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, 205 reviewsWrigleyville Southport Studio
Dec 15 – 22
Apartment in Lincoln Park
4.95 out of 5 average rating, 377 reviewsSophisticated Flat in Historic Building
Jul 28 – Aug 4
Guesthouse in Little Italy
4.99 out of 5 average rating, 784 reviewsPolk Street Coach House Apartment, Little Italy/Medical Dist
Feb 15 – 22
Guest suite in Lake View
4.91 out of 5 average rating, 358 reviewsContemporary, private suite w fireplace
Mar 26 – Apr 2
Apartment in West Town
4.96 out of 5 average rating, 262 reviewsTurquoise Wonder - Clean, Cozy & Stylish Apt
Apr 15 – 22
Apartment in Lincoln Park
4.98 out of 5 average rating, 300 reviewsLincoln Pk-parking-wifi-King bd-crib-kid friendly
Apartment in Humboldt Park
4.98 out of 5 average rating, 106 reviewsHumboldt Park Loft
Oct 10 – 17
Apartment in Lincoln Park
4.8 out of 5 average rating, 121 reviewsThe Biddle House (#2)
Dec 25 – Jan 1
Other great vacation rentals in Old Town, Chicago
Apartment in Lincoln Park
4.87 out of 5 average rating, 192 reviewsNew! Beautiful 2BR Apartment in Old Town
Oct 25 – Nov 1
Guesthouse in Lincoln Park
4.96 out of 5 average rating, 163 reviewsCoach House w/ Heated Garage & Pvt. Rooftop Deck
Oct 23 – 30
Guest suite in Lincoln Square
4.97 out of 5 average rating, 361 reviewsPrivate suite in Lincoln Square
Dec 30 – Jan 6
Townhouse in Lincoln Park
4.91 out of 5 average rating, 121 reviewsCheerful 3 story townhouse Old Town/LP
Nov 15 – 22
Condo in Lincoln Park
4.84 out of 5 average rating, 67 reviewsExclusive Condo Steps from Old Town + Lincoln Park
Dec 5 – 12
Apartment in Lincoln Park
4.91 out of 5 average rating, 23 reviewsOld Town Chicago Home
Oct 26 – Nov 2
Condo in Lincoln Park
4.94 out of 5 average rating, 50 reviewsNEW luxury Old Town 1-Bedroom condo
Nov 25 – Dec 2
Home in Lincoln Park
5.0 out of 5 average rating, 45 reviewsCharming 3-BED in Lincoln Park/ Old Town & Parking
Jan 8 – 15
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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