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$431+ 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 10/7. Fares are subject to change and may not be available on all flights or dates of travel.
NAP — CHI
jun. 17 — jun. 241
mar. 6/17
mar. 6/24
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 junio 12, 2025.

Round-trip from

$581
(American Airlines)

One-way from

$431
(Mytrip)

Popular in

November

Cheapest in

January

Average price

$695

Good round-trip deal

$729 or less

Good one-way deal

$487 or less
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 ($108 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($41 potential savings vs. average RT price).
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Average for round-trip flights in June 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 junio 12, 2025.

This American Airlines deal was found by Cheapflights users on 6/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 9/153:00 pmNAP - ORD
Nonstop10h 40mAmerican Airlines
lun. 9/228:40 pmORD - NAP
1 stop18h 20mAmerican Airlines
Deal found 6/10$581
This KLM deal was found by Cheapflights users on 6/12. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 8/2311:30 amNAP - ORD
1 stop33h 40mKLM
dom. 8/315:10 pmORD - NAP
1 stop21h 55mKLM
Deal found 6/12$622
This Finnair deal was found by Cheapflights users on 6/12. 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 Finnair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 8/2510:35 amNAP - ORD
1 stop14h 15mFinnair
lun. 9/18:35 pmORD - NAP
2 stops54h 15mFinnair
Deal found 6/12$625
This United Airlines deal was found by Cheapflights users on 6/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 9/106:40 amNAP - ORD
2 stops15h 15mUnited Airlines
mié. 9/248:40 amORD - NAP
1 stop18h 00mUnited Airlines
Deal found 6/11$627
This Mytrip deal was found by Cheapflights users on 6/11. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 8/226:40 amNAP - ORD
1 stop15h 15mLufthansa
dom. 8/319:40 pmORD - NAP
1 stop18h 15mLufthansa
Deal found 6/11$632
This lol.travel deal was found by Cheapflights users on 6/12. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 8/3011:35 amNAP - ORD
1 stop15h 41mAir Canada
vie. 9/51:05 pmORD - NAP
2 stops13h 35mAir Canada
Deal found 6/12$633
This British Airways deal was found by Cheapflights users on 6/10. 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.
lun. 9/157:50 amNAP - ORD
2 stops20h 11mBritish Airways
lun. 9/228:40 pmORD - NAP
1 stop18h 20mBritish Airways
Deal found 6/10$634
This SWISS deal was found by Cheapflights users on 6/10. 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 SWISS is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 8/239:35 amNAP - ORD
1 stop33h 35mSWISS
dom. 8/317:05 pmORD - NAP
1 stop30h 40mSWISS
Deal found 6/10$650
This Delta deal was found by Cheapflights users on 6/12. 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.
sáb. 8/309:00 amNAP - MDW
1 stop19h 12mDelta
vie. 9/56:00 amMDW - NAP
1 stop18h 00mDelta
Deal found 6/12$652
This Gotogate deal was found by Cheapflights users on 6/10. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 8/2311:35 amNAP - ORD
2 stops28h 34mMultiple Airlines
dom. 8/3110:30 pmORD - NAP
1 stop17h 25mMultiple Airlines
Deal found 6/10$664
This Delta deal was found by Cheapflights users on 6/10. 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.
lun. 9/156:10 amNAP - ORD
2 stops18h 26mDelta
lun. 9/2210:40 amORD - NAP
2 stops17h 55mDelta
Deal found 6/10$666
This Gotogate deal was found by Cheapflights users on 6/10. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 6/266:50 amNAP - ORD
1 stop14h 25mIberia
lun. 6/304:30 pmORD - NAP
1 stop22h 35mIberia
Deal found 6/10$724

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 junio 12, 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

lun. 9/15

3:00 pm-6:40 pm

Nonstop10h 40m

Chicago O'Hare Intl

lun. 9/22

8:40 pm-10:00 pm

1 stop18h 20m

$581

NaplesChicago

NAP - ORD

NAPORD

Naples

sáb. 8/23

11:30 am-2:10 pm

1 stop33h 40m

Chicago O'Hare Intl

dom. 8/31

5:10 pm-10:05 pm

1 stop21h 55m

$622

NaplesChicago

NAP - ORD

NAPORD

Naples

lun. 8/25

10:35 am-5:50 pm

1 stop14h 15m

Chicago O'Hare Intl

lun. 9/1

8:35 pm-9:50 am

2 stops54h 15m

$625

NaplesChicago

NAP - ORD

NAPORD

Naples

mié. 9/10

6:40 am-2:55 pm

2 stops15h 15m

Chicago O'Hare Intl

mié. 9/24

8:40 am-9:40 am

1 stop18h 00m

$627

NaplesChicago

NAP - ORD

NAPORD

Naples

vie. 8/22

6:40 am-2:55 pm

1 stop15h 15m

Chicago O'Hare Intl

dom. 8/31

9:40 pm-10:55 pm

1 stop18h 15m

$632

NaplesChicago

NAP - ORD

NAPORD

Naples

sáb. 8/30

11:35 am-8:16 pm

1 stop15h 41m

Chicago O'Hare Intl

vie. 9/5

1:05 pm-9:40 am

2 stops13h 35m

$633

NaplesChicago

NAP - ORD

NAPORD

Naples

lun. 9/15

7:50 am-9:01 pm

2 stops20h 11m

Chicago O'Hare Intl

lun. 9/22

8:40 pm-10:00 pm

1 stop18h 20m

$634

NaplesChicago

NAP - ORD

NAPORD

Naples

sáb. 8/23

9:35 am-12:10 pm

1 stop33h 35m

Chicago O'Hare Intl

dom. 8/31

7:05 pm-8:45 am

1 stop30h 40m

$650

NaplesChicago

NAP - MDW

NAPMDW

Naples

sáb. 8/30

9:00 am-9:12 pm

1 stop19h 12m

Chicago Midway

vie. 9/5

6:00 am-7:00 am

1 stop18h 00m

$652

NaplesChicago

NAP - ORD

NAPORD

Naples

sáb. 8/23

11:35 am-9:09 am

2 stops28h 34m

Chicago O'Hare Intl

dom. 8/31

10:30 pm-10:55 pm

1 stop17h 25m

$664

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

Showing 1-10 of 30 results
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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 junio 12, 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 26% 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 junio 12, 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).

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 junio 12, 2025.
Read through reviews of airlines operating flights from Naples to Chicago, such as Delta, KLM and Finnair. 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
7,950 reviews

Entertainment

7.9

Crew

8.5

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,950 reviews
Delta
8.0
Very good
7,950 reviews

Entertainment

7.9

Crew

8.5

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
KLM
7.8
Good
1,358 reviews
Delta
8.0
Very good
7,950 reviews

Entertainment

7.9

Crew

8.5

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Finnair
7.6
Good
1,290 reviews
Delta
8.0
Very good
7,950 reviews

Entertainment

7.9

Crew

8.5

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Air France
7.5
Good
1,463 reviews
Delta
8.0
Very good
7,950 reviews

Entertainment

7.9

Crew

8.5

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
SWISS
7.5
Good
1,623 reviews
Delta
8.0
Very good
7,950 reviews

Entertainment

7.9

Crew

8.5

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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.

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

    According to our current data, American Airlines ($581), KLM ($622), and Finnair ($625) offers the cheapest pricing from Naples to Chicago. Users have found that American Airlines is 17% 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 $509. Turkish Airlines flights start at $539 while deals on TAP AIR PORTUGAL start at $657 one-way.

  • What are the cheapest flights from Naples to Chicago?

    The cheapest flight price from Naples to Chicago is $382. On average you can expect to pay $693. The most popular route, (Naples - Chicago Midway), can usually be booked for $666.

  • 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
Lansing
Benton Harbor
Porter
Hammond
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 junio 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$664Average$919FlexibilityNo cancel feeOn-time71%

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