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Chicago Flights as Low as $161.97

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.

Cheap Chicago Flights

Celebrate your retirement, whether it’s a year away or a month, by exploring one of the most exciting cities in the Midwest: Chicago. With AARP Chicago flight deals, you don't have to put a dent in your savings to afford a memorable getaway to the Windy City. Low cost AARP member and senior flight deals in Chicago put more money in your travel fund. Use your extra cash and put it toward catching a baseball game at Wrigley Field, a Chicago Bulls basketball game, or even a football game played by the Chicago Bears. With the money you save on affordable Chicago vacations, you might as well get tickets for all three!

Right here at the AARP Travel Center Powered by Expedia, we offer a wide selection of Chicago flights for seniors and AARP members. We invite you to pair cheap flights for seniors and members to Chicago, IL with affordable Chicago car rentals and some of the best prices on Chicago hotels for a trip you won't be able to resist. Best of all, the cheapest airfare deals, vacation packages, and more are found right here in one convenient location. We want to leave you with more time to pick out the museums you want to visit in the Loop and whether your first meal in the Windy City will be a traditional hot dog with the works or a slice of deep dish pizza.