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
4.89 out of 5 average rating, 144 reviewsLincoln Paradise– Steps to Park & Zoo!
Jul 13 – 20
Guest suite in Lincoln Square
5.0 out of 5 average rating, 295 reviewsPrivate Lincoln Square one bed+bath studio apt.
Oct 2 – 9
Guesthouse in Lincoln Park
4.96 out of 5 average rating, 165 reviewsCoach House w/ Heated Garage & Pvt. Rooftop Deck
Sep 12 – 19
Guest suite in Lake View
4.95 out of 5 average rating, 176 reviews1 mile from Wrigley Field
Sep 5 – 12
Guest suite in Lincoln Square
4.97 out of 5 average rating, 362 reviewsPrivate suite in Lincoln Square
Mar 14 – 21
Guest suite in West Town
4.96 out of 5 average rating, 306 reviewsAugusta's Garden | Noble Square | Wicker Park
Aug 23 – 30
Guest suite in Lake View
4.91 out of 5 average rating, 359 reviewsContemporary, private suite w fireplace
Mar 8 – 15
Guest suite in Lincoln Square
4.94 out of 5 average rating, 178 reviewsLincoln Square In-laws Suite: Private Entrance
Sep 27 – Oct 4
Other great vacation rentals in Old Town, Chicago
Apartment in Old Town
4.91 out of 5 average rating, 158 reviewsOLD TOWN TRIUMPHANT 2BD/2BA (+Rooftop&Parking)
Jul 6 – 13
Condo in Lincoln Park
4.79 out of 5 average rating, 84 reviewsStylish Stay Steps from Old Town + Lincoln Park
Oct 17 – 24
Apartment in Lincoln Park
4.91 out of 5 average rating, 23 reviewsOld Town Chicago Home
Nov 25 – Dec 2
Condo in Lincoln Park
4.94 out of 5 average rating, 51 reviewsNEW luxury Old Town 1-Bedroom condo
Nov 25 – Dec 2
Apartment in Old Town
4.95 out of 5 average rating, 57 reviewsBreathtaking & Chic Oasis Loc in Desirable Old Twn
Dec 25 – Jan 1
Home in Lincoln Park
5.0 out of 5 average rating, 46 reviewsCharming 3-BED in Lincoln Park/ Old Town & Parking
Nov 9 – 16
Guest suite in Old Town
4.99 out of 5 average rating, 76 reviewsTravelers Retreat in Old Town Chicago
Jul 10 – 17
Apartment in Logan Square
5.0 out of 5 average rating, 22 reviewsThe Heart of Bucktown
Sep 21 – 28
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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