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Chicago Flights as Low as $167

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.

Chicago Flight Travel Guide

No matter how much you fight the travel bug, sometimes there's only one solution—to hop on the next plane to Chicago. AARP Travel Center Powered by Expedia® is here to help you cure that bug with great deals on flights and activities. AARP Travel features members-only discounts with the best rates from Expedia, so members will get the best price in travel, guaranteed.

As an AARP member, you'll have the opportunity to take advantage of exclusive rates on:

  • Hotels
  • Car rentals
  • Flights
  • Waived booking fees on flights

Once you have got your trip scheduled, we'll show you a full list of deals for your route. Do not forget to look at flights to alternative airports nearby, which can help you find a lower fare.

Transportation at the Airport

Once you've reserved plane tickets to Chicago, you might want to book a rental car so you can get around on your own. You can request Chicago car rentals under our cars tab and get in the car as soon as you step out of the airport. For more information, check out the Chicago (and vicinity) Car Rentals Guide.

Chicago Activities

If you aren't sure where to start, we can help you with that as well. Not to worry—there's lots to do in this city. Chicago has so much to do, and we can help you get started.

If you're looking for some fun activities to do in Chicago, make sure you look at our "Things to Do in Chicago (and vicinity)" page for activities and excursions for the whole crew.

Where to Stay in Chicago

Chicago has hotel to choose from, make sure you check out our hotel listings tab for some great recommendations from past visitors. Remember that you will get the best price out there when you stay with us.

Planning Your Trip to Chicago

Whether you are heading out on a business trip, exploring a place you have never been before or are bringing the family on the annual vacation, we have the perfect getaway waiting for you. There is no better time than now to start booking your next trip. Book one of our flights today.