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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 4/24. 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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Find the cheapest flights from Naples to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
ITA Airways Logo
6:35 am - 1:10 pm
NAP
-
ORD
13h 35m
1 stop
ITA Airways Logo
3:00 pm - 10:35 am
ORD
-
NAP
12h 35m
1 stop
$552ITA Airways
Mon, May 4 - Mon, May 11
ITA Airways Logo
6:35 am - 1:10 pm
NAP
-
ORD
13h 35m
1 stop
ITA Airways Logo
3:00 pm - 10:35 am
ORD
-
NAP
12h 35m
1 stop
$554ITA Airways
Mon, May 4 - Mon, May 11
ITA Airways Logo
6:35 am - 1:10 pm
NAP
-
ORD
13h 35m
1 stop
ITA Airways Logo
3:00 pm - 8:45 pm
ORD
-
NAP
22h 45m
2 stops
$564ITA Airways
Mon, May 4 - Mon, May 11
Finnair Logo
3:00 pm - 6:55 pm
NAP
-
ORD
10h 55mnonstop
Finnair Logo
5:25 pm - 10:00 am
ORD
-
NAP
9h 35mnonstop
$603Finnair
Sun, May 10 - Mon, May 18
Finnair Logo
10:35 am - 5:50 pm
NAP
-
ORD
14h 15m
1 stop
Finnair Logo
5:25 pm - 10:00 am
ORD
-
NAP
9h 35mnonstop
$604Finnair
Mon, May 4 - Mon, May 11
British Airways Logo
3:00 pm - 6:55 pm
NAP
-
ORD
10h 55mnonstop
British Airways Logo
5:25 pm - 10:00 am
ORD
-
NAP
9h 35mnonstop
$621British Airways
Sun, May 10 - Mon, May 18
British Airways Logo
3:00 pm - 6:55 pm
NAP
-
ORD
10h 55mnonstop
British Airways Logo
5:25 pm - 10:00 am
ORD
-
NAP
9h 35mnonstop
$626British Airways
Sun, May 10 - Mon, May 18
Delta Logo
10:15 am - 10:28 pm
NAP
-
MDW
19h 13m
2 stops
Delta Logo
1:59 pm - 3:15 pm
MDW
-
NAP
18h 16m
2 stops
$665Delta
Mon, May 4 - Mon, May 11
Delta Logo
6:05 am - 10:28 pm
NAP
-
MDW
23h 23m
2 stops
Delta Logo
1:59 pm - 3:15 pm
MDW
-
NAP
18h 16m
2 stops
$671Delta
Mon, May 4 - Mon, May 11
Multiple Airlines Logo
6:35 am - 6:33 pm
NAP
-
MDW
18h 58m
2 stops
Multiple Airlines Logo
5:11 pm - 6:15 pm
MDW
-
NAP
18h 04m
2 stops
$698Multiple Airlines
Fri, May 8 - Mon, Jun 8

British Airways flights from Naples to Chicago

Our best British Airways deals on Naples to Chicago flight tickets
British Airways
May 10
NAP3:00 pmNaples
10h 55m
ORD6:55 pmChicago O'Hare Intl
May 18
ORD5:25 pmChicago O'Hare Intl
9h 35m
NAP10:00 amNaples
$621
British Airways
May 10
NAP3:00 pmNaples
10h 55m
ORD6:55 pmChicago O'Hare Intl
May 18
ORD5:25 pmChicago O'Hare Intl
9h 35m
NAP10:00 amNaples
$626
British Airways
May 10
NAP3:00 pmNaples
10h 55m
ORD6:55 pmChicago O'Hare Intl
May 18
ORD5:25 pmChicago O'Hare Intl
9h 35m
NAP10:00 amNaples
$628

Air Canada flights from Naples to Chicago

Our best Air Canada deals on Naples to Chicago flight tickets
Air Canada
Sep 8
NAP6:00 amNaples
15h 52m
2 stops
ORD2:52 pmChicago O'Hare Intl
Sep 23
ORD10:43 amChicago O'Hare Intl
15h 57m
2 stops
NAP9:40 amNaples
$729
Air Canada
Apr 9
NAP6:00 amNaples
16h 48m
2 stops
ORD3:48 pmChicago O'Hare Intl
Apr 13
ORD12:50 pmChicago O'Hare Intl
16h 35m
2 stops
NAP12:25 pmNaples
$773

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 March 27, 2026.
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

Cheapest round-trip

NaplesChicago

NAP - ORD

NAPORD

Naples

Mon 5/4

6:35 am-1:10 pm

1 stop13h 35m

Chicago O'Hare Intl

Mon 5/11

3:00 pm-10:35 am

1 stop12h 35m

$552

NaplesChicago

NAP - ORD

NAPORD

Naples

Mon 5/4

6:35 am-1:10 pm

1 stop13h 35m

Chicago O'Hare Intl

Mon 5/11

3:00 pm-10:35 am

1 stop12h 35m

$554

NaplesChicago

NAP - ORD

NAPORD

Naples

Mon 5/4

6:35 am-1:10 pm

1 stop13h 35m

Chicago O'Hare Intl

Mon 5/11

3:00 pm-8:45 pm

2 stops22h 45m

$564
Quickest round-trip

NaplesChicago

NAP - ORD

NAPORD

Naples

Sun 5/10

3:00 pm-6:55 pm

Nonstop10h 55m

Chicago O'Hare Intl

Mon 5/18

5:25 pm-10:00 am

Nonstop9h 35m

$603

NaplesChicago

NAP - ORD

NAPORD

Naples

Mon 5/4

10:35 am-5:50 pm

1 stop14h 15m

Chicago O'Hare Intl

Mon 5/11

5:25 pm-10:00 am

Nonstop9h 35m

$604

NaplesChicago

NAP - ORD

NAPORD

Naples

Sun 5/10

3:00 pm-6:55 pm

Nonstop10h 55m

Chicago O'Hare Intl

Mon 5/18

5:25 pm-10:00 am

Nonstop9h 35m

$621

NaplesChicago

NAP - ORD

NAPORD

Naples

Sun 5/10

3:00 pm-6:55 pm

Nonstop10h 55m

Chicago O'Hare Intl

Mon 5/18

5:25 pm-10:00 am

Nonstop9h 35m

$626

NaplesChicago

NAP - MDW

NAPMDW

Naples

Mon 5/4

10:15 am-10:28 pm

2 stops19h 13m

Chicago Midway

Mon 5/11

1:59 pm-3:15 pm

2 stops18h 16m

$665

NaplesChicago

NAP - MDW

NAPMDW

Naples

Mon 5/4

6:05 am-10:28 pm

2 stops23h 23m

Chicago Midway

Mon 5/11

1:59 pm-3:15 pm

2 stops18h 16m

$671

NaplesChicago

NAP - MDW

NAPMDW

Naples

Fri 5/8

6:35 am-6:33 pm

2 stops18h 58m

Chicago Midway

Mon 6/8

5:11 pm-6:15 pm

2 stops18h 04m

$698

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 cheapest month to fly to Chicago?

The month of May is, on average, the cheapest month to fly to Chicago from Naples, with most prices found around $575. If you’re not able to fly to Chicago in May, then September is your next best option. Flight prices from Naples to Chicago during September average around $592.

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

Fastest flight time

10h 50m

Direct flights

Every day

Airports in Chicago

3 airports
The fastest flight from Naples to Chicago takes 10h 50m
Direct flights go from Naples to Chicago every day.
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?

  • 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 $639Free CancellationRating
7.1
11,507 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
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Schererville
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.

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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