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Chicago Vacation Packages for 2021

Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*

Choose two or more items and save on your trip:

Chicago Vacation Packages

Trying to figure out a way to package your flight and hotel, while saving some money? The AARP Travel Center Powered by Expedia® can help you get everything you need, while saving you both money and some time. We're here to book everything you'll need to make your Chicago trip one to remember. In only a few clicks, you can select the best Chicago vacation package for you. We have a huge list of flights and hotels, and Chicago activities to select from.

Chicago Hotel Deals

You can choose from around 2933 hotels. Whether you want to stay in the heart of the city or pick a spot that is near all the Chicago hot spots, we have plenty of options available.

We have fantastic rates on everything from family-friendly resorts that meet all the vacation must-haves to inexpensive hotels perfect for those on a budget. You can look through our vast catalog of options and pick the hotel that is perfect for you and your family. With AARP Travel Center's Chicago hotel packages, you not only get a great rate on your flight, but also a wonderful place to stay.

Things to do in Chicago

People from all over make this city their vacation destination, and with good reason. A little curiosity and asking the right people, like your hotel's concierge, goes a long way into having a unique experience.

If you need more suggestions, then make sure to click on AARP's "Things to Do" tab.

Book Together and Save

As an AARP Member, you get to take advantage of all the great deals. You'll save on select hotels worldwide, flights, and also car rentals. No matter what Chicago vacation package you pick, your membership savings helps you get a great deal. The hardest packing you'll have to do is for your suitcase. Bundle now and get ready for your Chicago vacation.

Top Hotel Deals

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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Top Flight Deals

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Spirit Airlines
Spirit Airlines
Spirit Airlines
United