Cheap Flights from Naples (NAP) to Chicago (MDW)

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

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Frequently asked questions

Is it cheaper to buy a plane ticket from Naples Intl. Airport (NAP) to Midway Airport last minute?
Booking your trip from Naples Intl. Airport (NAP) to Midway Airport at the last minute could save you some dough if you strike it lucky and find a terrific deal. However, tickets usually don't drop in price as the departure date nears. If you take a wait-and-see approach, flights could also be booked up or the best seats taken (we hope you like the middle seat!). If you'd prefer to play it safe, book well in advance of when you want to leave. In fact, some of the best deals are available on Expedia up to a year in advance. If your favorite airline hasn't released its fares yet, check back regularly as deals are updated on Expedia all the time.
What airports do you fly into for Chicago from Naples?
Midway Intl. Airport (MDW), O'Hare Intl. Airport (ORD) and Lewis University Airport (LOT) are your options when heading off from Naples to Chicago. Roughly 14 kilometers southwest of the heart of Chicago, Midway Intl. Airport (MDW) is the city's main gateway. Take into account factors such as flight departure and arrival times and the distance to your hotel before choosing your airport. Wrigley Field and Millennium Park are a couple of top attractions to put on your itinerary when you get to your destination.
Can I change the date of my flight from Naples Intl. Airport (NAP) to Chicago Airport?
We know plans can change, so Expedia is here to help make things easy. To start, find your Naples Intl. Airport (NAP) to MDW itinerary through the Expedia Trips portal and look up the fare rules about what changes can be made. If you booked in the last 24 hours, some carriers will let you cancel at no cost and organize new flights. If you bought your fare more than 24 hours ago, connect with us through our Customer Service portal to find out what your options are.

Travel information

Travel information

Origin airport
Naples Intl.
Destination airport
Midway Intl.
Distance
7894 km

Book with confidence

Book with confidence

Naples to Chicago Flights

Whether you’re looking for a grand adventure or just want to get away for a last-minute break, flights from Naples to Chicago offer the perfect respite. Not only does exploring Chicago provide the chance to make some magical memories, dip into delectable dishes, and tour the local landmarks, but the cheap airfare means you won’t bust your budget. So no matter whether your ideal itinerary involves flying one way, non-stop, or round trip, you’re bound to find flights that match your schedule on Expedia, and at prices that won’t shock your wallet.

Bagging a cheap flight from Naples to Chicago may mean more dollars to spend on for one-of-a-kind souvenirs when you arrive, but it doesn’t mean you have to skimp on your travel experience, as Expedia offers a sizzling selection of cheap airlines that’ll put you in your happy place on their planes, whether that’s getting lost in a hair-raising airport thriller, dreaming on the passing landscape over a glass of bubbly, or jotting down your vacation bucket list at 38,000 feet. There’s also bound to be plenty of opportunities to snap a few photos of the high life that will make your friends green with envy. After all, enjoying the journey is part of the fun.

With so many affordable flights and so many wonderful adventures awaiting you, there’s no reason to put off booking a fantastic flight from to today. So don’t leave it to the last minute to make your dream trip a reality: pack your bags with your go-to travel accessories, put together your list of must-see attractions and can’t-miss activities, and get ready to broaden your horizons – with Expedia, the wonders of Chicago are only a plane trip away. Book your travel arrangements with us today!

If you would like to book flights to Chicago more flexibly many prefer to purchase one-way tickets with options to take different airlines. A one way ticket to Chicago is now!

Naples to Chicago Flights

Explore a world of travel with Expedia

Explore a world of travel with Expedia