Old Town, Chicago vacation rentals
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Top-rated vacation rentals in Old Town, Chicago
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Old Town, Chicago vacation rentals
Other great vacation rentals in Old Town, Chicago
Apartment in Lincoln Park
4.89 out of 5 average rating, 148 reviewsChicago Lincoln Park North Pond 2 Bedroom Pied-à-Terre
Guest suite in Lincoln Square
4.99 out of 5 average rating, 300 reviewsPrivate Lincoln Square one bed+bath studio apt.
Apartment in Wicker Park
4.95 out of 5 average rating, 258 reviewsHeart of Bucktown
Apartment in Lincoln Park
4.98 out of 5 average rating, 173 reviewsLincoln Pk-Kingbd-fast WiFi-parking-crib/Highchair
Apartment in West Town
4.95 out of 5 average rating, 365 reviewsA Vintage Pink House in the Heart of Chicago
Condo in Lake View
4.99 out of 5 average rating, 571 reviewsUrban Comfort in the Heart of Chicago
Apartment in Near North Side
4.89 out of 5 average rating, 379 reviewsGreat Location Studio in the Gold Coast!!
Guest suite in Lake View
4.91 out of 5 average rating, 362 reviewsContemporary, private suite w fireplace
Other great vacation rentals in Old Town, Chicago
Guest suite in Lincoln Square
4.97 out of 5 average rating, 369 reviewsPrivate suite in Lincoln Square
Guest suite in West Town
4.96 out of 5 average rating, 310 reviewsAugusta's Garden | Noble Square | Wicker Park
Apartment in Lincoln Park
4.98 out of 5 average rating, 306 reviewsLincoln Pk-parking-wifi-King bd-crib-kid friendly
Condo in Lincoln Square
4.97 out of 5 average rating, 337 reviewsLincoln Square Gem!
Townhouse in Lincoln Park
4.91 out of 5 average rating, 131 reviewsCheerful 3 story townhouse Old Town/LP
Home in West Loop
4.97 out of 5 average rating, 319 reviewsCozy garden apartment historic Jackson Bvld.
Apartment in Wicker Park
4.97 out of 5 average rating, 237 reviewsStylish First Flr. Studio. Best Location Division+Hermitage.
Apartment in Lincoln Park
4.81 out of 5 average rating, 124 reviewsThe Biddle House (#2)
Quick stats about vacation 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
$70 before taxes and fees
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