United / JetBlue / American: Fly Between NYC and Chicago For Just $39-$44 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 just $39.20 – $44.20 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:

  • September: 12, 13, 19, 20, 25, 26, 27, 28, 30.
  • October: 2, 3, 4, 7, 10, 11, 12, 14, 16, 17, 18, 19, 21, 23, 24, 25, 26, 27, 28, 30, 31.
  • November: 1, 2, 4, 6, 7, 8, 11, 13, 14, 15, 28, 29.
  • December: 1, 2, 4, 5, 6, 7, 8, 9, 11, 12, 13, 14.
  • January: 4, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31.
  • February: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14.

Current valid dates from Chicago – New York:

  • September: 12, 13, 19, 20, 26, 6,7 28, 30.
  • October: 2, 3, 4, 5, 6, 7, 10, 11, 12, 13, 14, 16, 17, 18, 19, 210, 21, 23, 24, 25, 26, 27, 28, 30, 31.
  • November: 1, 2, 3, 4, 6, 7, 8, 9, 11, 13, 14, 15, 16, 28, 29, 30.
  • December: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 17, 18, 19, 20.
  • January: 3, 4, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31.
  • February: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14.

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