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Streeterville pickleball Stays, Resort Rentals, & Homes

About Streeterville Vacation Rentals

Discover over 357 amazing vacation rental options in Streeterville 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 Streeterville.

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 808.15 ft², with prices averaging $397 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 Streeterville.

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Top Pickleball-Ready Accommodation Types in Streeterville

Type Count
Holiday Apartments 185
Vacation Homes 105

Use these Quick Filters to Find a Vacation Rental in Streeterville

★ 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 Streeterville with PickleTrip™.

Weather in Streeterville, IL

View the weather forecast for Streeterville before booking your Streeterville 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 Streeterville, IL


Loyola University Museum of Art 4,190 Properties
Rush Street 4,167 Properties
Fourth Presbyterian Church 4,156 Properties
Wrigley Building 4,150 Properties
City Gallery 4,148 Properties
Shops at Northbridge 4,145 Properties
Chicago Place Mall 4,136 Properties
Museum of Contemporary Art 4,132 Properties
McCormick Freedom Project 4,131 Properties
McCormick Tribune Freedom Museum 4,129 Properties
Broadway Playhouse 4,120 Properties
John Hancock Center 4,112 Properties

Frequently Asked Questions About Streeterville?

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

How many pickleball-ready properties have private pools in Streeterville?

Discover 10 accommodations with private or nearby pickleball courts in Streeterville. Some of the best destinations to stay and play pickleball are:

Which vacation rentals, resorts, or hotels in Streeterville 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 Streeterville?

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 357 properties listed in Streeterville 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 1706
Near North Side Vacation Rentals in Chicago, Illinois 784
River North Vacation Rentals in Chicago, Illinois 434
Rush and Division Vacation Rentals in Chicago, Illinois 71
Gold Coast Vacation Rentals in Chicago, Illinois 54
Magnificent Mile Vacation Rentals in Chicago, Illinois 4128
Near East Side Vacation Rentals in Chicago, Illinois 735

People Also Ask

There are 357 Streeterville, IL Vacation Rentals

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