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Cheap flights from Naples to Chicago from $320

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 1/28. 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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0 bags

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Cheap round-trip flights

Enter your travel dates to find the best prices.
Scandinavian Airlines Logo
7:30 pm - 4:45 pmNAP-ORD
28h 15m1 stop
Scandinavian Airlines Logo
7:20 pm - 6:35 pmORD-NAP
16h 15m1 stop
$558Scandinavian Airlines
Find Deal
Thu, Nov 13 - Sat, Nov 22
Scandinavian Airlines Logo
7:30 pm - 4:45 pmNAP-ORD
28h 15m1 stop
Scandinavian Airlines Logo
7:20 pm - 6:35 pmORD-NAP
16h 15m1 stop
$559Scandinavian Airlines
Find Deal
Thu, Nov 13 - Sat, Nov 22
Multiple Airlines Logo
10:25 pm - 1:10 pmNAP-ORD
21h 45m2 stops
Multiple Airlines Logo
4:20 pm - 10:40 pmORD-NAP
23h 20m2 stops
$581Multiple Airlines
Find Deal
Mon, Nov 24 - Sun, Nov 30
Multiple Airlines Logo
3:05 pm - 1:10 pmNAP-ORD
29h 05m3 stops
Multiple Airlines Logo
4:20 pm - 10:40 pmORD-NAP
23h 20m2 stops
$615Multiple Airlines
Find Deal
Mon, Nov 24 - Sun, Nov 30
United Airlines Logo
2:15 pm - 8:05 pmNAP-ORD
12h 50m1 stop
United Airlines Logo
9:50 pm - 5:25 pmORD-NAP
12h 35m1 stop
$616United Airlines
Find Deal
Mon, Nov 24 - Sun, Nov 30
SWISS Logo
9:50 am - 12:45 pmNAP-ORD
33h 55m1 stop
SWISS Logo
6:50 pm - 2:10 pmORD-NAP
12h 20m1 stop
$626SWISS
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Wed, Feb 18 - Sun, Feb 22
SWISS Logo
9:50 am - 12:45 pmNAP-ORD
33h 55m1 stop
SWISS Logo
4:10 pm - 2:10 pmORD-NAP
15h 00m1 stop
$627SWISS
Find Deal
Wed, Feb 18 - Sun, Feb 22
Lufthansa Logo
2:15 pm - 1:10 pmNAP-ORD
29h 55m1 stop
Lufthansa Logo
9:50 pm - 5:25 pmORD-NAP
12h 35m1 stop
$632Lufthansa
Find Deal
Mon, Nov 24 - Sun, Nov 30
Lufthansa Logo
7:05 pm - 6:19 pmNAP-ORD
30h 14m2 stops
Lufthansa Logo
9:50 pm - 5:25 pmORD-NAP
12h 35m1 stop
$641Lufthansa
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Thu, Nov 20 - Wed, Nov 26
United Airlines Logo
6:35 am - 2:50 pmNAP-ORD
15h 15m1 stop
United Airlines Logo
6:00 am - 12:15 pmORD-NAP
23h 15m2 stops
$667United Airlines
Find Deal
Thu, Apr 2 - Mon, Apr 6

Scandinavian Airlines flights from Naples to Chicago

Our best Scandinavian Airlines deals on Naples to Chicago flight tickets
Scandinavian Airlines
Nov 13
NAP7:30 pmNaples
28h 15m
1 stop
ORD4:45 pmChicago O'Hare Intl
Nov 22
ORD7:20 pmChicago O'Hare Intl
16h 15m
1 stop
NAP6:35 pmNaples
$558
Find similar
Scandinavian Airlines
Nov 13
NAP7:30 pmNaples
28h 15m
1 stop
ORD4:45 pmChicago O'Hare Intl
Nov 22
ORD7:20 pmChicago O'Hare Intl
16h 15m
1 stop
NAP6:35 pmNaples
$559
Find similar
Scandinavian Airlines
Nov 20
NAP7:30 pmNaples
28h 15m
1 stop
ORD4:45 pmChicago O'Hare Intl
Nov 26
ORD7:20 pmChicago O'Hare Intl
16h 20m
1 stop
NAP6:40 pmNaples
$570
Find similar

United Airlines flights from Naples to Chicago

Our best United Airlines deals on Naples to Chicago flight tickets
United Airlines
Nov 24
NAP2:15 pmNaples
12h 50m
1 stop
ORD8:05 pmChicago O'Hare Intl
Nov 30
ORD9:50 pmChicago O'Hare Intl
12h 35m
1 stop
NAP5:25 pmNaples
$616
Find similar
United Airlines
Apr 2
NAP6:35 amNaples
15h 15m
1 stop
ORD2:50 pmChicago O'Hare Intl
Apr 6
ORD6:00 amChicago O'Hare Intl
23h 15m
2 stops
NAP12:15 pmNaples
$667
Find similar
United Airlines
Nov 24
NAP2:15 pmNaples
12h 50m
1 stop
ORD8:05 pmChicago O'Hare Intl
Nov 30
ORD6:25 pmChicago O'Hare Intl
16h 00m
2 stops
NAP5:25 pmNaples
$708
Find similar

momondo 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, momondo users made 832,500 searches. Data last updated November 2, 2025.
Use the filters below to find and compare flights from Naples to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

NaplesChicago

NAP - ORD

NAPORD

Naples

Thu 11/13

7:30 pm-4:45 pm

1 stop28h 15m

Chicago O'Hare Intl

Sat 11/22

7:20 pm-6:35 pm

1 stop16h 15m

$558

NaplesChicago

NAP - ORD

NAPORD

Naples

Thu 11/13

7:30 pm-4:45 pm

1 stop28h 15m

Chicago O'Hare Intl

Sat 11/22

7:20 pm-6:35 pm

1 stop16h 15m

$559

NaplesChicago

NAP - ORD

NAPORD

Naples

Mon 11/24

10:25 pm-1:10 pm

2 stops21h 45m

Chicago O'Hare Intl

Sun 11/30

4:20 pm-10:40 pm

2 stops23h 20m

$581

NaplesChicago

NAP - ORD

NAPORD

Naples

Mon 11/24

3:05 pm-1:10 pm

3 stops29h 05m

Chicago O'Hare Intl

Sun 11/30

4:20 pm-10:40 pm

2 stops23h 20m

$615

NaplesChicago

NAP - ORD

NAPORD

Naples

Mon 11/24

2:15 pm-8:05 pm

1 stop12h 50m

Chicago O'Hare Intl

Sun 11/30

9:50 pm-5:25 pm

1 stop12h 35m

$616

NaplesChicago

NAP - ORD

NAPORD

Naples

Wed 2/18

9:50 am-12:45 pm

1 stop33h 55m

Chicago O'Hare Intl

Sun 2/22

6:50 pm-2:10 pm

1 stop12h 20m

$626

NaplesChicago

NAP - ORD

NAPORD

Naples

Wed 2/18

9:50 am-12:45 pm

1 stop33h 55m

Chicago O'Hare Intl

Sun 2/22

4:10 pm-2:10 pm

1 stop15h 00m

$627

NaplesChicago

NAP - ORD

NAPORD

Naples

Mon 11/24

2:15 pm-1:10 pm

1 stop29h 55m

Chicago O'Hare Intl

Sun 11/30

9:50 pm-5:25 pm

1 stop12h 35m

$632

NaplesChicago

NAP - ORD

NAPORD

Naples

Thu 11/20

7:05 pm-6:19 pm

2 stops30h 14m

Chicago O'Hare Intl

Wed 11/26

9:50 pm-5:25 pm

1 stop12h 35m

$641

NaplesChicago

NAP - ORD

NAPORD

Naples

Thu 4/2

6:35 am-2:50 pm

1 stop15h 15m

Chicago O'Hare Intl

Mon 4/6

6:00 am-12:15 pm

2 stops23h 15m

$667

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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 typical price of a round-trip flight between Naples and Chicago?

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 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. 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 $897.

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

$450

Direct flights

None
The best one-way flight to Chicago from Naples in the past 72 hours is $450. The best round-trip flight deal from Naples to Chicago found on momondo in the last 72 hours is $757.
There are no direct flights from Naples to Chicago. There are no popular flight routes from Naples to Chicago.
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 12h 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?

  • 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?

  • 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
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $664Free CancellationRating
7.2
11,034 reviews
Search American Airlines flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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.

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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
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport