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 Chicago
4.82 out of 5 average rating, 437 reviewsLovely Andersonville Apt with Ideal Location
Dec 27 – Jan 3
Apartment in Edgewater
4.93 out of 5 average rating, 382 reviewsRavenswood Guest House Annex
Mar 6 – 13
Apartment in Lincoln Square
4.81 out of 5 average rating, 125 reviewsTranquil & Airy 1BR Apt in Lincoln Square
May 8 – 15
Apartment in Lake View
4.86 out of 5 average rating, 202 reviewsPrivate Queen Bedroom and En Suite Bath
Jul 12 – 19
Apartment in Lake View
4.97 out of 5 average rating, 329 reviewsCharming, Spacious 3BR Lakeview Apt Near Transit
Jan 2 – 9
Apartment in Chicago
4.9 out of 5 average rating, 283 reviewsModern Logan Square Apartment, steps from train!
Sep 27 – Oct 4
Apartment in Irving Park
4.89 out of 5 average rating, 177 reviewsHistoric Chicago neighborhood flat
Mar 1 – 8
Apartment in Logan Square
4.89 out of 5 average rating, 339 reviewsSunny Logan Square Artists' home
Feb 18 – 25
Private apartment rentals
Apartment in West Town
4.96 out of 5 average rating, 262 reviewsTurquoise Wonder - Clean, Cozy & Stylish Apt
Apr 21 – 28
Apartment in Irving Park
4.91 out of 5 average rating, 226 reviewsSkylights, King Bed, 2 bedrooms
Feb 21 – 28
Apartment in Logan Square
4.85 out of 5 average rating, 184 reviewsBucktown Retreat - Why The Buck Not? Sleeps 1-6
Dec 10 – 17
Apartment in Chicago
4.96 out of 5 average rating, 376 reviewsKing Bed, Huge Spa Shower, Dining Destination
Nov 12 – 19
Apartment in Roscoe Village
4.9 out of 5 average rating, 373 reviewsRelax and Enjoy Chicago in an Updated and Private Apartment in Roscoe Village
Oct 22 – 29
Apartment in Logan Square
4.87 out of 5 average rating, 287 reviewsSawyer Get-Away in Logan Square
Sep 9 – 16
Apartment in Logan Square
4.87 out of 5 average rating, 486 reviewsLogan Square Studio
Dec 1 – 8
Apartment in Chicago
4.86 out of 5 average rating, 324 reviewsThe Avondale Garden Unit
Jan 12 – 19
Apartment rentals with a hot tub
Apartment in West Town
4.88 out of 5 average rating, 394 reviewsCheckerboard Studio with Private Outdoor Hot Tub and Yard
Oct 24 – 31
Apartment in Near South Side
4.87 out of 5 average rating, 156 reviewsStunning Panoramic Chicago Views & Free Parking
Nov 15 – 22
Apartment in Berwyn
4.91 out of 5 average rating, 203 reviews“Dream slice of urban homesteading.”
Oct 24 – 31
Apartment in Logan Square
4.91 out of 5 average rating, 32 reviewsLuxe Suite + Spa House Retreat! Pets Welcome
Nov 25 – Dec 2
Apartment in West Rogers Park
4.9 out of 5 average rating, 20 reviewsSpacious Beautiful Condo
Oct 22 – 29
Apartment in Belmont Cragin
5.0 out of 5 average rating, 26 reviewsBelmont Pleasures - hot tub / arcade gaming room
Oct 23 – 30
Apartment in The Loop
5.0 out of 5 average rating, 7 reviewsThe Downtown Oasis (2BD / 2BA)
Feb 10 – 17
Apartment in West Town
4.88 out of 5 average rating, 42 reviewsCloud 9 | Presidential Penthouse Suite | The Iris
Feb 24 – Mar 3
Destinations to explore
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