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Cheapest prices ($44 One Way, $88 Round Trip) found within past 7 days. Prices and availability subject to change. Additional terms may apply.
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Planning a trip to Chicago? All you need is CheapTickets to get low fare deals on flights from New York to Chicago.
By booking early, you may find some real low-cost or even bargain offers from among the airlines that have scheduled flights from New York to Chicago. Most New York to Chicago flights take-off from La Guardia Airport (LGA) and arrive at O'Hare International Airport or Chicago Midway International Airport after about two hours. New York being the financial center, you can expect traffic going to the airport, although land transportation is easy with shuttles, cars, buses, railways, and taxis. Despite the announced traffic efficiency, it is safer to check-in early for your flights from New York to Chicago. LGA is an airport hub which means your time won't be wasted as you can enjoy or make use of the first-class facilities at the airport.
Your New York to Chicago flights will most likely land at O'Hare's Terminals 1, 2, or 3. Chicago is the third largest city in the U.S. and is known to be a windy city, so be ready with your clothing. Weather unpredictability demands you travel light with mixed clothes. The city is home to six major sports teams, including basketball and football, as well as the Chicago Blues Festival, the largest blues festival in the world. Your New York to Chicago flights are not complete if you miss the John Hancock Observatory and the Field Museum. Just a little reminder: Chicago is one place that is periodically visited by swarms of cicadas. Check out the timing of this phenomenon before you finalize your schedule.