Near West Side Vacation Rentals

Compare Vacation Rentals & Rent By Owner Homes in Near West Side, Chicago, Illinois, USA

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
GET THE BEST PRICE
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
GET THE BEST PRICE
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
GET THE BEST PRICE
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
GET THE BEST PRICE
New Spacious 2BR - 10 mins from Downtown
Apartment
Spacious 2BR - 10 mins from Downtown
From US $222 per night
New
2 Bedrooms 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 US $172 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 US $126 per night
|
9.6 (207 Reviews)
1 Bedroom 3 Guests
GET THE BEST PRICE
Top Floor Views + Central Comfort
Apartment
Top Floor Views + Central Comfort
From US $455 per night
10.0 (8 Reviews)
2 Bedrooms 6 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 US $336 per night
|
9.7 (14 Reviews)
6 Bedrooms 15 Guests
GET THE BEST PRICE
Stylish 1BR in West Loop
Apartment
Stylish 1BR in West Loop
From US $270 per night
10.0 (4 Reviews)
1 Bedroom 2 Guests
GET THE BEST PRICE
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
GET THE BEST PRICE
Stylish 2BR Retreat in Fulton Market for Getaways
Apartment
Stylish 2BR Retreat in Fulton Market for Getaways
From US $530 per night
10.0 (2 Reviews)
2 Bedrooms 5 Guests
GET THE BEST PRICE
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
GET THE BEST PRICE
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
GET THE BEST PRICE
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
GET THE BEST PRICE
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
GET THE BEST PRICE
High-End West Loop 2BR + City Views & Walkability
Apartment
High-End West Loop 2BR + City Views & Walkability
From US $441 per night
10.0 (1 Review)
2 Bedrooms 5 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 US $658 per night
|
9.0 (3 Reviews)
1 Bedroom 2 Guests
GET THE BEST PRICE
Panoramic City Views + Prime West Loop Location
Apartment
Panoramic City Views + Prime West Loop Location
From US $466 per night
10.0 (1 Review)
2 Bedrooms 5 Guests
GET THE BEST PRICE
New 3Bed 3Bath Condo with Parking by United Center
Apartment
New 3Bed 3Bath Condo with Parking by United Center
From US $180 per night
|
9.0 (2 Reviews)
3 Bedrooms 6 Guests
GET THE BEST PRICE
City Views + Walk to Dining, Ideal for All
Apartment
City Views + Walk to Dining, Ideal for All
From US $422 per night
10.0 (1 Review)
2 Bedrooms 5 Guests
GET THE BEST PRICE
The Upscale Getaway Near Downtown
Apartment
The Upscale Getaway Near Downtown
From US $371 per night
|
8.0 (3 Reviews)
2 Bedrooms 6 Guests
GET THE BEST PRICE
Brand New Building in the Medical District!
Apartment
Brand New Building in the Medical District!
From US $293 per night
10.0 (1 Review)
3 Bedrooms 4 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 US $679 per night
|
7.8 (10 Reviews)
13 Bedrooms 32 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 US $251 per night
10.0 (1 Review)
2 Bedrooms 4 Guests
GET THE BEST PRICE
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
GET THE BEST PRICE
Quick Drive to Downtown Chicago & Early Check-In
Apartment
Quick Drive to Downtown Chicago & Early Check-In
From US $240 per night
10.0 (1 Review)
2 Bedrooms 4 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 US $323 per night
7.0 (4 Reviews)
2 Bedrooms 6 Guests
GET THE BEST PRICE
Sun-Drenched 1BR Apartment
Apartment
Sun-Drenched 1BR Apartment
From US $234 per night
10.0 (1 Review)
1 Bedroom 2 Guests
GET THE BEST PRICE
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
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 US $173 per night
10.0 (1 Review)
1 Bedroom 2 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 US $104 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 US $97 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 US $305 per night
9.8 (89 Reviews)
2 Bedrooms 6 Guests
GET THE BEST PRICE
Nobu Hotel Chicago
Hotel
Nobu Hotel Chicago
From US $398 per night
|
9.4 (715 Reviews)
1 Bedroom 2 Guests
GET THE BEST PRICE
Go tel Private Chicago
Apartment
Go tel Private Chicago
From US $561 per night
New
2 Bedrooms 6 Guests
GET THE BEST PRICE
The Emily Hotel
Hotel
The Emily Hotel
From US $246 per night
|
9.2 (1141 Reviews)
1 Bedroom 2 Guests
GET THE BEST PRICE
Bright 2Bed 2Bath in Brand New Pilsen Development
Apartment
Bright 2Bed 2Bath in Brand New Pilsen Development
From US $389 per night
New
2 Bedrooms 4 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 US $150 per night
|
New
1 Bedroom 2 Guests
GET THE BEST PRICE
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
GET THE BEST PRICE
New Build in Pilsen! Spacious 2 Bed 2 Bath Unit
Apartment
New Build in Pilsen! Spacious 2 Bed 2 Bath Unit
From US $369 per night
New
2 Bedrooms 4 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 US $129 per night
|
New
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 US $100 per night
|
New
1 Bedroom 2 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 US $513 per night
|
New
3 Bedrooms 8 Guests
GET THE BEST PRICE
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
GET THE BEST PRICE
Gym Garage Parking Balcony Sleeps 4
Apartment
Gym Garage Parking Balcony Sleeps 4
From US $204 per night
New
1 Bedroom 4 Guests
GET THE BEST PRICE
Blueground | West Loop, rooftop pool & gym
Apartment
Blueground | West Loop, rooftop pool & gym
From US $308 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 US $147 per night
New
1 Bedroom 2 Guests
GET THE BEST PRICE
Modern 2BR2BA Condo Free Parking and Balcony
Apartment
Modern 2BR2BA Condo Free Parking and Balcony
From US $285 per night
New
2 Bedrooms 4 Guests
GET THE BEST PRICE
See More Properties

About Near West Side Vacation Rentals

With more than 527 Near West Side vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Rent By Owner Homes (RBOs) and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at an RBO property in Near West Side.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With RentByOwner Near West Side, you have the flexibility of comparing different options of various deals with a single click. Looking for an RBO with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner (RBOs), and other popular Airbnb-style properties in Near West Side. Places to stay near Near West Side are 657.86 ft² on average, with prices averaging US $319 a night.

RentByOwner makes it easy and safe to find and compare vacation rentals in Near West Side with prices often at a 30-40% discount versus the price of a hotel. Just 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 217 Properties
University Village / Little Italy 102 Properties
Tri-Taylor 32 Properties
West Loop Gate 28 Properties

Near West Side Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Near West Side?

How many Rentbyowner vacation rentals are available in Near West Side?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 527 in the Near West Side area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Near West Side. 

Nearby Neighborhood (13)

Neighborhood Property Count
Downtown Chicago Vacation Rentals in Chicago, Illinois 2261
West Loop Vacation Rentals in Chicago, Illinois 217
University Village / Little Italy Vacation Rentals in Chicago, Illinois 102
Lower West Side Vacation Rentals in Chicago, Illinois 53
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 28
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 527 Near West Side, IL Vacation Rentals

Recently Booked Vacation Rentals Near Near West Side