United / JetBlue / American: Fly Between NYC and Chicago For $56-$58 Each Way

Priceline Booking Link

You can currently snag flights on select dates from New York to Chicago, or vice versa from Chicago to New York for $56.20 – $58.20 each way. Flights are on either JetBlue, United or American airlines, depending on the date.

This fare is bookable on Priceline. With Priceline, tickets purchased are fully refundable until 11:29pm EST the next business day.

When searching for these flights, search as one way tickets, as round-trip may price out higher. There are limited seats available on each date, so initially try searching for one seat and then add one passenger at a time, to get as many seats as possible with the sale price.


Current valid dates from New York – Chicago:

  • March: 20, 21, 22, 23, 25, 26, 27, 28, 29, 30.
  • April: 4, 5, 11, 12, 18, 19, 25, 26, 29
  • May: 2, 3, 6, 9, 10, 13, 16, 17, 23, 24, 28, 31.
  • June: 6, 7, 13, 14.

Current valid dates from Chicago – New York:

  • March: 22, 23, 28, 29, 30, 31.
  • April: 1, 4, 5, 6, 8, 9, 10, 11, 12, 25, 26, 29.
  • May: 2, 3, 10, 31.
  • June: 14, 20, 27.

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