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
Flat in Skokie
4.89 out of 5 average rating, 56 reviewsCharming 2 bed/1 bath apt- walk 2 train/store/rest
Flat in West Lake View
4.95 out of 5 average rating, 102 reviewsChic retreat near the best of Lakeview & Wrigley
Flat in Lincoln Square
4.91 out of 5 average rating, 185 reviewsComfortable Vintage North Side Retreat for 8
Flat in Lincoln Park
4.95 out of 5 average rating, 110 reviewsElegant Depaul Apt on Jonquil Park
Flat in Irving Park
4.93 out of 5 average rating, 229 reviewsCool and Modern Chicago Apartment near Transit
Flat in West Town
4.85 out of 5 average rating, 161 reviews*Comfortable & Spacious Home Close to Downtown*
Flat in Bridgeport
4.93 out of 5 average rating, 107 reviewsCitySlickers Crash Pad /Free Parking /No Clean Fee
Flat in Lincoln Park
4.73 out of 5 average rating, 204 reviewsRare, Updated 1 BR Condo in Lincoln Park!
Private apartment rentals
Flat in Oak Park
4.87 out of 5 average rating, 273 reviewsCosmopolitan Nest in Oak Park North Side
Flat in Near North Side
4.91 out of 5 average rating, 121 reviewsModern 3BR with Private Rooftop & Free Parking
Flat in East Rogers Park
4.9 out of 5 average rating, 142 reviewsPrivate Garden Apartment GATED FREE Parking
Flat in Avondale
4.98 out of 5 average rating, 102 reviewsLovely 2bedroom 1bath Apt and outdoor seating.
Flat in Avondale
4.91 out of 5 average rating, 263 reviewsAvondale Gem: 2BR, Stylish Kitchen, Transit Nearby
Flat in West Town
4.75 out of 5 average rating, 138 reviewsWicker Park Historic, Art-Filled, Urban Oasis #2
Flat in Roscoe Village
4.75 out of 5 average rating, 251 reviewsNorth Side Pied-à-terre
Flat in Roscoe Village
4.77 out of 5 average rating, 267 reviewsClassic 2 Bedroom Roscoe Village Apartment
Apartment rentals with a hot tub
Flat in Lincoln Park
New place to stayDepaul SelfCheckin WasherDryer 15minstodowntown
Flat in West Loop
4.82 out of 5 average rating, 72 reviewsQuiet but in the Heart of City walk Everywhere
Flat in West Rogers Park
4.85 out of 5 average rating, 55 reviewsSpacious Beautiful Condo
Flat in West Loop
5 out of 5 average rating, 21 reviewsSkyline Oasis: City & Lake Views
Flat in Chicago
4.85 out of 5 average rating, 53 reviewsHoliday Parties Welcome with 3 nights or more!
Flat in Belmont Cragin
4.99 out of 5 average rating, 80 reviewsBelmont Pleasures - hot tub / arcade gaming room
Flat in Streeterville
5 out of 5 average rating, 21 reviewsLake, City, & River View Condo
Flat in The Loop
4.75 out of 5 average rating, 48 reviewsThe Professional's Playground
Quick stats about flat rentals in Old Town, Chicago
Total rentals
30 properties
Nightly prices starting at
₹8,543 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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