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Cheap JFK to MDW Flights

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

New York to Chicago route information

Origin Airport John F. Kennedy Intl.
Destination Airport Midway Intl.
Airlines Serving Delta
Flight Price $188
Distance 728 mi

Newark

$207.49

White Plains

$194.00

Islip

$16,311.96

New York

$270.40

Chicago

$171.00

Cheap JFK to MDW Flights

  • How long does the average person visit Chicago?

    Of course, you are not an average person, but if you were, you'd stay around five days.
  • What is the cheapest day to fly?

    The cheapest day to fly from New York to Chicago is on Monday. If you would like to save a bit of money on your next holiday look for flights on that day.
  • Which airline has the least delays from New York to Chicago?

    Booking with NetJets Aviation means you will arrive to Chicago . In fact, this timely airline has a 50% on-time average. Of course, it never hurts to be prepared. If you're on GoJet Airlines, be sure to sign up for the delay notifications to stay up to date with your flight's status.
  • Is there an alternative airport near Chicago?

    Chicago Midway International Airport is a fine airport, but there is a cheaper option -- O'Hare International Airport. It's only 16 miles away and flights are being booked 34% cheaper over the coming two months.
  • What is the cheapest airline flying from New York to Chicago?

    Delta Air Lines is the leader in keeping costs low for their passengers over the next three months. Bookings are being made at just $158 and, when compared to the pricier bookings of $934, it's a terrific deal.
  • What is the cheapest day to fly to Chicago?

    If you are needing to save some cash, look at Dec 9th. As of Nov 11th, it's showing the cheapest ticket sales at $164. That is 56% below the average for this route, so you can spend the savings on some souvenirs while in Chicago.
  • Can I change the date of my flight?

    Yes, you can adjust your departure date. If you wish to save some funds in doing so, the lowest-cost day to fly in November is Monday. You might think you're missing out taking off a day early, but we see it as just adding saving towards a future holiday. A penny saved is a vacation earned.

New York to Chicago Flights

Sometimes you just need to get out of town or maybe you’re looking for a change of scenery. Regardless of the reason, a flight from New York to Chicago will do just the trick! Go on, plan to see all the famous landmarks and eat your weight in the local cuisine. Your trip is beckoning, so answer the call by packing your suitcase and filling your travel itinerary with exploring Chicago.

Whether you’re flying for business or jet-setting on your personal time, you’ve come to the right place. Here at Expedia.com, we’ll pair you up with JFK to MDW flights that won’t make your bank account wince. Ready to temporarily leave behind New York for new horizons? Browse through our cheap airfare, and filter by flight times and dates until you find just what you had in mind. From flights without layovers to ones that arrive early in the morning, you’ll come across plane tickets that suit your travel preferences. You can even bundle your flight to MDW with hotels and car rentals to score even bigger savings.

All set to hit the clouds? Book your travel arrangements with us today and have left-over money to put toward your travel outings and adventures.

Package Disclaimer

*Savings amount equal to 100% when flight + hotel are booked together. Prices based on searches conducted by fellow shoppers within the past 24 hours. There is no guarantee that these prices will be in effect at the time of your search. Vacation package savings are based on comparison to prices on Expedia.com of the same components booked separately. Savings vary based on origin/destination, length of trip, stay dates and travel partners, and aren't available on all packages.