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
Get the amount of space that is right for you
Popular amenities for Old Town, Chicago apartment rentals
Weekly apartment rentals
Rental unit
4.95 out of 5 average rating, 397 reviewsA Vintage Pink House in the Heart of Chicago
Rental unit
4.96 out of 5 average rating, 519 reviewsStunning Retro Apartment in Andersonville
Rental unit
4.97 out of 5 average rating, 329 reviewsLincoln Park/Lake View/Wrigley/Walk to El/Parking
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4.96 out of 5 average rating, 275 reviewsRoscoe Village One Bed Lux Apartment Near Wrigley
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4.92 out of 5 average rating, 359 reviewsBright, Modern Apartment in a Vintage Greystone
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4.91 out of 5 average rating, 407 reviewsThe Grotto of Logan Square
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4.85 out of 5 average rating, 376 reviewsCozy Garden Apartment in Heart of Pilsen
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4.97 out of 5 average rating, 274 reviewsThe Garden on Wayne
Private apartment rentals
Rental unit
4.9 out of 5 average rating, 504 reviewsiKlektik House Chicago / Robin
Rental unit in Near North Side
4.91 out of 5 average rating, 117 reviewsModern 3BR with Private Rooftop & Free Parking
Rental unit in Lake View
4.87 out of 5 average rating, 275 reviewsWELCOME TO NANCY'S PAD!
Rental unit in Ukrainian Village
4.92 out of 5 average rating, 129 reviewsElegant Modern-Luxury Condo in Popular West Town
Rental unit
4.95 out of 5 average rating, 286 reviewsTurquoise Wonder - Clean, Cozy & Stylish Apt
Rental unit
4.86 out of 5 average rating, 516 reviewsLogan Square Studio
Rental unit in Near North Side
4.94 out of 5 average rating, 140 reviews*Steps to Mag Mile, 2 BD , fast Wi-Fi, W&D
Rental unit
4.94 out of 5 average rating, 234 reviewsUrban Chic Apartment by the Magnificent Mile
Apartment rentals with a hot tub
Rental unit
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 Belmont Cragin
4.99 out of 5 average rating, 71 reviewsBelmont Pleasures - hot tub / arcade gaming room
Rental unit
5 out of 5 average rating, 21 reviewsLake, City, & River View Condo
Rental unit
4.87 out of 5 average rating, 429 reviewsCheckerboard Studio with Private Outdoor Hot Tub and Yard
Rental unit in Logan Square
4.93 out of 5 average rating, 70 reviewsLuxe Suite + Spa House! Key West Vibes 4-Seasons
Rental unit in Albany Park
New place to stayVibrant 1BR Apt | Explore Chicago's Hidden Gems!
Quick stats about flat rentals in Old Town, Chicago
Total rentals
30 properties
Nightly prices starting at
£77 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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