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

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Frequently asked questions

Is it cheaper to buy a plane ticket from APF to Midway Intl. Airport (MDW) last minute?
Booking your flight from Naples Airport to Midway Airport at the last minute could save you a tidy sum if you stumble on a good deal. However, airfares usually don't drop in price as the departure date nears. If you take a wait-and-see approach, flights could also be booked solid or the best seats taken (we hope you like the middle seat!). If you'd rather play it safe, book well in advance of your departure date. In fact, you can find some of the biggest deals up to a year in advance. If your favorite carrier hasn't released its fares yet, check back regularly as offers are updated on Expedia constantly.
What airports do you fly into for Chicago from Naples?
From Naples, you can journey to Chicago via Midway Intl. Airport (MDW), O'Hare Intl. Airport (ORD) and Lewis University Airport (LOT). Research which hub is the best option for you before you make a decision. If you pick Midway Intl. Airport (MDW), it's approximately 14 kilometers southwest of the center of the city. Use the dough you save when booking your trip with Expedia to check out the city's top sights, such as Wrigley Field and Millennium Park.
Can I change the date of my flight from APF to Midway Airport?
Quickly and easily make changes to your Naples Municipal Airport (APF) to MDW flight through the Expedia Trips portal. But before amending dates or times, read over the rules and conditions in your itinerary to learn what the airline will allow you to do and if change fees apply. Some airlines have a change fee per person, plus any difference in fare prices. But if you booked in the last 24 hours, you may be able to cancel for free and arrange new flights. You can also stop by our Customer Service portal for further details and to chat with our Virtual Agent.

Travel information

Travel information

Origin airport
Naples Municipal
Destination airport
Midway Intl.
Distance
1811 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