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.

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 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.

When did momondo last update prices for flights from Naples Airport to Chicago O'Hare Intl Airport?

Prices for flights from Naples Airport to Chicago O'Hare Intl Airport were last updated today.

How many operators does momondo search for flights from Naples Airport to Chicago O'Hare Intl Airport?

The number of operators available for flights from Naples Airport to Chicago O'Hare Intl Airport is 1 as of December 2025.

How old do you have to be to fly from Naples Airport to Chicago O'Hare Intl Airport?

The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Naples Airport to Chicago O'Hare Intl Airport.

What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

The travel and health documents you'll need for your trip to Chicago O'Hare Intl Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago O'Hare Intl Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

$334 Cheap Flights from Naples to Chicago O'Hare Intl Airport in 2025/26

Q: What is the typical price of a round-trip flight between Naples and Chicago O'Hare Intl Airport?

Prices are currently low for flights on this route. Typical prices usually range from $826 to $1,062. The lowest price recently found on this route was $620.

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Find the cheapest flights from Naples to Chicago

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One-way

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

3:05 pm - 6:25 pm

NAP

ORD

34h 20m2 stops

10:40 am - 2:20 pm

ORD

NAP

20h 40m2 stops

$620ITA Airways

Mon, Apr 13 - Thu, Apr 30

6:35 am - 1:10 pm

NAP

ORD

13h 35m1 stop

11:15 am - 2:20 pm

ORD

NAP

20h 05m2 stops

$621ITA Airways

Wed, May 13 - Thu, Jun 4

8:00 am - 10:42 pm

NAP

ORD

45h 42m3 stops

6:30 pm - 7:10 pm

ORD

NAP

17h 40m2 stops

$639Multiple Airlines

Thu, Jan 15 - Thu, Jan 22

12:40 pm - 3:25 pm

NAP

ORD

33h 45m1 stop

11:40 am - 11:45 am

ORD

NAP

18h 05m2 stops

$640British Airways

Thu, Feb 26 - Wed, Mar 18

6:20 am - 2:55 pm

NAP

ORD

15h 35m1 stop

3:48 pm - 3:35 pm

ORD

NAP

16h 47m2 stops

$643American Airlines

Thu, Jan 15 - Thu, Jan 22

12:40 pm - 5:42 pm

NAP

ORD

36h 02m2 stops

4:14 pm - 3:35 pm

ORD

NAP

16h 21m2 stops

$646British Airways

Thu, Jan 15 - Thu, Jan 22

12:40 pm - 5:42 pm

NAP

ORD

36h 02m2 stops

11:44 am - 3:35 pm

ORD

NAP

20h 51m2 stops

$647British Airways

Thu, Jan 15 - Thu, Jan 22

6:15 am - 2:55 pm

NAP

ORD

15h 40m1 stop

8:16 am - 11:45 am

ORD

NAP

20h 29m2 stops

$648American Airlines

Sat, Jan 24 - Sat, Jan 31

6:15 am - 7:29 pm

NAP

ORD

20h 14m2 stops

8:16 am - 11:45 am

ORD

NAP

20h 29m2 stops

$658American Airlines

Sat, Jan 24 - Sat, Jan 31

6:35 am - 1:10 pm

NAP

ORD

13h 35m1 stop

10:40 am - 10:35 am

ORD

NAP

16h 55m2 stops

$669ITA Airways

Sun, May 10 - Wed, Jun 3

American Airlines flights from Naples to Chicago O'Hare Intl Airport

Our best American Airlines deals on Naples to Chicago O'Hare Intl Airport flight tickets

American Airlines

Jan 15

NAP6:20 amNaples

15h 35m

1 stop

ORD2:55 pmChicago O'Hare Intl

Jan 22

ORD3:48 pmChicago O'Hare Intl

16h 47m

2 stops

NAP3:35 pmNaples

$643

Find similar

American Airlines

Jan 24

NAP6:15 amNaples

15h 40m

1 stop

ORD2:55 pmChicago O'Hare Intl

Jan 31

ORD8:16 amChicago O'Hare Intl

20h 29m

2 stops

NAP11:45 amNaples

$648

Find similar

American Airlines

Jan 24

NAP6:15 amNaples

20h 14m

2 stops

ORD7:29 pmChicago O'Hare Intl

Jan 31

ORD8:16 amChicago O'Hare Intl

20h 29m

2 stops

NAP11:45 amNaples

$658

Find similar

British Airways flights from Naples to Chicago O'Hare Intl Airport

Our best British Airways deals on Naples to Chicago O'Hare Intl Airport flight tickets

British Airways

Feb 26

NAP12:40 pmNaples

33h 45m

1 stop

ORD3:25 pmChicago O'Hare Intl

Mar 18

ORD11:40 amChicago O'Hare Intl

18h 05m

2 stops

NAP11:45 amNaples

$640

Find similar

British Airways

Jan 15

NAP12:40 pmNaples

36h 02m

2 stops

ORD5:42 pmChicago O'Hare Intl

Jan 22

ORD4:14 pmChicago O'Hare Intl

16h 21m

2 stops

NAP3:35 pmNaples

$646

Find similar

British Airways

Jan 15

NAP12:40 pmNaples

36h 02m

2 stops

ORD5:42 pmChicago O'Hare Intl

Jan 22

ORD11:44 amChicago O'Hare Intl

20h 51m

2 stops

NAP3:35 pmNaples

$647

Find similar

momondo Fare Finder

Use the filters below to find and compare flights from Naples to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

NaplesChicago

NAP - ORD

NAPORD

Naples

Mon 4/13

3:05 pm-6:25 pm

2 stops34h 20m

Chicago O'Hare Intl

Thu 4/30

10:40 am-2:20 pm

2 stops20h 40m

$620

NaplesChicago

NAP - ORD

NAPORD

Naples

Wed 5/13

6:35 am-1:10 pm

1 stop13h 35m

Chicago O'Hare Intl

Thu 6/4

11:15 am-2:20 pm

2 stops20h 05m

$621

NaplesChicago

NAP - ORD

NAPORD

Naples

Thu 1/15

8:00 am-10:42 pm

3 stops45h 42m

Chicago O'Hare Intl

Thu 1/22

6:30 pm-7:10 pm

2 stops17h 40m

$639

NaplesChicago

NAP - ORD

NAPORD

Naples

Thu 2/26

12:40 pm-3:25 pm

1 stop33h 45m

Chicago O'Hare Intl

Wed 3/18

11:40 am-11:45 am

2 stops18h 05m

$640

NaplesChicago

NAP - ORD

NAPORD

Naples

Thu 1/15

6:20 am-2:55 pm

1 stop15h 35m

Chicago O'Hare Intl

Thu 1/22

3:48 pm-3:35 pm

2 stops16h 47m

$643

NaplesChicago

NAP - ORD

NAPORD

Naples

Thu 1/15

12:40 pm-5:42 pm

2 stops36h 02m

Chicago O'Hare Intl

Thu 1/22

4:14 pm-3:35 pm

2 stops16h 21m

$646

NaplesChicago

NAP - ORD

NAPORD

Naples

Thu 1/15

12:40 pm-5:42 pm

2 stops36h 02m

Chicago O'Hare Intl

Thu 1/22

11:44 am-3:35 pm

2 stops20h 51m

$647

NaplesChicago

NAP - ORD

NAPORD

Naples

Sat 1/24

6:15 am-2:55 pm

1 stop15h 40m

Chicago O'Hare Intl

Sat 1/31

8:16 am-11:45 am

2 stops20h 29m

$648

NaplesChicago

NAP - ORD

NAPORD

Naples

Sat 1/24

6:15 am-7:29 pm

2 stops20h 14m

Chicago O'Hare Intl

Sat 1/31

8:16 am-11:45 am

2 stops20h 29m

$658

NaplesChicago

NAP - ORD

NAPORD

Naples

Sun 5/10

6:35 am-1:10 pm

1 stop13h 35m

Chicago O'Hare Intl

Wed 6/3

10:40 am-10:35 am

2 stops16h 55m

$669

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 O'Hare Intl Airport

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 O'Hare Intl Airport?

What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Saturday when prices can be found for as low as $741. This is often the case because there is less demand to fly during this day of the week. On the other hand, Friday is the most expensive day to depart from Naples because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $999.

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

Flying to Chicago O'Hare Intl Airport from Naples in the morning is the least expensive time of day to depart. momondo users have found prices as low as $688 when looking at flights departing in the morning. Try not to purchase tickets in the afternoon because they tend to be around $897. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Naples to Chicago O'Hare Intl flight route?

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

What cabin class options are available on Naples to Chicago O'Hare Intl flights?

There are 3 cabin classes available to choose from on Naples to Chicago O'Hare Intl 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 O'Hare Intl Airport flights?

No. A direct flight is the cheapest option for a flight between Naples to Chicago O'Hare Intl Airport.

When to book flights from Naples to Chicago O'Hare Intl Airport

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

Estimated round-trip price

Cheap Naples to Chicago O'Hare Intl Airport (NAP to ORD) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Naples to Chicago O'Hare Intl Airport

Best Price Found	$549
Fastest flight time	10h 50m
Direct flights	Mon, Tue, Wed, Thu, Fri and Sun

The best one-way flight to Chicago O'Hare Intl Airport from Naples in the past 72 hours is $549. The best round-trip flight deal from Naples to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $757.

The fastest flight from Naples to Chicago O'Hare Intl Airport takes 10h 50m

Direct flights go from Naples to Chicago O'Hare Intl Airport on Monday, Tuesday, Wednesday, Thursday, Friday and Sunday. There are no airlines offering direct flights.

Search flight deals

How far is Naples to Chicago O'Hare Intl by plane?
Chicago O'Hare Intl is 4929.9 mi away from Naples. Flights usually cover this in 10h 50m, depending on flying conditions and air traffic around both airports.
When did momondo last update prices for flights from Naples Airport to Chicago O'Hare Intl Airport?
Prices for flights from Naples Airport to Chicago O'Hare Intl Airport were last updated today.
How many operators does momondo search for flights from Naples Airport to Chicago O'Hare Intl Airport?
The number of operators available for flights from Naples Airport to Chicago O'Hare Intl Airport is 1 as of December 2025.
How old do you have to be to fly from Naples Airport to Chicago O'Hare Intl Airport?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Naples Airport to Chicago O'Hare Intl Airport.
What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?
The travel and health documents you'll need for your trip to Chicago O'Hare Intl Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago O'Hare Intl Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Naples to Chicago O'Hare Intl Airport?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Naples to Chicago O'Hare Intl Airport is Boeing 787-9 Dreamliner (31.52% of total bookings). The next most popular plane models are Airbus A330-300 (11.96%), Airbus A330-900neo (9.78%), and Boeing 787-8 Dreamliner (9.78%).
What is the most popular airline from Naples to Chicago O'Hare Intl Airport?
Based on momondo bookings for flights between Naples and Chicago O'Hare Intl Airport, the leading airline is American Airlines, making up 100% of the total bookings.

Best airlines flying from Naples to Chicago O'Hare Intl Airport

Compare and see reviews for airlines that fly from Naples to Chicago O'Hare Intl Airport with momondo

Airline	Rating	Free Cancellation	Price
American Airlines	PriceFrom $664	Free Cancellation	Rating 7.2 11,050 reviews		Search American Airlines flights

Lake Geneva

South Haven

Schaumburg

Rockford

Merrillville

Gurnee

Naperville

Rosemont

Kenosha

New Buffalo

Joliet

Oak Brook

Orland Park

Racine

Hammond

Tinley Park

Janesville

Aurora

Elgin

Benton Harbor

Why use momondo?

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

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Naples.

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

Yes. momondo enables you to select and highlight flights to Chicago from Naples with this policy.

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

Once all potential Naples to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

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 O'Hare Intl Airport trip

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Cheap flights from Naples to Chicago from $334

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 2/9. 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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Filter for what you want

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American Airlines flights from Naples to Chicago O'Hare Intl Airport

Our best American Airlines deals on Naples to Chicago O'Hare Intl Airport flight tickets

British Airways flights from Naples to Chicago O'Hare Intl Airport

Our best British Airways deals on Naples to Chicago O'Hare Intl Airport flight tickets

momondo Fare Finder

Use the filters below to find and compare flights from Naples to Chicago O'Hare Intl Airport that are best for you.

See travel insights to Chicago from

How to get the cheapest flight ticket from Naples to Chicago O'Hare Intl Airport

What is the typical price of a round-trip flight between Naples and Chicago O'Hare Intl Airport?

What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

What is the cheapest Naples to Chicago O'Hare Intl flight route?

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

What cabin class options are available on Naples to Chicago O'Hare Intl flights?

There are 3 cabin classes available to choose from on Naples to Chicago O'Hare Intl 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 O'Hare Intl Airport flights?

No. A direct flight is the cheapest option for a flight between Naples to Chicago O'Hare Intl Airport.

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 O'Hare Intl Airport

Cheap Naples to Chicago O'Hare Intl Airport (NAP to ORD) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Naples to Chicago O'Hare Intl Airport

Best Price Found

Fastest flight time

Direct flights

How far is Naples to Chicago O'Hare Intl by plane?

When did momondo last update prices for flights from Naples Airport to Chicago O'Hare Intl Airport?

How many operators does momondo search for flights from Naples Airport to Chicago O'Hare Intl Airport?

How old do you have to be to fly from Naples Airport to Chicago O'Hare Intl Airport?

What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

What is the most popular plane model from Naples to Chicago O'Hare Intl Airport?

What is the most popular airline from Naples to Chicago O'Hare Intl Airport?

Best airlines flying from Naples to Chicago O'Hare Intl Airport

Compare and see reviews for airlines that fly from Naples to Chicago O'Hare Intl Airport 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 O'Hare Intl Airport 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 Chicago

Popular cities in the United States

Popular flights according to clicks in the last 7 days on momondo