What’s the cost of a flight from Naples to Chicago Midway?

Prices vary based on date, airline, and availability. Compare several options if you're flying between Naples 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.

Is there more than one airport in Naples or Chicago?

Even short-haul routes can benefit from considering secondary airports. It may open up more flight times or cheaper fares.

• Airports in Naples: Only Naples - Capodichino is currently operational.
• Airports in Chicago: Chicago has 3 airports - Midway, O'Hare, Rockford.

Airports with more daily flights offer more flexibility if plans change or delays occur. If you’re flexible, consider airports near Chicago as well.

Refine your flight search from Naples to Chicago Midway

With Jetcost, it’s easy to narrow down results to find flights that match your schedule and preferences. You can filter by airline, price, trip type, and more — including offers from the best airlines and travel agencies.

Other popular destinations

Also looking at United States? These cities are trending: Las Vegas, Los Angeles, Miami, New York City, Orlando.

Online agencies can show different offers for the same flight — it’s worth comparing. Filters let you narrow things down further, like selecting a specific time slot to find flights that suit you best.