Sister Bay Condo Rentals - Vacation Rentals in West Loop

Modern West Loop Gem-City Views & Prime Location 6 From US $483
         

10.0 (13 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Security/Safety
Freshly Minted 2BR - Elegance & Comfort in Central Chicago From US $349
         

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10.0 (4 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • Accessibility
The Publishing House B&B From US $208
         

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9.8 (199 Reviews)
Bed & Breakfast
  • Air Conditioner
  • TV
  • Wheelchair Accessible
West Loop Living – Bright 1BR From US $201
         

10.0 (8 Reviews)
Apartment
  • Pet Friendly
  • 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
Designer Loft in Fulton Market with Parking From US $1,023
         

10.0 (6 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly
Modern West Loop Gem-City Views & Prime Location 3 From US $549
         

10.0 (5 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Wheelchair Accessible
Sunlit 1BR Apartment | Warm & Welcoming Space From US $234
         

10.0 (2 Reviews)
Apartment
  • Pet Friendly
  • TV
  • Security/Safety

Luxury Places to Stay in West Loop

Over 312+ Luxury Places to Stay in or Near West Loop
Huge 5BR Heart of Fulton Market Duplex of Dreams From US $2,674
         

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New
Apartment
  • Air Conditioner
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  • Balcony/Terrace
West Loop - City Views With In & Out Parking 6 From US $1,123
         

9.5 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Accessibility
West Loop - City Views With In & Out Parking 2 From US $1,059
         

1.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Accessibility
Beautiful Downtown 3BR with Free Parking From US $997
         

9.6 (28 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV

Top-Rated Vacation Rentals with a Pool in West Loop

Over 168+ Top-Rated Vacation Rentals with a Pool in or Near West Loop
Cozy West Loop 1BR w/Pool, Gym, nr. Restaurant Row, by Blueground From US $210
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Hip West Loop Studio w/Gym & Coworking, nr UIC, by Blueground From US $189
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Pet Friendly
  • Pool
Smart West Loop Studio w/Pool, Gym, nr. Fulton Market, by Blueground From US $150
         

Hampton Inn Chicago West Loop Fulton Market Area From US $217
         

9.4 (1008 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Nobu Hotel Chicago From US $398
         

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9.4 (814 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in West Loop

Over 178+ Pet-Friendly Vacation Rentals in or Near West Loop
Modern Comfort: 1BR Unit w/Laundry From US $238
         

9.4 (16 Reviews)
Apartment
  • Pet Friendly
  • TV
  • 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
1BR Modern Luxe Apt with In-Unit Laundry From US $234
         

8.0 (2 Reviews)
Apartment
  • Pet Friendly
  • TV
  • Security/Safety
Blueground | West Loop, pool, nr Millennium Park From US $469
         

Large Vacation Homes & Villas in West Loop

Over 26+ Large Vacation Homes & Villas in or Near West Loop
West Loop - City Views With In & Out Parking 4 From US $309
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Accessibility
Modern West Loop Gem-City Views & Prime Location 2 From US $913
         

9.4 (8 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Wheelchair Accessible
Modern West Loop Gem-City Views & Prime Location 5 From US $924
         

9.4 (3 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV

Wheelchair Accessible Vacation Homes in West Loop

Over 199+ Wheelchair Accessible Vacation Homes in or Near West Loop
The Publishing House Bed and Breakfast From US $139
         

9.4 (39 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • TV
LIVN - West Loop Chicago From US $130
         

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10.0 (10 Reviews)
Hotel
  • Air Conditioner
  • Wheelchair Accessible
  • Accessibility
LIVN West Loop Chicago Queen Superior Studio From US $184
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • TV
  • Wheelchair Accessible
LIVN West Loop Chicago 1 BR From US $470
         

New
Apartment
  • Air Conditioner
  • TV
  • Wheelchair Accessible
Blueground | West Loop, pool, nr Union Park From US $256
         

New
Apartment
  • Air Conditioner
  • Pet Friendly
  • Pool
Blueground | West Loop, rooftop pool & gym From US $255
         

New
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Blueground | West Loop, rooftop pool & gym From US $252
         

New
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly

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

Over 151+ West Loop Vacation Rentals and Airbnb Places to Stay Under $200
W Loop 2BR w pool gym lounge nr L CHI-748 From US $200
         

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New
Apartment
  • Air Conditioner
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  • Pet Friendly
Chicago Parthenon Hostel From US $156
         

8.2 (452 Reviews)
Hostel
  • Air Conditioner
  • Security/Safety
  • Wellness Facilities
Blueground | West Loop, pool & AC, nr Willis From US $193
         

New
Apartment
  • Air Conditioner
  • Pet Friendly
  • Pool
Blueground | West Loop, pool, nr Chicago River From US $190
         

Blueground | Greektown, bbq, gym, nr Willis Tower From US $187
         

New
Apartment
  • Air Conditioner
  • TV
  • Wheelchair Accessible

Instantly Bookable Vacation Homes in West Loop

Over 175+ Instantly Bookable Vacation Homes in or Near West Loop
Near Fulton Market! Walkable West Loop Condo From US $372
         

10.0 (1 Review)
Condo
  • Air Conditioner
  • TV
  • Security/Safety
Blueground | West Loop, rooftop pool & gym From US $241
         

New
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
LIVN West Loop Chicago 2 BR City View From US $229
         

New
Apartment
  • Air Conditioner
  • TV
  • Wheelchair Accessible

About West Loop Vacation Rentals

With more than 321 West Loop vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Sisterbaycondorentals 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 West Loop.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Sisterbaycondorentals West Loop, 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 Loop. Places to stay near West Loop are 713.91 ft² on average, with prices averaging $384 a night.

Sisterbaycondorentals makes it easy and safe to find and compare vacation rentals in West Loop 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 Loop

Type Count
Holiday Apartments 260
Hotels with Suites 28
Vacation Homes 13
B&B 2
Hostels 2

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

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

Weather in West Loop

View the weather forecast for West Loop before booking your West Loop 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 Loop Vacation Rental Frequently Asked Questions

What are the top vacation rentals in West Loop?
How many vacation rentals are available in West Loop?

Currently, the total number of properties listed in 2026 is over 321 in the West Loop area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in West Loop.