Cheap Flights from Naples to Chicago from $603

Frequently Asked Questions

• What are the cheapest flights from Naples to Chicago (NAP-CHI)?

  Based on Trip.com data, Turkish Airlines offers one-way fares as low as $603 on Cheapest nonstop routes (e.g. NAP to ORD on Thu, Jul 2), while KLM offers Cheapest nonstop round-trips from $732 departing on Sat, Jun 20 and returning on Sat, Jun 27.

• Which airlines offer direct flights from Naples to Chicago?

  At the moment, you can catch a nonstop flight from Naples to Chicago with the following airlines, including: American Airlines Selected airlines are based on historical data collected from flight bookings users made on Trip.com within the last 90 days.

• How long does it take to fly from Naples (NAP) to Chicago (CHI) and what is the distance?

  It takes around 10 hours 55 minutes to fly from Naples (NAP) to Chicago (CHI).

• When is the best time to book flights from Naples to Chicago?

  By analyzing data from all airlines on the Trip.com flight calendar, it looks like the best time to book a flight from Naples to Chicago is around 40 days (6 weeks) in advance, and the best time to fly is usually on Tuesday, Wednesday, and Saturday. Tuesday typically offers the cheapest flights for departure, while Saturday offers the best return deals.

• How many flights are there per week from Naples to Chicago?

  Based on Trip.com data in the past 4 weeks, there is 7 flight per week flying from Naples to Chicago. You can check the weekly schedule for popular airlines on this route below: American Airlines: S/M/T/W/T/F/S -- AA181 (15:16)

• How can I find the best deals on flights from Naples to Chicago?

  To find best deals on flights from Naples to Chicago, you can use various tools on Trip.com:
  · Be flexible with your travel dates to get the cheapest flight deal. Now the cheapest flight deal is on Thu, Jul 2, with one-way flights priced at just $603.
  · Compare airlines strategically. Budget carriers often provide the lowest base fares, while we found the most affordable airline currently operating on this route is Iberia.
  · Set up price alerts to easily monitor ticket prices without having to check every day.
  · Check Trip.com flight deals and promo codes frequently.
  · Avoid peak season unless you book very early. It seems the peak season for Chicago travel is around July.
  · Get exclusive promo codes for Trip.com app users.

• When are flight tickets from Naples (NAP) to Chicago (CHI) the cheapest?

  The cheapest months to fly from Naples to Chicago is November, when demand for travel is lower.

• Which upcoming date is cheapest to fly from Naples to Chicago on?

  After crunching the numbers on our June flight calendar, it's currently cheapest to fly from Naples to Chicago on June 27, 2026 with Wizz Air Malta, with prices starting at $549.

• Which airports can I fly to for Chicago from Naples?

  You can land at any one of the following hubs in Chicago, with Naples International Airport to Chicago O'Hare International Airport (NAP-ORD) is by far the most common option on this route: Chicago O'Hare International Airport (ORD) Chicago Midway International Airport (MDW) Chicago Rockford International Airport (RFD).

• Is there any time difference between Naples and Chicago?

  The time difference between Chicago and Naples is 7h.

• How do I change or cancel my ticket from Naples to Chicago?

  Tickets can only be changed or canceled if permitted by airline policy. To submit a change or cancellation request, go to the flight bookings page, select the option to change or cancel your booking, choose the relevant passengers and segment, and submit a request. Please note that additional charges may apply according to the airline ticket policy. However, if the flight has been rescheduled and you would like to change or cancel your ticket, you can submit an involuntary cancellation request. For more details about change and cancellation policies, please check the customer support pages.