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$334+ Cheap flights from Naples (NAP) to Illinois

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 11/17. Fares are subject to change and may not be available on all flights or dates of travel.
NAP — ORD
Oct 23 — Oct 301
Thu 10/23
Thu 10/30
1 adult, Economy
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Cheap flight deals from Naples to Illinois

Keep the following information in mind while searching for Naples to Illinois flight deals. Data was last updated September 23, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$525
(lol.travel)

One-way from

$334
(eDestinos)

Popular in

November

Cheapest in

January

Average price

$592

Good one-way deal

$728 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 Illinois
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One-way flight from Naples to Illinois
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Highest demand for flights based on searches. 12% potential increase in price ($101 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($30 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a one-way flight from Naples to Illinois.
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Find flight deals from Naples to Illinois

Cheapest flights from Naples to Illinois
Explore the most affordable flight options available from Naples to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 23, 2025.

This lol.travel deal was found by Cheapflights users on 9/21. 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 10/166:40 amNAP - ORD
1 stop13h 15mUnited Airlines
Mon 10/201:17 pmORD - NAP
1 stop15h 23mUnited Airlines
Deal found 9/21$525
This lol.travel deal was found by Cheapflights users on 9/23. 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 10/236:40 amNAP - ORD
1 stop15h 15mUnited Airlines
Tue 10/2810:50 pmORD - NAP
1 stop12h 35mUnited Airlines
Deal found 9/23$533
This lol.travel deal was found by Cheapflights users on 9/22. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/88:50 pmNAP - ORD
2 stops26h 55mScandinavian Airlines
Wed 11/267:20 pmORD - NAP
1 stop16h 20mScandinavian Airlines
Deal found 9/22$534
This lol.travel deal was found by Cheapflights users on 9/23. 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 10/92:00 pmNAP - ORD
1 stop14h 26mUnited Airlines
Fri 10/178:40 amORD - NAP
1 stop18h 00mUnited Airlines
Deal found 9/23$543
This American Airlines deal was found by Cheapflights users on 9/22. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/33:00 pmNAP - ORD
Nonstop10h 50mAmerican Airlines
Tue 10/78:40 pmORD - NAP
1 stop14h 30mAmerican Airlines
Deal found 9/22$557
This Gotogate deal was found by Cheapflights users on 9/21. 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.
Wed 11/59:50 amNAP - ORD
1 stop13h 30mSWISS
Wed 11/126:50 pmORD - NAP
1 stop12h 25mSWISS
Deal found 9/21$567
This American Airlines deal was found by Cheapflights users on 9/22. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/163:00 pmNAP - ORD
Nonstop10h 50mAmerican Airlines
Mon 10/208:50 pmORD - NAP
Nonstop9h 10mAmerican Airlines
Deal found 9/22$570
This United Airlines deal was found by Cheapflights users on 9/23. 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.
Thu 10/162:00 pmNAP - ORD
1 stop16h 30mUnited Airlines
Fri 10/243:35 pmORD - NAP
1 stop11h 05mUnited Airlines
Deal found 9/23$576
This Delta deal was found by Cheapflights users on 9/21. 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 10/169:00 amNAP - MDW
1 stop20h 14mDelta
Fri 10/246:23 pmMDW - NAP
2 stops16h 52mDelta
Deal found 9/21$583
This Delta deal was found by Cheapflights users on 9/23. 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.
Thu 10/169:00 amNAP - MDW
1 stop20h 14mDelta
Mon 10/209:35 amMDW - NAP
2 stops19h 00mDelta
Deal found 9/23$585
This KLM deal was found by Cheapflights users on 9/21. 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 10/169:00 amNAP - MDW
1 stop20h 14mKLM
Fri 10/2410:35 amMDW - NAP
1 stop13h 25mKLM
Deal found 9/21$587
This flugladen.de deal was found by Cheapflights users on 9/23. 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 flugladen.de is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/36:10 amNAP - MDW
2 stops22h 26mMultiple Airlines
Tue 10/76:23 pmMDW - NAP
2 stops16h 52mMultiple Airlines
Deal found 9/23$589

Cheapflights Fare Finder

 
Customize your flight search to find flights from Naples to Illinois 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 September 23, 2025.
Use the filters below to find and compare flights from Naples to Illinois that are best for you.

Fly from

Naples

Fly to

Illinois

Route

Depart

Return

Price

NaplesChicago

NAP - ORD

NAPORD

Naples

Thu 10/16

6:40 am-12:55 pm

1 stop13h 15m

Chicago O'Hare Intl

Mon 10/20

1:17 pm-11:40 am

1 stop15h 23m

$525

NaplesChicago

NAP - ORD

NAPORD

Naples

Sat 11/8

8:50 pm-4:45 pm

2 stops26h 55m

Chicago O'Hare Intl

Wed 11/26

7:20 pm-6:40 pm

1 stop16h 20m

$534

NaplesChicago

NAP - ORD

NAPORD

Naples

Fri 10/3

3:00 pm-6:50 pm

Nonstop10h 50m

Chicago O'Hare Intl

Tue 10/7

8:40 pm-6:10 pm

1 stop14h 30m

$557

NaplesChicago

NAP - ORD

NAPORD

Naples

Thu 2/19

12:40 pm-5:00 pm

1 stop35h 20m

Chicago O'Hare Intl

Mon 2/23

11:45 am-11:50 am

2 stops17h 05m

$558

NaplesChicago

NAP - ORD

NAPORD

Naples

Thu 10/16

6:40 am-12:55 pm

1 stop13h 15m

Chicago O'Hare Intl

Fri 10/24

10:40 am-9:40 am

1 stop16h 00m

$558

NaplesChicago

NAP - ORD

NAPORD

Naples

Wed 11/5

9:50 am-4:20 pm

1 stop13h 30m

Chicago O'Hare Intl

Wed 11/12

6:50 pm-2:15 pm

1 stop12h 25m

$567

NaplesChicago

NAP - ORD

NAPORD

Naples

Thu 10/16

3:00 pm-6:50 pm

Nonstop10h 50m

Chicago O'Hare Intl

Mon 10/20

2:41 pm-10:00 am

1 stop12h 19m

$570

NaplesChicago

NAP - ORD

NAPORD

Naples

Thu 2/19

3:05 pm-4:20 pm

1 stop32h 15m

Chicago O'Hare Intl

Mon 2/23

6:50 pm-2:00 pm

1 stop12h 10m

$570

NaplesChicago

NAP - MDW

NAPMDW

Naples

Thu 10/16

9:00 am-10:14 pm

1 stop20h 14m

Chicago Midway

Fri 10/24

6:23 pm-6:15 pm

2 stops16h 52m

$583

NaplesChicago

NAP - MDW

NAPMDW

Naples

Thu 10/16

9:00 am-10:14 pm

1 stop20h 14m

Chicago Midway

Mon 10/20

6:23 pm-6:15 pm

2 stops16h 52m

$583

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/22

Showing 1-10 of 27 results
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Best time to book a flight from Naples to Illinois

Have a flexible travel schedule? Discover the best time to fly to Illinois 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 Illinois

What is the cheapest time of day to fly from NAP to IL?

Find hourly flight availability from Naples to Illinois. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 23, 2025.

When flying from Naples to Illinois, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Weekly flight availability from Naples to Illinois

Explore weekly flight availability from Naples to Illinois. 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 September 23, 2025.

The most flights from NAP to USIL 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 Naples to Illinois?

Reviews of airlines servicing Illinois

Get insights into the airlines that provide service to Illinois. 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 Illinois. Reviews last updated September 23, 2025.
Peruse reviews from past customers who have flown with American Airlines from Naples to Illinois to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
10,000 reviews

Crew

8.0

Boarding

7.5

Comfort

7.2

Food

6.4

Overall

7.2

Entertainment

6.9

Reviews

1 / 20
2.0
Mediocre

Nordia,Sep 2025

KIN - MIA

We were to land in Miami sometime after 3pm but couldn’t due to bad weather, we flew around for 2 hrs until we had to land in Forth Myers to refuel, we had to sit another 2 hrs at Forth Myers until given the clearance to refuel, we were hungry, thirsty and frustrated at that point. All the had on the flight to offer was a small plastic glass of water and a pack of biscoff, I requested a cup of tea and was told none was there. We were basically at another airport and not one of the staff could consider that the passengers might be hungry or thirsty being on a plane for around 8 hrs, which you weren’t prepared for, at least find some hot water on board.
American Airlines
7.2
Good
10,000 reviews
American Airlines
7.2
Good
10,000 reviews

Crew

8.0

Boarding

7.5

Comfort

7.2

Food

6.4

Overall

7.2

Entertainment

6.9

Reviews

1 / 20
2.0
Mediocre

Nordia,Sep 2025

KIN - MIA

We were to land in Miami sometime after 3pm but couldn’t due to bad weather, we flew around for 2 hrs until we had to land in Forth Myers to refuel, we had to sit another 2 hrs at Forth Myers until given the clearance to refuel, we were hungry, thirsty and frustrated at that point. All the had on the flight to offer was a small plastic glass of water and a pack of biscoff, I requested a cup of tea and was told none was there. We were basically at another airport and not one of the staff could consider that the passengers might be hungry or thirsty being on a plane for around 8 hrs, which you weren’t prepared for, at least find some hot water on board.

Related info for your journey

Find useful and relevant information for your journey from Naples to Illinois. 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 Illinois?

    Most people fly from Naples (NAP) if they book a flight from Naples to Illinois. Naples is conveniently located just 2.9 mi from Naples’s city center.

  • How long is the flight from Naples to Illinois?

    There are many flights that can get you from Naples to Illinois in 10h 50m. Fly via United Airlines, Scandinavian Airlines, or American Airlines to get the fastest option. Airlines will cover a distance of 4929 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest flights from Naples to Illinois?

    Looking at all options, your cheapest flight can be booked for $562. While the most popular route (Naples - Chicago O'Hare Intl) can be booked for $525 on average, our data indicates $1,083 when flying from Naples to Illinois.

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

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

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

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

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

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

    Currently, August is the cheapest month in which you can book a flight from Naples to Illinois (average of $245). Flying from Naples to Illinois 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

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Alternative routes for Naples to Illinois

See prices for flight routes from nearby airports that may be better suited for you.
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Top airline flying from Naples to Illinois

Discover the top airline that operate flights from Naples to Illinois. 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 September 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$664Average$877FlexibilityNo cancel feeOn-time71%

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