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
Home in Lake View
4.98 out of 5 average rating, 209 reviewsWrigleyville Southport Studio
Apartment in West Town
4.92 out of 5 average rating, 310 reviewsSpacious & private! Free parking! Great location!
Apartment in Lincoln Park
4.89 out of 5 average rating, 149 reviewsLincoln Paradise– Steps to Park & Zoo!
Apartment in Lincoln Park
4.96 out of 5 average rating, 385 reviewsSophisticated Flat in Historic Building
Apartment in Lincoln Park
4.89 out of 5 average rating, 149 reviewsChicago Lincoln Park North Pond 2 Bedroom Pied-à-Terre
Condo in Lake View
4.99 out of 5 average rating, 575 reviewsUrban Comfort in the Heart of Chicago
Guesthouse in Little Italy
4.99 out of 5 average rating, 795 reviewsPolk Street Coach House Apartment, Little Italy/Medical Dist
Home in West Loop
4.98 out of 5 average rating, 320 reviewsCozy garden apartment historic Jackson Bvld.
Other great vacation rentals in Old Town, Chicago
Townhouse in Lincoln Park
4.91 out of 5 average rating, 131 reviewsCheerful 3 story townhouse Old Town/LP
Apartment in Roscoe Village
4.96 out of 5 average rating, 246 reviewsRoscoe Village One Bed Lux Apartment Near Wrigley
Apartment in Gold Coast
4.89 out of 5 average rating, 143 reviewsCharming Gold Coast One-Bedroom Near Downtown!
Apartment in Old Town
4.91 out of 5 average rating, 159 reviewsOLD TOWN TRIUMPHANT 2BD/2BA (+Rooftop&Parking)
Condo in Lincoln Square
4.97 out of 5 average rating, 337 reviewsLincoln Square Gem!
Guest suite in Lake View
4.91 out of 5 average rating, 362 reviewsContemporary, private suite w fireplace
Apartment in Lincoln Park
4.98 out of 5 average rating, 307 reviewsLincoln Pk-parking-wifi-King bd-crib-kid friendly
Guest suite in West Town
4.96 out of 5 average rating, 311 reviewsAugusta's Garden | Noble Square | Wicker Park
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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