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$356+ 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 8/28. Fares are subject to change and may not be available on all flights or dates of travel.
NAP — CHI
Aug 4 — Aug 111
Mon 8/4
Mon 8/11
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 July 30, 2025.

Round-trip from

$509
(lol.travel)

One-way from

$356
(Kiwi.com)

Popular in

November

Cheapest in

January

Average price

$779

Good round-trip deal

$718 or less

Good one-way deal

$721 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. 15% potential increase in price ($124 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($38 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 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 July 30, 2025.

This lol.travel 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/186:40 amNAP - ORD
1 stop15h 15mUnited Airlines
Wed 10/1510:40 amORD - NAP
1 stop13h 20mUnited Airlines
Deal found 7/30$509
This Gotogate 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1811:35 amNAP - ORD
1 stop15h 36mMultiple Airlines
Wed 10/1510:40 amORD - NAP
2 stops15h 05mMultiple Airlines
Deal found 7/30$534
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/73:00 pmNAP - ORD
Nonstop10h 50mAmerican Airlines
Sat 8/1611:44 amORD - NAP
1 stop15h 16mAmerican Airlines
Deal found 7/30$535
This British Airways 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 British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/1412:00 pmNAP - ORD
1 stop34h 45mBritish Airways
Mon 8/187:19 pmORD - NAP
1 stop31h 41mBritish Airways
Deal found 7/29$545
This SWISS 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 SWISS is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/207:15 pmNAP - ORD
1 stop24h 35mSWISS
Sun 8/317:05 pmORD - NAP
1 stop30h 40mSWISS
Deal found 7/30$565
This Gotogate 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/216:40 amNAP - ORD
1 stop20h 15mLufthansa
Fri 11/79:50 pmORD - NAP
1 stop12h 35mLufthansa
Deal found 7/28$572
This Booking.com 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/411:35 amNAP - ORD
1 stop15h 36mAir Canada
Mon 9/86:06 pmORD - NAP
2 stops32h 34mAir Canada
Deal found 7/29$577
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.
Tue 10/216:10 amNAP - ORD
1 stop15h 50mDelta
Tue 11/410:30 amORD - NAP
2 stops22h 20mDelta
Deal found 7/29$608
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.
Thu 9/186:10 amNAP - MDW
2 stops19h 25mDelta
Wed 10/1512:48 pmMDW - NAP
2 stops15h 47mDelta
Deal found 7/30$610
This KLM 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/49:00 amNAP - MDW
1 stop19h 26mKLM
Mon 9/86:00 amMDW - NAP
1 stop18h 00mKLM
Deal found 7/30$673
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/1411:25 amNAP - MDW
2 stops17h 19mAir France
Mon 8/1810:31 amMDW - NAP
1 stop13h 29mAir France
Deal found 7/29$850
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/226:35 amNAP - MDW
2 stops18h 12mMultiple Airlines
Sun 8/314:25 pmMDW - NAP
1 stop31h 35mMultiple Airlines
Deal found 7/30$911

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 July 30, 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

Thu 9/18

6:40 am-2:55 pm

1 stop15h 15m

Chicago O'Hare Intl

Wed 10/15

10:40 am-7:00 am

1 stop13h 20m

$509

NaplesChicago

NAP - ORD

NAPORD

Naples

Thu 9/18

11:35 am-8:11 pm

1 stop15h 36m

Chicago O'Hare Intl

Wed 10/15

10:40 am-8:45 am

2 stops15h 05m

$534

NaplesChicago

NAP - ORD

NAPORD

Naples

Thu 8/7

3:00 pm-6:50 pm

Nonstop10h 50m

Chicago O'Hare Intl

Sat 8/16

11:44 am-10:00 am

1 stop15h 16m

$535

NaplesChicago

NAP - ORD

NAPORD

Naples

Thu 8/14

12:00 pm-3:45 pm

1 stop34h 45m

Chicago O'Hare Intl

Mon 8/18

7:19 pm-10:00 am

1 stop31h 41m

$545

NaplesChicago

NAP - ORD

NAPORD

Naples

Wed 8/20

7:15 pm-12:50 pm

1 stop24h 35m

Chicago O'Hare Intl

Mon 9/1

7:05 pm-8:45 am

1 stop30h 40m

$565

NaplesChicago

NAP - ORD

NAPORD

Naples

Tue 10/21

6:40 am-7:55 pm

1 stop20h 15m

Chicago O'Hare Intl

Fri 11/7

9:50 pm-5:25 pm

1 stop12h 35m

$572

NaplesChicago

NAP - ORD

NAPORD

Naples

Thu 9/4

11:35 am-8:11 pm

1 stop15h 36m

Chicago O'Hare Intl

Mon 9/8

6:06 pm-9:40 am

2 stops32h 34m

$577

NaplesChicago

NAP - ORD

NAPORD

Naples

Tue 10/21

6:10 am-3:00 pm

1 stop15h 50m

Chicago O'Hare Intl

Tue 11/4

10:30 am-3:50 pm

2 stops22h 20m

$608

NaplesChicago

NAP - MDW

NAPMDW

Naples

Thu 9/18

6:10 am-6:35 pm

2 stops19h 25m

Chicago Midway

Wed 10/15

12:48 pm-11:35 am

2 stops15h 47m

$610

NaplesChicago

NAP - MDW

NAPMDW

Naples

Thu 9/4

9:00 am-9:26 pm

1 stop19h 26m

Chicago Midway

Mon 9/8

6:00 am-7:00 am

1 stop18h 00m

$673

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

Showing 1-10 of 18 results
1
2

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 July 30, 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 25% 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 July 30, 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 July 30, 2025.
See what other customers who have flown with Delta, KLM, and Air France 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.
Delta
8.0
Very good
7,980 reviews

Crew

8.5

Boarding

8.2

Comfort

7.9

Overall

8.0

Entertainment

7.9

Food

7.3

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.
Delta
8.0
Very good
7,980 reviews
Delta
8.0
Very good
7,980 reviews

Crew

8.5

Boarding

8.2

Comfort

7.9

Overall

8.0

Entertainment

7.9

Food

7.3

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.
KLM
7.8
Good
1,383 reviews
Delta
8.0
Very good
7,980 reviews

Crew

8.5

Boarding

8.2

Comfort

7.9

Overall

8.0

Entertainment

7.9

Food

7.3

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.
Air France
7.5
Good
1,465 reviews
Delta
8.0
Very good
7,980 reviews

Crew

8.5

Boarding

8.2

Comfort

7.9

Overall

8.0

Entertainment

7.9

Food

7.3

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.
SWISS
7.5
Good
1,686 reviews
Delta
8.0
Very good
7,980 reviews

Crew

8.5

Boarding

8.2

Comfort

7.9

Overall

8.0

Entertainment

7.9

Food

7.3

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.
United Airlines
7.4
Good
8,896 reviews
Delta
8.0
Very good
7,980 reviews

Crew

8.5

Boarding

8.2

Comfort

7.9

Overall

8.0

Entertainment

7.9

Food

7.3

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.

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, United Airlines ($509), Scandinavian Airlines ($519), and American Airlines ($535) offers the cheapest pricing from Naples to Chicago. Users have found that United Airlines is 26% 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 TAP AIR PORTUGAL, which is currently one of the cheapest options available, starting at $407. Delta flights start at $850 while deals on KLM start at $867 one-way.

  • What are the cheapest flights from Naples to Chicago?

    The cheapest flight price from Naples to Chicago is $651. On average you can expect to pay $845. The most popular route, (Naples - Chicago O'Hare Intl), can usually be booked for $496.

  • 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
Valparaiso
Chesterton

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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 July 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$664Average$899FlexibilityNo cancel feeOn-time71%

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