What is the cheapest airline that flies from Naples to Chicago?

TAP AIR PORTUGAL is the most popular carrier operating from Naples to Chicago

Which layover airport has the shortest travel time from Naples to Chicago?

Flights connecting via Zurich (ZRH) have the shortest average one-way travel time: 13h 05m.

Which layover airport has the shortest connection time from Naples to Chicago?

Zurich (ZRH) has the shortest average layover time for this route: 1h 03m.

How many flights depart from Naples to Chicago on average per day?

1 flights are operational daily from Naples to Chicago as of July 2025. The most popular departure time for this route is 3:00PM, with 100% of flights per day taking off in the afternoon.

How many flights depart from Naples to Chicago on average per week?

As of July 2025, there are 7 flights per week flying from Naples to Chicago. The most common day of the week flights depart is Mon, with 14% of flights taking off on this day.

Which airport is the most popular layover for flights between Naples and Chicago?

Dublin (DUB) was the most common stop: 33% of momondo users choosing 1-stop flights on this route connected there.

Which layover airport offers the lowest fares from Naples to Chicago?

Flights via Copenhagen (CPH) offer the lowest average round-trip price of $481.

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 July 2025, 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.

$333 Cheap Flights from Naples to Chicago in 2025

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Find the cheapest flights from Naples to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

6:40 am - 2:55 pmNAP-ORD

15h 15m1 stop

10:40 am - 7:00 amORD-NAP

13h 20m1 stop

$509United Airlines

Find Deal

jue., sep. 18 - mié., oct. 15

7:35 pm - 4:10 pmNAP-ORD

27h 35m1 stop

7:15 pm - 6:45 pmORD-NAP

16h 30m1 stop

$519Scandinavian Airlines

Find Deal

jue., sep. 4 - lun., sep. 8

6:40 am - 2:55 pmNAP-ORD

15h 15m1 stop

8:15 pm - 7:00 amORD-NAP

27h 45m1 stop

$527United Airlines

Find Deal

vie., sep. 12 - vie., sep. 19

3:00 pm - 6:50 pmNAP-ORD

10h 50mnonstop

10:35 pm - 10:00 pmORD-NAP

16h 25m1 stop

$529American Airlines

Find Deal

mar., ago. 19 - mar., sep. 2

11:35 am - 8:11 pmNAP-ORD

15h 36m1 stop

10:40 am - 8:45 amORD-NAP

15h 05m2 stops

$534

Find Deal

jue., sep. 18 - mié., oct. 15

12:00 pm - 7:58 amNAP-ORD

26h 58m2 stops

10:35 pm - 10:00 pmORD-NAP

16h 25m1 stop

$535American Airlines

Find Deal

mié., ago. 20 - mar., sep. 2

12:00 pm - 8:11 pmNAP-ORD

15h 11m1 stop

9:15 pm - 7:25 pmORD-NAP

15h 10m1 stop

$536British Airways

Find Deal

mié., ago. 20 - dom., ago. 31

12:00 pm - 3:45 pmNAP-ORD

34h 45m1 stop

8:35 pm - 10:00 pmORD-NAP

18h 25m1 stop

$538British Airways

Find Deal

mié., ago. 20 - dom., ago. 31

6:40 am - 2:55 pmNAP-ORD

15h 15m1 stop

7:05 pm - 8:45 amORD-NAP

30h 40m1 stop

$556

Find Deal

sáb., ago. 23 - dom., ago. 31

7:15 pm - 12:50 pmNAP-ORD

24h 35m1 stop

7:05 pm - 8:45 amORD-NAP

30h 40m1 stop

$565SWISS

Find Deal

mié., ago. 20 - lun., sep. 1

Air Canada flights from Naples to Chicago

Our best Air Canada deals on Naples to Chicago flight tickets

Air Canada

Aug 20

NAP11:35 amNaples

41h 32m

2 stops

ORD10:07 pmChicago O'Hare Intl

Sep 2

ORD9:55 amChicago O'Hare Intl

16h 45m

2 stops

NAP9:40 amNaples

$576

Find similar

Air Canada

Sep 4

NAP11:35 amNaples

15h 36m

1 stop

ORD8:11 pmChicago O'Hare Intl

Sep 8

ORD6:06 pmChicago O'Hare Intl

32h 34m

2 stops

NAP9:40 amNaples

$577

Find similar

Air Canada

Sep 4

NAP11:35 amNaples

17h 32m

2 stops

ORD10:07 pmChicago O'Hare Intl

Sep 8

ORD9:12 pmChicago O'Hare Intl

29h 28m

2 stops

NAP9:40 amNaples

$578

Find similar

United Airlines flights from Naples to Chicago

Our best United Airlines deals on Naples to Chicago flight tickets

United Airlines

Sep 18

NAP6:40 amNaples

15h 15m

1 stop

ORD2:55 pmChicago O'Hare Intl

Oct 15

ORD10:40 amChicago O'Hare Intl

13h 20m

1 stop

NAP7:00 amNaples

$509

Find similar

United Airlines

Sep 12

NAP6:40 amNaples

15h 15m

1 stop

ORD2:55 pmChicago O'Hare Intl

Sep 19

ORD8:15 pmChicago O'Hare Intl

27h 45m

1 stop

NAP7:00 amNaples

$527

Find similar

United Airlines

Oct 2

NAP6:40 amNaples

15h 15m

1 stop

ORD2:55 pmChicago O'Hare Intl

Oct 10

ORD10:40 amChicago O'Hare Intl

16h 00m

1 stop

NAP9:40 amNaples

$552

Find similar

Fly from

Fly to

Route

Depart

Return

Price

NaplesChicago

NAP - ORD

NAPORD

Naples

jue. 9/18

6:40 am-2:55 pm

1 stop15h 15m

Chicago O'Hare Intl

mié. 10/15

10:40 am-7:00 am

1 stop13h 20m

$509

NaplesChicago

NAP - ORD

NAPORD

Naples

jue. 9/4

7:35 pm-4:10 pm

1 stop27h 35m

Chicago O'Hare Intl

lun. 9/8

7:15 pm-6:45 pm

1 stop16h 30m

$519

NaplesChicago

NAP - ORD

NAPORD

Naples

vie. 9/12

6:40 am-2:55 pm

1 stop15h 15m

Chicago O'Hare Intl

vie. 9/19

8:15 pm-7:00 am

1 stop27h 45m

$527

NaplesChicago

NAP - ORD

NAPORD

Naples

mar. 8/19

3:00 pm-6:50 pm

Nonstop10h 50m

Chicago O'Hare Intl

mar. 9/2

10:35 pm-10:00 pm

1 stop16h 25m

$529

NaplesChicago

NAP - ORD

NAPORD

Naples

jue. 9/18

11:35 am-8:11 pm

1 stop15h 36m

Chicago O'Hare Intl

mié. 10/15

10:40 am-8:45 am

2 stops15h 05m

$534

NaplesChicago

NAP - ORD

NAPORD

Naples

mié. 8/20

12:00 pm-7:58 am

2 stops26h 58m

Chicago O'Hare Intl

mar. 9/2

10:35 pm-10:00 pm

1 stop16h 25m

$535

NaplesChicago

NAP - ORD

NAPORD

Naples

mié. 8/20

12:00 pm-8:11 pm

1 stop15h 11m

Chicago O'Hare Intl

dom. 8/31

9:15 pm-7:25 pm

1 stop15h 10m

$536

NaplesChicago

NAP - ORD

NAPORD

Naples

mié. 8/20

12:00 pm-3:45 pm

1 stop34h 45m

Chicago O'Hare Intl

dom. 8/31

8:35 pm-10:00 pm

1 stop18h 25m

$538

NaplesChicago

NAP - ORD

NAPORD

Naples

sáb. 8/23

6:40 am-2:55 pm

1 stop15h 15m

Chicago O'Hare Intl

dom. 8/31

7:05 pm-8:45 am

1 stop30h 40m

$556

NaplesChicago

NAP - ORD

NAPORD

Naples

mié. 8/20

7:15 pm-12:50 pm

1 stop24h 35m

Chicago O'Hare Intl

lun. 9/1

7:05 pm-8:45 am

1 stop30h 40m

$565

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

Airlines

Layovers

Other information

What is the cheapest month to fly to Chicago?

The month of January is, on average, the cheapest month to fly to Chicago from Naples, with most prices found around $566. If you’re not able to fly to Chicago in January, then March is your next best option. Flight prices from Naples to Chicago during March average around $572.

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 Wednesday when prices can be found for as low as $692. 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 time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the morning. Flights from Naples to Chicago during this time can be as low as $709. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $937.

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	$333
Fastest flight time	10h 50m
Direct flights	Every day
Airports in Chicago	2 airports

The best one-way flight to Chicago from Naples in the past 72 hours is $333. The best round-trip flight deal from Naples to Chicago found on momondo in the last 72 hours is $509.

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

Direct flights go from Naples to Chicago every day.

There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)

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 July 2025, 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 (32.17% of total bookings). The next most popular plane models are Boeing 787-8 Dreamliner (16.52%), Boeing 767-300 (winglets) (11.30%), and Airbus A330-300 (8.70%).

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 $664	Free Cancellation	Rating 7.2 10,000 reviews		Search American Airlines flights

American Airlines Flights From Naples to Chicago
American Airlines flies from Naples to Chicago around 7 times per week, with 10,000 momondo users rating the airline 7.2/10. The cheapest American Airlines deal from Naples to Chicago in the last 72 hours was $664 (round-trip), much lower than the average airfare cost of $899 for American Airlines flights on this route.

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Portage

Lansing

Schererville

Valparaiso

Crown Point

Munster

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

Popular cities in the United States

Flights to New Yorkfrom $39

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Flights to Las Vegasfrom $35

Flights to San Franciscofrom $49

Flights to Washington, D.C.from $49

Flights to Bostonfrom $77

Flights to Atlantafrom $29

Flights to Dallasfrom $55

Flights to Seattlefrom $93

Flights to Denverfrom $49

Cheap flights from Naples to Chicago from $333

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 11/4. 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

Filter for what you want

Filter for what you want

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Find the cheapest flights from Naples to Chicago

Cheap round-trip flights

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Cheap last minute flights

Cheap direct flights

Air Canada flights from Naples to Chicago

Our best Air Canada deals on Naples to Chicago flight tickets

United Airlines flights from Naples to Chicago

Our best United Airlines deals on Naples to Chicago flight tickets

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Use the filters below to find and compare flights from Naples to Chicago that are best for you.

See travel insights to Chicago from

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

What is the cheapest month to fly to Chicago?

The month of January is, on average, the cheapest month to fly to Chicago from Naples, with most prices found around $566. If you’re not able to fly to Chicago in January, then March is your next best option. Flight prices from Naples to Chicago during March average around $572.

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

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

Our most recent data shows that the best time of day to fly to Chicago is in the morning. Flights from Naples to Chicago during this time can be as low as $709. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $937.

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.

What is the cheapest airline that flies from Naples to Chicago?

TAP AIR PORTUGAL is the most popular carrier operating from Naples to Chicago

Which airport is the most popular layover for flights between Naples and Chicago?

Dublin (DUB) was the most common stop: 33% of momondo users choosing 1-stop flights on this route connected there.

Which layover airport offers the lowest fares from Naples to Chicago?

Flights via Copenhagen (CPH) offer the lowest average round-trip price of $481.

Which layover airport has the shortest travel time from Naples to Chicago?

Flights connecting via Zurich (ZRH) have the shortest average one-way travel time: 13h 05m.

Which layover airport has the shortest connection time from Naples to Chicago?

Zurich (ZRH) has the shortest average layover time for this route: 1h 03m.

How many flights depart from Naples to Chicago on average per day?

1 flights are operational daily from Naples to Chicago as of July 2025. The most popular departure time for this route is 3:00PM, with 100% of flights per day taking off in the afternoon.

How many flights depart from Naples to Chicago on average per week?

As of July 2025, there are 7 flights per week flying from Naples to Chicago. The most common day of the week flights depart is Mon, with 14% of flights taking off on this day.

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?

Best airlines flying from Naples to Chicago

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

American Airlines Flights From Naples to Chicago

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