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$306+ 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 5/7. Fares are subject to change and may not be available on all flights or dates of travel.
NAP — CHI
Apr 29 — May 61
Tue 4/29
Tue 5/6
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 April 24, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$539
(American Airlines)

One-way from

$306
(Kiwi.com)

Popular in

November

Cheapest in

January

Average price

$621

Good round-trip deal

$825 or less

Good one-way deal

$714 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. 24% potential increase in price ($226 potential increase over avg. RT price).
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Cheapest flight prices on average. 8% potential price decrease ($54 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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Price to beat on a round-trip flight from Naples to Chicago (CHI).
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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 April 24, 2025.

This American Airlines deal was found by Cheapflights users on 4/23. 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 8/253:00 pmNAP - ORD
Nonstop10h 40mAmerican Airlines
Sun 8/319:15 pmORD - NAP
1 stop15h 10mAmerican Airlines
Deal found 4/23$539
This Iberia deal was found by Cheapflights users on 4/23. 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 Iberia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/86:50 amNAP - ORD
1 stop14h 25mMultiple Airlines
Mon 5/127:15 pmORD - NAP
1 stop19h 45mMultiple Airlines
Deal found 4/23$550
This British Airways deal was found by Cheapflights users on 4/23. 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 5/811:10 amNAP - ORD
1 stop14h 05mBritish Airways
Mon 5/1211:45 amORD - NAP
2 stops19h 40mBritish Airways
Deal found 4/23$582
This lol.travel deal was found by Cheapflights users on 4/23. 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.
Sat 5/176:40 amNAP - ORD
2 stops15h 25mAir Canada
Sat 5/2410:40 amORD - NAP
1 stop16h 00mAir Canada
Deal found 4/23$613
This Gotogate deal was found by Cheapflights users on 4/23. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/178:00 pmNAP - ORD
1 stop26h 55mSWISS
Sat 5/317:05 pmORD - NAP
1 stop16h 45mSWISS
Deal found 4/23$638
This United Airlines deal was found by Cheapflights users on 4/23. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/1711:35 amNAP - ORD
1 stop34h 12mUnited Airlines
Sun 6/110:42 amORD - NAP
1 stop13h 18mUnited Airlines
Deal found 4/23$639
This Delta deal was found by Cheapflights users on 4/23. 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.
Sat 5/176:10 amNAP - ORD
2 stops22h 23mDelta
Sun 6/17:00 amORD - NAP
1 stop18h 10mDelta
Deal found 4/23$660
This Delta deal was found by Cheapflights users on 4/23. 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 6/186:35 amNAP - MDW
2 stops22h 10mDelta
Wed 7/165:59 pmMDW - NAP
2 stops17h 16mDelta
Deal found 4/23$669
This Gurufare deal was found by Cheapflights users on 4/23. 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 Gurufare is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/166:35 amNAP - ORD
1 stop13h 35mITA Airways
Wed 7/163:00 pmORD - NAP
1 stop20h 50mITA Airways
Deal found 4/23$726
This Lufthansa deal was found by Cheapflights users on 4/22. 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 Lufthansa is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/36:00 amNAP - ORD
1 stop13h 30mLufthansa
Tue 6/109:40 pmORD - NAP
1 stop11h 55mLufthansa
Deal found 4/22$729
This KLM deal was found by Cheapflights users on 4/23. 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.
Sat 7/1910:15 amNAP - ORD
1 stop18h 19mKLM
Wed 7/305:10 pmORD - NAP
1 stop21h 55mKLM
Deal found 4/23$748
This lol.travel deal was found by Cheapflights users on 4/23. 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 5/811:40 amNAP - ORD
1 stop14h 20mAer Lingus
Mon 5/129:15 pmORD - NAP
1 stop30h 25mAer Lingus
Deal found 4/23$762

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 April 24, 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 8/25

3:00 pm-6:40 pm

Nonstop10h 40m

Chicago O'Hare Intl

Sun 8/31

9:15 pm-7:25 pm

1 stop15h 10m

$539

NaplesChicago

NAP - ORD

NAPORD

Naples

Thu 5/8

6:50 am-2:15 pm

1 stop14h 25m

Chicago O'Hare Intl

Mon 5/12

7:15 pm-10:00 pm

1 stop19h 45m

$550

NaplesChicago

NAP - ORD

NAPORD

Naples

Thu 5/8

11:10 am-6:15 pm

1 stop14h 05m

Chicago O'Hare Intl

Mon 5/12

11:45 am-2:25 pm

2 stops19h 40m

$582

NaplesChicago

NAP - ORD

NAPORD

Naples

Sat 5/17

6:40 am-3:05 pm

2 stops15h 25m

Chicago O'Hare Intl

Sat 5/24

10:40 am-9:40 am

1 stop16h 00m

$613

NaplesChicago

NAP - ORD

NAPORD

Naples

Sat 5/17

8:00 pm-3:55 pm

1 stop26h 55m

Chicago O'Hare Intl

Sat 5/31

7:05 pm-6:50 pm

1 stop16h 45m

$638

NaplesChicago

NAP - ORD

NAPORD

Naples

Sat 5/17

11:35 am-2:47 pm

1 stop34h 12m

Chicago O'Hare Intl

Sun 6/1

10:42 am-7:00 am

1 stop13h 18m

$639

NaplesChicago

NAP - ORD

NAPORD

Naples

Sat 5/17

6:10 am-9:33 pm

2 stops22h 23m

Chicago O'Hare Intl

Sun 6/1

7:00 am-8:10 am

1 stop18h 10m

$660

NaplesChicago

NAP - MDW

NAPMDW

Naples

Wed 6/18

6:35 am-9:45 pm

2 stops22h 10m

Chicago Midway

Wed 7/16

5:59 pm-6:15 pm

2 stops17h 16m

$669

NaplesChicago

NAP - ORD

NAPORD

Naples

Mon 6/16

6:35 am-1:10 pm

1 stop13h 35m

Chicago O'Hare Intl

Wed 7/16

3:00 pm-6:50 pm

1 stop20h 50m

$726

NaplesChicago

NAP - ORD

NAPORD

Naples

Tue 6/3

6:00 am-12:30 pm

1 stop13h 30m

Chicago O'Hare Intl

Tue 6/10

9:40 pm-4:35 pm

1 stop11h 55m

$729

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/23

Showing 1-10 of 30 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 April.
ProviderPrice AccuracyTrust Score*
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 stars
AranGrantPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust 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 AranGrant to be most consistent on Cheapflights vs. AranGrant Users can find the same prices on Naples-Chicago flight deals on Cheapflights vs. AranGrant >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 AranGrant the most. AranGrant 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 April 24, 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 21% versus a flight at noon.

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 April 24, 2025.
Read through reviews of airlines operating flights from Naples to Chicago, such as Delta, KLM and SWISS. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,920 reviews

Overall

8.0

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Delta
8.0
Very good
7,920 reviews
Delta
8.0
Very good
7,920 reviews

Overall

8.0

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
KLM
7.8
Good
1,333 reviews
Delta
8.0
Very good
7,920 reviews

Overall

8.0

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
SWISS
7.5
Good
1,582 reviews
Delta
8.0
Very good
7,920 reviews

Overall

8.0

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
United Airlines
7.4
Good
8,685 reviews
Delta
8.0
Very good
7,920 reviews

Overall

8.0

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Turkish Airlines
7.3
Good
3,775 reviews
Delta
8.0
Very good
7,920 reviews

Overall

8.0

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

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.

  • What are the cheapest airlines flying from Naples to Chicago round-trip?

    According to our current data, American Airlines ($539), British Airways ($582), and Air Canada ($613) offers the cheapest pricing from Naples to Chicago. Users have found that American Airlines is 22% 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 Aer Lingus, which is currently one of the cheapest options available, starting at $489. TAP AIR PORTUGAL flights start at $494 while deals on Turkish Airlines start at $540 one-way.

  • What are the cheapest flights from Naples to Chicago?

    The cheapest flight price from Naples to Chicago is $527. On average you can expect to pay $1,085. The most popular route, (Naples - Chicago O'Hare Intl), can usually be booked for $548.

  • 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 Naples?

Book flights to Naples if you plan to visit one of these locations
Merrillville
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
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 April 24, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$673Average$951FlexibilityNo cancel feeOn-time71%

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