531+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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  4. South Loop

South Loop pickleball Stays, Resort Rentals, & Homes

About South Loop Vacation Rentals

Discover over 531 amazing vacation rental options in South 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 South 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 917.18 ft², with prices averaging US $386 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 South Loop.

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Top Pickleball-Ready Accommodation Types in South Loop

Type Count
Holiday Apartments 445
Vacation Homes 13

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

Weather in South Loop, IL

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


Pontiac Building 4,073 Properties
Mergenthaler Lofts 4,056 Properties
Second Franklin Building 4,054 Properties
Dearborn St Station 4,040 Properties
Printers Row 4,021 Properties
Spertus Institute of Jewish Studies 3,953 Properties
Columbia College Chicago 3,947 Properties
Museum of Contemporary Photography 3,946 Properties
Dearborn Park 3,938 Properties
South Side 403 Properties
Near South Side 381 Properties
Prairie District 280 Properties

Frequently Asked Questions About South Loop?

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

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

Discover 5 accommodations with private or nearby pickleball courts in South Loop. Some of the best destinations to stay and play pickleball are:

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

Looking for a fun and active getaway with pickleball courts in South 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 South 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 531 properties listed in South 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 (7) 
Neighborhood Property Count
Downtown Chicago Vacation Rentals in Chicago, Illinois 2318
The Loop Vacation Rentals in Chicago, Illinois 1336
Near South Side Vacation Rentals in Chicago, Illinois 381
Prairie District Vacation Rentals in Chicago, Illinois 280
Printers Row Vacation Rentals in Chicago, Illinois 4021
Ickes Praire Homes Vacation Rentals in Chicago, Illinois 2027
Chicago Museum Campus Vacation Rentals in Chicago, Illinois 3407

People Also Ask

There are 531 South Loop, IL Vacation Rentals

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