VersusFly

Flights New York to Chicago

The best month to fly from New York to Chicago is November: as low as €190, compared with €215 in September.

Thursday is on average the cheapest day to leave (€190).

3 prices were recorded on this route over the last 60 days.

Updated September 23, 2026

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  • New York (all)
  • Chicago (all)

Optional – to calculate the real cost of getting to the airport.

Trip type
Dates
Nights there
More options
Departure days
Return days
€190Lowest price seen (60 d)
€202Median price
—Direct flight
3Prices recorded

Prices by departure month

Sept 26 : €215 €215 Sept 26 Octo 26 : €202 €202 Octo 26 Nove 26 : €190 €190 Nove 26
Lowest price seen per month

Prices by departure day

Wed : €215 €215 Wed Thu : €190 €190 Thu Sat : €202 €202 Sat
Median price by weekday

Airlines seen

  • Frontier Airlines
  • jetBlue

Door-to-door cost

The real cost includes getting to the airport (fuel, tolls, parking or train), luggage and the transfer on arrival. Add your address in the form to calculate it.

Frequently asked questions

What is the cheapest month to fly New York – Chicago?

Based on prices seen, November (from €190).

Which airport is closest to Chicago city centre?

Chicago Midway (MDW), 14 km from Chicago centre.

Nearby destinations, same departure

See also

Prices are indicative and dated. The final price is confirmed on the partner’s site.