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Flights from Naples to Chicago

We've found these cheap flights for you. You can book one-way or round-trip flight tickets.

      • NAP 13:00
        17h 25m
        1 stop
        CHI 14:00
        Naples - Chicago | Sun, Jul 19 | Normal Airline
        CHI 15:00
        6h
        Nonstop
        NAP 16:00
        Chicago - Naples | Tue, Jul 21 | Normal Airline
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        Search
      • NAP 13:00
        17h 25m
        1 stop
        CHI 14:00
        Naples - Chicago | Sun, Jul 19 | Normal Airline
        CHI 15:00
        6h
        Nonstop
        NAP 16:00
        Chicago - Naples | Tue, Jul 21 | Normal Airline
        Search
        Search
      • NAP 13:00
        17h 25m
        1 stop
        CHI 14:00
        Naples - Chicago | Sun, Jul 19 | Normal Airline
        CHI 15:00
        6h
        Nonstop
        NAP 16:00
        Chicago - Naples | Tue, Jul 21 | Normal Airline
        Search
        Search
      • NAP 13:00
        17h 25m
        1 stop
        CHI 14:00
        Naples - Chicago | Sun, Jul 19 | Normal Airline
        CHI 15:00
        6h
        Nonstop
        NAP 16:00
        Chicago - Naples | Tue, Jul 21 | Normal Airline
        Search
        Search
      • NAP 13:00
        17h 25m
        1 stop
        CHI 14:00
        Naples - Chicago | Sun, Jul 19 | Normal Airline
        CHI 15:00
        6h
        Nonstop
        NAP 16:00
        Chicago - Naples | Tue, Jul 21 | Normal Airline
        Search
        Search
      • NAP 13:00
        17h 25m
        1 stop
        CHI 14:00
        Naples - Chicago | Sun, Jul 19 | Normal Airline
        CHI 15:00
        6h
        Nonstop
        NAP 16:00
        Chicago - Naples | Tue, Jul 21 | Normal Airline
        Search
        Search
      • NAP 13:00
        17h 25m
        1 stop
        CHI 14:00
        Naples - Chicago | Sun, Jul 19 | Normal Airline
        CHI 15:00
        6h
        Nonstop
        NAP 16:00
        Chicago - Naples | Tue, Jul 21 | Normal Airline
        Search
        Search
      • NAP 13:00
        17h 25m
        1 stop
        CHI 14:00
        Naples - Chicago | Sun, Jul 19 | Normal Airline
        CHI 15:00
        6h
        Nonstop
        NAP 16:00
        Chicago - Naples | Tue, Jul 21 | Normal Airline
        Search
        Search
      • NAP 13:00
        17h 25m
        1 stop
        CHI 14:00
        Naples - Chicago | Sun, Jul 19 | Normal Airline
        CHI 15:00
        6h
        Nonstop
        NAP 16:00
        Chicago - Naples | Tue, Jul 21 | Normal Airline
        Search
        Search
      • Cheapest nonstop
        NAP 15:00
        10h 45m
        Nonstop
        ORD 18:45
        Naples - Chicago | Sat, Aug 29 | Iberia
        US$398 US$589
        32% off
        32% off
        US$589 US$398
      • NAP 15:00
        10h 45m
        Nonstop
        ORD 18:45
        Naples - Chicago | Sat, Aug 29 | British Airways
        US$481 US$589
        18% off
        18% off
        US$589 US$481
      • NAP 15:00
        10h 45m
        Nonstop
        ORD 18:45
        Naples - Chicago | Sun, Aug 30 | British Airways
        US$485 US$589
        18% off
        18% off
        US$589 US$485
      • NAP 15:00
        10h 45m
        Nonstop
        ORD 18:45
        Naples - Chicago | Sun, Aug 30 | American Airlines
        US$488
        17% off
        US$589 US$488
      • NAP 15:00
        10h 45m
        Nonstop
        ORD 18:45
        Naples - Chicago | Fri, Aug 21 | American Airlines
        US$498
        15% off
        US$589 US$498
      • NAP 15:00
        10h 45m
        Nonstop
        ORD 18:45
        Naples - Chicago | Sat, Aug 29 | Finnair
        US$498
        15% off
        US$589 US$498
      • NAP 15:00
        10h 45m
        Nonstop
        ORD 18:45
        Naples - Chicago | Sun, Aug 30 | Finnair
        US$503
        15% off
        US$589 US$503
      • NAP 15:00
        10h 45m
        Nonstop
        ORD 18:45
        Naples - Chicago | Sun, Aug 30 | Iberia
        US$505
        14% off
        US$589 US$505
      • NAP 06:50
        16h 10m
        1 stop
        ORD 16:00
        Naples - Chicago | Sat, Aug 29 | American Airlines
        US$481
        18% off
        US$589 US$481
      • NAP 19:15
        27h 45m
        1 stop
        ORD 16:00
        Naples - Chicago | Thu, Sep 3 | TAP Air Portugal
        US$524
        11% off
        US$589 US$524
      • NAP 13:00
        17h 25m
        1 stop
        CHI 14:00
        Naples - Chicago | Sun, Jul 19 | Normal Airline
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Cheapest airlines flights from Naples to Chicago

You can choose from 1 airlines that fly from Naples to Chicago, including Turkish Airlines, Iberia has lowest fares on this route.
Turkish Airlines logo Turkish Airlines
Airlines are determined based on actual purchased flight tickets from Naples to Chicago according to previous 12 months data from Trip.com.

Naples to Chicago Flight Details

The distance between Naples and Chicago is about 7,928.35 km. The average flying time from Naples to Chicago is around 10 hours 50 minutes. Based on Trip.com's latest data, travel demand is highest in July. The off-season for travel is November.

Cheapest one-way flight priceUS$398
Cheapest monthNovember
Peak season for travelJuly
Flight distance7,928.35 km
Average flight time10 hours 50 minutes
Popular airlineTurkish Airlines
Flight statistics for the Naples–Chicago route are based on aggregated booking data from Trip.com over the past 12 months.

Frequently Asked Questions

  • Which airlines offer flights from Naples to Chicago?

    At the moment, several airlines serve connecting flights from Naples to Chicago, including: ITA Airways Turkish Airlines Selected airlines are based on historical data collected from flight bookings made by users on Trip.com within the last 90 days.
  • It takes about 10 hours 50 minutes to fly 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.
  • 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 Sat, Aug 29, with one-way flights priced at just US$398.
    · 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.
  • The cheapest months to fly from Naples to Chicago is November, when demand for travel is lower.
  • After crunching the numbers on our July flight calendar, it's currently cheapest to fly from Naples to Chicago on July 25, 2026 with British Airways, with prices starting at US$635.
  • You can land at any one of the following hubs in Chicago, with Naples International Airport to O'Hare International Airport (NAP-ORD) is by far the most common option on this route: Chicago Midway International Airport (MDW) O'Hare International Airport (ORD) Chicago Rockford International Airport (RFD).
  • The time difference between Chicago and Naples is 7h.
  • 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.

Trip.com Airline Insights on Flights from Naples to Chicago

Which airline offers the cheapest direct flights from Naples to Chicago?

Data is based on the average price of all nonstop flights from Naples to Chicago on Trip.com over the past 12 months.

Based on Trip.com’s data from the past 12 months, Turkish Airlines provides the lowest-priced direct flights from Naples to Chicago, with fares starting at US$672.

US$84
US$672
US$1,260
US$1,848
US$2,436
Turkish Airlines
US$672
Turkish Airlines
Aer Lingus
US$786
Aer Lingus
ITA Airways
US$927
ITA Airways
Iberia
US$2,436
Iberia

Which airline operates the most flights from Naples to Chicago?

Total flights from Naples to Chicago across all airlines. (Based on Trip.com data from the past month)

Based on Trip.com’s data from the past month, American Airlines/Iberia/British Airways/Finnair operates the most frequent flights from Naples to Chicago, with 8 flights per week.

8
American Airlines
8
American Airlines
Iberia
8
Iberia
British Airways
8
British Airways
Finnair
8
Finnair

How many flights fly from Naples to Chicago daily?

The data is based on the flight numbers for each day of the week from Naples to Chicago within the Trip.com database over the past month.

Based on the past month's historical data from Trip.com, the number of flights from Naples to Chicago is the highest on Friday/Saturday/Sunday and the lowest on Monday.

20
16
12
8
Highest
12
Mon
16
Tue
16
Wed
16
Thu
20
Fri
20
Sat
20
Sun

Explore More Popular Flights

Note: Prices shown on this page are the estimated lowest prices found in the last 24 hours and include all taxes and fees.

Book with no extra fees

Prices displayed on this page are all-inclusive (incl. taxes, fuel surcharges, Civil Aviation Development Fund, etc.), and all fees are clearly shown before you pay. Charges for checked baggage, onboard meals, Wi‑Fi, and other optional services are also included where applicable in the flight cards.

Real-time pricing updates

Prices, availability, and travel details on this page have been updated within the last 24 hours, and for many routes are refreshed in real time. The more popular the route, the more accurate and up-to-date the data.

Change & Cancellation Policy

Trip.com shows the change and cancellation rules for each ticket during the booking process, including all related fees and conditions. Please refer to the following scenarios:
Voluntary cancellation/change:
To request a change or cancellation, go to the flight bookings page, select the option to change or cancel your booking, choose the relevant passengers and flight segment, and submit your request. Please note that additional charges may apply based on the airline’s fare rules.
Cancellation/change due to a flight schedule change:
If your flight has been rescheduled and you would like to change or cancel your ticket, you can submit an involuntary cancellation request. For full details of change and cancellation policies, please refer to the customer support pages.