Near West Side Vacation Rentals

Compare Vacation Rentals & Rent By Owner 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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Designer 2BR in Walkable Fulton Market
Apartment
Designer 2BR in Walkable Fulton Market
From US $590 per night
10.0 (2 Reviews)
2 Bedrooms 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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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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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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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 $510 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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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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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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Prime Location 2BR: Balcony, Restful Night
Apartment
Prime Location 2BR: Balcony, Restful Night
From US $489 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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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
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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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Quick Drive to Downtown Chicago & Early Check-In
Apartment
Quick Drive to Downtown Chicago & Early Check-In
From US $274 per night
10.0 (1 Review)
2 Bedrooms 4 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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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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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 $234 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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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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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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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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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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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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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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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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West Loop Oasis: Walk to Dining, Private Balcony
Apartment
West Loop Oasis: Walk to Dining, Private Balcony
From US $488 per night
9.6 (4 Reviews)
2 Bedrooms 5 Guests
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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
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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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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 $240 per night
9.2 (1012 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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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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Modern 2BR2BA Condo Free Parking and Balcony
Apartment
Modern 2BR2BA Condo Free Parking and Balcony
From US $287 per night
New
2 Bedrooms 4 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 (498 Reviews)
6 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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West Loop Living – Bright 1BR
Apartment
West Loop Living – Bright 1BR
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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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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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

With more than 518 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 652.27 ft² on average, with prices averaging US $325 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 Gate 2,257 Properties
Tri-Taylor 1,078 Properties
University Village / Little Italy 743 Properties
West Loop 36 Properties

Frequently Asked Questions About Near West Side?

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 518 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 411
West Loop Vacation Rentals in Chicago, Illinois 36
University Village / Little Italy Vacation Rentals in Chicago, Illinois 743
Illinois Medical District Vacation Rentals in Chicago, Illinois 3502
West Loop Gate Vacation Rentals in Chicago, Illinois 2257
Lower West Side Vacation Rentals in Chicago, Illinois 909
Tri-Taylor Vacation Rentals in Chicago, Illinois 1078
North Lawndale Vacation Rentals in Chicago, Illinois 443
Lawndale Vacation Rentals in Chicago, Illinois 435
Heart of Chicago Vacation Rentals in Chicago, Illinois 691
Greektown Vacation Rentals in Chicago, Illinois 4320
Pilsen Vacation Rentals in Chicago, Illinois 3300
Fulton Market Vacation Rentals in Chicago, Illinois 4451

There are 518 Near West Side, IL Vacation Rentals

Recently Booked Vacation Rentals Near Near West Side