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
4.98 out of 5 average rating, 298 reviewsLincoln Pk-parking-wifi-King bd-crib-kid friendly
Jun 16 – 21
Apartment in Wicker Park
4.95 out of 5 average rating, 171 reviewsWicker Park/Bucktown Location
Jul 10 – 17
Apartment in Lincoln Park
4.89 out of 5 average rating, 144 reviewsLincoln Paradise– Steps to Park & Zoo!
Dec 30 – Jan 6
Guest suite in Lincoln Square
5.0 out of 5 average rating, 292 reviewsPrivate Lincoln Square one bed+bath studio apt.
Sep 29 – Oct 6
Apartment in Lincoln Park
4.87 out of 5 average rating, 192 reviewsNew! Beautiful 2BR Apartment in Old Town
Oct 22 – 29
Guest suite in West Town
4.96 out of 5 average rating, 305 reviewsAugusta's Garden | Noble Square | Wicker Park
Jul 14 – 21
Apartment in Roscoe Village
4.96 out of 5 average rating, 236 reviewsRoscoe Village One Bed Lux Apartment Near Wrigley
Dec 13 – 20
Home in Lake View
4.98 out of 5 average rating, 203 reviewsWrigleyville Southport Studio
Oct 18 – 25
Other great vacation rentals in Old Town, Chicago
Condo in Lincoln Park
4.79 out of 5 average rating, 82 reviewsStylish Stay Steps from Old Town + Lincoln Park
Nov 8 – 15
Apartment in Lincoln Park
4.91 out of 5 average rating, 23 reviewsOld Town Chicago Home
Nov 17 – 24
Condo in Lincoln Park
4.94 out of 5 average rating, 49 reviewsNEW luxury Old Town 1-Bedroom condo
Dec 12 – 19
Apartment in Lincoln Park
4.9 out of 5 average rating, 42 reviewsEntire Apartment in Lincoln Park
Sep 29 – Oct 6
Home in Lincoln Park
5.0 out of 5 average rating, 44 reviewsCharming 3-BED in Lincoln Park/ Old Town & Parking
Dec 26 – Jan 2
Apartment in Lincoln Park
4.96 out of 5 average rating, 69 reviewsEnglish garden apt. in the heart of Lincoln Park
Sep 16 – 23
Apartment in Old Town
4.85 out of 5 average rating, 52 reviewsOld Town/Gold Coast Masterpiece (+private rooftop)
Apr 23 – 30
Guest suite in West Loop
4.91 out of 5 average rating, 80 reviewsCozy one-bedroom suite in the heart of West Loop
Jan 26 – Feb 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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