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Chicago Resorts & All Inclusive Resorts

Discover the 33 Best Resorts in Chicago

About Chicago Resorts on PickleTrip

PickleTrip™ makes it easy to compare and book resorts in Chicago. You can filter your search by location, price, amenities, and more to find the perfect resort for your needs. Our user-friendly website allows you to view detailed descriptions, photos, and customer reviews of each resort, so you can make an informed decision before booking. Additionally, we offer special deals and discounts on many resorts, so you can save money on your next vacation.

Whether you're looking for a romantic getaway or a family vacation, you'll find the perfect resort on PickleTrip™. We also have a great selection of all-inclusive resorts, where everything from meals to activities is included in the price. This can be a great option for those who want to relax and not have to worry about budgeting for extra expenses. Browse our selection of resorts today and start planning your next trip to Chicago.

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Frequently Asked Questions About Chicago Resorts

There are a lot of options in Chicago. If you plan on staying in the Chicago area, consider making a reservation for a few nights at one of these properties as these have been rated the top Resort Rentals in Chicago:

Most of our listed resorts are suitable for families in Chicago. Filter your all-inclusive resorts Chicago with a family-friendly option to see which ones are right for you.
Yes, there are more than 33 resorts in Chicago that have indoor and private swimming pools. Check out our filter option and find your best resort near Chicago.
At PickleTrip, the rate for luxury resorts in Chicago per night starts from $119. Our partner provides these prices & we calculated the average daily rate in Chicago. Please see our partner's price for more details.
Yes. We have all-inclusive resorts in Chicago that allow pets. Some of the top pet-friendly resorts in Chicago are:

You can see all pet-friendly places to stayin Chicago on PickleTrip

Most of the resorts are perfect for travelers, but based on guest reviews in 2026, the best resorts in or near Chicago are:
Some of the resorts in Chicago have been described as romantic by other travelers: