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
Loft in Lake View
4.96 out of 5 average rating, 422 reviewsLakeview Loft-Vintage Chicago, Modern Amenities
Home in Roscoe Village
4.94 out of 5 average rating, 214 reviewsModern Home RoscoeVillage/Wrigley Free St Parking
Apartment in Lincoln Park
4.96 out of 5 average rating, 382 reviewsSophisticated Flat in Historic Building
Home in Lake View
4.98 out of 5 average rating, 208 reviewsWrigleyville Southport Studio
Apartment in Lincoln Park
4.83 out of 5 average rating, 213 reviewsCozy Lincoln Park Studio - Steps to Zoo!
Apartment in West Town
4.96 out of 5 average rating, 266 reviewsTurquoise Wonder - Clean, Cozy & Stylish Apt
Condo in Lake View
4.99 out of 5 average rating, 567 reviewsUrban Comfort in the Heart of Chicago
Guesthouse in Little Italy
4.99 out of 5 average rating, 791 reviewsPolk Street Coach House Apartment, Little Italy/Medical Dist
Other great vacation rentals in Old Town, Chicago
Guest suite in Lincoln Square
4.97 out of 5 average rating, 366 reviewsPrivate suite in Lincoln Square
Condo in Lincoln Square
4.97 out of 5 average rating, 334 reviewsLincoln Square Gem!
Apartment in Wicker Park
4.97 out of 5 average rating, 237 reviewsStylish First Flr. Studio. Best Location Division+Hermitage.
Guest suite in West Town
4.96 out of 5 average rating, 310 reviewsAugusta's Garden | Noble Square | Wicker Park
Guest suite in Lincoln Square
4.95 out of 5 average rating, 243 reviewsGreat location, private entry and patio!
Apartment in Humboldt Park
4.98 out of 5 average rating, 110 reviewsHumboldt Park Loft
Apartment in Old Town
4.91 out of 5 average rating, 158 reviewsOLD TOWN TRIUMPHANT 2BD/2BA (+Rooftop&Parking)
Condo in Lincoln Park
4.79 out of 5 average rating, 86 reviewsStylish Stay Steps from Old Town + Lincoln 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
ﺩ.ﺇ257 before taxes and fees
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