North Side Vacation Rentals & Ski-in/Ski-out Homes

Compare Vacation Rentals & Ski-in/Ski-out Homes in North Side, Illinois, USA

The Sono Chicago
Bed & Breakfast
The Sono Chicago
From US $266 per night
|
10.0 (465 Reviews)
1 Bedroom 2 Guests
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Modern 3BR Apt in Boystown, 12-min walk to Wrigley - Stratford 1S
Apartment
Modern 3BR Apt in Boystown, 12-min walk to Wrigley - Stratford 1S
From US $517 per night
|
10.0 (4 Reviews)
3 Bedrooms 6 Guests
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Wrigleyville Inn
House
Wrigleyville Inn
From US $531 per night
|
10.0 (19 Reviews)
1 Bedroom 2 Guests
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New Mid-Century Gem in Avondale - 2BR - Office - Free Parking
Apartment
Mid-Century Gem in Avondale - 2BR - Office - Free Parking
From US $247 per night
New
2 Bedrooms 4 Guests
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The Logandale: HUGE Mid-Century Home, sleeps 15
House
The Logandale: HUGE Mid-Century Home, sleeps 15
From US $484 per night
|
10.0 (4 Reviews)
4 Bedrooms 15 Guests
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Ray's Bucktown B&B
Bed & Breakfast
Ray's Bucktown B&B
From US $202 per night
|
9.8 (370 Reviews)
1 Bedroom 2 Guests
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Lyons' Den
House
Lyons' Den
From US $245 per night
10.0 (4 Reviews)
1 Bedroom 2 Guests
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New Charming Garden Flat w/King Bed
House
Charming Garden Flat w/King Bed
From US $181 per night
New
2 Bedrooms 2 Guests
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Bootlegger House Sleeps 10-20 Free TV & Parking
Apartment
Bootlegger House Sleeps 10-20 Free TV & Parking
From US $645 per night
|
10.0 (3 Reviews)
6 Bedrooms 20 Guests
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The Wrigleyville Deluxe -Steps from Wrigley Sleeps 10
Apartment
The Wrigleyville Deluxe -Steps from Wrigley Sleeps 10
From US $853 per night
|
10.0 (2 Reviews)
5 Bedrooms 10 Guests
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North Center - Modern, Safe, Family-Friendly, Solar-Powered Apartment
Apartment
North Center - Modern, Safe, Family-Friendly, Solar-Powered Apartment
From US $226 per night
10.0 (116 Reviews)
2 Bedrooms 6 Guests
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The Village Inn by Dakota Gal Digs
House
The Village Inn by Dakota Gal Digs
From US $710 per night
|
10.0 (2 Reviews)
3 Bedrooms 8 Guests
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Comfy 2BR Apartment near Wrigley Field - Grace 3
Apartment
Comfy 2BR Apartment near Wrigley Field - Grace 3
From US $500 per night
|
10.0 (2 Reviews)
2 Bedrooms 4 Guests
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Trendy 2BR Apartment in Logan Square!
Apartment
Trendy 2BR Apartment in Logan Square!
From US $233 per night
10.0 (84 Reviews)
2 Bedrooms 5 Guests
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MTM Fully Furnished Rental in Old Town - 2 beds
Apartment
MTM Fully Furnished Rental in Old Town - 2 beds
From US $90 per night
|
10.0 (1 Review)
2 Bedrooms 4 Guests
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Stylish, Inviting 2-BR near Logan Square and Wrigley Field
Apartment
Stylish, Inviting 2-BR near Logan Square and Wrigley Field
From US $219 per night
10.0 (58 Reviews)
2 Bedrooms 4 Guests
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EAST LAKEVIEW DESIGNER CONDO 2 BED/2 BATH, SLEEPS 6!
Condo
EAST LAKEVIEW DESIGNER CONDO 2 BED/2 BATH, SLEEPS 6!
From US $433 per night
10.0 (56 Reviews)
2 Bedrooms 6 Guests
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The Wrigleyville VIP-200 Steps from Wrigley Field
Apartment
The Wrigleyville VIP-200 Steps from Wrigley Field
From US $308 per night
|
9.7 (13 Reviews)
2 Bedrooms 6 Guests
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Stylish and Cute 2BR Apartment Near Wrigley!
Apartment
Stylish and Cute 2BR Apartment Near Wrigley!
From US $276 per night
10.0 (45 Reviews)
2 Bedrooms 4 Guests
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Lincoln Park Light-Filled Loft
Apartment
Lincoln Park Light-Filled Loft
From US $257 per night
9.7 (9 Reviews)
1 Bedroom 4 Guests
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The Roscoe Village Guesthouse
Apartment
The Roscoe Village Guesthouse
From US $360 per night
|
9.7 (8 Reviews)
3 Bedrooms 6 Guests
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Wrigley Field Views & Cubs Vibes – Stay Across the Street!
Apartment
Wrigley Field Views & Cubs Vibes – Stay Across the Street!
From US $564 per night
10.0 (40 Reviews)
2 Bedrooms 4 Guests
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Entire Apartment in heart of Lincoln Park & Lake Sea and beach
Apartment
Entire Apartment in heart of Lincoln Park & Lake Sea and beach
From US $181 per night
9.7 (3 Reviews)
1 Bedroom 4 Guests
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LOGAN SQUARE: Chic, Comfy 1st Floor 2 BDRM APT! Parking Incld!
House
LOGAN SQUARE: Chic, Comfy 1st Floor 2 BDRM APT! Parking Incld!
From US $185 per night
10.0 (38 Reviews)
2 Bedrooms 6 Guests
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4 Bedroom Home in Best Location Parking Fireplace Back Yard Pets Welcome
House
4 Bedroom Home in Best Location Parking Fireplace Back Yard Pets Welcome
From US $1,199 per night
|
9.6 (5 Reviews)
4 Bedrooms 18 Guests
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Bright and Cozy 1BR Apartment in Logan Square!
Apartment
Bright and Cozy 1BR Apartment in Logan Square!
From US $142 per night
10.0 (36 Reviews)
1 Bedroom 2 Guests
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Wrigley Oasis! Steps from the Field! - 3BD 1BA
Apartment
Wrigley Oasis! Steps from the Field! - 3BD 1BA
From US $131 per night
|
9.5 (40 Reviews)
3 Bedrooms 6 Guests
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Cozy two bedroom close to Wrigley Field
Apartment
Cozy two bedroom close to Wrigley Field
From US $385 per night
10.0 (35 Reviews)
2 Bedrooms 6 Guests
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Bucktown Private Condo
Apartment
Bucktown Private Condo
From US $151 per night
9.5 (23 Reviews)
2 Bedrooms 4 Guests
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❤️ Stylish and Cozy 2BR in Logan Square!
Apartment
❤️ Stylish and Cozy 2BR in Logan Square!
From US $191 per night
10.0 (35 Reviews)
2 Bedrooms 4 Guests
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Stone Mansion Sleeps 10-20 Free TV & Parking
Apartment
Stone Mansion Sleeps 10-20 Free TV & Parking
From US $447 per night
|
9.5 (2 Reviews)
4 Bedrooms 20 Guests
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Lovely Minimalist Loft in the heart of Lakeview
Apartment
Lovely Minimalist Loft in the heart of Lakeview
From US $320 per night
10.0 (33 Reviews)
2 Bedrooms 4 Guests
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Wrigleyville Inn - Garden Unit
Condo
Wrigleyville Inn - Garden Unit
From US $352 per night
10.0 (29 Reviews)
2 Bedrooms 4 Guests
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Chic Urban Retreat Near Wrigley Field w/Parking
Condo
Chic Urban Retreat Near Wrigley Field w/Parking
From US $449 per night
10.0 (23 Reviews)
2 Bedrooms 5 Guests
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Stylish Two Bedroom - A block from Wrigley Field
Apartment
Stylish Two Bedroom - A block from Wrigley Field
From US $405 per night
10.0 (23 Reviews)
2 Bedrooms 5 Guests
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1BR City Loft With Modern Glass Views
Apartment
1BR City Loft With Modern Glass Views
From US $267 per night
10.0 (1 Review)
1 Bedroom 4 Guests
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Ray's Bucktown Bed and Breakfast
Bed & Breakfast
Ray's Bucktown Bed and Breakfast
From US $271 per night
|
9.4 (202 Reviews)
11 Bedrooms 31 Guests
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Villa D' Citta
Bed & Breakfast
Villa D' Citta
From US $336 per night
|
9.4 (103 Reviews)
1 Bedroom 2 Guests
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Chic & Fully Furnished Urban Studio Apartment
Apartment
Chic & Fully Furnished Urban Studio Apartment
From US $263 per night
10.0 (1 Review)
2 Bedrooms 2 Guests
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The Avondale Guesthouse
House
The Avondale Guesthouse
From US $283 per night
|
9.4 (135 Reviews)
3 Bedrooms 6 Guests
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Dorothy's
Bed & Breakfast
Dorothy's
From US $116 per night
|
8.2 (73 Reviews)
1 Bedroom 2 Guests
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1BR Stylishly Apt in Lakeview
Apartment
1BR Stylishly Apt in Lakeview
From US $260 per night
10.0 (1 Review)
1 Bedroom 2 Guests
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Luxurious Lincoln Park Home with Gourmet Kitchen
Apartment
Luxurious Lincoln Park Home with Gourmet Kitchen
From US $683 per night
|
9.4 (5 Reviews)
4 Bedrooms 10 Guests
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The Villa Toscana
Bed & Breakfast
The Villa Toscana
From US $134 per night
7.8 (602 Reviews)
1 Bedroom 2 Guests
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Chic & Fully Furnished 2BR Apt!
Apartment
Chic & Fully Furnished 2BR Apt!
From US $218 per night
10.0 (1 Review)
2 Bedrooms 4 Guests
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The Sono Chicago
Bed & Breakfast
The Sono Chicago
From US $371 per night
|
9.3 (325 Reviews)
8 Bedrooms 7 Guests
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Chic & Stylish Studio w/Modern Kitchen
Apartment
Chic & Stylish Studio w/Modern Kitchen
From US $214 per night
10.0 (1 Review)
1 Bedroom 2 Guests
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Designer Themed 4 Bedroom in Best Location with Patio and Fireplace
House
Designer Themed 4 Bedroom in Best Location with Patio and Fireplace
From US $852 per night
|
9.3 (29 Reviews)
4 Bedrooms 14 Guests
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1BR Unit w/2 Comfy Beds
Apartment
1BR Unit w/2 Comfy Beds
From US $210 per night
10.0 (1 Review)
1 Bedroom 4 Guests
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Inspiring Grotto Sleeps 10-20 Free TV & Parking
Apartment
Inspiring Grotto Sleeps 10-20 Free TV & Parking
From US $360 per night
|
9.3 (3 Reviews)
4 Bedrooms 20 Guests
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The Lyons' Lair
Apartment
The Lyons' Lair
From US $239 per night
9.2 (17 Reviews)
2 Bedrooms 6 Guests
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One block from Lincoln Park and the zoo
Apartment
One block from Lincoln Park and the zoo
From US $302 per night
9.8 (112 Reviews)
1 Bedroom 3 Guests
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Boho Bliss - 1Br, 1Bath w/Patio!
Apartment
Boho Bliss - 1Br, 1Bath w/Patio!
From US $149 per night
9.2 (17 Reviews)
1 Bedroom 4 Guests
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Unique Chicago Penthouse Loft - Amazing Deal & Location
Bed & Breakfast
Unique Chicago Penthouse Loft - Amazing Deal & Location
From US $422 per night
9.8 (98 Reviews)
1 Bedroom 2 Guests
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City-View Chicago 3-BR Rooftop
Apartment
City-View Chicago 3-BR Rooftop
From US $519 per night
|
9.2 (16 Reviews)
3 Bedrooms 6 Guests
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The Wrigleyville VIP- 200 steps to Wrigley- Super Clean!
House
The Wrigleyville VIP- 200 steps to Wrigley- Super Clean!
From US $652 per night
9.8 (81 Reviews)
2 Bedrooms 6 Guests
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City Villa Sleeps 10-20 Free TV & Parking
Apartment
City Villa Sleeps 10-20 Free TV & Parking
From US $1,040 per night
|
9.2 (13 Reviews)
4 Bedrooms 20 Guests
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Classic Lincoln Park 2 bedroom condo- parking included
Condo
Classic Lincoln Park 2 bedroom condo- parking included
From US $355 per night
9.8 (74 Reviews)
2 Bedrooms 4 Guests
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Lincoln Park Light Filled Loft
Apartment
Lincoln Park Light Filled Loft
From US $326 per night
9.8 (67 Reviews)
1 Bedroom 4 Guests
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MAGNIFICENT NEW Home w/8 Beds & Free Parking
House
MAGNIFICENT NEW Home w/8 Beds & Free Parking
From US $900 per night
|
9.1 (6 Reviews)
4 Bedrooms 15 Guests
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About North Side Vacation Rentals

Explore over 1062 vacation rentals in North Side with SunSki Resorts. These accommodations, comprising vacation homes, cottages, cabins, and condos, boast excellent amenities at great value, ensuring comfort and luxury. Enhance your stay with SunSki Resorts in North Side for more space and value.

In search of last-minute deals or the best bargains on vacation rentals? With SunSki Resorts, you can conveniently compare various options and deals in North Side. Discover rentals with desirable amenities like swimming pools, hot tubs, and pet-friendly options. Find the ideal vacation rental in North Side tailored to your preferences. On average, these rentals offer 829.45 ft² of space, and are priced at an average of US $492 per night.

SunSki Resorts simplifies and secures the process of finding and comparing vacation rentals in North Side at prices typically 30-40% lower than hotels. Discover your perfect vacation rental and book now.

Other Places to Stay in North Side, IL


Lakeview 247 Properties
Lincoln Park 147 Properties
Logan Square 76 Properties
Lake View East 68 Properties
Old Town 53 Properties
Old Town Triangle 53 Properties
North Center 53 Properties
Wrigleyville 46 Properties
Avondale 44 Properties
Sheffield and DePaul 39 Properties
West Bucktown 33 Properties
Park West 24 Properties

Frequently Asked Questions About North Side?

What are the top vacation rentals in North Side?

How many SunSkiResorts vacation rentals or resorts are available in North Side?

Discover the ideal vacation rental in North Side with SunSki Resorts™. We provide an extensive selection of over 1062 properties, encompassing vacation homes, private villas, cottages, and more. Explore our listings to find the perfect place to stay for your upcoming trip to North Side.

Nearby Neighborhood (16)

Neighborhood Property Count
Downtown Chicago Vacation Rentals in Chicago, Illinois 1794
Near North Side Vacation Rentals in Chicago, Illinois 818
River North Vacation Rentals in Chicago, Illinois 486
West Town Vacation Rentals in Chicago, Illinois 298
Lakeview Vacation Rentals in Chicago, Illinois 247
Lincoln Park Vacation Rentals in Chicago, Illinois 147
Logan Square Vacation Rentals in Chicago, Illinois 76
Lake View East Vacation Rentals in Chicago, Illinois 68
Old Town Vacation Rentals in Chicago, Illinois 53
North Center Vacation Rentals in Chicago, Illinois 53
Wrigleyville Vacation Rentals in Chicago, Illinois 46
Avondale Vacation Rentals in Chicago, Illinois 44
Irving Park Vacation Rentals in Chicago, Illinois 43
Wicker Park Vacation Rentals in Chicago, Illinois 42
Gold Coast Vacation Rentals in Chicago, Illinois 38
Uptown Vacation Rentals in Chicago, Illinois 35

There are 1062 North Side, IL Vacation Rentals

Recently Booked Hotels, Resorts, or Rentals in North Side