$1,382 Cheap Flights from Naples (NAP) to Chicago (MDW)

View $1,382 flight on Mon, Jan 12, 2026Opens in a new window

Popular airlines from Naples Intl. Airport (NAP) to Chicago Midway Airport (MDW)

Cheap Flights from Naples to Chicago (NAP-MDW)

Prices were available within the past 7 days and start at $1,382 for one-way flights and $972 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Air France
Fri, Jul 11 - Thu, Jul 17
NAP
Naples
MDW
Chicago
$972 Roundtrip, found 1 day ago
$972
Roundtrip
found 1 day ago
Select Air France flight, departing Fri, Jul 11 from Naples to Chicago, returning Thu, Jul 17, priced at $972 found 1 day ago
Air France
Fri, Jul 11 - Thu, Jul 17
NAP
Naples
MDW
Chicago
$1,062 Roundtrip, found 1 day ago
$1,062
Roundtrip
found 1 day ago
Select Air France flight, departing Fri, Jul 11 from Naples to Chicago, returning Thu, Jul 17, priced at $1,062 found 1 day ago
Delta
Sat, Jul 19 - Fri, Jul 25
NAP
Naples
MDW
Chicago
$1,079 Roundtrip, found 5 days ago
$1,079
Roundtrip
found 5 days ago
Select Delta flight, departing Sat, Jul 19 from Naples to Chicago, returning Fri, Jul 25, priced at $1,079 found 5 days ago
Delta
Sat, Jul 19 - Fri, Jul 25
NAP
Naples
MDW
Chicago
$1,125 Roundtrip, found 5 days ago
$1,125
Roundtrip
found 5 days ago
Select Delta flight, departing Sat, Jul 19 from Naples to Chicago, returning Fri, Jul 25, priced at $1,125 found 5 days ago
Air France
Fri, Jul 11 - Thu, Jul 17
NAP
Naples
MDW
Chicago
$1,200 Roundtrip, found 1 day ago
$1,200
Roundtrip
found 1 day ago
Select Air France flight, departing Fri, Jul 11 from Naples to Chicago, returning Thu, Jul 17, priced at $1,200 found 1 day ago
Delta
Fri, Aug 8 - Wed, Aug 20
NAP
Naples
MDW
Chicago
$1,275 Roundtrip, found 2 days ago
$1,275
Roundtrip
found 2 days ago
Select Delta flight, departing Fri, Aug 8 from Naples to Chicago, returning Wed, Aug 20, priced at $1,275 found 2 days ago
Delta
Fri, Aug 8 - Wed, Aug 20
NAP
Naples
MDW
Chicago
$1,304 Roundtrip, found 2 days ago
$1,304
Roundtrip
found 2 days ago
Select Delta flight, departing Fri, Aug 8 from Naples to Chicago, returning Wed, Aug 20, priced at $1,304 found 2 days ago
Delta
Fri, Aug 8 - Wed, Aug 20
NAP
Naples
MDW
Chicago
$1,306 Roundtrip, found 2 days ago
$1,306
Roundtrip
found 2 days ago
Select Delta flight, departing Fri, Aug 8 from Naples to Chicago, returning Wed, Aug 20, priced at $1,306 found 2 days ago
Delta
Fri, Jul 11 - Thu, Jul 17
NAP
Naples
MDW
Chicago
$1,308 Roundtrip, found 1 day ago
$1,308
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, Jul 11 from Naples to Chicago, returning Thu, Jul 17, priced at $1,308 found 1 day ago
Delta
Fri, Aug 8 - Wed, Aug 20
NAP
Naples
MDW
Chicago
$1,348 Roundtrip, found 2 days ago
$1,348
Roundtrip
found 2 days ago
Select Delta flight, departing Fri, Aug 8 from Naples to Chicago, returning Wed, Aug 20, priced at $1,348 found 2 days ago
Flights from Naples (NAP) to Chicago (MDW)
Origin airport
Naples Intl.
Destination airport
Midway Intl.
Airlines serving
KLM
Roundtrip price
$972
Distance
4934 mi

Naples to Chicago Flights

The cheapest times to fly from Naples to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Naples to Chicago are during the month of July. You can find some of the cheapest flights from Naples to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Naples to Chicago

Sunday is one of the best days to book for cheap flights from Naples to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Naples to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Naples to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $1,382 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Naples to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Naples to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from Naples Intl. Airport (NAP) to Midway Intl. Airport (MDW) cost?
Discover the latest flight deals from NAP to MDW by entering your preferred travel dates and searching on Expedia. Easily compare prices by departure date if you have flexibility with your schedule and use handy filters to explore prices for your preferred journey. As a member of One Key™, our free loyalty program, you can use Price Tracking to watch fares and receive notifications if prices go up or down.
What is the cheapest month to fly from NAP to MDW?
The cheapest flights from NAP to MDW are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
What is the cheapest airline that flies from NAP to MDW?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that'll take you from NAP to MDW. Sort your results by "Price (lowest to highest)" to snap up a great deal.
How many flights per day from Naples Intl. Airport (NAP) to Midway Intl. Airport (MDW)?
There are no daily nonstop flights available from Naples Intl. Airport (NAP) to Midway Intl. Airport (MDW). But you can opt for flights with layovers. Filter your search results on Expedia to include one or two stops, and you'll be cruising above the clouds in no time.
What day of the week has the most flights from NAP to MDW?
Friday is usually the busiest day for flights, while Tuesday tends to be the quietest.* Keep in mind that flight schedules can change depending on a number of factors, including the time of year and airline.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Naples Intl. Airport (NAP) to Midway Intl. Airport (MDW)?
To land at Midway Intl. Airport (MDW) on time, choose a flight that takes off from Naples Intl. Airport (NAP) before 3 PM. The chance of cancellations is 22% higher, on average, for departures after this time.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from Naples Intl. Airport (NAP) to Midway Intl. Airport (MDW) last-minute?
Booking your flight from NAP to MDW shortly before your trip is typically more expensive. However, if there's some wiggle room with your departure times and dates, you could grab a cheap last-minute fare.
Is it cheaper to book a NAP to MDW flight and hotel package?
Compared with arranging flights and hotels separately, booking a NAP to MDW flight and hotel package with Expedia could lead to significant savings. Better still, having everything in one place will take the hassle out of travel planning. Just secure your flights and select from our wide range of hotels, then personalize your trip with other add-ons like car rentals and activities.
Can I cancel or change the date of my flight from Naples Intl. Airport (NAP) to Midway Intl. Airport (MDW)?
You can usually reschedule or cancel your NAP to MDW flight. However, for bookings made more than 24 hours ago, additional fees may apply. Check your airline's policies in your itinerary to see what changes are possible and whether any costs are involved. You'll also find further details on our Customer Service portal.

Explore a world of travel with Expedia

*Available to One Key members.