Central Chicago Summer Rentals, Cottages & Cabins

Book a Place to Stay in Central Chicago for Your Summer Getaway

About Central Chicago Summer Rental on PickleTrip

PickleTrip™'s summer rentals in Central Chicago are perfect for your next summer getaway. We offer a wide range of properties to choose from, including homes with top-notch pickleball courts or nearby facilities, private pools, indoor/outdoor pools, hot tubs, WiFi, beach access, and more. Whether you're traveling with family, friends, or a group, we have a rental that will suit your needs.

Enjoy the perfect summer vacation in Central Chicago with PickleTrip™. Our summer rental homes are designed to provide you with maximum comfort and relaxation. Choose from a variety of properties, including condos, resorts, villas, bungalows, cozy cabins, RVs, and cottages. Stay and play pickleball when you travel with PickleTrip™.

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Frequently Asked Questions About Central Chicago Luxury Rentals

In 2025, PickleTrip offers 2205 summer rentals in or around Central Chicago. Find unique home rentals for your summer holiday or a weekend getaway with family and friends.
The average price per night for a summer rental in Central Chicago is $448. Check the full list of summer accommodations in Central Chicago.
There are 2205 summer rentals, cabins, cottages and properties that are available to rent. Book for your next trip with PickleTrip.

Yes, here are some popular summer holiday rentals in Central Chicago that have a private or indoor pool:

Check all holiday rentals with a pool in Central Chicago on PickleTrip.

Yes, We have 2205 summer rental homes in Central Chicago and types of place to stay in Central Chicago include:

  • Vacation Homes: 2205 available for rent
  • Villas: 2205 Rentals available for rent
  • Holiday Apartments: 2205 Rentals available for rent
  • Hotels with Suites: 2205 Rentals available for book
Yes, of course! There are many luxury summer rental properties in Central Chicago. Use our search filter to discover all of our luxury summer accommodations with an indoor/outdoor pool. Sorting by price is another way to find the most and least expensive luxury summer rentals in Central Chicago.