Near West Side Holiday Rentals

Compare Villas, Resorts, & Rentals in Near West Side, Chicago, Illinois, USA

New Gym, Garage Parking, Balcony, Sleeps 4
Apartment
Gym, Garage Parking, Balcony, Sleeps 4
From US $356 per night
New
2 Bedrooms 4 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 $230 per night
|
9.8 (186 Reviews)
1 Bedroom 2 Guests
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New Gym | Garage Parking | Balcony | Sleeps 6
Apartment
Gym | Garage Parking | Balcony | Sleeps 6
From US $348 per night
New
2 Bedrooms 6 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 $105 per night
9.6 (306 Reviews)
1 Bedroom 2 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 (215 Reviews)
1 Bedroom 3 Guests
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New Arcade, Free Parking, Sleeps 8!
Apartment
Arcade, Free Parking, Sleeps 8!
From US $391 per night
New
2 Bedrooms 8 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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Top Floor Views + Central Comfort
Apartment
Top Floor Views + Central Comfort
From US $438 per night
10.0 (8 Reviews)
2 Bedrooms 6 Guests
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Cozy 1 BR 1 Parking Sleeps 4
Apartment
Cozy 1 BR 1 Parking Sleeps 4
From US $265 per night
9.7 (10 Reviews)
1 Bedroom 4 Guests
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Stylish 1BR in West Loop
Apartment
Stylish 1BR in West Loop
From US $219 per night
10.0 (6 Reviews)
1 Bedroom 2 Guests
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Chic 2 BR 1 Parking Sleeps 6
Apartment
Chic 2 BR 1 Parking Sleeps 6
From US $368 per night
|
9.7 (4 Reviews)
2 Bedrooms 6 Guests
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Stylish 2BR Retreat in Fulton Market for Getaways
Apartment
Stylish 2BR Retreat in Fulton Market for Getaways
From US $520 per night
10.0 (2 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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Relaxing Studio with Private Patio Downtown Chicago
Apartment
Relaxing Studio with Private Patio Downtown Chicago
From US $507 per night
10.0 (2 Reviews)
1 Bedroom 4 Guests
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New 3Bed 3Bath Condo with Parking by United Center
Apartment
New 3Bed 3Bath Condo with Parking by United Center
From US $180 per night
|
9.3 (3 Reviews)
3 Bedrooms 6 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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Brand New Building in the Medical District!
Apartment
Brand New Building in the Medical District!
From US $225 per night
10.0 (2 Reviews)
3 Bedrooms 4 Guests
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High-End West Loop 2BR + City Views & Walkability
Apartment
High-End West Loop 2BR + City Views & Walkability
From US $420 per night
10.0 (1 Review)
2 Bedrooms 5 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
Apartment
The Upscale Getaway Near Downtown
From US $371 per night
|
8.0 (3 Reviews)
2 Bedrooms 6 Guests
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Panoramic City Views + Prime West Loop Location
Apartment
Panoramic City Views + Prime West Loop Location
From US $433 per night
10.0 (1 Review)
2 Bedrooms 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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City Views + Walk to Dining, Ideal for All
Apartment
City Views + Walk to Dining, Ideal for All
From US $388 per night
10.0 (1 Review)
2 Bedrooms 5 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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Sun-Drenched 1BR Apartment
Apartment
Sun-Drenched 1BR Apartment
From US $261 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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Quick Drive to Downtown Chicago & Early Check-In
Apartment
Quick Drive to Downtown Chicago & Early Check-In
From US $191 per night
10.0 (1 Review)
2 Bedrooms 4 Guests
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New Sleek 2BR - Perfect Blend of Comfort & Style in Chicago
Apartment
New Sleek 2BR - Perfect Blend of Comfort & Style in Chicago
From US $500 per night
|
5.5 (2 Reviews)
2 Bedrooms 6 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 $113 per night
10.0 (1 Review)
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 $96 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 $217 per night
9.8 (94 Reviews)
2 Bedrooms 6 Guests
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Chic 1 BR w Parking S
Apartment
Chic 1 BR w Parking S
From US $243 per night
New
1 Bedroom 4 Guests
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Nobu Hotel Chicago
Hotel
Nobu Hotel Chicago
From US $605 per night
|
9.4 (736 Reviews)
1 Bedroom 2 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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The Emily Hotel
Hotel
The Emily Hotel
From US $237 per night
|
9.2 (1256 Reviews)
1 Bedroom 2 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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Hampton Inn Chicago West Loop Fulton Market Area
Hotel
Hampton Inn Chicago West Loop Fulton Market Area
From US $243 per night
9.2 (1009 Reviews)
1 Bedroom 2 Guests
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New Blueground | Greektown, rooftop, nr Grant Park
Apartment
Blueground | Greektown, rooftop, nr Grant Park
From US $112 per night
New
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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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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Go tel Private Chicago
Apartment
Go tel Private Chicago
From US $561 per night
New
2 Bedrooms 6 Guests
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Modern West Loop Gem-City Views & Prime Location 4
Apartment
Modern West Loop Gem-City Views & Prime Location 4
From US $309 per night
New
1 Bedroom 10 Guests
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Gym Garage Parking Balcony Sleeps 4
Apartment
Gym Garage Parking Balcony Sleeps 4
From US $204 per night
New
1 Bedroom 4 Guests
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Elegant Escape Minutes from Downtown & UIC
Apartment
Elegant Escape Minutes from Downtown & UIC
From US $179 per night
New
1 Bedroom 6 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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W Loop 1BR w Pool Gym nr Restaurant Row CHI-294
Apartment
W Loop 1BR w Pool Gym nr Restaurant Row CHI-294
From US $154 per night
New
1 Bedroom 2 Guests
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Blueground | West Loop, pool & gym, nr Willis
Apartment
Blueground | West Loop, pool & gym, nr Willis
From US $281 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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About Casai's Private Villas and Holiday Rentals in Near West Side

Discover more than 531 vacation rentals available in Near West Side. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Near West Side.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Near West Side, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Near West Side. On average, places to stay near Near West Side offer 660.22 ft², with nightly prices averaging US $302.

With Casai, finding and comparing holiday rentals in Near West Side is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.

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 209 Properties
University Village / Little Italy 96 Properties
Tri-Taylor 32 Properties
West Loop Gate 25 Properties

Frequently Asked Questions About Near West Side?

What are the top holiday rentals in Near West Side?

How many Casai.com holiday rentals are available in Near West Side?

As of 2025, Casai boasts over 531 properties listed in the Near West Side area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Near West Side.

Nearby Neighborhood (13)

Neighborhood Property Count
Downtown Chicago Vacation Rentals in Chicago, Illinois 2228
West Loop Vacation Rentals in Chicago, Illinois 209
University Village / Little Italy Vacation Rentals in Chicago, Illinois 96
Lower West Side Vacation Rentals in Chicago, Illinois 50
Tri-Taylor Vacation Rentals in Chicago, Illinois 32
Heart of Chicago Vacation Rentals in Chicago, Illinois 32
West Loop Gate Vacation Rentals in Chicago, Illinois 25
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 531 Near West Side, IL Vacation Rentals

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