$95 Cheap Flights from Fort Myers (RSW) to Chicago (MDW)

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Cheap Flights from Fort Myers to Chicago (RSW-MDW)

Prices were available within the past 7 days and start at $95 for one-way flights and $155 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Frontier Airlines
Frontier Airlines
Frontier Airlines
Frontier Airlines
Frontier Airlines
Frontier Airlines
Frontier Airlines
Frontier Airlines
Frontier Airlines
Flights from Fort Myers (RSW) to Chicago (MDW)
Origin airport
Southwest Florida Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, Frontier Airlines
Roundtrip price
$155
Distance
1107 mi
Average flight time
2 hours 52 mins

Fort Myers to Chicago Flights

Whether you’re looking for a grand adventure or just want to get away for a last-minute break, flights from Fort Myers 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 Fort Myers 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 RSW to MDW 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 $95 now!

Frequently asked questions

How much is a flight from Southwest Florida Intl. Airport to MDW?
Round-trip tickets from Southwest Florida Intl. Airport (RSW) to Midway Intl. Airport (MDW) start from $155. This price is based on fares listed within the last 7 days on Expedia for flights departing within the next year — book now to avoid missing out. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from Southwest Florida Intl. Airport to MDW?
Most flights can be conveniently canceled online, but whether you incur a fee differs between airlines. If you do need to cancel your break, follow the instructions in the Customer Service Portal.
How do I find cheap flights from Southwest Florida Intl. Airport to Midway Airport that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you’re searching for Southwest Florida Intl. Airport to Midway Intl. Airport (MDW) flights, you’ll see a “no change fees” filter for you to select.
How far is the flight from Southwest Florida Intl. Airport (RSW) to Midway Airport?
The flight distance from Fort Myers to Chicago is 1119 mi. Pack yourself a drink, a snack and a few good podcasts. Keep yourself entertained and time will zip by.
Which airlines fly direct from RSW to MDW?
Check out the fares with Southwest Airlines (WN) if you want to fly directly from Southwest Florida Intl. Airport to Midway Airport. This top airline operates 104 flights monthly, so you’re sure to find one that fits your travel plans.
Are RSW to Chicago Airport flight tickets cheaper when they're purchased at the last minute?
Booking last minute from RSW to MDW can be hit-or-miss. You may be able to score a bargain, but you could also miss out entirely! If you’d rather start your trip planning ahead of time, Expedia compares flight deals up to a year in advance. Just keep in mind that not all airlines issue their prices that far in advance. Our top tip? Check back often as updates are made regularly.
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