Near West Side Holiday Rentals

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

Unbeatable Top Floor: Views, Central, Modern
Apartment
Unbeatable Top Floor: Views, Central, Modern
From ZA R10,728 per night
10.0 (6 Reviews)
2 Bedrooms 6 Guests
GET THE BEST PRICE
Freshly Minted 2BR - Elegance & Comfort in Central Chicago
Apartment
Freshly Minted 2BR - Elegance & Comfort in Central Chicago
From ZA R6,052 per night
|
10.0 (2 Reviews)
2 Bedrooms 6 Guests
GET THE BEST PRICE
The Publishing House B&B
Bed & Breakfast
The Publishing House B&B
From ZA R4,141 per night
|
9.8 (181 Reviews)
1 Bedroom 2 Guests
GET THE BEST PRICE
Stylish 1BR in West Loop
Apartment
Stylish 1BR in West Loop
From ZA R4,688 per night
10.0 (4 Reviews)
1 Bedroom 2 Guests
GET THE BEST PRICE
2 Bedroom Home near West Loop with Parking
Apartment
2 Bedroom Home near West Loop with Parking
From ZA R6,099 per night
10.0 (1 Review)
2 Bedrooms 4 Guests
GET THE BEST PRICE
Hampton Inn & Suites Chicago Medical District UIC
Hotel
Hampton Inn & Suites Chicago Medical District UIC
From ZA R3,730 per night
9.6 (246 Reviews)
1 Bedroom 2 Guests
GET THE BEST PRICE
Relaxing Studio with Private Patio Downtown Chicago
Apartment
Relaxing Studio with Private Patio Downtown Chicago
From ZA R9,125 per night
10.0 (2 Reviews)
1 Bedroom 4 Guests
GET THE BEST PRICE
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 ZA R2,983 per night
|
9.9 (74 Reviews)
3 Bedrooms 6 Guests
GET THE BEST PRICE
The Neighborhood Hotel-Little Italy
Apartment
The Neighborhood Hotel-Little Italy
From ZA R2,185 per night
|
9.6 (202 Reviews)
1 Bedroom 2 Guests
GET THE BEST PRICE
Sage Modern Apartments Near Union Park in West Loop
Apartment
Sage Modern Apartments Near Union Park in West Loop
From ZA R5,827 per night
|
9.7 (14 Reviews)
6 Bedrooms 15 Guests
GET THE BEST PRICE
West Loop High-End 2BR: Walkable, City Views
Apartment
West Loop High-End 2BR: Walkable, City Views
From ZA R9,379 per night
10.0 (1 Review)
2 Bedrooms 5 Guests
GET THE BEST PRICE
Luxury West Loop Rentals: Modern Suites w/City Views & Resort Amenities
Apartment
Luxury West Loop Rentals: Modern Suites w/City Views & Resort Amenities
From ZA R12,052 per night
10.0 (1 Review)
2 Bedrooms 4 Guests
GET THE BEST PRICE
Fulbrix Bright Designer Apartments with West Loop Views
Apartment
Fulbrix Bright Designer Apartments with West Loop Views
From ZA R15,123 per night
|
9.5 (34 Reviews)
13 Bedrooms 32 Guests
GET THE BEST PRICE
West Loop Charm: Dining & Nightlife, Balcony
Apartment
West Loop Charm: Dining & Nightlife, Balcony
From ZA R8,929 per night
10.0 (1 Review)
2 Bedrooms 5 Guests
GET THE BEST PRICE
Quick Drive to Downtown Chicago & Early Check-In
Apartment
Quick Drive to Downtown Chicago & Early Check-In
From ZA R5,093 per night
9.3 (3 Reviews)
2 Bedrooms 4 Guests
GET THE BEST PRICE
Prime Location 2BR: Balcony, Restful Night
Apartment
Prime Location 2BR: Balcony, Restful Night
From ZA R8,888 per night
10.0 (1 Review)
2 Bedrooms 5 Guests
GET THE BEST PRICE
Quick Drive to Downtown Chicago & Early Check-In
Apartment
Quick Drive to Downtown Chicago & Early Check-In
From ZA R4,430 per night
10.0 (1 Review)
2 Bedrooms 4 Guests
GET THE BEST PRICE
1BR Adorable Apt with In-unit Laundry - Lake 206 rep
Apartment
1BR Adorable Apt with In-unit Laundry - Lake 206 rep
From ZA R11,417 per night
|
9.0 (3 Reviews)
1 Bedroom 2 Guests
GET THE BEST PRICE
Cozy 2 Bed Home by West Loop with Parking & Laundry
Apartment
Cozy 2 Bed Home by West Loop with Parking & Laundry
From ZA R4,361 per night
10.0 (1 Review)
2 Bedrooms 4 Guests
GET THE BEST PRICE
The Upscale Getaway Near Downtown
Apartment
The Upscale Getaway Near Downtown
From ZA R6,434 per night
|
8.0 (3 Reviews)
2 Bedrooms 6 Guests
GET THE BEST PRICE
Chicago 1BR Condo w Free Gated Parking & Highspeed Internet
Condo
Chicago 1BR Condo w Free Gated Parking & Highspeed Internet
From ZA R4,102 per night
10.0 (1 Review)
1 Bedroom 5 Guests
GET THE BEST PRICE
Avra Stylish Apartments Prime West Loop Location Near Union Park
Apartment
Avra Stylish Apartments Prime West Loop Location Near Union Park
From ZA R11,775 per night
|
7.8 (10 Reviews)
13 Bedrooms 32 Guests
GET THE BEST PRICE
2BR Chic New Apartment With Rooftop Pool & Gym
Apartment
2BR Chic New Apartment With Rooftop Pool & Gym
From ZA R6,035 per night
|
7.8 (4 Reviews)
2 Bedrooms 6 Guests
GET THE BEST PRICE
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 ZA R2,998 per night
10.0 (1 Review)
1 Bedroom 2 Guests
GET THE BEST PRICE
Jeffjack Heated Pool Penthouse in Chicago's West Loop
Apartment
Jeffjack Heated Pool Penthouse in Chicago's West Loop
From ZA R5,602 per night
7.0 (4 Reviews)
2 Bedrooms 6 Guests
GET THE BEST PRICE
EMALUX Condo Near Downtown,Bus,Train,Hospitals,United-Center,Fulton Market
Apartment
EMALUX Condo Near Downtown,Bus,Train,Hospitals,United-Center,Fulton Market
From ZA R8,741 per night
|
6.8 (10 Reviews)
3 Bedrooms 6 Guests
GET THE BEST PRICE
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 ZA R1,798 per night
10.0 (1 Review)
1 Bedroom 2 Guests
GET THE BEST PRICE
Hip West Loop Studio w/Gym & Coworking, nr UIC, by Blueground
Apartment
Hip West Loop Studio w/Gym & Coworking, nr UIC, by Blueground
From ZA R1,680 per night
10.0 (1 Review)
1 Bedroom 2 Guests
GET THE BEST PRICE
The Upscale Getaway Near Downtown
Condo
The Upscale Getaway Near Downtown
From ZA R5,290 per night
9.8 (89 Reviews)
2 Bedrooms 6 Guests
GET THE BEST PRICE
W Loop 1BR w Pool Gym nr Fulton Mkt CHI-293
Apartment
W Loop 1BR w Pool Gym nr Fulton Mkt CHI-293
From ZA R2,601 per night
|
New
1 Bedroom 2 Guests
GET THE BEST PRICE
Sleek 2 Bed, 2 Bath Condo in Trendy Fulton Market
Apartment
Sleek 2 Bed, 2 Bath Condo in Trendy Fulton Market
From ZA R7,255 per night
9.6 (11 Reviews)
2 Bedrooms 6 Guests
GET THE BEST PRICE
West Loop Oasis: Walk to Dining, Private Balcony
Apartment
West Loop Oasis: Walk to Dining, Private Balcony
From ZA R9,747 per night
9.6 (4 Reviews)
2 Bedrooms 5 Guests
GET THE BEST PRICE
2 Bedroom Medical District
Apartment
2 Bedroom Medical District
From ZA R4,795 per night
9.6 (4 Reviews)
2 Bedrooms 7 Guests
GET THE BEST PRICE
Unforgettable Stay: High End 2BR, Easy City Access
Apartment
Unforgettable Stay: High End 2BR, Easy City Access
From ZA R9,212 per night
9.4 (3 Reviews)
2 Bedrooms 5 Guests
GET THE BEST PRICE
Breathtaking & Bright: Designer 2BD with Garage
Apartment
Breathtaking & Bright: Designer 2BD with Garage
From ZA R3,658 per night
9.4 (3 Reviews)
1 Bedroom 6 Guests
GET THE BEST PRICE
Elizabeth by Coast to Cactus | Chic Artists Loft
Condo
Elizabeth by Coast to Cactus | Chic Artists Loft
From ZA R4,587 per night
9.2 (21 Reviews)
2 Bedrooms 6 Guests
GET THE BEST PRICE
W Loop Studio w Gym Pool Coworking nr UIC CHI-439
Apartment
W Loop Studio w Gym Pool Coworking nr UIC CHI-439
From ZA R2,237 per night
|
New
1 Bedroom 2 Guests
GET THE BEST PRICE
Nobu Hotel Chicago
Hotel
Nobu Hotel Chicago
From ZA R6,902 per night
|
9.4 (715 Reviews)
1 Bedroom 2 Guests
GET THE BEST PRICE
W Loop Studio w Gym Pool Coworking nr UIC CHI-397
Apartment
W Loop Studio w Gym Pool Coworking nr UIC CHI-397
From ZA R1,734 per night
|
New
1 Bedroom 2 Guests
GET THE BEST PRICE
The Emily Hotel
Hotel
The Emily Hotel
From ZA R4,270 per night
|
9.2 (1141 Reviews)
1 Bedroom 2 Guests
GET THE BEST PRICE
Modern 2BR2BA Condo Free Parking and Balcony
Apartment
Modern 2BR2BA Condo Free Parking and Balcony
From ZA R5,867 per night
New
2 Bedrooms 4 Guests
GET THE BEST PRICE
Spacious 3-Bed West Loop Townhouse, 1 Car Garage
House
Spacious 3-Bed West Loop Townhouse, 1 Car Garage
From ZA R8,899 per night
|
New
3 Bedrooms 8 Guests
GET THE BEST PRICE
Hampton Inn Chicago West Loop Fulton Market Area
Hotel
Hampton Inn Chicago West Loop Fulton Market Area
From ZA R2,924 per night
9.2 (1008 Reviews)
1 Bedroom 2 Guests
GET THE BEST PRICE
2 Br 1 Free Parking Gym
Apartment
2 Br 1 Free Parking Gym
From ZA R5,109 per night
|
New
2 Bedrooms 4 Guests
GET THE BEST PRICE
Chicago Modern Condo 2BR2BA, Balcony, Free Park
Apartment
Chicago Modern Condo 2BR2BA, Balcony, Free Park
From ZA R5,734 per night
New
2 Bedrooms 4 Guests
GET THE BEST PRICE
W Loop Studio w Pool Gym nr Restaurant Row CHI-264
Apartment
W Loop Studio w Pool Gym nr Restaurant Row CHI-264
From ZA R2,549 per night
New
1 Bedroom 2 Guests
GET THE BEST PRICE
Sun-Drenched 1BR Apartment
Apartment
Sun-Drenched 1BR Apartment
From ZA R5,462 per night
New
1 Bedroom 2 Guests
GET THE BEST PRICE
Hampton Inn & Suites Chicago Medical District Uic
Hotel
Hampton Inn & Suites Chicago Medical District Uic
From ZA R4,126 per night
|
9.1 (136 Reviews)
135 Bedrooms 32 Guests
GET THE BEST PRICE
Blueground | West Loop, rooftop pool & gym
Apartment
Blueground | West Loop, rooftop pool & gym
From ZA R5,339 per night
New
2 Bedrooms 4 Guests
GET THE BEST PRICE
Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area
Hotel
Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area
From ZA R3,662 per night
|
8.9 (500 Reviews)
7 Bedrooms 30 Guests
GET THE BEST PRICE
Nobu Hotel Chicago
Hotel
Nobu Hotel Chicago
From ZA R7,631 per night
|
8.9 (428 Reviews)
104 Bedrooms 14 Guests
GET THE BEST PRICE
The Emily Hotel
Hotel
The Emily Hotel
From ZA R4,901 per night
|
8.9 (358 Reviews)
150 Bedrooms 18 Guests
GET THE BEST PRICE
1BR Modern Luxe Apt with In-Unit Laundry
Apartment
1BR Modern Luxe Apt with In-Unit Laundry
From ZA R4,761 per night
New
1 Bedroom 2 Guests
GET THE BEST PRICE
Level Chicago Fulton Market
Hotel
Level Chicago Fulton Market
From ZA R4,072 per night
|
8.9 (58 Reviews)
56 Bedrooms 26 Guests
GET THE BEST PRICE
See More Properties

About Casai's Private Villas and Holiday Rentals in Near West Side

Discover more than 517 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 653.53 ft², with nightly prices averaging ZA R5,684.

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 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 holiday rentals in Near West Side?

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

As of 2025, Casai boasts over 517 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 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