What is the most punctual flight time for Naples to Chicago flights?

Generally, flights departing in the early afternoon tend to experience fewer delays. Flights in the morning have, in the past, seen delays more frequently in comparison.

Which airline has the best punctuality record on Naples to Chicago flights?

According to our data, American Airlines have had the least number of delays on this route over the last 12 months; with about 23% of their flights experiencing any sort of delay.

What day of the week experiences the fewest flight delays on this route?

Thursday is statistically the day of the week which experiences the fewest number of delays on this flight route. Friday has historically seen more delays on average compared to the rest of the week.

How often are flights from Naples to Chicago delayed?

Historically, on average around 23% of flights between Naples and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 222 minutes.

When did momondo last update prices for flights from Naples Airport to Chicago?

Prices for flights from Naples Airport to Chicago were last updated today.

How many operators does momondo search for flights from Naples Airport to Chicago?

As of February 2026, there is 1 operator available to choose from for flights from Naples Airport to Chicago.

How old do you have to be to fly from Naples Airport to Chicago?

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Naples Airport to Chicago.

What documentation or ID do you need to fly to Chicago?

The travel and health documents required for your trip to Chicago can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$324 Cheap Flights from Naples to Chicago in 2026

Q: What is the typical price of a round-trip flight between Naples and Chicago?

Prices are currently typical for flights on this route. Typical prices usually range from $582 to $788. The lowest price recently found on this route was $605.

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Find the cheapest flights from Naples to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

2:15 pm - 8:05 pm

NAP

ORD

12h 50m

1 stop

7:50 pm - 2:10 pm

ORD

NAP

12h 20m

1 stop

$605Multiple Airlines

Mon, Mar 2 - Sun, Mar 8

2:15 pm - 8:05 pm

NAP

ORD

12h 50m

1 stop

10:50 pm - 5:25 pm

ORD

NAP

12h 35m

1 stop

$608Lufthansa

Mon, Mar 2 - Sun, Mar 8

6:20 am - 2:55 pm

NAP

ORD

15h 35m

1 stop

6:30 pm - 1:05 pm

ORD

NAP

11h 35m

1 stop

$621American Airlines

Fri, Feb 13 - Sun, Feb 22

3:00 pm - 4:20 pm

NAP

ORD

32h 20m

1 stop

7:50 pm - 2:10 pm

ORD

NAP

12h 20m

1 stop

$625SWISS

Mon, Mar 2 - Sun, Mar 8

6:20 am - 2:55 pm

NAP

ORD

15h 35m

1 stop

8:35 pm - 2:10 pm

ORD

NAP

34h 35m

2 stops

$635American Airlines

Fri, Feb 13 - Fri, Feb 20

6:45 am - 2:53 pm

NAP

ORD

15h 08m

2 stops

9:55 am - 9:40 am

ORD

NAP

16h 45m

2 stops

$638Air Canada

Sat, May 9 - Sat, May 23

2:15 pm - 8:05 pm

NAP

ORD

12h 50m

1 stop

4:45 pm - 5:25 pm

ORD

NAP

18h 40m

2 stops

$641United Airlines

Mon, Mar 2 - Sun, Mar 8

2:15 pm - 8:05 pm

NAP

ORD

12h 50m

1 stop

5:05 pm - 5:25 pm

ORD

NAP

18h 20m

2 stops

$646Lufthansa

Mon, Mar 2 - Sun, Mar 8

6:20 am - 7:48 pm

NAP

ORD

20h 28m

2 stops

6:40 pm - 10:25 pm

ORD

NAP

21h 45m

1 stop

$653Iberia

Mon, Mar 2 - Sun, Mar 8

2:15 pm - 12:45 pm

NAP

ORD

29h 30m

2 stops

7:50 pm - 2:10 pm

ORD

NAP

12h 20m

1 stop

$659SWISS

Mon, Mar 2 - Sun, Mar 8

TAP AIR PORTUGAL flights from Naples to Chicago

Our best TAP AIR PORTUGAL deals on Naples to Chicago flight tickets

TAP AIR PORTUGAL

May 9

NAP7:10 pmNaples

27h 50m

1 stop

ORD4:00 pmChicago O'Hare Intl

May 23

ORD6:15 pmChicago O'Hare Intl

17h 05m

1 stop

NAP6:20 pmNaples

$796

TAP AIR PORTUGAL

Mar 2

NAP6:35 amNaples

32h 10m

3 stops

ORD7:45 amChicago O'Hare Intl

Mar 8

ORD9:25 pmChicago O'Hare Intl

19h 15m

2 stops

NAP10:40 pmNaples

$1,439

TAP AIR PORTUGAL

Feb 12

NAP6:35 amNaples

33h 35m

3 stops

ORD9:10 amChicago O'Hare Intl

Feb 21

ORD10:00 amChicago O'Hare Intl

26h 20m

3 stops

NAP7:20 pmNaples

$2,886

American Airlines flights from Naples to Chicago

Our best American Airlines deals on Naples to Chicago flight tickets

American Airlines

Feb 13

NAP6:20 amNaples

15h 35m

1 stop

ORD2:55 pmChicago O'Hare Intl

Feb 22

ORD6:30 pmChicago O'Hare Intl

11h 35m

1 stop

NAP1:05 pmNaples

$621

American Airlines

Feb 13

NAP6:20 amNaples

15h 35m

1 stop

ORD2:55 pmChicago O'Hare Intl

Feb 20

ORD8:35 pmChicago O'Hare Intl

34h 35m

2 stops

NAP2:10 pmNaples

$635

American Airlines

Feb 12

NAP6:20 amNaples

15h 35m

1 stop

ORD2:55 pmChicago O'Hare Intl

Feb 21

ORD5:40 pmChicago O'Hare Intl

13h 30m

1 stop

NAP2:10 pmNaples

$653

Fly from

Fly to

Route

Depart

Return

Price

NaplesChicago

NAP - ORD

NAPORD

Naples

Mon 3/2

2:15 pm-8:05 pm

1 stop12h 50m

Chicago O'Hare Intl

Sun 3/8

7:50 pm-2:10 pm

1 stop12h 20m

$605

NaplesChicago

NAP - ORD

NAPORD

Naples

Mon 3/2

2:15 pm-8:05 pm

1 stop12h 50m

Chicago O'Hare Intl

Sun 3/8

10:50 pm-5:25 pm

1 stop12h 35m

$608

NaplesChicago

NAP - ORD

NAPORD

Naples

Fri 2/13

6:20 am-2:55 pm

1 stop15h 35m

Chicago O'Hare Intl

Sun 2/22

6:30 pm-1:05 pm

1 stop11h 35m

$621

NaplesChicago

NAP - ORD

NAPORD

Naples

Mon 3/2

3:00 pm-4:20 pm

1 stop32h 20m

Chicago O'Hare Intl

Sun 3/8

7:50 pm-2:10 pm

1 stop12h 20m

$625

NaplesChicago

NAP - ORD

NAPORD

Naples

Fri 2/13

6:20 am-2:55 pm

1 stop15h 35m

Chicago O'Hare Intl

Fri 2/20

8:35 pm-2:10 pm

2 stops34h 35m

$635

NaplesChicago

NAP - ORD

NAPORD

Naples

Sat 5/9

6:45 am-2:53 pm

2 stops15h 08m

Chicago O'Hare Intl

Sat 5/23

9:55 am-9:40 am

2 stops16h 45m

$638

NaplesChicago

NAP - ORD

NAPORD

Naples

Mon 3/2

2:15 pm-8:05 pm

1 stop12h 50m

Chicago O'Hare Intl

Sun 3/8

4:45 pm-5:25 pm

2 stops18h 40m

$641

NaplesChicago

NAP - ORD

NAPORD

Naples

Mon 3/2

2:15 pm-8:05 pm

1 stop12h 50m

Chicago O'Hare Intl

Sun 3/8

5:05 pm-5:25 pm

2 stops18h 20m

$646

NaplesChicago

NAP - ORD

NAPORD

Naples

Mon 3/2

6:20 am-7:48 pm

2 stops20h 28m

Chicago O'Hare Intl

Sun 3/8

6:40 pm-10:25 pm

1 stop21h 45m

$653

NaplesChicago

NAP - ORD

NAPORD

Naples

Mon 3/2

2:15 pm-12:45 pm

2 stops29h 30m

Chicago O'Hare Intl

Sun 3/8

7:50 pm-2:10 pm

1 stop12h 20m

$659

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Naples to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Delays

What is the typical price of a round-trip flight between Naples and Chicago?

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Saturday when prices can be found for as low as $732. This is often the case because there is less demand to fly during this day of the week. When flying out on a Friday, the most expensive travel day of the week, you can expect to see flight prices from Naples to Chicago for around $999.

What is the cheapest Naples to Chicago flight route?

Fly from Naples to Chicago O'Hare Intl for the best Naples - Chicago flight prices

What cabin class options are available on Naples to Chicago flights?

There are 3 cabin classes available to choose from on Naples to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Naples to Chicago flights?

No. A direct flight is the cheapest option for a flight between Naples to Chicago.

When to book flights from Naples to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Naples to Chicago according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap Naples to Chicago (NAP to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Naples to Chicago

Best Price Found	$519
Fastest flight time	10h 50m
Direct flights	Mon, Wed, Thu, Fri, Sat and Sun
Airports in Chicago	3 airports

The best one-way flight to Chicago from Naples in the past 72 hours is $519. The best round-trip flight deal from Naples to Chicago found on momondo in the last 72 hours is $757.

The fastest flight from Naples to Chicago takes 10h 50m

Direct flights go from Naples to Chicago on Monday, Wednesday, Thursday, Friday, Saturday and Sunday. There are no airlines offering direct flights.

There are 3 airports in Chicago. From Naples there are direct flights to Chicago O'Hare Intl (ORD).

Search flight deals

How far is Naples to Chicago by plane?
The straight-line distance from Naples to Chicago is 4923.3 mi. Typically, this will take 10h 50m by plane in normal conditions.
When did momondo last update prices for flights from Naples Airport to Chicago?
Prices for flights from Naples Airport to Chicago were last updated today.
How many operators does momondo search for flights from Naples Airport to Chicago?
As of February 2026, there is 1 operator available to choose from for flights from Naples Airport to Chicago.
How old do you have to be to fly from Naples Airport to Chicago?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Naples Airport to Chicago.
What documentation or ID do you need to fly to Chicago?
The travel and health documents required for your trip to Chicago can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from Naples to Chicago?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Naples to Chicago is Boeing 787-9 Dreamliner (25.89% of total bookings). The next most popular plane models are Boeing 767-300 (winglets) (16.07%), Boeing 787-8 Dreamliner (10.71%), and Airbus A330-300 (9.82%).
What is the most popular airline from Naples to Chicago?
Based on momondo bookings for flights between Naples and Chicago, the leading airline is Turkish Airlines, making up 52% of the total bookings. Other popular airlines include American Airlines with 48%.

Best airlines flying from Naples to Chicago

Compare and see reviews for airlines that fly from Naples to Chicago with momondo

Airline	Rating	Free Cancellation	Price
American Airlines	PriceFrom $647	Free Cancellation	Rating 7.2 11,216 reviews		Search American Airlines flights

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Portage

Lansing

Schererville

Valparaiso

Munster

Crown Point

Chesterton

Monticello

Porter

Griffith

Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Naples to Chicago?

It is quick and easy to find Naples to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

Can I find flights from Naples to Chicago with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Naples to Chicago flights to just show those with flexible booking policies.

How can momondo help me find flights from Naples to Chicago?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Naples to Chicago.

I’m not ready to book a flight from Naples to Chicago right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Chicago from Naples. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Chicago Midway Airport

Chicago O'Hare Intl Airport

Chicago Greater Rockford Airport

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Flights to New Yorkfrom $49

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Flights to Las Vegasfrom $49

Flights to Washington, D.C.from $51

Flights to Bostonfrom $51

Flights to Atlantafrom $42

Flights to Dallasfrom $51

Flights to Seattlefrom $73

Flights to Denverfrom $41

Cheap flights from Naples to Chicago from $324

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Naples to Chicago departing on 2/28. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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Big names and deals

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Filter for what you want

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TAP AIR PORTUGAL flights from Naples to Chicago

Our best TAP AIR PORTUGAL deals on Naples to Chicago flight tickets

American Airlines flights from Naples to Chicago

Our best American Airlines deals on Naples to Chicago flight tickets

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See travel insights to Chicago from

How to get the cheapest flight ticket from Naples to Chicago

What is the typical price of a round-trip flight between Naples and Chicago?

What is the cheapest day to depart on your flight to Chicago?

What is the cheapest Naples to Chicago flight route?

Fly from Naples to Chicago O'Hare Intl for the best Naples - Chicago flight prices

What cabin class options are available on Naples to Chicago flights?

There are 3 cabin classes available to choose from on Naples to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Naples to Chicago flights?

No. A direct flight is the cheapest option for a flight between Naples to Chicago.

How often are flights from Naples to Chicago delayed?

Historically, on average around 23% of flights between Naples and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 222 minutes.

What is the most punctual flight time for Naples to Chicago flights?

Generally, flights departing in the early afternoon tend to experience fewer delays. Flights in the morning have, in the past, seen delays more frequently in comparison.

What day of the week experiences the fewest flight delays on this route?

Thursday is statistically the day of the week which experiences the fewest number of delays on this flight route. Friday has historically seen more delays on average compared to the rest of the week.

Which airline has the best punctuality record on Naples to Chicago flights?

According to our data, American Airlines have had the least number of delays on this route over the last 12 months; with about 23% of their flights experiencing any sort of delay.

When to book flights from Naples to Chicago

Cheap Naples to Chicago (NAP to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Naples to Chicago

Best Price Found

Fastest flight time

Direct flights

Airports in Chicago

How far is Naples to Chicago by plane?

When did momondo last update prices for flights from Naples Airport to Chicago?

How many operators does momondo search for flights from Naples Airport to Chicago?

How old do you have to be to fly from Naples Airport to Chicago?

What documentation or ID do you need to fly to Chicago?

What is the most popular plane model from Naples to Chicago?

What is the most popular airline from Naples to Chicago?

Best airlines flying from Naples to Chicago

Compare and see reviews for airlines that fly from Naples to Chicago with momondo

Traveling to a place near Chicago?

Why use momondo?

Why should I use momondo to find a flight deal from Naples to Chicago?

Can I find flights from Naples to Chicago with flexible booking policies on momondo?

How can momondo help me find flights from Naples to Chicago?

I’m not ready to book a flight from Naples to Chicago right now. Can momondo alert me if prices change?

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago