Compare prices across airlines and find the best deals
Our best American Airlines deals on New York to Chicago tickets
Our best Frontier Airlines deals on New York to Chicago tickets
If your flying dates are flexible, you should consider flying to Chicago on a Fri, as we generally find the cheapest rates on that day. On the other hand, Sun is the most expensive day to fly.
The cheapest month for flights from New York to Chicago is Oct, where tickets cost $109 on average. The most expensive months are Dec.
Compare prices across airlines to find the best deal. Prices can vary significantly.
Flying midweek or in off-peak seasons can save you up to 30% on airfare.
Booking 3+ weeks in advance typically offers the best prices.
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