Holiday houses in North Side
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Top-rated holiday rentals in North Side
Guests agree: these stays are highly rated for location, cleanliness and more.
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Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for North Side holiday rentals
Other great holiday rentals in North Side
Guest favourite
Apartment in Uptown
4.96 out of 5 average rating, 264 reviewsCozy loft in Chicago's Uptown
7–14 Oct
$240 NZD per night
Guest favourite
Apartment in Lincoln Square
4.96 out of 5 average rating, 320 reviewsBright family-friendly Lincoln Square 2-bed 1-bath
28 Sep – 5 Oct
$288 NZD per night
Guest favourite
Guest suite in Portage Park
4.93 out of 5 average rating, 350 reviewsPeaceful Portage Park Apartment
3–10 Feb
$246 NZD per night
Guest favourite
Guesthouse in Edgewater
4.95 out of 5 average rating, 366 reviewsCozy Coach House
19–26 Aug
$244 NZD per night
Guest favourite
Apartment in Logan Square
4.96 out of 5 average rating, 255 reviewsLogan Square 2nd Floor Chicago Victorian
22–29 Mar
$271 NZD per night
Guest favourite
Apartment in Irving Park
4.89 out of 5 average rating, 176 reviewsHistoric Chicago neighborhood flat
25 Sep – 2 Oct
$259 NZD per night
Superhost
Apartment in Logan Square
4.9 out of 5 average rating, 282 reviewsModern Logan Square Apartment, steps from train!
9–16 Nov
$297 NZD per night
Guest favourite
Apartment in Lincoln Square
4.95 out of 5 average rating, 22 reviewsLincoln Square Oasis - Bright, clean studio
5–12 Jan
$201 NZD per night
Destinations to explore
- Downtown Chicago Holiday rentals
- Milwaukee Holiday rentals
- Lake Geneva Holiday rentals
- Lake Michigan Beach Holiday rentals
- Saugatuck Holiday rentals
- Evanston Holiday rentals
- South Haven Holiday rentals
- Naperville Holiday rentals
- South Side Holiday rentals
- South Bend Holiday rentals
- New Buffalo Holiday rentals
- Chicago Holiday rentals
- Rentals with a balcony North Side
- Kid-friendly rentals North Side
- Hotel rentals North Side
- Rentals with lake access North Side
- Beachfront rentals North Side
- Bed and breakfasts North Side
- Wheelchair accessible rentals North Side
- Rentals with a fire pit North Side
- Fitness-friendly rentals North Side
- Condo rentals North Side
- Smoking-friendly rentals North Side
- House rentals North Side
- Rentals with a patio North Side
- Rentals with a washing machine and dryer North Side
- Apartment rentals North Side
- Family-friendly rentals North Side
- Rentals with beach access North Side
- Rentals with pools North Side
- Pet-friendly rentals North Side
- Rentals with a fireplace North Side
- Loft rentals North Side
- Rentals with an EV charger North Side
- Guesthouse rentals North Side
- Rentals with a hot tub North Side
- Waterfront rentals North Side
- Monthly Rentals North Side
- Private suite rentals North Side
- Townhouse rentals North Side
- Rentals with breakfast North Side
- Rentals with outdoor seating North Side
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