Carolina Log Cabins - Vacation Rentals in West Side

Cabin 105 by 747 Lofts From US $244
         

5.8 (13 Reviews)
Hotel
  • Air Conditioner
  • Accessibility
  • Security/Safety

Luxury Places to Stay in West Side

Over 1555+ Luxury Places to Stay in or Near West Side
: The Wolcott : Modern Elegance at Its Finest From US $3,490
         

9.4 (14 Reviews)
House
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Unique Luxury Fulton Market Penthouse - Sleeps 32 From US $2,944
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Huge 5BR Heart of Fulton Market Duplex of Dreams From US $2,674
         

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New
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3 Flat Building Downtown - With Private Patios From US $2,412
         

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New
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Stunning 5BR Home in Heart of Chicago with 2 Rooftops From US $2,234
         

Top-Rated Vacation Rentals with a Pool in West Side

Over 238+ Top-Rated Vacation Rentals with a Pool in or Near West Side
BlueJay/Unique One Bedroom Full of Amazing Art From US $203
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Cozy West Loop 1BR w/Pool, Gym, nr. Restaurant Row, by Blueground From US $241
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Hip West Loop Studio w/Gym & Coworking, nr UIC, by Blueground From US $225
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Pet Friendly
  • Pool
Smart West Loop Studio w/Pool, Gym, nr. Fulton Market, by Blueground From US $209
         

Pet-Friendly Vacation Rentals in West Side

Over 613+ Pet-Friendly Vacation Rentals in or Near West Side
Chicago Quick Stay From US $130
         

6.3 (47 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • Internet
The Neighborhood Hotel-Little Italy From US $126
         

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9.6 (268 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • Wheelchair Accessible
NEW LUXURY PENTHOUSE CONDO From US $631
         

10.0 (215 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly
NEW LUXURY CONDO WITH PATIO DECK From US $395
         

10.0 (199 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly
Ukrainian Village 3BR/3BA Private Patio, Parking From US $790
         

10.0 (35 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly
Vital Urban: Spa Inspired Retreat From US $617
         

10.0 (12 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Designer Loft in Fulton Market with Parking From US $1,120
         

10.0 (7 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in West Side

Over 224+ Large Vacation Homes & Villas in or Near West Side
Homan Square From US $7
         

3.0 (193 Reviews)
House
  • Parking
  • Child Friendly
  • Internet
Modern 3 BR Apt - 5 Mins to Downtown Sleeps 10 From US $309
         

New
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Spacious 4-Level/4-Bedroom Townhouse in West Loop From US $1,217
         

Modern West Loop Gem-City Views & Prime Location 6 From US $1,014
         

10.0 (22 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Security/Safety
Modern West Loop Gem-City Views & Prime Location 4 From US $810
         

10.0 (7 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Wheelchair Accessible
Modern West Loop Gem-City Views & Prime Location 3 From US $693
         

10.0 (7 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Wheelchair Accessible
2 Suites, 2 Floors in Downtown Chicago From US $914
         

10.0 (6 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV

Wheelchair Accessible Vacation Homes in West Side

Over 460+ Wheelchair Accessible Vacation Homes in or Near West Side
Modern River West 2BR with W&D by Zencity From US $77
         

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10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Wheelchair Accessible
The Publishing House B&B From US $338
         

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9.8 (206 Reviews)
Bed & Breakfast
  • Air Conditioner
  • TV
  • Wheelchair Accessible
The Cornerstone - Designer 4BR Flat in Bucktown/WP From US $960
         

10.0 (11 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Wheelchair Accessible
Cabin 104 by 747 Lofts From US $275
         

10.0 (9 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Cabin 302 by 747 Lofts From US $298
         

10.0 (6 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
LIVN West Loop Chicago Queen Superior Studio From US $438
         

10.0 (5 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Wheelchair Accessible
LIVN West Loop Chicago King Studio From US $558
         

10.0 (4 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Wheelchair Accessible
1 Garage Parking/Skyline Rooftop/PingPong/Balcony From US $643
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV

West Side Vacation Rentals and Airbnb Places to Stay Under $200

Over 559+ West Side Vacation Rentals and Airbnb Places to Stay Under $200
Modern River West 2BR with W&D by Zencity From US $76
         

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9.0 (4 Reviews)
Apartment
  • Air Conditioner
  • Wheelchair Accessible
  • Internet
Chicago Parthenon Hostel From US $163
         

8.2 (465 Reviews)
Hostel
  • Air Conditioner
  • Security/Safety
  • Wellness Facilities
King Comfort apartment, Quiet, Clean, AC & WiFi From US $136
         

10.0 (5 Reviews)
House
  • Air Conditioner
  • TV
  • Security/Safety
✨ Beautiful 2BR Apartment with Laundry From US $170
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Security/Safety
Pilsen Gem Near the Loop and Chinatown From US $175
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • TV
  • Balcony/Terrace
Flexhome Wicker Park Stylish 2BR Sleeps 6 From US $198
         

9.8 (6 Reviews)
Apartment
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  • Parking
  • TV

Instantly Bookable Vacation Homes in West Side

Over 848+ Instantly Bookable Vacation Homes in or Near West Side
3 BD condo near to downtown, Gold Coast and Michigan Avenue. From US $284
         

Entire Below Level Studio w/Private Sauna From US $287
         

10.0 (76 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Private Historic Coach House Wicker Park From US $432
         

10.0 (71 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Vibrant 3BR Pilsen Stay Free Parking Near Downtown From US $485
         

10.0 (35 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV

About West Side Vacation Rentals

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Carolinalogcabins 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 West Side. Places to stay near West Side with prices averaging US $244 a night.

Carolinalogcabins makes it easy and safe to find and compare vacation rentals in 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 West Side

Type Count
Hotels 1

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

Pro Tip: Carolinalogcabins makes it easy to compare the best listings on Carolinalogcabins homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Carolinalogcabins 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 West Side.

Weather in West Side

View the weather forecast for West Side before booking your 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

West Side Vacation Rental Frequently Asked Questions

What are the top vacation rentals in West Side?

There are a lot of options in West Side. If you plan on staying in the West Side area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in West Side:

How many vacation rentals are available in West Side?

Currently, the total number of properties listed in 2026 is over 1 in the West Side area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in West Side.