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$371+ Cheap flights from Naples (NAP) to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/9. Fares are subject to change and may not be available on all flights or dates of travel.
NAP — CHI
Aug 22 — Aug 291
Sat 8/22
Sat 8/29
1 adult, Economy
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Cheap flight deals from Naples to Chicago

Cheapest flights from Naples to Chicago
Explore the most affordable flight options available from Naples to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 23, 2026.

This lol.travel deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/212:30 pm
NAP
-
ORD
1 stop31h 10m
TAP AIR PORTUGAL
Sun 9/66:00 pm
ORD
-
NAP
1 stop34h 40m
TAP AIR PORTUGAL
Deal found 7/22$544
This lol.travel deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/310:35 am
NAP
-
ORD
1 stop14h 15m
Finnair
Thu 9/109:30 pm
ORD
-
NAP
1 stop14h 35m
Finnair
Deal found 7/20$594
This Flightnetwork deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/36:35 am
NAP
-
ORD
1 stop13h 35m
ITA Airways
Tue 9/83:00 pm
ORD
-
NAP
1 stop12h 35m
ITA Airways
Deal found 7/22$595
This lol.travel deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/310:35 am
NAP
-
ORD
1 stop14h 15m
Finnair
Wed 9/95:35 pm
ORD
-
NAP
Nonstop9h 25m
Finnair
Deal found 7/22$597
This lol.travel deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/310:35 am
NAP
-
ORD
1 stop14h 15m
Finnair
Mon 9/75:30 pm
ORD
-
NAP
Nonstop9h 30m
Finnair
Deal found 7/19$598
This lol.travel deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/33:00 pm
NAP
-
ORD
Nonstop10h 45m
Finnair
Fri 9/115:35 pm
ORD
-
NAP
Nonstop9h 25m
Finnair
Deal found 7/22$604
This lol.travel deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/212:00 pm
NAP
-
ORD
1 stop14h 46m
Finnair
Wed 9/95:35 pm
ORD
-
NAP
Nonstop9h 25m
Finnair
Deal found 7/20$608
This Delta deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/249:05 am
NAP
-
MDW
1 stop20h 31m
Delta
Mon 8/315:45 pm
MDW
-
NAP
2 stops17h 30m
Delta
Deal found 7/21$660
This Delta deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/66:05 am
NAP
-
MDW
2 stops17h 15m
Delta
Tue 10/2010:58 am
MDW
-
NAP
2 stops17h 32m
Delta
Deal found 7/22$661
This Air France deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air France is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/66:05 am
NAP
-
MDW
2 stops17h 15m
Air France
Tue 10/2010:58 am
MDW
-
NAP
1 stop13h 07m
Air France
Deal found 7/22$664
This Trip.com deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/39:00 am
NAP
-
MDW
2 stops20h 36m
Multiple Airlines
Wed 9/95:37 pm
MDW
-
NAP
2 stops17h 38m
Multiple Airlines
Deal found 7/22$692
This Trip.com deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/66:35 am
NAP
-
MDW
2 stops18h 30m
Multiple Airlines
Tue 10/2012:28 pm
MDW
-
NAP
2 stops16h 02m
Multiple Airlines
Deal found 7/19$703

Find flight deals from Naples to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Naples (NAP) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated July 23, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$544
(lol.travel)

One-way from

$371
(Kiwi.com)

Popular in

December

Cheapest in

February

Average price

$886

Good round-trip deal

$689 or less

Good one-way deal

$594 or less
Provider with most accurate pricing for Naples-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Naples-Chicago (CHI) flights.
Search Deals
From Naples to Chicago (CHI)
Search Deals
One-way flight from Naples to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($90 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($23 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
Search Deals
Price to beat on a round-trip flight from Naples to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Naples to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Naples to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 23, 2026.
Use the filters below to find and compare flights from Naples to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

NaplesChicago

NAP - ORD

NAPORD

Naples

Thu 9/3

6:35 am-1:10 pm

1 stop13h 35m

Chicago O'Hare Intl

Sun 9/6

3:00 pm-10:40 pm

1 stop24h 40m

$624
Quickest round-trip

NaplesChicago

NAP - ORD

NAPORD

Naples

Thu 9/3

3:00 pm-6:45 pm

Nonstop10h 45m

Chicago O'Hare Intl

Fri 9/11

9:15 pm-10:00 pm

1 stop17h 45m

$648

NaplesChicago

NAP - ORD

NAPORD

Naples

Thu 9/3

3:00 pm-6:45 pm

Nonstop10h 45m

Chicago O'Hare Intl

Mon 9/7

9:15 pm-2:00 pm

1 stop33h 45m

$648

NaplesChicago

NAP - ORD

NAPORD

Naples

Wed 9/2

12:00 pm-2:15 pm

1 stop33h 15m

Chicago O'Hare Intl

Wed 9/9

9:15 pm-7:05 pm

1 stop14h 50m

$649

NaplesChicago

NAP - ORD

NAPORD

Naples

Thu 9/3

12:00 pm-7:46 pm

1 stop14h 46m

Chicago O'Hare Intl

Tue 9/8

9:15 pm-10:00 pm

1 stop17h 45m

$654

NaplesChicago

NAP - ORD

NAPORD

Naples

Thu 9/3

6:05 am-3:10 pm

1 stop16h 05m

Chicago O'Hare Intl

Tue 9/8

5:10 pm-6:15 pm

2 stops18h 05m

$658

NaplesChicago

NAP - MDW

NAPMDW

Naples

Tue 10/6

6:05 am-4:20 pm

2 stops17h 15m

Chicago Midway

Tue 10/20

10:58 am-11:30 am

2 stops17h 32m

$662

NaplesChicago

NAP - ORD

NAPORD

Naples

Thu 9/3

6:05 am-8:30 pm

2 stops21h 25m

Chicago O'Hare Intl

Fri 9/11

5:10 pm-6:15 pm

2 stops18h 05m

$663

NaplesChicago

NAP - MDW

NAPMDW

Naples

Sat 9/5

6:05 am-4:59 pm

2 stops17h 54m

Chicago Midway

Sat 9/12

5:37 pm-6:15 pm

2 stops17h 38m

$663

NaplesChicago

NAP - MDW

NAPMDW

Naples

Sat 8/29

6:05 am-6:33 pm

2 stops19h 28m

Chicago Midway

Mon 9/7

1:19 pm-3:15 pm

2 stops18h 56m

$663

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/21

Showing 1-10 of 31 resultsSorted by cheapest first
1
2
3
4
  • Most accurate provider: When it comes to deals on Naples-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Naples-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Naples-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Naples-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Naples-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Naples to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Naples with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Naples to Chicago

What is the cheapest month to book a flight from Naples to Chicago?

Currently, February is the cheapest month in which you can book a flight from Naples to Chicago (average of $607). Flying from Naples to Chicago in September is currently the most expensive (average of $1,027). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from NAP to CHI?

Find hourly flight availability from Naples to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 23, 2026.

When flying from Naples to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Weekly flight availability from Naples to Chicago

Explore weekly flight availability from Naples to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated July 23, 2026.

The most flights from NAP to CHI are scheduled on a Monday (4 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (4 on average).

How much does it cost to fly round-trip from Naples to Chicago?

How often are flights from Naples to Chicago delayed?

About 22% of weekly flights between Naples and Chicago have experienced delays in the past year, with the average delay time being 230 minutes.

What is the most punctual flight time for Naples to Chicago flights?

Historically, flights departing in the early afternoon are less likely to be delayed, whereas flights leaving in the morning tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Sunday tends to have the lowest number of delays on this route, whereas Friday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on Naples to Chicago flights?

Over the last year, American Airlines have had the lowest number of delays on this route, with just 22% of flights being delayed.

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated July 23, 2026.
See what other customers who have flown with Turkish Airlines from Naples to Chicago have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Turkish Airlines
7.4
Good
4,447 reviews

Boarding

7.3

Overall

7.4

Entertainment

7.5

Comfort

7.3

Crew

7.8

Food

7.5

Reviews

1 / 20
8.0
Excellent

Muhammad,Jan 2026

ORD - DFW

Great, customer service agent at O’hare was able to change the flight due to snow storm. Thank you
Turkish Airlines
7.4
Good
4,447 reviews
Turkish Airlines
7.4
Good
4,447 reviews

Boarding

7.3

Overall

7.4

Entertainment

7.5

Comfort

7.3

Crew

7.8

Food

7.5

Reviews

1 / 20
8.0
Excellent

Muhammad,Jan 2026

ORD - DFW

Great, customer service agent at O’hare was able to change the flight due to snow storm. Thank you

Related info for your journey

Find useful and relevant information for your journey from Naples to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Naples to Chicago?

    Located just 2.9 mi from the city center, Naples is the airport most travelers will use when flying to Chicago from Naples. Booking flights from Naples (NAP) to Chicago should be relatively easy as there are 4 daily outbound flights to Chicago from 0 different airlines.

  • How long is the flight from Naples to Chicago?

    There are many flights that can get you from Naples to Chicago in 10h 45m. Fly via ITA Airways, British Airways, or Delta to get the fastest option. There are 4929 mi between Naples and Chicago. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Naples to Chicago one-way?

    To fly one-way, consider booking your trip with Finnair, which is currently one of the cheapest options available, starting at $430. American Airlines flights start at $480 while deals on Aer Lingus start at $518 one-way.

  • What are the most reliable airlines from Naples to Chicago?

    Before booking your flight to Chicago from Naples, check out the most reliable airlines to get you to your destination on time: American Airlines (80%), Finnair (80%), Iberia( 80%).

  • What are the cheapest flights from Naples to Chicago?

    The cheapest flight price from Naples to Chicago is $411. On average you can expect to pay $797. The most popular route, (Naples - Chicago O'Hare Intl), can usually be booked for $544.

  • Can I find deals for flights from Naples to Chicago that include hotel bookings?

    Yes. In addition to deals on Naples to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Naples to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Naples to Chicago.

  • Can I find deals for business class flights from Naples to Chicago?

    Yes. Cheapflights offers flight deals from Naples to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Naples to Chicago?

    Currently, February is the cheapest month in which you can book a flight from Naples to Chicago (average of $607). Flying from Naples to Chicago in September is currently the most expensive (average of $1,027). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Benton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter

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