Chicago Vacation Rentals & Ski-in/Ski-out Homes

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

Modern One Bedroom Apartment 35 miles to Chicago
Apartment
Modern One Bedroom Apartment 35 miles to Chicago
From US $80 per night
10.0 (2 Reviews)
1 Bedroom 2 Guests
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Hip Urban Loft-Small Town Charm-124 LOFTS #2
Apartment
Hip Urban Loft-Small Town Charm-124 LOFTS #2
From US $171 per night
|
10.0 (20 Reviews)
1 Bedroom 2 Guests
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2 Bedroom Modern Apartment 35 miles to Chicago
Apartment
2 Bedroom Modern Apartment 35 miles to Chicago
From US $79 per night
10.0 (2 Reviews)
2 Bedrooms 2 Guests
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King Bed, Personal Parking & In-Unit Laundry!
Apartment
King Bed, Personal Parking & In-Unit Laundry!
From US $190 per night
10.0 (6 Reviews)
1 Bedroom 5 Guests
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1BR+Office Apt. Chicago South Suburbs Near Indiana
Apartment
1BR+Office Apt. Chicago South Suburbs Near Indiana
From US $161 per night
10.0 (1 Review)
1 Bedroom 3 Guests
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Hip Urban Loft - Small Town Charm -124 LOFTS #3
Apartment
Hip Urban Loft - Small Town Charm -124 LOFTS #3
From US $160 per night
|
10.0 (16 Reviews)
1 Bedroom 2 Guests
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Dubois Guest House Room 202
Bed & Breakfast
Dubois Guest House Room 202
From US $194 per night
2.0 (1 Review)
1 Bedroom 2 Guests
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Relaxing 2 Bdrm Guest Suite w/Kit. & Pvt. Entry
House
Relaxing 2 Bdrm Guest Suite w/Kit. & Pvt. Entry
From US $143 per night
10.0 (1 Review)
2 Bedrooms 4 Guests
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Private lower level 2 Bedroom guest space.
Apartment
Private lower level 2 Bedroom guest space.
From US $174 per night
9.8 (17 Reviews)
2 Bedrooms 4 Guests
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Uptown Gem
Apartment
Uptown Gem
From US $117 per night
|
10.0 (12 Reviews)
1 Bedroom 4 Guests
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Relaxing Riverfront Home with Pier
House
Relaxing Riverfront Home with Pier
From US $242 per night
9.8 (15 Reviews)
2 Bedrooms 5 Guests
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Well-Appointed Cozy Portage Park Apt, Dogs, Kids, Free Parking, 420 Compliant
Apartment
Well-Appointed Cozy Portage Park Apt, Dogs, Kids, Free Parking, 420 Compliant
From US $107 per night
|
10.0 (10 Reviews)
3 Bedrooms 10 Guests
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Private Plainfield Retreat w/Gas Grill + Patio
House
Private Plainfield Retreat w/Gas Grill + Patio
From US $213 per night
9.4 (6 Reviews)
1 Bedroom 3 Guests
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Historic Oakpark Home
Apartment
Historic Oakpark Home
From US $268 per night
|
10.0 (6 Reviews)
3 Bedrooms 8 Guests
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Cozy Steger Apartment w/Patio: 30 Mi to Chicago!
Apartment
Cozy Steger Apartment w/Patio: 30 Mi to Chicago!
From US $218 per night
8.0 (3 Reviews)
3 Bedrooms 4 Guests
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Stunning home in Skokie
House
Stunning home in Skokie
From US $727 per night
10.0 (6 Reviews)
4 Bedrooms 8 Guests
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An Intimate & cozy event space
House
An Intimate & cozy event space
From US $387 per night
New
1 Bedroom 1 Guest
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Friendly Suite Home Chicago
Apartment
Friendly Suite Home Chicago
From US $113 per night
10.0 (6 Reviews)
2 Bedrooms 6 Guests
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Large Private Studio Apartment
Apartment
Large Private Studio Apartment
From US $262 per night
New
1 Bedroom 2 Guests
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Downtown Luxury Farmhouse Apartment #3
Apartment
Downtown Luxury Farmhouse Apartment #3
From US $192 per night
|
10.0 (5 Reviews)
1 Bedroom 2 Guests
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Downtown Luxury Farmhouse Apartment #2
Apartment
Downtown Luxury Farmhouse Apartment #2
From US $191 per night
|
10.0 (5 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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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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2BR+Office Apt. Chicago South Suburbs Near Indiana
Apartment
2BR+Office Apt. Chicago South Suburbs Near Indiana
From US $195 per night
New
2 Bedrooms 5 Guests
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Fenced Yard Fox River Grove Home, Dogs Welcome
House
Fenced Yard Fox River Grove Home, Dogs Welcome
From US $338 per night
|
10.0 (4 Reviews)
3 Bedrooms 7 Guests
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Elegant and Chic 2Bed 2Bath steps from the lake!
Apartment
Elegant and Chic 2Bed 2Bath steps from the lake!
From US $263 per night
10.0 (4 Reviews)
2 Bedrooms 4 Guests
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Odd Fellows Retreat
Apartment
Odd Fellows Retreat
From US $139 per night
New
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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Newly updated surrounded by nature
House
Newly updated surrounded by nature
From US $95 per night
New
2 Bedrooms 5 Guests
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Lux Apts with Lake Views and Top Amenities
Apartment
Lux Apts with Lake Views and Top Amenities
From US $1,582 per night
|
10.0 (3 Reviews)
13 Bedrooms 32 Guests
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In Town Apartment in downtown Geneva!
Apartment
In Town Apartment in downtown Geneva!
From US $187 per night
10.0 (47 Reviews)
2 Bedrooms 6 Guests
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Urban Oasis - Kid Friendly - Quiet Street
House
Urban Oasis - Kid Friendly - Quiet Street
From US $715 per night
|
10.0 (3 Reviews)
3 Bedrooms 8 Guests
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Tudor house stay-In Town Location!
Apartment
Tudor house stay-In Town Location!
From US $201 per night
10.0 (46 Reviews)
2 Bedrooms 4 Guests
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The Tailor House
House
The Tailor House
From US $278 per night
10.0 (44 Reviews)
2 Bedrooms 5 Guests
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Horse Country Quonset Home
House
Horse Country Quonset Home
From US $142 per night
10.0 (37 Reviews)
1 Bedroom 3 Guests
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- Fully-Equipped Condo - King Bed - Massive yard -
House
- Fully-Equipped Condo - King Bed - Massive yard -
From US $304 per night
10.0 (31 Reviews)
2 Bedrooms 8 Guests
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The Yates Loft - Downtown Geneva
Apartment
The Yates Loft - Downtown Geneva
From US $355 per night
10.0 (20 Reviews)
2 Bedrooms 4 Guests
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Hip Urban Loft-Small Town Charm - 124 LOFTS #3
Apartment
Hip Urban Loft-Small Town Charm - 124 LOFTS #3
From US $209 per night
10.0 (17 Reviews)
1 Bedroom 2 Guests
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Spacious Ranch blocks away from downtown McHenry
House
Spacious Ranch blocks away from downtown McHenry
From US $351 per night
9.8 (15 Reviews)
2 Bedrooms 7 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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Charming Downtown Farmhouse Apartment #1
Apartment
Charming Downtown Farmhouse Apartment #1
From US $243 per night
9.8 (10 Reviews)
1 Bedroom 2 Guests
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Luxurious New Remodeled
Apartment
Luxurious New Remodeled
From US $312 per night
|
10.0 (3 Reviews)
1 Bedroom 4 Guests
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Villa Dubois Guest House Room 5
Bed & Breakfast
Villa Dubois Guest House Room 5
From US $241 per night
New
1 Bedroom 2 Guests
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Stylish 2BR stunner in unbeatable location
Apartment
Stylish 2BR stunner in unbeatable location
From US $194 per night
|
10.0 (3 Reviews)
2 Bedrooms 6 Guests
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Modern 3 BR Apt - 5 Mins to Downtown Sleeps 10
Apartment
Modern 3 BR Apt - 5 Mins to Downtown Sleeps 10
From US $309 per night
New
3 Bedrooms 10 Guests
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The Brown House - A luxurious UChicago Campus stay
Apartment
The Brown House - A luxurious UChicago Campus stay
From US $407 per night
10.0 (3 Reviews)
3 Bedrooms 6 Guests
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Luxury Suite in Glen Ellyn
Apartment
Luxury Suite in Glen Ellyn
From US $293 per night
10.0 (3 Reviews)
2 Bedrooms 2 Guests
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Beautiful lake house tucked away in quiet neighborhood
House
Beautiful lake house tucked away in quiet neighborhood
From US $106 per night
9.6 (19 Reviews)
2 Bedrooms 6 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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*Cozy home near downtown and fox river*
House
*Cozy home near downtown and fox river*
From US $193 per night
9.6 (13 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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Riverfront Cottage/sauna/nkayaks/dock/firepit
Cottage
Riverfront Cottage/sauna/nkayaks/dock/firepit
From US $233 per night
9.6 (4 Reviews)
1 Bedroom 4 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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Keyless, KING bd, WIFI, desk, Fox River Bike Trail, near MetraTrain
Apartment
Keyless, KING bd, WIFI, desk, Fox River Bike Trail, near MetraTrain
From US $213 per night
9.4 (29 Reviews)
2 Bedrooms 6 Guests
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House in the Park 5 Min from O'Hare
House
House in the Park 5 Min from O'Hare
From US $342 per night
|
10.0 (2 Reviews)
4 Bedrooms 10 Guests
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About Chicago Vacation Rentals

Explore over 10575 vacation rentals in Chicago 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 Chicago 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 Chicago. Discover rentals with desirable amenities like swimming pools, hot tubs, and pet-friendly options. Find the ideal vacation rental in Chicago tailored to your preferences. On average, these rentals offer 754.97 ft² of space, and are priced at an average of US $362 per night.

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

Other Places to Stay in Chicago, IL


Cook County 5,637 Properties
Chicago 4,272 Properties
Central Chicago 1,959 Properties
Downtown Chicago 1,794 Properties
Near North Side 818 Properties
The Loop 776 Properties
West Side 742 Properties
North Side 589 Properties
Lake County 562 Properties
DuPage County 538 Properties
River North 486 Properties
South Side 381 Properties

Frequently Asked Questions About Chicago?

What are the top vacation rentals in Chicago?

How many SunSkiResorts vacation rentals or resorts are available in Chicago?

Discover the ideal vacation rental in Chicago with SunSki Resorts™. We provide an extensive selection of over 10575 properties, encompassing vacation homes, private villas, cottages, and more. Explore our listings to find the perfect place to stay for your upcoming trip to Chicago.

Nearby Neighborhood (16)

Neighborhood Property Count
Downtown Chicago Vacation Rentals in Chicago, Illinois 1794
Near North Side Vacation Rentals in Chicago, Illinois 818
The Loop Vacation Rentals in Chicago, Illinois 776
River North Vacation Rentals in Chicago, Illinois 486
South Loop Vacation Rentals in Chicago, Illinois 375
Near South Side Vacation Rentals in Chicago, Illinois 363
Lakeview Vacation Rentals in Chicago, Illinois 247
West Loop Vacation Rentals in Chicago, Illinois 200
Lincoln Park Vacation Rentals in Chicago, Illinois 147
Hyde Park Vacation Rentals in Chicago, Illinois 86
Logan Square Vacation Rentals in Chicago, Illinois 76
Rogers Park Vacation Rentals in Chicago, Illinois 67
O'Hare Vacation Rentals in Chicago, Illinois 66
Edgewater Vacation Rentals in Chicago, Illinois 55
Wrigleyville Vacation Rentals in Chicago, Illinois 46
Wicker Park Vacation Rentals in Chicago, Illinois 42

There are 10575 Chicago, IL Vacation Rentals

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