Cheap flights from New York to Chicago

One-way fares from $105 · NYC → CHI · prices found by travellers in the last 48 hours

Compare all dates Chicago → New York
Cheapest fare
$105

Frontier Airlines · Wed, Dec 9

Cheapest month
December

from $105

Direct flights
Yes

American Airlines and Southwest Airlines

Flight time
2h 30m

1,140 km

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Cheapest month to fly from New York to Chicago

Lowest one-way fare per person in each month. Choose a month to see every date.

  1. November 2026 $108
  2. December 2026 Cheapest $105
  3. January 2027 $111
  4. February 2027 $108
  5. March 2027 $113
  6. April 2027 $175
  7. May 2027 $175
  8. July 2027 $175

Cheapest dates in December 2026

The lowest fares we've seen for each day, cheapest first.

Frontier Airlines
Depart06:00 Tue, Dec 8EWR → MDW 5h 08m · 1 stop
$105one way, per person
View deal
Frontier Airlines
Depart06:00 Wed, Dec 9EWR → MDW 5h 08m · 1 stop
$105one way, per person
View deal
Frontier Airlines
Depart06:00 Wed, Dec 16EWR → MDW 5h 08m · 1 stop
$105one way, per person
View deal
Frontier Airlines
Depart09:15 Thu, Dec 10LGA → MDW 4h 50m · 1 stop
$119one way, per person
View deal
Southwest Airlines
Depart18:35 Fri, Dec 25LGA → MDW 2h 40m · Direct
$146one way, per person
View deal
American Airlines
Depart19:30 Tue, Dec 29JFK → ORD 3h 07m · Direct
$157one way, per person
View deal
American Airlines
Depart06:45 Fri, Dec 18EWR → ORD 3h 10m · Direct
$167one way, per person
View deal
American Airlines
Depart17:55 Thu, Dec 24LGA → ORD 2h 59m · Direct
$168one way, per person
View deal
See every date in December 2026 →

Plan the rest of your trip to Chicago

Where to stay, what to do and getting around, from our travel partners.

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Getting around

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About flights from New York to Chicago

New York (NYC) and Chicago (CHI) are about 1,140 km apart. Direct flights take around 2h 30m, and recent direct fares were with American Airlines and Southwest Airlines. Over the next few months, one-way fares start from $105, and December 2026 is currently the cheapest month to fly.

These prices come from searches travellers made in the last 48 hours, so they move quickly. If you see a good fare, it's worth booking soon. FlightsExp is free to use: you book directly with our travel partner.

Frequently asked questions

How much is a flight from New York to Chicago?

The cheapest one-way fare we've seen recently is $105 with Frontier Airlines, departing Wednesday, December 9, 2026. Over the coming months, the lowest fare in each month ranges from $105 to $175.

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

December 2026 currently has the lowest fares, from $105 one way.

Are there direct flights from New York to Chicago?

Yes. Recent direct fares were with American Airlines and Southwest Airlines.

How long is the flight from New York to Chicago?

A direct flight takes about 2h 30m. New York and Chicago are around 1,140 km apart.

Which airlines fly from New York to Chicago?

Recent fares on this route were with Frontier Airlines, American Airlines and Southwest Airlines.

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