96 out of 5 average rating, 262 reviewsTurquoise Wonder - Clean, Cozy & Stylish Apt
15–22 Apr
$238 NZD per night
Superhost
Apartment in Lincoln Park
4.8 out of 5 average rating, 121 reviewsThe Biddle House (#2)
25 Dec – 1 Jan
$458 NZD per night
Guest favourite
Apartment in Humboldt Park
4.98 out of 5 average rating, 106 reviewsHumboldt Park Loft
10–17 Oct
$275 NZD per night
Guest favourite
Apartment in Wicker Park
4.97 out of 5 average rating, 236 reviewsStylish First Flr. Studio. Best Location Division+Hermitage.
2–9 Feb
$361 NZD per night
Guest favourite
Apartment in Lincoln Park
4.98 out of 5 average rating, 300 reviewsLincoln Pk-parking-wifi-King bd-crib-kid friendly
$339 NZD per night
Quick stats about holiday rentals in Old Town, Chicago
Total rentals
70 properties
Rentals with dedicated workspaces
40 properties have a dedicated workspace
Pet-friendly rentals
20 properties allow pets
Family-friendly rentals
50 properties are a good fit for families
Total number of reviews
5.5K reviews
Nightly prices starting at
$118 NZD before taxes and fees
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