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Cheap Flights from New York to Chicago $143.6

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Cheapest Flights from New York to Chicago (JFK to MDW)

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Interesting Facts About Flights from New York to Chicago (JFK to MDW)

Question : Should you take that vacation to Chicago in the next 30 days?
Answer : Since low prices are preferred, look at February 10th. As of January 23rd, the cheapest ticket sales are coming in 43% below the average price for this route, so you can spend that extra money on an adventure rather than the flight.

Question : How long are most people's visits to Chicago when they fly in from New York?
Answer : The average time spent in Chicago by passengers flying from JFK is four days.

Question : Would you be willing to change your travel days if it saved you money?
Answer : The lowest-cost day to fly in February is Wednesday. Having flexibility in your travel plans means you can save, so be sure to plan ahead when possible.

Question : Are prices changing frequently for this route?
Answer : Prices are fluctuating much more for this route than the majority of routes. Remember, you can save by booking further in advance.

Question : Is this route your best bet for getting to Chicago with minimal delays?
Answer : The best way to measure a flight's promptness combines both on-time percentage and total delay minutes. JFK to MDW currently has 0.2 stars out of 5, earning the route one of the lower scores in the world.