Owner Direct Vacation Rentals in Near West Side

The Best Owner Direct Vacation Rentals in Near West Side. Explore thousands of vacation home rentals, large cabins, and villas near Near West Side

Freshly Minted 2BR - Elegance & Comfort in Central Chicago From US $349
         

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10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Accessibility
  • Security/Safety
The Publishing House B&B From US $217
         

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9.8 (188 Reviews)
Bed & Breakfast
  • Air Conditioner
  • TV
  • Wheelchair Accessible
2 Bedroom Home near West Loop with Parking From US $352
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
1F Cozy Home in Little Italy near Downtown West Loop United Center From US $172
         

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9.9 (74 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Security/Safety
Stylish Penthouse Loft Tri-Taylor 2BR 2BA, Parking
New
From US $242
         

New
Condo
  • Air Conditioner
  • Pet Friendly
  • Security/Safety
Sage Modern Apartments Near Union Park in West Loop From US $336
         

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9.7 (14 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly

Luxury Places to Stay in Near West Side

Over 573+ Luxury Places to Stay in or Near Near West Side
6 Luxe Apts, Perfect Group Solution, Sleeps 30 From US $3,735
         

New
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Exclusive Group Getaway in Vibrant West Loop From US $3,433
         

New
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
High-End 2BR Apartments in West Loop From US $1,641
         

2.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Prime West Loop 2BR Apts + Event Convenience From US $1,632
         

New
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Hotel Chicago West Loop, SureStay Collection by Best Western From US $1,436
         

7.3 (901 Reviews)
Hotel
  • Air Conditioner
  • Pet Friendly
  • Wheelchair Accessible
Spacious West Loop Retreat for Business Groups From US $1,326
         

New
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly

Top-Rated Vacation Rentals with a Pool in Near West Side

Over 204+ Top-Rated Vacation Rentals with a Pool in or Near Near West Side
Top Floor Views + Central Comfort From US $459
         

10.0 (8 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • Pool
Relaxing Studio with Private Patio Downtown Chicago From US $507
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Stylish 2BR Retreat in Fulton Market for Getaways From US $485
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • Pool
Luxury West Loop Rentals: Modern Suites w/City Views & Resort Amenities From US $793
         

Skyline Views in 3BR Apartment w/Top Amenities From US $732
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Pet Friendly
  • Pool
Cozy West Loop 1BR w/Pool, Gym, nr. Restaurant Row, by Blueground From US $123
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly

Pet-Friendly Vacation Rentals in Near West Side

Over 308+ Pet-Friendly Vacation Rentals in or Near Near West Side
Fulbrix Bright Designer Apartments with West Loop Views From US $872
         

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9.5 (34 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Blueground | West Loop, pool, nr Grant Park
New
From US $177
         

New
Apartment
  • Air Conditioner
  • Pet Friendly
  • Pool
The Neighborhood Hotel-Little Italy From US $126
         

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9.6 (221 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • Wheelchair Accessible
Blueground | West Loop, pool, nr Chicago River
New
From US $123
         

1BR Adorable Apt with In-unit Laundry - Lake 206 rep From US $658
         

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9.0 (3 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • Security/Safety
Stylish 1BR in West Loop From US $180
         

10.0 (10 Reviews)
Apartment
  • Pet Friendly
  • TV
  • Security/Safety
Jeffjack Heated Pool Penthouse in Chicago's West Loop From US $323
         

7.0 (4 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in Near West Side

Over 44+ Large Vacation Homes & Villas in or Near Near West Side
Chicago Parthenon Hostel From US $116
         

7.9 (357 Reviews)
Hostel
  • Air Conditioner
  • Parking
  • TV
Chic Modern Loft near United Center, UIC/IMD & Downtown W/Parking From US $265
         

West Loop - City Views With In & Out Parking 4 From US $309
         

New
Apartment
  • Air Conditioner
  • Parking
  • Accessibility
Remodeled 1890 Chicago Greystone, 4bd 3.5ba & Gym From US $568
         

10.0 (8 Reviews)
House
  • Air Conditioner
  • TV
  • Security/Safety

Wheelchair Accessible Vacation Homes in Near West Side

Over 316+ Wheelchair Accessible Vacation Homes in or Near Near West Side
Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area From US $211
         

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9.0 (491 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Brand New Building in the Medical District! From US $219
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Nobu Hotel Chicago From US $440
         

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8.9 (417 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
High-End West Loop 2BR + City Views & Walkability From US $408
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
The Emily Hotel From US $283
         

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8.9 (358 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
City Views + Walk to Dining, Ideal for All From US $398
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
Hampton Inn Chicago West Loop Fulton Market Area From US $257
         

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8.8 (733 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly

Near West Side Varoom and Airbnb Places to Stay Under $200

Over 319+ Near West Side Varoom and Airbnb Places to Stay Under $200
New 3Bed 3Bath Condo with Parking by United Center From US $180
         

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9.5 (4 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Security/Safety
Chicago Parthenon Hostel From US $139
         

8.2 (441 Reviews)
Hostel
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
Chicago 1BR Condo w Free Gated Parking & WiFi
New
From US $193
         

New
Condo
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
W Loop Studio w Gym Pool Coworking nr UIC CHI-439 From US $129
         

W Loop Studio w Gym Pool Coworking nr UIC CHI-397 From US $100
         

Instantly Bookable Vacation Homes in Near West Side

Over 343+ Instantly Bookable Vacation Homes in or Near Near West Side
Quick Drive to Downtown Chicago & Early Check-In From US $191
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
West Loop Living – Bright 1BR From US $159
         

10.0 (2 Reviews)
Apartment
  • Pet Friendly
  • TV
  • Security/Safety
Sun-Drenched 1BR Apartment From US $159
         

10.0 (2 Reviews)
Apartment
  • Pet Friendly
  • TV
  • Security/Safety
Panoramic City Views + Prime West Loop Location From US $397
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
1BR Modern Luxe Apt with In-Unit Laundry From US $159
         

10.0 (1 Review)
Apartment
  • Pet Friendly
  • TV
  • Security/Safety
Hip West Loop Studio w/Gym & Coworking, nr UIC, by Blueground From US $103
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Pet Friendly
  • Pool

About Near West Side Vacation Rentals

With more than 582 Near West Side vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Ownerdirect 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 a rental 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 Ownerdirect Near West Side, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner 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, and other popular Airbnb-style properties in Near West Side. Places to stay near Near West Side are 676.51 ft² on average, with prices averaging $287 a night.

Ownerdirect 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.

Top Rental Accommodation Types in Near West Side

Type Count
Holiday Apartments 456
Vacation Homes 39
Hotels with Suites 37
B&B 2
Hostels 2

Use these Quick Filters to Find a Vacation Rental in Near West Side

Pro Tip: Ownerdirect makes it easy to compare the best listings on Ownerdirect homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Ownerdirect homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Near West Side.

Weather in Near West Side

View the weather forecast for Near West Side before booking your Near West Side Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F