2880+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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  2. Illinois
  3. Chicago
  4. Downtown Chicago

Downtown Chicago pickleball Stays, Resort Rentals, & Homes

About Downtown Chicago Vacation Rentals

Discover over 2880 amazing vacation rental options in Downtown Chicago 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 Downtown Chicago.

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 751.94 ft², with prices averaging $433 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 Downtown Chicago.

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Top Pickleball-Ready Accommodation Types in Downtown Chicago

Type Count
Holiday Apartments 1871
Vacation Homes 540
Villas 7

Use these Quick Filters to Find a Vacation Rental in Downtown Chicago

★ 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 Downtown Chicago with PickleTrip™.

Weather in Downtown Chicago, IL

View the weather forecast for Downtown Chicago before booking your Downtown Chicago 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 Downtown Chicago, IL


Chicago 7,401 Properties
Chicago 4,334 Properties
West Loop Gate 2,257 Properties
Central Chicago 1,865 Properties
Near North Side 785 Properties
The Loop 715 Properties
River North 434 Properties
Streeterville 211 Properties
West Loop 206 Properties
Rush and Division 71 Properties
Gold Coast 54 Properties
Killgubbin 33 Properties

Frequently Asked Questions About Downtown Chicago?

What are the top vacation rentals, resorts, and hotels in Downtown Chicago 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 Downtown Chicago. 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 Downtown Chicago!

How many pickleball-ready properties have private pools in Downtown Chicago?

Discover 66 accommodations with private or nearby pickleball courts in Downtown Chicago. Some of the best destinations to stay and play pickleball are:

Which vacation rentals, resorts, or hotels in Downtown Chicago 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 Downtown Chicago?

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 2880 properties listed in Downtown Chicago 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 (16) 
Neighborhood Property Count
Near North Side Vacation Rentals in Chicago, Illinois 785
The Loop Vacation Rentals in Chicago, Illinois 715
River North Vacation Rentals in Chicago, Illinois 434
South Loop Vacation Rentals in Chicago, Illinois 372
Near South Side Vacation Rentals in Chicago, Illinois 363
Near West Side Vacation Rentals in Chicago, Illinois 362
West Town Vacation Rentals in Chicago, Illinois 317
Streeterville Vacation Rentals in Chicago, Illinois 211
West Loop Vacation Rentals in Chicago, Illinois 206
Lincoln Park Vacation Rentals in Chicago, Illinois 158
University Village / Little Italy Vacation Rentals in Chicago, Illinois 113
Gold Coast Vacation Rentals in Chicago, Illinois 54
River West Vacation Rentals in Chicago, Illinois 53
Old Town Vacation Rentals in Chicago, Illinois 51
Magnificent Mile Vacation Rentals in Chicago, Illinois 4128
Lakeshore East Vacation Rentals in Chicago, Illinois 735

People Also Ask

There are 2880 Downtown Chicago, IL Vacation Rentals

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