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$332+ 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 11/25. Fares are subject to change and may not be available on all flights or dates of travel.
NAP — CHI
Oct 29 — Nov 51
Wed 10/29
Wed 11/5
1 adult, Economy
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Cheap 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 September 29, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$525
(lol.travel)

One-way from

$332
(Kiwi.com)

Popular in

November

Cheapest in

January

Average price

$592

Good one-way deal

$728 or less
Provider with most accurate pricing for Naples-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Naples-Chicago (CHI) flights.
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From Naples to Chicago (CHI)
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One-way flight from Naples to Chicago (CHI)
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Highest demand for flights based on searches. 13% potential increase in price ($102 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($31 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a one-way flight from Naples to Chicago (CHI).
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Find 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 September 29, 2025.

This lol.travel deal was found by Cheapflights users on 9/29. 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 10/156:40 amNAP - ORD
1 stop15h 15mUnited Airlines
Sun 10/196:00 amORD - NAP
1 stop18h 00mUnited Airlines
Deal found 9/29$525
This lol.travel deal was found by Cheapflights users on 9/28. 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 10/236:40 amNAP - ORD
1 stop13h 15mUnited Airlines
Tue 10/2810:50 pmORD - NAP
1 stop12h 35mUnited Airlines
Deal found 9/28$529
This lol.travel deal was found by Cheapflights users on 9/28. 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.
Mon 12/82:15 pmNAP - ORD
1 stop12h 50mUnited Airlines
Mon 12/153:20 pmORD - NAP
1 stop15h 30mUnited Airlines
Deal found 9/28$531
This American Airlines deal was found by Cheapflights users on 9/27. 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.
Mon 10/63:00 pmNAP - ORD
Nonstop10h 50mAmerican Airlines
Sun 10/1210:35 pmORD - NAP
1 stop13h 50mAmerican Airlines
Deal found 9/27$554
This Flighttix deal was found by Cheapflights users on 9/28. 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 Flighttix is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/63:00 pmNAP - ORD
Nonstop10h 50mBritish Airways
Sun 10/128:50 pmORD - NAP
Nonstop9h 10mBritish Airways
Deal found 9/28$559
This Expedia deal was found by Cheapflights users on 9/29. 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.
Wed 10/226:40 amNAP - ORD
1 stop13h 15mLufthansa
Thu 12/116:00 pmORD - NAP
1 stop11h 30mLufthansa
Deal found 9/29$561
This American Airlines deal was found by Cheapflights users on 9/27. 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 10/163:00 pmNAP - ORD
Nonstop10h 50mAmerican Airlines
Mon 10/209:45 amORD - NAP
1 stop17h 15mAmerican Airlines
Deal found 9/27$567
This Air France deal was found by Cheapflights users on 9/28. 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.
Wed 11/124:45 pmNAP - ORD
1 stop29h 25mAir France
Wed 11/195:20 pmORD - NAP
1 stop20h 55mAir France
Deal found 9/28$570
This Flighttix deal was found by Cheapflights users on 9/28. 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 Flighttix is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/66:50 amNAP - ORD
1 stop14h 25mMultiple Airlines
Sun 10/129:45 amORD - NAP
1 stop17h 15mMultiple Airlines
Deal found 9/28$572
This Delta deal was found by Cheapflights users on 9/29. 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.
Wed 10/1510:15 amNAP - MDW
2 stops18h 59mDelta
Sun 10/199:35 amMDW - NAP
2 stops19h 00mDelta
Deal found 9/29$582
This Delta deal was found by Cheapflights users on 9/27. 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 10/169:00 amNAP - MDW
1 stop20h 14mDelta
Fri 10/246:00 amMDW - NAP
2 stops19h 10mDelta
Deal found 9/27$596
This Delta deal was found by Cheapflights users on 9/27. 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 10/66:10 amNAP - MDW
2 stops23h 04mDelta
Sun 10/126:00 amMDW - NAP
2 stops19h 10mDelta
Deal found 9/27$600

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 September 29, 2025.
Use the filters below to find and compare flights from Naples to Chicago that are best for you.

Fly from

Naples

Fly to

Chicago

Route

Depart

Return

Price

NaplesChicago

NAP - ORD

NAPORD

Naples

Mon 12/8

2:15 pm-8:05 pm

1 stop12h 50m

Chicago O'Hare Intl

Mon 12/15

3:20 pm-1:50 pm

1 stop15h 30m

$531

NaplesChicago

NAP - ORD

NAPORD

Naples

Wed 10/15

3:00 pm-6:50 pm

Nonstop10h 50m

Chicago O'Hare Intl

Sun 10/19

7:15 pm-12:00 pm

1 stop33h 45m

$555

NaplesChicago

NAP - ORD

NAPORD

Naples

Wed 10/22

6:40 am-12:55 pm

1 stop13h 15m

Chicago O'Hare Intl

Thu 12/11

7:15 am-9:15 am

2 stops19h 00m

$559

NaplesChicago

NAP - ORD

NAPORD

Naples

Wed 10/22

6:40 am-12:55 pm

1 stop13h 15m

Chicago O'Hare Intl

Thu 12/11

6:00 pm-12:30 pm

1 stop11h 30m

$561

NaplesChicago

NAP - ORD

NAPORD

Naples

Thu 10/9

3:00 pm-6:50 pm

Nonstop10h 50m

Chicago O'Hare Intl

Mon 10/13

11:55 am-10:00 am

1 stop15h 05m

$567

NaplesChicago

NAP - ORD

NAPORD

Naples

Thu 10/23

6:40 am-12:55 pm

1 stop13h 15m

Chicago O'Hare Intl

Tue 10/28

2:39 pm-2:05 pm

2 stops17h 26m

$567

NaplesChicago

NAP - ORD

NAPORD

Naples

Thu 10/16

3:00 pm-6:50 pm

Nonstop10h 50m

Chicago O'Hare Intl

Mon 10/20

9:45 am-10:00 am

1 stop17h 15m

$567

NaplesChicago

NAP - ORD

NAPORD

Naples

Wed 2/18

9:50 am-12:45 pm

1 stop33h 55m

Chicago O'Hare Intl

Sun 2/22

6:50 pm-2:10 pm

1 stop12h 20m

$568

NaplesChicago

NAP - ORD

NAPORD

Naples

Thu 10/16

3:00 pm-6:50 pm

Nonstop10h 50m

Chicago O'Hare Intl

Fri 10/24

8:50 pm-1:00 pm

Nonstop9h 10m

$568

NaplesChicago

NAP - MDW

NAPMDW

Naples

Wed 10/15

10:15 am-10:14 pm

2 stops18h 59m

Chicago Midway

Sun 10/19

9:35 am-11:35 am

2 stops19h 00m

$582

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/27

Showing 1-10 of 31 results
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Compare providers for flights from Naples to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Naples to Chicago in September.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • 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 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 September 29, 2025.

When flying from Naples to Chicago, the time of day you fly usually plays a role in the price. Save by searching for a flight in the morning, which can drop the price by up to 23% versus a flight at noon.

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 September 29, 2025.

The most flights from NAP to CHI are scheduled on a Monday (1 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (1 on average).

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 September 29, 2025.
See what other customers who have flown with 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.
American Airlines
7.2
Good
10,000 reviews

Boarding

7.5

Entertainment

6.9

Food

6.4

Overall

7.2

Comfort

7.2

Crew

8.0

Reviews

1 / 20
2.0
Mediocre

Nordia,Sep 2025

KIN - MIA

We were to land in Miami sometime after 3pm but couldn’t due to bad weather, we flew around for 2 hrs until we had to land in Forth Myers to refuel, we had to sit another 2 hrs at Forth Myers until given the clearance to refuel, we were hungry, thirsty and frustrated at that point. All the had on the flight to offer was a small plastic glass of water and a pack of biscoff, I requested a cup of tea and was told none was there. We were basically at another airport and not one of the staff could consider that the passengers might be hungry or thirsty being on a plane for around 8 hrs, which you weren’t prepared for, at least find some hot water on board.
American Airlines
7.2
Good
10,000 reviews
American Airlines
7.2
Good
10,000 reviews

Boarding

7.5

Entertainment

6.9

Food

6.4

Overall

7.2

Comfort

7.2

Crew

8.0

Reviews

1 / 20
2.0
Mediocre

Nordia,Sep 2025

KIN - MIA

We were to land in Miami sometime after 3pm but couldn’t due to bad weather, we flew around for 2 hrs until we had to land in Forth Myers to refuel, we had to sit another 2 hrs at Forth Myers until given the clearance to refuel, we were hungry, thirsty and frustrated at that point. All the had on the flight to offer was a small plastic glass of water and a pack of biscoff, I requested a cup of tea and was told none was there. We were basically at another airport and not one of the staff could consider that the passengers might be hungry or thirsty being on a plane for around 8 hrs, which you weren’t prepared for, at least find some hot water on board.

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 is 1 daily outbound flight 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 10h 50m. Fly via United Airlines, American Airlines, or Lufthansa 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 ($664), offers the cheapest pricing from Naples to Chicago. Users have found that American Airlines is 2% cheaper than the other options available to this destination.

  • What are the cheapest flights from Naples to Chicago?

    The cheapest flight price from Naples to Chicago is $562. On average you can expect to pay $1,150. The most popular route, (Naples - Chicago Midway), can usually be booked for $597.

  • 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, August is the cheapest month in which you can book a flight from Naples to Chicago (average of $245). Flying from Naples to Chicago in March is currently the most expensive (average of $321). 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
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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 September 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$664Average$877FlexibilityNo cancel feeOn-time71%

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