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$302+ 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 7/29. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — NAP
May 6 — May 131
Tue 5/6
Tue 5/13
1 adult, Economy
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1. Tell us where you want to go

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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 Sunday or Saturday and return on a Monday

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 May 1, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$823
(Mytrip)

One-way from

$316
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$1,092

Good round-trip deal

$1,039 or less

Good one-way deal

$588 or less
Provider with most accurate pricing for Chicago (CHI)-Naples flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Naples flights.
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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. 2% potential increase in price ($25 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($51 potential savings vs. average RT price).
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Average for round-trip flights in May 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 May 1, 2025.

This FlightHub deal was found by Cheapflights users on 4/30. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/116:00 pmORD - NAP
1 stop34h 40mTAP AIR PORTUGAL
Wed 10/83:05 pmNAP - ORD
2 stops28h 30mTAP AIR PORTUGAL
Deal found 4/30$813
This Ovago deal was found by Cheapflights users on 4/30. 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 Ovago is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/127:25 pmORD - NAP
2 stops16h 25mIcelandair
Tue 8/2611:20 amNAP - ORD
2 stops16h 55mIcelandair
Deal found 4/30$816
This Scandinavian Airlines deal was found by Cheapflights users on 4/30. 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 Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/17:30 amORD - NAP
2 stops28h 15mScandinavian Airlines
Sun 10/123:55 pmNAP - ORD
1 stop31h 15mScandinavian Airlines
Deal found 4/30$818
This oojo deal was found by Cheapflights users on 4/30. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/113:00 pmORD - NAP
1 stop24h 40mITA Airways
Sun 8/2411:40 amNAP - ORD
2 stops32h 30mITA Airways
Deal found 4/30$820
This Booking.com deal was found by Cheapflights users on 4/30. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2111:25 amORD - NAP
1 stop20h 35mTurkish Airlines
Fri 9/129:20 amNAP - ORD
1 stop31h 20mTurkish Airlines
Deal found 4/30$821
This Mytrip deal was found by Cheapflights users on 4/30. 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.
Tue 5/610:37 amORD - NAP
3 stops26h 13mMultiple Airlines
Thu 5/82:20 pmNAP - ORD
3 stops40h 45mMultiple Airlines
Deal found 4/30$823
This Iberia deal was found by Cheapflights users on 4/30. 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 Iberia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/64:30 pmORD - NAP
1 stop22h 35mIberia
Wed 10/2210:10 amNAP - ORD
2 stops19h 41mIberia
Deal found 4/30$824
This American Airlines deal was found by Cheapflights users on 4/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/238:30 pmORD - NAP
Nonstop9h 30mAmerican Airlines
Wed 10/13:00 pmNAP - ORD
Nonstop10h 40mAmerican Airlines
Deal found 4/30$826
This Air Canada deal was found by Cheapflights users on 4/30. 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.
Thu 10/161:55 pmORD - NAP
2 stops36h 45mAir Canada
Sat 10/2511:35 amNAP - ORD
2 stops27h 25mAir Canada
Deal found 4/30$831
This United Airlines deal was found by Cheapflights users on 4/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/2810:55 amORD - NAP
1 stop13h 05mUnited Airlines
Fri 10/106:40 amNAP - ORD
2 stops34h 11mUnited Airlines
Deal found 4/30$838
This Delta deal was found by Cheapflights users on 4/29. 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.
Fri 10/179:30 amMDW - NAP
2 stops14h 30mDelta
Fri 10/246:10 amNAP - MDW
2 stops18h 57mDelta
Deal found 4/29$853
This KAYAK deal was found by Cheapflights users on 4/30. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/257:55 pmORD - NAP
1 stop31h 05mBritish Airways
Wed 8/2012:00 pmNAP - ORD
1 stop15h 08mBritish Airways
Deal found 4/30$861

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 May 1, 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

Tue 5/6

7:10 am-7:50 pm

3 stops29h 40m

Naples

Thu 5/8

4:15 pm-11:29 pm

2 stops38h 14m

$823

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Tue 7/15

4:30 pm-2:00 pm

1 stop14h 30m

Naples

Tue 9/2

10:05 am-10:51 pm

2 stops19h 46m

$850

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Tue 5/13

7:00 am-12:00 pm

2 stops22h 00m

Naples

Thu 5/22

7:35 pm-11:59 pm

2 stops35h 24m

$851

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Fri 10/17

9:30 am-7:00 am

2 stops14h 30m

Naples

Fri 10/24

6:10 am-6:07 pm

2 stops18h 57m

$853

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Fri 7/25

7:55 pm-10:00 am

1 stop31h 05m

Naples

Wed 8/20

12:00 pm-8:08 pm

1 stop15h 08m

$861

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Fri 7/25

6:00 pm-6:50 pm

2 stops17h 50m

Naples

Wed 8/20

12:30 pm-12:35 pm

1 stop31h 05m

$865

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Fri 7/25

8:40 pm-1:00 pm

Nonstop9h 20m

Naples

Wed 8/20

3:00 pm-6:40 pm

Nonstop10h 40m

$889

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Fri 7/25

6:15 pm-9:40 am

2 stops32h 25m

Naples

Wed 8/20

11:35 am-12:01 pm

2 stops31h 26m

$890

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Sun 5/4

7:50 pm-8:20 am

1 stop29h 30m

Naples

Wed 5/14

4:00 pm-9:40 am

1 stop24h 40m

$933

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Sat 9/27

6:00 am-7:00 am

1 stop18h 00m

Naples

Tue 10/7

9:00 am-5:58 pm

1 stop15h 58m

$950

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

Showing 1-10 of 32 results
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Compare providers for flights from Chicago to Naples

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 Chicago to Naples in May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 stars
AranGrantPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
OvagoPrice Accuracy2 starsTrust Score*2 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 Chicago-Naples flights, users find the pricing of AranGrant to be most consistent on Cheapflights vs. AranGrant Users can find the same prices on Chicago-Naples flight deals on Cheapflights vs. AranGrant >95% of the time. Price accuracy is based on data collected from Chicago-Naples flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Naples 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 Chicago-Naples 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 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 April 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 $1,238). 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 May 1, 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 46% on your trip compared to booking a flight in the evening.

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 June 30, 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.

Rainfall in Naples by month

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

In terms of precipitation, rainfall in Naples ranges from 0.9 - 6.4 inches per month. November is typically the wettest month, when rainfall can reach 6.4 in. July is typically the driest time to visit Naples when rainfall is around 0.9 in.

Temperature in Naples by month

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

If weather is an important factor for your trip to Naples, 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 75.2 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 46.4 F).

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 May 1, 2025.
Peruse reviews from past customers who have flown with Delta, KLM and Austrian Airlines from Chicago to Naples to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,934 reviews

Entertainment

7.9

Overall

8.0

Boarding

8.2

Crew

8.5

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Delta
8.0
Very good
7,934 reviews
Delta
8.0
Very good
7,934 reviews

Entertainment

7.9

Overall

8.0

Boarding

8.2

Crew

8.5

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
KLM
7.8
Good
1,334 reviews
Delta
8.0
Very good
7,934 reviews

Entertainment

7.9

Overall

8.0

Boarding

8.2

Crew

8.5

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Austrian Airlines
7.6
Good
781 reviews
Delta
8.0
Very good
7,934 reviews

Entertainment

7.9

Overall

8.0

Boarding

8.2

Crew

8.5

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Air France
7.4
Good
1,446 reviews
Delta
8.0
Very good
7,934 reviews

Entertainment

7.9

Overall

8.0

Boarding

8.2

Crew

8.5

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
United Airlines
7.4
Good
8,696 reviews
Delta
8.0
Very good
7,934 reviews

Entertainment

7.9

Overall

8.0

Boarding

8.2

Crew

8.5

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

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. 11 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 0 inbound flights from Chicago per day.

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

    Currently priced at $850, Iberia will fly you from Chicago to Naples and back. In addition to Iberia, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from Scandinavian Airlines and Delta - these airlines can fly you to your destination from $851 and $853, respectively. Iberia is 8% 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?

    $406 is the cheapest one-way deal found within the past few days, from Turkish Airlines. You may also be able to find cheap deals on TAP AIR PORTUGAL and ITA Airways, with prices starting from $529 and $582, respectively.

  • What are the cheapest flights from Chicago to Naples?

    The cheapest flight price from Chicago to Naples is $499. On average you can expect to pay $1,000. The most popular route, (Chicago O'Hare Intl - Naples), can usually be booked for $546.

  • 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 $1,238). 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
Ravello
Caserta
Conca Dei Marini
Praiano
Sant'Agnello
Vico Equense
Procida

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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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
Turkish AirlinesCheapest$546Average$635FlexibilityNo cancel feeOn-time77%
IberiaCheapest$570Average$618FlexibilityNo cancel feeOn-time77%
KLMCheapest$581Average$934FlexibilityNo cancel feeOn-time75%
SWISSCheapest$602Average$1,081FlexibilityNo cancel feeOn-time79%
LufthansaCheapest$623Average$988FlexibilityNo cancel feeOn-time76%
United AirlinesCheapest$644Average$1,199FlexibilityNo cancel feeOn-time69%
Aer LingusCheapest$699Average$936FlexibilityNo cancel feeOn-timeN/A
ITA AirwaysCheapest$727Average$982FlexibilityNo cancel feeOn-time81%
British AirwaysCheapest$739Average$810FlexibilityNo cancel feeOn-time70%
DeltaCheapest$865Average$973FlexibilityNo cancel feeOn-timeN/A

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