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$340+ 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 5/10. Fares are subject to change and may not be available on all flights or dates of travel.
NAP — CHI
Apr 12 — Apr 191
Sun 4/12
Sun 4/19
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 March 13, 2026.

This lol.travel deal was found by Cheapflights users on 3/10. 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 4/167:15 pm
NAP
-
ORD
1 stop27h 45m
TAP AIR PORTUGAL
Wed 4/226:00 pm
ORD
-
NAP
1 stop17h 25m
TAP AIR PORTUGAL
Deal found 3/10$507
This Finnair deal was found by Cheapflights users on 3/8. 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 Finnair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/2310:35 am
NAP
-
ORD
1 stop14h 15m
Finnair
Thu 4/309:30 pm
ORD
-
NAP
1 stop14h 35m
Finnair
Deal found 3/8$598
This American Airlines deal was found by Cheapflights users on 3/8. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/167:40 am
NAP
-
ORD
1 stop16h 55m
American Airlines
Wed 4/2210:30 pm
ORD
-
NAP
1 stop16h 30m
American Airlines
Deal found 3/8$602
This British Airways deal was found by Cheapflights users on 3/10. 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 British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/166:00 am
NAP
-
ORD
1 stop15h 25m
Multiple Airlines
Wed 4/229:15 pm
ORD
-
NAP
1 stop17h 45m
Multiple Airlines
Deal found 3/10$623
This American Airlines deal was found by Cheapflights users on 3/8. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/223:00 pm
NAP
-
ORD
Nonstop10h 50m
American Airlines
Mon 10/266:40 pm
ORD
-
NAP
1 stop13h 25m
American Airlines
Deal found 3/8$627
This KLM deal was found by Cheapflights users on 3/8. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/2210:40 am
NAP
-
ORD
1 stop34h 35m
KLM
Wed 4/295:10 pm
ORD
-
NAP
1 stop15h 35m
KLM
Deal found 3/8$634
This Trip.com deal was found by Cheapflights users on 3/10. 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 4/166:05 am
NAP
-
MDW
2 stops19h 31m
Air France
Wed 4/221:24 pm
MDW
-
NAP
2 stops19h 21m
Air France
Deal found 3/10$667
This Delta deal was found by Cheapflights users on 3/11. 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.
Thu 4/1610:15 am
NAP
-
MDW
2 stops19h 13m
Delta
Wed 4/226:00 am
MDW
-
NAP
2 stops19h 10m
Delta
Deal found 3/11$695
This Delta deal was found by Cheapflights users on 3/10. 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.
Fri 4/2410:15 am
NAP
-
MDW
2 stops19h 13m
Delta
Fri 5/11:24 pm
MDW
-
NAP
2 stops18h 51m
Delta
Deal found 3/10$743
This Delta deal was found by Cheapflights users on 3/12. 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.
Fri 5/86:05 am
NAP
-
MDW
2 stops22h 04m
Delta
Thu 6/45:15 pm
MDW
-
NAP
2 stops18h 00m
Delta
Deal found 3/12$1,047
This Expedia deal was found by Cheapflights users on 3/9. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/219:05 am
NAP
-
MDW
2 stops16h 28m
Multiple Airlines
Sat 5/3010:45 am
MDW
-
NAP
1 stop13h 20m
Multiple Airlines
Deal found 3/9$1,091
This Trip.com deal was found by Cheapflights users on 3/11. 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.
Fri 3/136:15 am
NAP
-
MDW
2 stops22h 16m
Multiple Airlines
Tue 3/171:10 pm
MDW
-
NAP
2 stops20h 40m
Multiple Airlines
Deal found 3/11$1,109

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 March 13, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$507
(lol.travel)

One-way from

$340
(Kiwi.com)

Popular in

December

Cheapest in

May

Average price

$765

Good one-way deal

$552 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. 15% potential increase in price ($135 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($21 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
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 March 13, 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 4/23

10:35 am-5:50 pm

1 stop14h 15m

Chicago O'Hare Intl

Thu 4/30

9:30 pm-7:05 pm

1 stop14h 35m

$598

NaplesChicago

NAP - ORD

NAPORD

Naples

Thu 4/16

2:50 pm-2:25 pm

1 stop30h 35m

Chicago O'Hare Intl

Wed 4/22

10:30 pm-10:00 pm

1 stop16h 30m

$617

NaplesChicago

NAP - ORD

NAPORD

Naples

Thu 4/16

6:00 am-2:25 pm

1 stop15h 25m

Chicago O'Hare Intl

Wed 4/22

9:15 pm-10:00 pm

1 stop17h 45m

$623

NaplesChicago

NAP - ORD

NAPORD

Naples

Wed 4/22

10:40 am-2:15 pm

1 stop34h 35m

Chicago O'Hare Intl

Wed 4/29

5:10 pm-3:45 pm

1 stop15h 35m

$634

NaplesChicago

NAP - ORD

NAPORD

Naples

Thu 4/16

6:05 am-3:10 pm

1 stop16h 05m

Chicago O'Hare Intl

Wed 4/22

1:36 pm-3:45 pm

2 stops19h 09m

$635

NaplesChicago

NAP - ORD

NAPORD

Naples

Wed 4/22

6:05 am-3:10 pm

1 stop16h 05m

Chicago O'Hare Intl

Wed 4/29

3:30 pm-6:15 pm

2 stops19h 45m

$638

NaplesChicago

NAP - MDW

NAPMDW

Naples

Thu 4/16

10:15 am-10:28 pm

2 stops19h 13m

Chicago Midway

Wed 4/22

6:00 am-8:10 am

2 stops19h 10m

$695

NaplesChicago

NAP - ORD

NAPORD

Naples

Sun 4/26

6:00 am-2:50 pm

1 stop15h 50m

Chicago O'Hare Intl

Sun 5/3

6:15 pm-6:20 pm

2 stops17h 05m

$732

NaplesChicago

NAP - ORD

NAPORD

Naples

Fri 4/24

6:00 am-8:05 pm

2 stops21h 05m

Chicago O'Hare Intl

Fri 5/1

6:15 pm-6:15 pm

2 stops17h 00m

$734

NaplesChicago

NAP - MDW

NAPMDW

Naples

Fri 4/24

10:15 am-10:28 pm

2 stops19h 13m

Chicago Midway

Fri 5/1

1:24 pm-3:15 pm

2 stops18h 51m

$743

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/9

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

How often are flights from Naples to Chicago delayed?

About 23% of weekly flights between Naples and Chicago have experienced delays in the past year, with the average delay time being 222 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?

Thursday 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 23% 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 March 13, 2026.
See what other customers who have flown with Turkish Airlines and American 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
7.3
Good
4,254 reviews

Food

7.5

Entertainment

7.5

Overall

7.3

Boarding

7.3

Comfort

7.3

Crew

7.8

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
7.3
Good
4,254 reviews
Turkish Airlines
7.3
Good
4,254 reviews

Food

7.5

Entertainment

7.5

Overall

7.3

Boarding

7.3

Comfort

7.3

Crew

7.8

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
American Airlines
7.1
Good
11,446 reviews
Turkish Airlines
7.3
Good
4,254 reviews

Food

7.5

Entertainment

7.5

Overall

7.3

Boarding

7.3

Comfort

7.3

Crew

7.8

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 0 daily outbound flights to Chicago from 1 airline.

  • How long is the flight from Naples to Chicago?

    There are many flights that can get you from Naples to Chicago in 14h 15m. Fly via Finnair, American Airlines, or KLM 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 is the cheapest airline to fly from Naples to Chicago round-trip?

    According to our current data, American Airlines ($639), offers the cheapest pricing from Naples to Chicago. Users have found that American Airlines is 14% cheaper than the other options available to this destination.

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

    To fly one-way, consider booking your trip with American Airlines, which is currently one of the cheapest options available, starting at $391. Aer Lingus flights start at $495 while deals on Turkish Airlines start at $509 one-way.

  • What are the cheapest flights from Naples to Chicago?

    The cheapest flight price from Naples to Chicago is $422. On average you can expect to pay $635. The most popular route, (Naples - Chicago O'Hare Intl), can usually be booked for $512.

  • 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.

See more FAQs

Traveling to a place near Chicago?

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

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Naples to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Naples to O'Hare Intl flights

Top airline flying from Naples to Chicago

Discover the top airline that operate flights from Naples to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated March 13, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$639Average$952FlexibilityNo cancel feeOn-time71%

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