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 Gold Coast
4.88 out of 5 average rating, 145 reviewsCharming Gold Coast One-Bedroom Near Downtown!
Apartment in Wicker Park
4.97 out of 5 average rating, 239 reviewsStylish First Flr. Studio. Best Location Division+Hermitage.
Guest suite in Lake View
4.95 out of 5 average rating, 179 reviews1 mile from Wrigley Field
Guesthouse in Little Italy
4.99 out of 5 average rating, 795 reviewsPolk Street Coach House Apartment, Little Italy/Medical Dist
Apartment in Roscoe Village
4.96 out of 5 average rating, 246 reviewsRoscoe Village One Bed Lux Apartment Near Wrigley
Townhouse in Lincoln Park
4.91 out of 5 average rating, 133 reviewsCheerful 3 story townhouse Old Town/LP
Apartment in Lincoln Park
4.98 out of 5 average rating, 311 reviewsLincoln Pk-parking-wifi-King bd-crib-kid friendly
Guest suite in West Town
4.96 out of 5 average rating, 312 reviewsAugusta's Garden | Noble Square | Wicker Park
Other great vacation rentals in Old Town, Chicago
Apartment in Lincoln Park
4.89 out of 5 average rating, 151 reviewsLincoln Paradise– Steps to Park & Zoo!
Apartment in Lincoln Park
4.87 out of 5 average rating, 277 reviewsHistoric Old Town Flat - Minutes from Downtown!
Apartment in Logan Square
4.92 out of 5 average rating, 497 reviews2BR Bursting w/ Character in Hip Logan Square!
Apartment in West Loop
4.87 out of 5 average rating, 221 reviewsGarden Apartment in the Historic Heart of the City
Apartment in Old Town
4.91 out of 5 average rating, 161 reviewsOLD TOWN TRIUMPHANT 2BD/2BA (+Rooftop&Parking)
Home in West Town
4.95 out of 5 average rating, 179 reviewsParadise on the Park
Condo in Lincoln Square
4.97 out of 5 average rating, 338 reviewsLincoln Square Gem!
Apartment in Roscoe Village
4.92 out of 5 average rating, 260 reviewsA+Posh Chicago Home Roscoe Village Wrigley Classic
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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