Apartment holiday 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.
Holiday rentals for every style
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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
$167 NZD 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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