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$227+ Cheap flights from Chicago (CHI) to Naples (NAP)

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 10/27. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — NAP
ago. 4 — ago. 111
lun. 8/4
lun. 8/11
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Naples are usually found in January or March, booked 79 days in advance, depart on a Monday or Tuesday and return on a Wednesday

Cheap flight deals from Chicago to Naples

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Naples (NAP). 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 julio 30, 2025.

Round-trip from

$628
(Air Canada)

One-way from

$227
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$1,065

Good round-trip deal

$745 or less

Good one-way deal

$438 or less
From Chicago (CHI) to Naples
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One-way flight from Chicago (CHI) to Naples
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Highest demand for flights based on searches. 1% potential increase in price ($14 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($48 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Price to beat on a round-trip flight from Chicago (CHI) to Naples.
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Price to beat on a one-way flight from Chicago (CHI) to Naples.
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Find flight deals from Chicago to Naples

Cheapest flights from Chicago to Naples
Explore the most affordable flight options available from Chicago to Naples. Find the lowest fares from popular airlines and budget airlines, with prices last updated on julio 30, 2025.

This Air Canada deal was found by Cheapflights users on 7/30. 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 Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 8/2010:40 amORD - NAP
1 stop16h 00mAir Canada
mié. 9/1011:35 amNAP - ORD
2 stops27h 25mAir Canada
Deal found 7/30$628
This American Airlines deal was found by Cheapflights users on 7/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 9/88:40 pmORD - NAP
Nonstop9h 20mAmerican Airlines
vie. 9/193:00 pmNAP - ORD
Nonstop10h 50mAmerican Airlines
Deal found 7/29$629
This Lufthansa deal was found by Cheapflights users on 7/30. 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.
dom. 8/109:40 pmORD - NAP
1 stop18h 15mLufthansa
sáb. 8/236:00 amNAP - ORD
2 stops20h 55mLufthansa
Deal found 7/30$631
This Turkish Airlines deal was found by Cheapflights users on 7/29. 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 Turkish Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 9/2611:25 amORD - NAP
1 stop13h 55mTurkish Airlines
mié. 10/19:20 amNAP - ORD
1 stop31h 20mTurkish Airlines
Deal found 7/29$632
This Delta deal was found by Cheapflights users on 7/30. 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.
dom. 8/106:20 pmMDW - NAP
2 stops16h 55mDelta
mar. 8/269:00 amNAP - MDW
1 stop19h 44mDelta
Deal found 7/30$635
This Mytrip deal was found by Cheapflights users on 7/30. 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.
mié. 10/159:55 amORD - NAP
3 stops29h 45mMultiple Airlines
mié. 10/293:10 pmNAP - ORD
3 stops29h 00mMultiple Airlines
Deal found 7/30$638
This United Airlines deal was found by Cheapflights users on 7/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 9/97:11 amORD - NAP
1 stop19h 29mUnited Airlines
vie. 9/266:40 amNAP - ORD
2 stops21h 36mUnited Airlines
Deal found 7/28$647
This Delta deal was found by Cheapflights users on 7/29. 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.
dom. 8/104:15 pmORD - NAP
1 stop11h 25mDelta
mar. 8/2610:15 amNAP - ORD
2 stops31h 05mDelta
Deal found 7/29$649
This Iberia deal was found by Cheapflights users on 7/28. 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 Iberia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 9/234:30 pmORD - NAP
1 stop22h 35mIberia
mié. 10/110:10 amNAP - ORD
2 stops17h 33mIberia
Deal found 7/28$654
This FlightHub deal was found by Cheapflights users on 7/29. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 8/253:00 pmORD - NAP
1 stop20h 50mITA Airways
dom. 8/316:35 amNAP - ORD
1 stop13h 35mITA Airways
Deal found 7/29$656
This deal was found by Cheapflights users on 7/28. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 9/109:15 pmORD - NAP
1 stop14h 50mBritish Airways
vie. 9/267:35 amNAP - ORD
1 stop17h 40mBritish Airways
Deal found 7/28$661
This KLM deal was found by Cheapflights users on 7/29. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 8/256:00 amMDW - NAP
1 stop18h 00mKLM
dom. 8/319:00 amNAP - MDW
1 stop19h 12mKLM
Deal found 7/29$793

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Naples 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 julio 30, 2025.
Use the filters below to find and compare flights from Chicago to Naples that are best for you.

Fly from

Chicago

Fly to

Naples

Route

Depart

Return

Price

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

mié. 8/20

10:40 am-9:40 am

1 stop16h 00m

Naples

mié. 9/10

11:35 am-8:00 am

2 stops27h 25m

$628

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

lun. 9/8

8:40 pm-1:00 pm

Nonstop9h 20m

Naples

vie. 9/19

3:00 pm-6:50 pm

Nonstop10h 50m

$629

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

dom. 8/10

9:40 pm-10:55 pm

1 stop18h 15m

Naples

sáb. 8/23

6:00 am-7:55 pm

2 stops20h 55m

$631

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

vie. 9/26

11:25 am-8:20 am

1 stop13h 55m

Naples

mié. 10/1

9:20 am-9:40 am

1 stop31h 20m

$632

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

dom. 8/10

6:20 pm-6:15 pm

2 stops16h 55m

Naples

mar. 8/26

9:00 am-9:44 pm

1 stop19h 44m

$635

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

mié. 10/15

9:55 am-10:40 pm

3 stops29h 45m

Naples

mié. 10/29

3:10 pm-2:10 pm

3 stops29h 00m

$638

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

mar. 9/9

7:11 am-9:40 am

1 stop19h 29m

Naples

vie. 9/26

6:40 am-9:16 pm

2 stops21h 36m

$647

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

dom. 8/10

4:15 pm-10:40 am

1 stop11h 25m

Naples

mar. 8/26

10:15 am-10:20 am

2 stops31h 05m

$649

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

mar. 9/23

4:30 pm-10:05 pm

1 stop22h 35m

Naples

mié. 10/1

10:10 am-8:43 pm

2 stops17h 33m

$654

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

lun. 8/25

3:00 pm-6:50 pm

1 stop20h 50m

Naples

dom. 8/31

6:35 am-1:10 pm

1 stop13h 35m

$656

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/28

Showing 1-10 of 19 results
1
2

Best time to book a flight from Chicago to Naples

Have a flexible travel schedule? Discover the best time to fly to Naples from Chicago 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 Chicago to Naples

How far ahead should I book a flight from Chicago to Naples?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Naples. Price data was last updated on July 25, 2025.

The price you pay for your flight from Chicago to Naples may vary depending on when you book. For the best chance of a lower fare, look to book 79 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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

Currently, January is the cheapest month in which you can book a flight from Chicago to Naples (average of $703). Flying from Chicago to Naples in June is currently the most expensive (average of $1,210). 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 CHI to NAP?

Find hourly flight availability from Chicago to Naples. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated julio 30, 2025.

A simple way to save on the total cost of your ticket is to fly from Chicago to Naples in the morning. If you’re flexible enough to do this you can expect to save up to 43% on your trip compared to booking a flight at noon.

What is the cheapest day to fly from Chicago to Naples?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Naples. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Chicago to Naples flight should consider departing on Wednesday mornings when fares are most often at their lowest. Friday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Chicago to Naples

Explore weekly flight availability from Chicago to Naples. 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 julio 30, 2025.

The most flights from CHI to NAP 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).

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

Reviews of airlines servicing Naples

Get insights into the airlines that provide service to Naples. 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 Naples. Reviews last updated julio 30, 2025.
See what other customers who have flown with Delta, KLM, and Air France from Chicago to Naples have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,980 reviews

Food

7.3

Comfort

7.9

Boarding

8.2

Overall

8.0

Entertainment

7.9

Crew

8.5

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
7,980 reviews
Delta
8.0
Very good
7,980 reviews

Food

7.3

Comfort

7.9

Boarding

8.2

Overall

8.0

Entertainment

7.9

Crew

8.5

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
1,383 reviews
Delta
8.0
Very good
7,980 reviews

Food

7.3

Comfort

7.9

Boarding

8.2

Overall

8.0

Entertainment

7.9

Crew

8.5

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
1,465 reviews
Delta
8.0
Very good
7,980 reviews

Food

7.3

Comfort

7.9

Boarding

8.2

Overall

8.0

Entertainment

7.9

Crew

8.5

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!
United Airlines
7.4
Good
8,896 reviews
Delta
8.0
Very good
7,980 reviews

Food

7.3

Comfort

7.9

Boarding

8.2

Overall

8.0

Entertainment

7.9

Crew

8.5

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!
Turkish Airlines
7.3
Good
3,928 reviews
Delta
8.0
Very good
7,980 reviews

Food

7.3

Comfort

7.9

Boarding

8.2

Overall

8.0

Entertainment

7.9

Crew

8.5

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 Chicago to Naples. 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 into for flights to Naples from Chicago?

    Naples (NAP), located 2.9 mi from the city center, is the airport you fly into when you book flights from Chicago to Naples. 10 airlines have flights to Naples from Chicago on a regular basis. Booking flights from Chicago to Naples should not be difficult; the airport handles an average of 1 inbound flight from Chicago per day.

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

    Currently priced at $628, Air Canada will fly you from Chicago to Naples and back. In addition to Air Canada, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from American Airlines and Lufthansa - these airlines can fly you to your destination from $629 and $631, respectively. Air Canada is 32% cheaper than the average price of flights available within the next 90 days to this destination.

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

    $243 is the cheapest one-way deal found within the past few days, from ITA Airways. You may also be able to find cheap deals on KLM and Delta, with prices starting from $430 and $431, respectively.

  • What are the cheapest flights from Chicago to Naples?

    The cheapest flight price from Chicago to Naples is $438. On average you can expect to pay $726. The most popular route, (Chicago O'Hare Intl - Naples), can usually be booked for $455.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Chicago to Naples 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 Chicago to Naples?

    Currently, January is the cheapest month in which you can book a flight from Chicago to Naples (average of $703). Flying from Chicago to Naples in June is currently the most expensive (average of $1,210). 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
Praiano
Conca Dei Marini
Caserta
Maiori
Ravello
Sant'Agnello
Vico Equense

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Alternative routes for Chicago to Naples

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

Top 10 airlines flying from Chicago to Naples

Discover the top 10 airlines that operate flights from Chicago to Naples. 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 julio 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Scandinavian AirlinesCheapest$414Average$522FlexibilityNo cancel feeOn-time77%
British AirwaysCheapest$497Average$763FlexibilityNo cancel feeOn-time70%
KLMCheapest$525Average$777FlexibilityNo cancel feeOn-time75%
Turkish AirlinesCheapest$535Average$626FlexibilityNo cancel feeOn-time77%
LufthansaCheapest$594Average$812FlexibilityNo cancel feeOn-time76%
SWISSCheapest$602Average$1,086FlexibilityNo cancel feeOn-time79%
United AirlinesCheapest$612Average$954FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$633Average$1,142FlexibilityNo cancel feeOn-time71%
Aer LingusCheapest$657Average$861FlexibilityNo cancel feeOn-timeN/A
ITA AirwaysCheapest$727Average$970FlexibilityNo cancel feeOn-time81%

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