52+ Chicagoland Speedway Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near Chicagoland Speedway

Discover more than 52 holiday rentals in Chicagoland Speedway. PickleTrip™ holiday homes has everything you need to find a place to stay near Chicagoland Speedway, IL.

Whether you are looking for luxury villas in Chicagoland Speedway, furnished homes, unique style condos, flats, cozy cottages for a romantic getaway, spacious apartment for family holidays, or stylish accommodation for a business trip, we can help you find the perfect place with private pickleball courts or nearby facilities. Our holiday rentals include top amenities such as indoor/outdoor swimming pools, kitchen facilities, gyms, hot tubs, Internet connectivity, and more.

If you are planning to travel to Chicagoland Speedway with a whole family or group, PickleTrip™ holiday accommodations can make your trip more memorable. We have plenty of places to stay in Chicagoland Speedway for families, large parties, or private owner accommodations for long or short trips. Pet-friendly holiday rentals are available as well. Book your favorite vacation rentals in Chicagoland Speedway with PickleTrip™. Stay and play pickleball when you travel.

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Frequently Asked Questions About Chicagoland Speedway Holiday Rentals

There are many holiday rentals available in Chicagoland Speedway; however, here are a few of the most popular holiday homes listed in Chicagoland Speedway on our website:
At PickleTrip most of our places to stay are perfect for families. Check out the complete list of holiday homes in Chicagoland Speedway to find one that works for you.
Yes, there are 52 self-catering family homes and holiday rentals in Chicagoland Speedway.
There are more than 52 luxury holiday homes in or near Chicagoland Speedway, according to 2025 data from PickleTrip. Consider these homes for your next holiday:
Yes, there are 52 pet friendly rentals that are available in Chicagoland Speedway.