Apartment vacation rentals in North Side
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Top-rated apartment rentals in North Side
Guests agree: these apartments are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for North Side apartment rentals
Weekly apartment rentals
Apartment in Humboldt Park
4.98 out of 5 average rating, 107 reviewsHumboldt Park Loft
Sep 28 – Oct 5
Apartment in Andersonville
4.98 out of 5 average rating, 250 reviewsAndersonville Cozy 1 bedroom basement suite
Dec 11 – 18
Apartment in Logan Square
4.91 out of 5 average rating, 372 reviewsThe Grotto of Logan Square
Sep 2 – 7
Apartment in Irving Park
4.86 out of 5 average rating, 101 reviews⭐️⭐️Entire Unite 2-Bdr. HORNER PARK⭐️⭐️
Apr 4 – 11
Apartment in Logan Square
4.93 out of 5 average rating, 207 reviewsCozy Private Coach House
Sep 24 – Oct 1
Apartment in Chicago
4.8 out of 5 average rating, 385 reviews'Secret Garden' Apartment in Wrigleyville
Oct 2 – 9
Apartment in Lake View
4.86 out of 5 average rating, 201 reviewsPrivate Queen Bedroom and En Suite Bath
Jul 10 – 17
Apartment in Logan Square
4.96 out of 5 average rating, 256 reviewsLogan Square 2nd Floor Chicago Victorian
Mar 16 – 23
Private apartment rentals
Apartment in Logan Square
4.9 out of 5 average rating, 283 reviewsModern Logan Square Apartment, steps from train!
Feb 6 – 13
Apartment in Logan Square
4.87 out of 5 average rating, 485 reviewsLogan Square Studio
Feb 26 – Mar 5
Apartment in Edgewater
4.93 out of 5 average rating, 382 reviewsRavenswood Guest House Annex
Jan 29 – Feb 5
Apartment in Logan Square
4.89 out of 5 average rating, 339 reviewsSunny Logan Square Artists' home
Feb 12 – 19
Apartment in West Town
4.89 out of 5 average rating, 473 reviewsiKlektik House Chicago / Robin
Jan 1 – 8
Apartment in Norwood Park
4.95 out of 5 average rating, 196 reviewsFree Parking & King Bed in Desirable Norwood Park!
Jul 14 – 21
Apartment in Edgewater
4.9 out of 5 average rating, 294 reviewsEdgewater escape, charming 2 BR, Rooftop Solar
Dec 3 – 10
Apartment in Chicago
4.86 out of 5 average rating, 324 reviewsThe Avondale Garden Unit
Apr 9 – 16
Apartment rentals with a hot tub
Apartment in West Town
4.88 out of 5 average rating, 393 reviewsCheckerboard Studio with Private Outdoor Hot Tub and Yard
Sep 19 – 26
Apartment in Chicago
4.87 out of 5 average rating, 156 reviewsStunning Panoramic Chicago Views & Free Parking
Mar 11 – 18
Apartment in West Loop
4.87 out of 5 average rating, 106 reviewsCloud9 |XL Penthouse+Movie Theater+Gym |The Harper
Dec 21 – 28
Apartment in Berwyn
4.91 out of 5 average rating, 202 reviews“Dream slice of urban homesteading.”
Apr 9 – 16
Apartment in Logan Square
4.9 out of 5 average rating, 30 reviewsLuxe Suite + Spa House Retreat! Pets Welcome
Jan 11 – 18
Apartment in West Rogers Park
5.0 out of 5 average rating, 17 reviewsSpacious Beautiful Condo
Oct 17 – 24
Apartment in Streeterville
5.0 out of 5 average rating, 10 reviewsLake, City, & River View Condo
Jul 9 – 16
Apartment in Belmont Cragin
5.0 out of 5 average rating, 25 reviewsBelmont Pleasures - hot tub / arcade gaming room
Dec 3 – 10
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