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

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

New Blueground | West Town, pets allowed, nr Park
Apartment
Blueground | West Town, pets allowed, nr Park
From US $158 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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New Blueground | West Town, washer, nr Chicago River
Apartment
Blueground | West Town, washer, nr Chicago River
From US $111 per night
New
1 Bedroom 2 Guests
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Freshly Minted 2BR - Elegance & Comfort in Central Chicago
Apartment
Freshly Minted 2BR - Elegance & Comfort in Central Chicago
From US $349 per night
|
10.0 (2 Reviews)
2 Bedrooms 6 Guests
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The Publishing House B&B
Bed & Breakfast
The Publishing House B&B
From US $239 per night
|
9.8 (181 Reviews)
1 Bedroom 2 Guests
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New Blueground | West Town, washer, nr Chicago River
Apartment
Blueground | West Town, washer, nr Chicago River
From US $106 per night
New
1 Bedroom 2 Guests
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Wicker Park Inn
Bed & Breakfast
Wicker Park Inn
From US $307 per night
|
9.0 (249 Reviews)
1 Bedroom 2 Guests
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New Spacious Pilsen 4 Bed 4 Bath Family Retreat
Apartment
Spacious Pilsen 4 Bed 4 Bath Family Retreat
From US $479 per night
New
4 Bedrooms 8 Guests
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Luxury 2BD-2BA View-Gym-Rooftop
Apartment
Luxury 2BD-2BA View-Gym-Rooftop
From US $590 per night
|
10.0 (1 Review)
2 Bedrooms 4 Guests
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New Chicago Citrus Charm 2BR WestTown
Apartment
Chicago Citrus Charm 2BR WestTown
From US $249 per night
New
2 Bedrooms 6 Guests
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Modern River West 2BR with W&D by Zencity
Apartment
Modern River West 2BR with W&D by Zencity
From US $77 per night
|
10.0 (1 Review)
2 Bedrooms 3 Guests
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New Cozy Garden Apartment in Chicago
Apartment
Cozy Garden Apartment in Chicago
From US $177 per night
New
2 Bedrooms 4 Guests
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Amazing Penthouse Skyline Views!
House
Amazing Penthouse Skyline Views!
From US $1,237 per night
10.0 (1 Review)
3 Bedrooms 14 Guests
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New Artsy Chicago - 1BR/1BATH
Condo
Artsy Chicago - 1BR/1BATH
From US $163 per night
New
1 Bedroom 4 Guests
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2 Bedroom Home near West Loop with Parking
Apartment
2 Bedroom Home near West Loop with Parking
From US $352 per night
10.0 (1 Review)
2 Bedrooms 4 Guests
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NEW LUXURY PENTHOUSE CONDO
Condo
NEW LUXURY PENTHOUSE CONDO
From US $385 per night
10.0 (189 Reviews)
2 Bedrooms 9 Guests
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Spacious and Modern 3BD 2BA Home- Garage Parking!
Apartment
Spacious and Modern 3BD 2BA Home- Garage Parking!
From US $299 per night
10.0 (1 Review)
3 Bedrooms 8 Guests
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NEW LUXURY CONDO WITH PATIO DECK
Condo
NEW LUXURY CONDO WITH PATIO DECK
From US $304 per night
10.0 (180 Reviews)
1 Bedroom 5 Guests
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1F Cozy Home in Little Italy near Downtown West Loop United Center
Apartment
1F Cozy Home in Little Italy near Downtown West Loop United Center
From US $172 per night
|
9.9 (74 Reviews)
3 Bedrooms 6 Guests
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Private Historic Coach House Wicker Park
House
Private Historic Coach House Wicker Park
From US $411 per night
10.0 (65 Reviews)
2 Bedrooms 5 Guests
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Avenir West Loop Penthouses with Iconic City Views
Apartment
Avenir West Loop Penthouses with Iconic City Views
From US $1,192 per night
|
9.8 (6 Reviews)
10 Bedrooms 24 Guests
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Entire Below Level Studio w/Private Sauna
Apartment
Entire Below Level Studio w/Private Sauna
From US $248 per night
10.0 (51 Reviews)
1 Bedroom 3 Guests
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First Floor Condo In Chicago
Apartment
First Floor Condo In Chicago
From US $178 per night
9.7 (15 Reviews)
2 Bedrooms 12 Guests
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Sage Modern Apartments Near Union Park in West Loop
Apartment
Sage Modern Apartments Near Union Park in West Loop
From US $336 per night
|
9.7 (14 Reviews)
6 Bedrooms 15 Guests
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Cozy Vintage Chicago Apartment near Downtown
Apartment
Cozy Vintage Chicago Apartment near Downtown
From US $202 per night
10.0 (25 Reviews)
1 Bedroom 4 Guests
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Spacious & private! Free parking! Great location!
Apartment
Spacious & private! Free parking! Great location!
From US $169 per night
10.0 (25 Reviews)
2 Bedrooms 2 Guests
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Spacious 5-BR House near Transit w Parking
House
Spacious 5-BR House near Transit w Parking
From US $941 per night
|
9.6 (13 Reviews)
5 Bedrooms 16 Guests
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Trendy West Town Flat - 2 bed/1.5 bath with parking
Condo
Trendy West Town Flat - 2 bed/1.5 bath with parking
From US $331 per night
10.0 (23 Reviews)
2 Bedrooms 5 Guests
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Fulbrix Bright Designer Apartments with West Loop Views
Apartment
Fulbrix Bright Designer Apartments with West Loop Views
From US $872 per night
|
9.5 (34 Reviews)
13 Bedrooms 32 Guests
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iKlektik House/Cardinal
Apartment
iKlektik House/Cardinal
From US $199 per night
|
9.5 (4 Reviews)
1 Bedroom 3 Guests
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Bucktown Private Condo
Condo
Bucktown Private Condo
From US $379 per night
10.0 (11 Reviews)
2 Bedrooms 4 Guests
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Superior
Apartment
Superior
From US $120 per night
|
9.4 (35 Reviews)
3 Bedrooms 9 Guests
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Unbeatable Top Floor: Views, Central, Modern
Apartment
Unbeatable Top Floor: Views, Central, Modern
From US $619 per night
10.0 (6 Reviews)
2 Bedrooms 6 Guests
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The Velvet Jazz Haus
Apartment
The Velvet Jazz Haus
From US $281 per night
|
9.4 (8 Reviews)
1 Bedroom 6 Guests
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Vital Urban: Spa Inspired Retreat
House
Vital Urban: Spa Inspired Retreat
From US $485 per night
10.0 (6 Reviews)
2 Bedrooms 6 Guests
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Spacious loft in the heart of West Town, Noble Square Chicago
Apartment
Spacious loft in the heart of West Town, Noble Square Chicago
From US $210 per night
10.0 (6 Reviews)
1 Bedroom 4 Guests
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Ukrainian Village Hideaway
House
Ukrainian Village Hideaway
From US $186 per night
10.0 (5 Reviews)
1 Bedroom 4 Guests
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River North Central Home With Balcony
Apartment
River North Central Home With Balcony
From US $347 per night
10.0 (4 Reviews)
2 Bedrooms 5 Guests
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Charming 2-bedroom apartment in hip Chicago
Apartment
Charming 2-bedroom apartment in hip Chicago
From US $288 per night
10.0 (4 Reviews)
2 Bedrooms 4 Guests
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Stylish 1BR in West Loop
Apartment
Stylish 1BR in West Loop
From US $270 per night
10.0 (4 Reviews)
1 Bedroom 2 Guests
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Cozy West Loop 1BR w/Pool, Gym, nr. Restaurant Row, by Blueground
Apartment
Cozy West Loop 1BR w/Pool, Gym, nr. Restaurant Row, by Blueground
From US $173 per night
10.0 (1 Review)
1 Bedroom 2 Guests
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Quick Drive to Downtown Chicago & Early Check-In
Apartment
Quick Drive to Downtown Chicago & Early Check-In
From US $294 per night
9.3 (3 Reviews)
2 Bedrooms 4 Guests
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Art Villa
Apartment
Art Villa
From US $1,240 per night
|
10.0 (2 Reviews)
1 Bedroom 2 Guests
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iKlektik House/Robin
Apartment
iKlektik House/Robin
From US $166 per night
10.0 (1 Review)
1 Bedroom 2 Guests
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Cabin 105 by 747 Lofts
Apartment
Cabin 105 by 747 Lofts
From US $139 per night
10.0 (1 Review)
1 Bedroom 2 Guests
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Fresh Stylish Apartment
Apartment
Fresh Stylish Apartment
From US $108 per night
10.0 (1 Review)
2 Bedrooms 5 Guests
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Private Balcony 1 Garage Parking Sleeps 6
Apartment
Private Balcony 1 Garage Parking Sleeps 6
From US $328 per night
|
9.2 (8 Reviews)
2 Bedrooms 8 Guests
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Hampton Inn & Suites Chicago Medical District UIC
Hotel
Hampton Inn & Suites Chicago Medical District UIC
From US $215 per night
9.6 (246 Reviews)
1 Bedroom 2 Guests
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Rustic Mix
Apartment
Rustic Mix
From US $206 per night
|
9.1 (42 Reviews)
2 Bedrooms 4 Guests
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Smart West Loop Studio w/Pool, Gym, nr. Fulton Market, by Blueground
Apartment
Smart West Loop Studio w/Pool, Gym, nr. Fulton Market, by Blueground
From US $104 per night
10.0 (1 Review)
1 Bedroom 2 Guests
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Chicago Treasure 4 Bed Getaway
House
Chicago Treasure 4 Bed Getaway
From US $290 per night
|
9.1 (6 Reviews)
4 Bedrooms 10 Guests
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Wicker Park 2BR Modern Apartment DV3
Apartment
Wicker Park 2BR Modern Apartment DV3
From US $396 per night
9.0 (18 Reviews)
2 Bedrooms 5 Guests
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Hip West Loop Studio w/Gym & Coworking, nr UIC, by Blueground
Apartment
Hip West Loop Studio w/Gym & Coworking, nr UIC, by Blueground
From US $97 per night
10.0 (1 Review)
1 Bedroom 2 Guests
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Charming Chicago Apt
Apartment
Charming Chicago Apt
From US $353 per night
|
9.0 (8 Reviews)
2 Bedrooms 6 Guests
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Cozy Charming Art 🎨 Food🌮 Close to Train 🚉 Parking!
Apartment
Cozy Charming Art 🎨 Food🌮 Close to Train 🚉 Parking!
From US $211 per night
9.8 (93 Reviews)
2 Bedrooms 4 Guests
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1BR Adorable Apt with In-unit Laundry - Lake 206 rep
Apartment
1BR Adorable Apt with In-unit Laundry - Lake 206 rep
From US $658 per night
|
9.0 (3 Reviews)
1 Bedroom 2 Guests
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The Upscale Getaway Near Downtown
Condo
The Upscale Getaway Near Downtown
From US $305 per night
9.8 (89 Reviews)
2 Bedrooms 6 Guests
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Spacious Chicago Condo with Deck Less Than 9 Mi to Downtown!
Apartment
Spacious Chicago Condo with Deck Less Than 9 Mi to Downtown!
From US $267 per night
|
9.0 (3 Reviews)
4 Bedrooms 12 Guests
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iKlektik House/Robin
Apartment
iKlektik House/Robin
From US $281 per night
|
9.0 (1 Review)
1 Bedroom 2 Guests
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Wicker Park Inn
Bed & Breakfast
Wicker Park Inn
From US $306 per night
|
8.9 (48 Reviews)
8 Bedrooms 18 Guests
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Bucktown Condo Just Two Blocks from the L by AllSet Turnover
Condo
Bucktown Condo Just Two Blocks from the L by AllSet Turnover
From US $254 per night
9.8 (9 Reviews)
2 Bedrooms 4 Guests
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Red Robin Rentals - Wicker Park
Apartment
Red Robin Rentals - Wicker Park
From US $308 per night
|
8.7 (15 Reviews)
3 Bedrooms 10 Guests
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About West Side Vacation Rentals

Explore over 1281 vacation rentals in West 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 West 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 West Side. Discover rentals with desirable amenities like swimming pools, hot tubs, and pet-friendly options. Find the ideal vacation rental in West Side tailored to your preferences. On average, these rentals offer 762.12 ft² of space, and are priced at an average of US $367 per night.

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

Other Places to Stay in West Side, IL


Near West Side 331 Properties
West Town 298 Properties
West Loop 200 Properties
East Village 153 Properties
University Village / Little Italy 88 Properties
River West 51 Properties
Lower West Side 44 Properties
Wicker Park 42 Properties
Pulaski Park 33 Properties
Noble Square 33 Properties
Tri-Taylor 26 Properties
Heart of Chicago 26 Properties

Frequently Asked Questions About West Side?

What are the top vacation rentals in West Side?

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

Discover the ideal vacation rental in West Side with SunSki Resorts™. We provide an extensive selection of over 1281 properties, encompassing vacation homes, private villas, cottages, and more. Explore our listings to find the perfect place to stay for your upcoming trip to West Side.

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
Near West Side Vacation Rentals in Chicago, Illinois 331
West Town Vacation Rentals in Chicago, Illinois 298
West Loop Vacation Rentals in Chicago, Illinois 200
Lincoln Park Vacation Rentals in Chicago, Illinois 147
University Village / Little Italy Vacation Rentals in Chicago, Illinois 88
Logan Square Vacation Rentals in Chicago, Illinois 76
Wicker Park Vacation Rentals in Chicago, Illinois 42
Belmont Cragin Vacation Rentals in Chicago, Illinois 24
Bucktown Vacation Rentals in Chicago, Illinois 1151
Austin Vacation Rentals in Chicago, Illinois 159
Pilsen Vacation Rentals in Chicago, Illinois 3300
Chinatown Vacation Rentals in Chicago, Illinois 3053

There are 1281 West Side, IL Vacation Rentals

Recently Booked Hotels, Resorts, or Rentals in West Side