What’s the cost of a flight from New York JFK to Chicago Midway?

Prices vary based on date, airline, and availability. Compare several options if you're flying between New York City and Chicago.

Choose a date to explore the best fares now.

If possible, avoid holiday periods: ticket prices tend to rise quickly and availability drops, especially on busy routes. Morning and evening flights are often in high demand too — book early to get a good fare.

Which airports near New York City or Chicago offer flights?

In many cases, using a nearby airport can improve your chances of finding direct flights or better rates.

• Airports in New York City: 3 airports are active - John F. Kennedy, La Guardia, Newark.
• Airports in Chicago: 3 options available in Chicago - Midway, O'Hare, Rockford.

Secondary airports can offer faster travel thanks to shorter lines and quicker boarding times than major ones.

Find flights from New York JFK to Chicago Midway that suit your schedule

Use Jetcost to sort and filter results based on your preferred flight time, number of stops, price range, or airline. View deals from the best airlines and travel agencies.

Other popular destinations

Interested in United States? These cities are also in demand: Las Vegas, Los Angeles, Miami, New York City, Orlando.

Connecting flights can be cheaper but often mean longer layovers. You can easily select either direct or connecting flights with a single click using the filters.