Beginning of main content

Search over 1,000,000 properties worldwide and 550 airlines worldwide.

Search over a million flights, hotels, packages, and more

No Expedia cancellation fee to change or cancel almost any hotel reservation.

Check prices on hotels in Chicago

Best deal Jul 5 - Jul 7
Tonight May 26 - May 27
This weekend May 31 - Jun 2
Next weekend Jun 7 - Jun 9

Featured Chicago All-inclusive Resorts

See all 1,654 Properties in Chicago

Estimated price for 1 night/2 adults

Pheasant Run Resort
Pheasant Run Resort
3.0 out of 5.0 4051 E Main Street, West Chicago, IL
Free Cancellation
3.4/5 (857 reviews)
$139/ night for 2 guests

Property is old and would benefit from some remodeling.

Reviewed on May 19, 2019

Chicago All Inclusive Resort Information

We get that preparation is the fun part when it's time to consider your next adventure. Choosing your region, seeking out hotels and airfares, and unearthing the perfect things to do are all a part of making memories that will last forever. But you definitely don’t want to use all your time thinking about what’s included in your hotel. Have no fear: All-inclusive hotels in Chicago are here to help. And our awesome rates and easy payment process are here for you as well.

It's Time to Get the Best Chicago All-Inclusive Hotel

We have 4 Chicago hotels that have it all, and our deals can't be topped. Be sure you find what you really want by taking a look at our review section, where you can learn tons of helpful things to know about Chicago and the Chicago area. The fact that Chicago is also known as "Chi-Town" is just one of the fun things you'll learn, plus:

  • Our reviews are certified and truthful.
  • Uncover recommendations and guidance for visiting Chicago.
  • The frills you require are at your fingertips.
  • Out on the grounds, amenities also abound.
  • Look to Expedia as your partner in planning, and we're certain you will find what you're searching for.

Reserve Your Chicago Holiday Today

Chicago has seen interest holding constant throughout the last twelve months, but it's always been a fashionable area. We'll continue to give you the most amazing deals around, whenever and however you want to tour this holiday hideout. If some time spent away from the office is nearly here, it's a splendid opportunity to get an all-inclusive hotel in Chicago. Then adjust your new camera for stunning vistas and your belly for savory meals—it's vacation time!