Chicago All inclusive Holidays

Use the all-inclusive filter to find amazing all-inclusive package holidays to Chicago, then just add on your flights with a few simple clicks. With everything from cocktails to car hire booked in one go, all you need to decide is whether you’ll be sipping a mojito or a margarita at sunset.

If screaming kids is your holiday nightmare, book a peaceful adults-only all-inclusive holiday to Chicago and you’re pretty much guaranteed a dreamy retreat. With those thoughtful grownup touches – beachside massage beds and live after-dinner music – an adults-only hotel levels up the sophistication on your holiday.

Last-minute breaks are a great way to find very cheap all-inclusive holidays to Chicago. If you can be flexible with your holiday dates, browse our best Chicago deals and use the all-inclusive filter to add everything that makes your hols perfect.

There are some nifty little tricks to find pocket-friendly all-inclusive breaks in Chicago. Try hunting around for cheaper deals in the off season by playing with your dates. Or you could also choose an all-inclusive hotel or resort a little off the beaten track. We have some top value deals starting at – and they’re easy to find if you sort your results by price. Prices and availability are subject to change. Additional terms may apply.

All-inclusive holidays are such a treat, but a 5-star all-inclusive is a whole other level of luxury. Think butlers waiting on your every whim, infinity pools with epic ocean views and unlimited spa-ing for holiday heaven on cloud nine.

If you’re holidaying with tots in tow, book an all-inclusive Chicago package with all the kid-friendly amenities. The action-packed kids’ clubs, the slide-tastic water parks, the fussy-eater-friendly restaurants: we have a stack of deals specifically designed with kids in mind.

There are great all-inclusive deals galore in Chicago. Sort by price to see the cheapest places to stay, and consider travelling during the less popular months when there’s often more availability and better prices.

Flexibility is key to a stress-free holiday. Look for properties with free cancellation or book now, pay later options. Then, if your plans change, just login to make changes in a few clicks.

With a huge range of all-inclusive Chicago trips on offer, Expedia is your go-to place to find and book your trip. It’s super easy … and it’s all here.