1112+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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  2. Illinois
  3. Chicago
  4. The Loop

The Loop pickleball Stays, Resort Rentals, & Homes

About The Loop Vacation Rentals

Discover over 1112 amazing vacation rental options in The 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 The 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 639.39 ft², with prices averaging $378 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 The Loop.

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Top Pickleball-Ready Accommodation Types in The Loop

Type Count
Holiday Apartments 689
Vacation Homes 188

Use these Quick Filters to Find a Vacation Rental in The 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 The Loop with PickleTrip™.

Weather in The Loop, IL

View the weather forecast for The Loop before booking your The 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 The Loop, IL


Chicago 7,399 Properties
Chicago 4,331 Properties
333 West Wacker Drive 4,290 Properties
Civic Opera House 4,251 Properties
Cadillac Palace Theatre 4,224 Properties
Chicago City Hall 4,216 Properties
Monument with Standing Beast 4,207 Properties
Printers Row 4,021 Properties
Central Chicago 1,863 Properties
Downtown Chicago 1,703 Properties
Lakeshore East 735 Properties
Near East Side 735 Properties

Frequently Asked Questions About The Loop?

What are the top vacation rentals, resorts, and hotels in The 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 The 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 The Loop!

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

Discover 28 accommodations with private or nearby pickleball courts in The Loop. Some of the best destinations to stay and play pickleball are:

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

Looking for a fun and active getaway with pickleball courts in ? 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 The 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 1112 properties listed in The Loop in 2025, 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 (10) 
Neighborhood Property Count
Downtown Chicago Vacation Rentals in Chicago, Illinois 1703
Near North Side Vacation Rentals in Chicago, Illinois 785
River North Vacation Rentals in Chicago, Illinois 434
South Loop Vacation Rentals in Chicago, Illinois 372
West Loop Vacation Rentals in Chicago, Illinois 205
West Loop Gate Vacation Rentals in Chicago, Illinois 2257
Lakeshore East Vacation Rentals in Chicago, Illinois 735
Near East Side Vacation Rentals in Chicago, Illinois 735
Printers Row Vacation Rentals in Chicago, Illinois 4021
Chicago Museum Campus Vacation Rentals in Chicago, Illinois 3407

People Also Ask

There are 1112 The Loop, IL Vacation Rentals

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