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Cheap flights from Naples to Chicago from $311

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 4/29. 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

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Multiple Airlines Logo
7:40 am - 2:55 pm
NAP
-
ORD
14h 15m
1 stop
Multiple Airlines Logo
5:25 pm - 10:00 am
ORD
-
NAP
9h 35mnonstop
$563Multiple Airlines
Wed, May 20 - Sat, Jun 6
Multiple Airlines Logo
7:40 am - 2:55 pm
NAP
-
ORD
14h 15m
1 stop
Multiple Airlines Logo
5:00 pm - 10:00 pm
ORD
-
NAP
22h 00m
1 stop
$591Multiple Airlines
Wed, May 20 - Sat, Jun 6
British Airways Logo
1:55 pm - 3:25 pm
NAP
-
ORD
32h 30m
1 stop
British Airways Logo
10:45 pm - 11:50 am
ORD
-
NAP
31h 05m
1 stop
$602British Airways
Mon, Mar 2 - Sun, Mar 8
Iberia Logo
2:55 pm - 2:55 pm
NAP
-
ORD
31h 00m
1 stop
Iberia Logo
6:40 pm - 2:10 pm
ORD
-
NAP
13h 30m
1 stop
$615Iberia
Mon, Mar 2 - Sun, Mar 8
Finnair Logo
3:00 pm - 6:50 pm
NAP
-
ORD
10h 50mnonstop
Finnair Logo
5:25 pm - 10:00 am
ORD
-
NAP
9h 35mnonstop
$616Finnair
Wed, May 20 - Sat, Jun 6
United Airlines Logo
2:15 pm - 8:05 pm
NAP
-
ORD
12h 50m
1 stop
United Airlines Logo
10:50 pm - 5:25 pm
ORD
-
NAP
12h 35m
1 stop
$622United Airlines
Mon, Mar 2 - Sun, Mar 8
American Airlines Logo
6:20 am - 2:55 pm
NAP
-
ORD
15h 35m
1 stop
American Airlines Logo
6:30 pm - 11:45 am
ORD
-
NAP
34h 15m
1 stop
$623American Airlines
Fri, Feb 13 - Fri, Feb 20
United Airlines Logo
2:15 pm - 8:05 pm
NAP
-
ORD
12h 50m
1 stop
United Airlines Logo
10:50 pm - 5:25 pm
ORD
-
NAP
12h 35m
1 stop
$625United Airlines
Mon, Mar 2 - Sun, Mar 8
American Airlines Logo
6:20 am - 2:55 pm
NAP
-
ORD
15h 35m
1 stop
American Airlines Logo
6:30 pm - 11:45 am
ORD
-
NAP
34h 15m
1 stop
$626American Airlines
Fri, Feb 13 - Fri, Feb 20
United Airlines Logo
6:25 am - 6:33 pm
NAP
-
ORD
19h 08m
2 stops
United Airlines Logo
11:03 am - 11:40 am
ORD
-
NAP
17h 37m
2 stops
$627United Airlines
Wed, May 20 - Sat, Jun 6

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
Mar 2
NAP1:55 pmNaples
32h 30m
1 stop
ORD3:25 pmChicago O'Hare Intl
Mar 8
ORD10:45 pmChicago O'Hare Intl
31h 05m
1 stop
NAP11:50 amNaples
$602
British Airways
Mar 2
NAP1:55 pmNaples
32h 30m
1 stop
ORD3:25 pmChicago O'Hare Intl
Mar 8
ORD8:58 pmChicago O'Hare Intl
32h 52m
2 stops
NAP11:50 amNaples
$674
British Airways
May 5
NAP7:40 amNaples
13h 10m
1 stop
ORD1:50 pmChicago O'Hare Intl
May 19
ORD5:25 pmChicago O'Hare Intl
9h 35m
NAP10:00 amNaples
$699

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

Our best United Airlines deals on Naples to Chicago O'Hare Intl Airport flight tickets
United Airlines
Mar 2
NAP2:15 pmNaples
12h 50m
1 stop
ORD8:05 pmChicago O'Hare Intl
Mar 8
ORD10:50 pmChicago O'Hare Intl
12h 35m
1 stop
NAP5:25 pmNaples
$622
United Airlines
Mar 2
NAP2:15 pmNaples
12h 50m
1 stop
ORD8:05 pmChicago O'Hare Intl
Mar 8
ORD10:50 pmChicago O'Hare Intl
12h 35m
1 stop
NAP5:25 pmNaples
$625
United Airlines
May 20
NAP6:25 amNaples
19h 08m
2 stops
ORD6:33 pmChicago O'Hare Intl
Jun 6
ORD11:03 amChicago O'Hare Intl
17h 37m
2 stops
NAP11:40 amNaples
$627

momondo Fare Finder

 
Customize your flight search to find flights from Naples to Chicago O'Hare Intl Airport 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 January 29, 2026.
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

Wed 5/20

7:40 am-2:55 pm

1 stop14h 15m

Chicago O'Hare Intl

Sat 6/6

5:25 pm-10:00 am

Nonstop9h 35m

$563

NaplesChicago

NAP - ORD

NAPORD

Naples

Wed 5/20

7:40 am-2:55 pm

1 stop14h 15m

Chicago O'Hare Intl

Sat 6/6

5:00 pm-10:00 pm

1 stop22h 00m

$591

NaplesChicago

NAP - ORD

NAPORD

Naples

Mon 3/2

1:55 pm-3:25 pm

1 stop32h 30m

Chicago O'Hare Intl

Sun 3/8

10:45 pm-11:50 am

1 stop31h 05m

$602

NaplesChicago

NAP - ORD

NAPORD

Naples

Mon 3/2

2:55 pm-2:55 pm

1 stop31h 00m

Chicago O'Hare Intl

Sun 3/8

6:40 pm-2:10 pm

1 stop13h 30m

$615

NaplesChicago

NAP - ORD

NAPORD

Naples

Wed 5/20

3:00 pm-6:50 pm

Nonstop10h 50m

Chicago O'Hare Intl

Sat 6/6

5:25 pm-10:00 am

Nonstop9h 35m

$616

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

$622

NaplesChicago

NAP - ORD

NAPORD

Naples

Fri 2/13

6:20 am-2:55 pm

1 stop15h 35m

Chicago O'Hare Intl

Fri 2/20

6:30 pm-11:45 am

1 stop34h 15m

$623

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

$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

6:30 pm-11:45 am

1 stop34h 15m

$626

NaplesChicago

NAP - ORD

NAPORD

Naples

Wed 5/20

6:25 am-6:33 pm

2 stops19h 08m

Chicago O'Hare Intl

Sat 6/6

11:03 am-11:40 am

2 stops17h 37m

$627

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 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

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 $737. 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 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

$491

Fastest flight time

10h 50m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Naples in the past 72 hours is $491. 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 every day.
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?

  • 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?

  • 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
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $647Free CancellationRating
7.2
11,206 reviews
Search American Airlines flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lake Geneva
Schaumburg
South Haven
Rockford
Merrillville
Gurnee
Naperville
Rosemont
New Buffalo
Kenosha
Joliet
Oak Brook
Orland Park
Racine
Hammond
Janesville
Tinley Park
Elgin
Aurora
South Holland

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.

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