$1,399 Cheap Flights from Naples (NAP) to Chicago (MDW)

View $1,399 flight on Thu, Sep 11, 2025Opens in a new window

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

  • Plan, book, fly with confidence

  • trending down icon

    Be in the know

    Get alerts if flight prices drop or rise*
  • bex rewards loyalty icon

    Book smarter

    Save up to 30% on select hotels after you book a flight*
  • one key icon

    Earn twice

    Earn your airline miles on top of our OneKeyCash
    Learn about One Key

Cheap Flights from Naples to Chicago (NAP-MDW)

Prices were available within the past 7 days and start at $1,399 for one-way flights and $711 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Thu, Sep 11 - Mon, Sep 15
NAP
Naples
MDW
Chicago
$711 Roundtrip, found 5 days ago
$711
Roundtrip
found 5 days ago
Select Delta flight, departing Thu, Sep 11 from Naples to Chicago, returning Mon, Sep 15, priced at $711 found 5 days ago
ITA Airways
Thu, Sep 11 - Mon, Sep 15
NAP
Naples
MDW
Chicago
$722 Roundtrip, found 5 days ago
$722
Roundtrip
found 5 days ago
Select ITA Airways flight, departing Thu, Sep 11 from Naples to Chicago, returning Mon, Sep 15, priced at $722 found 5 days ago
KLM
Thu, Sep 11 - Mon, Sep 15
NAP
Naples
MDW
Chicago
$739 Roundtrip, found 5 days ago
$739
Roundtrip
found 5 days ago
Select KLM flight, departing Thu, Sep 11 from Naples to Chicago, returning Mon, Sep 15, priced at $739 found 5 days ago
Delta
Tue, Aug 26 - Sun, Aug 31
NAP
Naples
MDW
Chicago
$752 Roundtrip, found 6 days ago
$752
Roundtrip
found 6 days ago
Select Delta flight, departing Tue, Aug 26 from Naples to Chicago, returning Sun, Aug 31, priced at $752 found 6 days ago
Delta
Sat, Aug 23 - Sat, Aug 30
NAP
Naples
MDW
Chicago
$752 Roundtrip, found 6 days ago
$752
Roundtrip
found 6 days ago
Select Delta flight, departing Sat, Aug 23 from Naples to Chicago, returning Sat, Aug 30, priced at $752 found 6 days ago
Delta
Sat, Aug 23 - Sat, Aug 30
NAP
Naples
MDW
Chicago
$757 Roundtrip, found 6 days ago
$757
Roundtrip
found 6 days ago
Select Delta flight, departing Sat, Aug 23 from Naples to Chicago, returning Sat, Aug 30, priced at $757 found 6 days ago
Delta
Sat, Aug 23 - Sat, Aug 30
NAP
Naples
MDW
Chicago
$758 Roundtrip, found 6 days ago
$758
Roundtrip
found 6 days ago
Select Delta flight, departing Sat, Aug 23 from Naples to Chicago, returning Sat, Aug 30, priced at $758 found 6 days ago
Delta
Sat, Aug 23 - Sat, Aug 30
NAP
Naples
MDW
Chicago
$762 Roundtrip, found 6 days ago
$762
Roundtrip
found 6 days ago
Select Delta flight, departing Sat, Aug 23 from Naples to Chicago, returning Sat, Aug 30, priced at $762 found 6 days ago
Delta
Sun, Aug 24 - Sun, Aug 31
NAP
Naples
MDW
Chicago
$764 Roundtrip, found 6 days ago
$764
Roundtrip
found 6 days ago
Select Delta flight, departing Sun, Aug 24 from Naples to Chicago, returning Sun, Aug 31, priced at $764 found 6 days ago
Air France
Sat, Aug 23 - Sat, Aug 30
NAP
Naples
MDW
Chicago
$782 Roundtrip, found 6 days ago
$782
Roundtrip
found 6 days ago
Select Air France flight, departing Sat, Aug 23 from Naples to Chicago, returning Sat, Aug 30, priced at $782 found 6 days ago

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $694
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $694
Flights from Naples (NAP) to Chicago (MDW)
Origin airport
Naples Intl.
Destination airport
Midway Intl.
Roundtrip price
$711
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 September. 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 $1,399 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?
Get a cheap one-way flight from $1,399 or cheap return flight from $711 from Naples Intl. Airport (NAP) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight deals on this route.
What is the cheapest month to fly from Naples Intl. Airport (NAP) to Midway Intl. Airport (MDW)?
Planning your getaway for September may help you find better deals, as it's the cheapest month for flights between NAP and MDW. You'll often find the lowest fares during off-peak months.
What is the cheapest airline that flies from Naples Intl. Airport (NAP) to Midway Intl. Airport (MDW)?
Expedia's filter tool lets you easily compare travel time, airlines and fares all in one place. Customize the search to your preferences, then sort by "Price (lowest to highest)" to find the carrier with the cheapest NAP to MDW flight.
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.