How much should you expect to spend for a flight from New York to Chicago Midway?

Flight prices from New York City to Chicago change depending on demand and time of booking.

Pick a travel date to see today’s available fares.

Studies show that flying midweek — like on a Tuesday or Wednesday — can be cheaper than weekend flights. Still, airfares change frequently, so check updated prices on Jetcost.

What are the airport options between New York City and Chicago?

If both departure and destination cities offer multiple airports, comparing them can help you save time and money.

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

Some airports have different terminals for low-cost and traditional airlines — knowing in advance can save time. You can filter results to see only the airports that suit you.

Smart ways to search flights from New York to Chicago Midway

Use Jetcost to view tailored results based on what you care about — time, duration, number of stops, or even your preferred booking agency. Results include carriers like American, Delta, United, and more.

Other popular destinations

Flying to United States? Other travelers also searched: Atlanta, Los Angeles, Miami, New York City, Orlando.

Prefer non-stop flights? Just activate the filter to skip unnecessary layovers. If your dates are flexible, you can also explore different departure and return combinations to find the best fit.