Apartment vacation rentals in Old Town, Chicago
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Top-rated apartment rentals in Old Town, Chicago
Guests agree: these apartments 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 apartment rentals
Weekly apartment rentals
Rental unit in West Town
4.95 out of 5 average rating, 397 reviewsA Vintage Pink House in the Heart of Chicago
Rental unit in Near North Side
4.91 out of 5 average rating, 117 reviewsModern 3BR with Private Rooftop & Free Parking
Rental unit in Roscoe Village
4.96 out of 5 average rating, 275 reviewsRoscoe Village One Bed Lux Apartment Near Wrigley
Rental unit in Lake View
4.83 out of 5 average rating, 429 reviewsLakeview Charmer -with parking!
Rental unit in West Town
4.95 out of 5 average rating, 286 reviewsTurquoise Wonder - Clean, Cozy & Stylish Apt
Rental unit in Wicker Park
4.96 out of 5 average rating, 129 reviewsCOZY Bright*BOLD*FUN* Eclectic Wicker Park Home
Rental unit in Uptown
4.89 out of 5 average rating, 495 reviewsWhole Flat in Private Club. Walk to L, Dining & Shows
Rental unit in Uptown
4.96 out of 5 average rating, 280 reviewsCozy loft in Chicago's Uptown
Private apartment rentals
Rental unit in Lake View
4.97 out of 5 average rating, 330 reviewsLincoln Park/Lake View/Wrigley/Walk to El/Parking
Rental unit in Logan Square
4.86 out of 5 average rating, 516 reviewsLogan Square Studio
Rental unit in West Town
4.92 out of 5 average rating, 359 reviewsBright, Modern Apartment in a Vintage Greystone
Rental unit in Logan Square
4.91 out of 5 average rating, 407 reviewsThe Grotto of Logan Square
Rental unit in Pilsen Historic District
4.85 out of 5 average rating, 376 reviewsCozy Garden Apartment in Heart of Pilsen
Rental unit in Logan Square
4.9 out of 5 average rating, 317 reviewsModern Logan Square Apartment, steps from train!
Rental unit in Magnificent Mile
4.94 out of 5 average rating, 234 reviewsUrban Chic Apartment by the Magnificent Mile
Rental unit in Logan Square
4.83 out of 5 average rating, 513 reviewsRelaxed Bucktown/Wicker Park 1B Apt
Apartment rentals with a hot tub
Rental unit in West Rogers Park
4.88 out of 5 average rating, 48 reviewsSpacious Beautiful Condo
Rental unit in Chicago
4.85 out of 5 average rating, 53 reviewsPrivate Rooftop Views from Penthouse Suite
Rental unit in West Loop
5 out of 5 average rating, 20 reviewsSkyline Oasis: City & Lake Views
Rental unit in Magnificent Mile
4.86 out of 5 average rating, 96 reviews4Br Gold Coast Duplex w Jacuzzi in the Bedroom!
Rental unit in Belmont Cragin
4.99 out of 5 average rating, 72 reviewsBelmont Pleasures - hot tub / arcade gaming room
Rental unit in Streeterville
5 out of 5 average rating, 21 reviewsLake, City, & River View Condo
Rental unit in The Loop
4.73 out of 5 average rating, 40 reviewsThe Professional's Playground
Rental unit in West Town
4.87 out of 5 average rating, 430 reviewsCheckerboard Studio with Private Outdoor Hot Tub and Yard
Quick stats about apartment rentals in Old Town, Chicago
Total rentals
30 properties
Nightly prices starting at
ﺩ.ﺇ367 before taxes and fees
Total number of reviews
3.5K reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
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