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

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

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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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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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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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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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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Relaxing Studio with Private Patio Downtown Chicago
Apartment
Relaxing Studio with Private Patio Downtown Chicago
From US $526 per night
10.0 (2 Reviews)
1 Bedroom 4 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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The Neighborhood Hotel-Little Italy
Apartment
The Neighborhood Hotel-Little Italy
From US $126 per night
|
9.6 (202 Reviews)
1 Bedroom 2 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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West Loop High-End 2BR: Walkable, City Views
Apartment
West Loop High-End 2BR: Walkable, City Views
From US $541 per night
10.0 (1 Review)
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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West Loop Charm: Dining & Nightlife, Balcony
Apartment
West Loop Charm: Dining & Nightlife, Balcony
From US $516 per night
10.0 (1 Review)
2 Bedrooms 5 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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Prime Location 2BR: Balcony, Restful Night
Apartment
Prime Location 2BR: Balcony, Restful Night
From US $513 per night
10.0 (1 Review)
2 Bedrooms 5 Guests
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Quick Drive to Downtown Chicago & Early Check-In
Apartment
Quick Drive to Downtown Chicago & Early Check-In
From US $255 per night
10.0 (1 Review)
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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Cozy 2 Bed Home by West Loop with Parking & Laundry
Apartment
Cozy 2 Bed Home by West Loop with Parking & Laundry
From US $251 per night
10.0 (1 Review)
2 Bedrooms 4 Guests
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The Upscale Getaway Near Downtown
Apartment
The Upscale Getaway Near Downtown
From US $371 per night
|
8.0 (3 Reviews)
2 Bedrooms 6 Guests
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Chicago 1BR Condo w Free Gated Parking & Highspeed Internet
Condo
Chicago 1BR Condo w Free Gated Parking & Highspeed Internet
From US $237 per night
10.0 (1 Review)
1 Bedroom 5 Guests
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Avra Stylish Apartments Prime West Loop Location Near Union Park
Apartment
Avra Stylish Apartments Prime West Loop Location Near Union Park
From US $679 per night
|
7.8 (10 Reviews)
13 Bedrooms 32 Guests
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2BR Chic New Apartment With Rooftop Pool & Gym
Apartment
2BR Chic New Apartment With Rooftop Pool & Gym
From US $348 per night
|
7.8 (4 Reviews)
2 Bedrooms 6 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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Jeffjack Heated Pool Penthouse in Chicago's West Loop
Apartment
Jeffjack Heated Pool Penthouse in Chicago's West Loop
From US $323 per night
7.0 (4 Reviews)
2 Bedrooms 6 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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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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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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W Loop 1BR w Pool Gym nr Fulton Mkt CHI-293
Apartment
W Loop 1BR w Pool Gym nr Fulton Mkt CHI-293
From US $150 per night
|
New
1 Bedroom 2 Guests
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Sleek 2 Bed, 2 Bath Condo in Trendy Fulton Market
Apartment
Sleek 2 Bed, 2 Bath Condo in Trendy Fulton Market
From US $418 per night
9.6 (11 Reviews)
2 Bedrooms 6 Guests
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West Loop Oasis: Walk to Dining, Private Balcony
Apartment
West Loop Oasis: Walk to Dining, Private Balcony
From US $562 per night
9.6 (4 Reviews)
2 Bedrooms 5 Guests
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Unforgettable Stay: High End 2BR, Easy City Access
Apartment
Unforgettable Stay: High End 2BR, Easy City Access
From US $508 per night
9.6 (4 Reviews)
2 Bedrooms 5 Guests
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2 Bedroom Medical District
Apartment
2 Bedroom Medical District
From US $276 per night
9.6 (4 Reviews)
2 Bedrooms 7 Guests
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Breathtaking & Bright: Designer 2BD with Garage
Apartment
Breathtaking & Bright: Designer 2BD with Garage
From US $211 per night
9.4 (3 Reviews)
1 Bedroom 6 Guests
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Elizabeth by Coast to Cactus | Chic Artists Loft
Condo
Elizabeth by Coast to Cactus | Chic Artists Loft
From US $265 per night
9.2 (21 Reviews)
2 Bedrooms 6 Guests
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W Loop Studio w Gym Pool Coworking nr UIC CHI-439
Apartment
W Loop Studio w Gym Pool Coworking nr UIC CHI-439
From US $129 per night
|
New
1 Bedroom 2 Guests
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Nobu Hotel Chicago
Hotel
Nobu Hotel Chicago
From US $398 per night
|
9.4 (715 Reviews)
1 Bedroom 2 Guests
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W Loop Studio w Gym Pool Coworking nr UIC CHI-397
Apartment
W Loop Studio w Gym Pool Coworking nr UIC CHI-397
From US $100 per night
|
New
1 Bedroom 2 Guests
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The Emily Hotel
Hotel
The Emily Hotel
From US $246 per night
|
9.2 (1141 Reviews)
1 Bedroom 2 Guests
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Modern 2BR2BA Condo Free Parking and Balcony
Apartment
Modern 2BR2BA Condo Free Parking and Balcony
From US $338 per night
New
2 Bedrooms 4 Guests
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Spacious 3-Bed West Loop Townhouse, 1 Car Garage
House
Spacious 3-Bed West Loop Townhouse, 1 Car Garage
From US $513 per night
|
New
3 Bedrooms 8 Guests
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Hampton Inn Chicago West Loop Fulton Market Area
Hotel
Hampton Inn Chicago West Loop Fulton Market Area
From US $169 per night
9.2 (1008 Reviews)
1 Bedroom 2 Guests
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2 Br 1 Free Parking Gym
Apartment
2 Br 1 Free Parking Gym
From US $295 per night
|
New
2 Bedrooms 4 Guests
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Chicago Modern Condo 2BR2BA, Balcony, Free Park
Apartment
Chicago Modern Condo 2BR2BA, Balcony, Free Park
From US $331 per night
New
2 Bedrooms 4 Guests
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W Loop Studio w Pool Gym nr Restaurant Row CHI-264
Apartment
W Loop Studio w Pool Gym nr Restaurant Row CHI-264
From US $147 per night
New
1 Bedroom 2 Guests
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Sun-Drenched 1BR Apartment
Apartment
Sun-Drenched 1BR Apartment
From US $315 per night
New
1 Bedroom 2 Guests
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Blueground | West Loop, rooftop pool & gym
Apartment
Blueground | West Loop, rooftop pool & gym
From US $308 per night
New
2 Bedrooms 4 Guests
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Hampton Inn & Suites Chicago Medical District Uic
Hotel
Hampton Inn & Suites Chicago Medical District Uic
From US $238 per night
|
9.1 (136 Reviews)
135 Bedrooms 32 Guests
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Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area
Hotel
Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area
From US $211 per night
|
8.9 (500 Reviews)
7 Bedrooms 30 Guests
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Nobu Hotel Chicago
Hotel
Nobu Hotel Chicago
From US $440 per night
|
8.9 (428 Reviews)
104 Bedrooms 14 Guests
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1BR Modern Luxe Apt with In-Unit Laundry
Apartment
1BR Modern Luxe Apt with In-Unit Laundry
From US $275 per night
New
1 Bedroom 2 Guests
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The Emily Hotel
Hotel
The Emily Hotel
From US $283 per night
|
8.9 (358 Reviews)
150 Bedrooms 18 Guests
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Level Chicago Fulton Market
Hotel
Level Chicago Fulton Market
From US $235 per night
|
8.9 (58 Reviews)
56 Bedrooms 26 Guests
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About Near West Side Vacation Rentals

Explore over 517 vacation rentals in Near 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 Near 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 Near West Side. Discover rentals with desirable amenities like swimming pools, hot tubs, and pet-friendly options. Find the ideal vacation rental in Near West Side tailored to your preferences. On average, these rentals offer 653.53 ft² of space, and are priced at an average of US $327 per night.

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

Other Places to Stay in Near West Side, IL


Mars Gallery 4,474 Properties
Fulton Market 4,451 Properties
Packer Schopf Gallery 4,446 Properties
Union Park 4,396 Properties
threewalls 4,391 Properties
Pitchfork Music Festival 4,374 Properties
Greektown 4,320 Properties
Illinois Medical District 3,502 Properties
West Loop 200 Properties
University Village / Little Italy 88 Properties
Tri-Taylor 26 Properties
West Loop Gate 24 Properties

Frequently Asked Questions About Near West Side?

What are the top vacation rentals in Near West Side?

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

Discover the ideal vacation rental in Near West Side with SunSki Resorts™. We provide an extensive selection of over 517 properties, encompassing vacation homes, private villas, cottages, and more. Explore our listings to find the perfect place to stay for your upcoming trip to Near West Side.

Nearby Neighborhood (13)

Neighborhood Property Count
Downtown Chicago Vacation Rentals in Chicago, Illinois 1794
West Loop Vacation Rentals in Chicago, Illinois 200
University Village / Little Italy Vacation Rentals in Chicago, Illinois 88
Lower West Side Vacation Rentals in Chicago, Illinois 44
Tri-Taylor Vacation Rentals in Chicago, Illinois 26
Heart of Chicago Vacation Rentals in Chicago, Illinois 26
West Loop Gate Vacation Rentals in Chicago, Illinois 24
Pilsen Vacation Rentals in Chicago, Illinois 3300
Illinois Medical District Vacation Rentals in Chicago, Illinois 3502
North Lawndale Vacation Rentals in Chicago, Illinois 443
Lawndale Vacation Rentals in Chicago, Illinois 435
Greektown Vacation Rentals in Chicago, Illinois 4320
Fulton Market Vacation Rentals in Chicago, Illinois 4451

There are 517 Near West Side, IL Vacation Rentals

Recently Booked Hotels, Resorts, or Rentals in Near West Side