306+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. USA
  2. Illinois
  3. Chicago
  4. West Loop

West Loop pickleball Stays, Resort Rentals, & Homes

About West Loop Vacation Rentals

Discover over 306 amazing vacation rental options in West Loop with pickleball courts or nearby facilities. From resorts to hotels, villas to condos, PickleTrip connects you with a vast selection of pickleball-ready amenities at great prices, providing you with the perfect spot to base your next pickleball vacation. Stay and Play pickleball When You Travel and uncover great stays in West Loop.

Find exclusive last-minute deals on vacation rentals, resorts, and hotels with private courts and nearby facilities with PickleTrip™, whether you're traveling solo or with a group. Our platform offers a variety of stay options, from vacation rentals to Airbnb-style properties, all with private pickleball courts or nearby facilities. Compare options from multiple suppliers with a single click to find the perfect stay that fits your budget and style. Places to stay near pickleball courts are an average of 726.04 ft², with prices averaging US $313 per night.

With PickleTrip™, you can easily search for and book your next pickleball vacation rental with courts or nearby facilities. Our platform connects you with the ideal holiday rental to create a lifetime of travel memories. Prices listed are often discounted versus rack rates, so you can secure your perfect place to stay today and get ready to play pickleball in West Loop.

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Top Pickleball-Ready Accommodation Types in West Loop

Type Count
Holiday Apartments 251
Vacation Homes 15

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

★ Pro Tip: PickleTrip™ is a travel platform, connecting avid pickleball players and enthusiasts with a variety of vacation rentals, resorts, and hotels featuring private pickleball courts or nearby facilities. We curate a vast selection of properties from trusted sources, providing you with unbeatable options and pricing to find the perfect pickleball getaway. Experience unforgettable pickleball matches in West Loop with PickleTrip™.

Weather in West Loop, IL

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

Other Places to Stay in West Loop, IL


Fulton Market 4,292 Properties
Mars Gallery 4,290 Properties
Union Park 4,287 Properties
Packer Schopf Gallery 4,269 Properties
Pitchfork Music Festival 4,268 Properties
Threewalls 4,213 Properties
Mary Bartelme Park 4,192 Properties
Greektown 4,157 Properties
Batcolumn 4,148 Properties
Old St Patrick’s Church 4,133 Properties
Union Station 4,072 Properties
West Loop Gate 33 Properties

Frequently Asked Questions About West Loop?

What are the top vacation rentals, resorts, and hotels in West Loop with Courts?

Experience the ultimate pickleball vacation with PickleTrip™. We offer a variety of premium rental properties, resorts, and hotels with private pickleball courts or nearby facilities in West Loop. Whether you're a beginner or a seasoned player, we have the perfect destination for you to stay and play. Book now and discover the best pickleball vacation spots in West Loop!

How many pickleball-ready properties have private pools in West Loop?

Discover 3 accommodations with private or nearby pickleball courts in West Loop. Some of the best destinations to stay and play pickleball are:

Which vacation rentals, resorts, or hotels in West Loop is best for families looking for a pickleball-getaway?

Looking for a fun and active getaway with pickleball courts in West Loop? With PickleTrip™, you'll have access to a wide selection of top-rated properties that offer private pickleball courts or nearby facilities. Make the most of you getaway and ace your A-game while you travel.

How many PickleTrip vacation rentals or resorts are available in West Loop?

PickleTrip™ offers a diverse selection of properties with private pickleball courts or nearby facilities to enhance your pickleball experience on your next trip. With a combination of established great stays and new options in top locations, PickleTrip™ has over 306 properties listed in West Loop in 2026, and the number only continues to grow. By consolidating listings from various providers, PickleTrip™ brings you the best luxury stays for a sporty, professional, and fun travel experience.

Nearby Neighborhood (12) 
Neighborhood Property Count
Downtown Chicago Vacation Rentals in Chicago, Illinois 1527
The Loop Vacation Rentals in Chicago, Illinois 703
Near North Side Vacation Rentals in Chicago, Illinois 605
Near West Side Vacation Rentals in Chicago, Illinois 370
River North Vacation Rentals in Chicago, Illinois 317
West Town Vacation Rentals in Chicago, Illinois 314
University Village / Little Italy Vacation Rentals in Chicago, Illinois 103
Lower West Side Vacation Rentals in Chicago, Illinois 52
West Loop Gate Vacation Rentals in Chicago, Illinois 33
Chinatown Vacation Rentals in Chicago, Illinois 2948
Greektown Vacation Rentals in Chicago, Illinois 4157
Fulton Market Vacation Rentals in Chicago, Illinois 4292

People Also Ask

There are 306 West Loop, IL Vacation Rentals

Recently Booked Vacation Rentals in West Loop