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Amazing RSW to MDW Flight Deals

The cheapest flights to Midway Intl. found within the past 7 days were $158 round trip and $79 one way. Prices and availability subject to change. Additional terms may apply.

Best Midway Intl. Flight and Hotel Packages

Midway Intl. flight + hotel packages - economy flights

FAQs about flights from Southwest Florida Intl. Airport (RSW) to Midway Intl. Airport (MDW)

Are there direct flights from Fort Myers, FL (RSW-Southwest Florida Intl.) to Chicago Airport?

Wander wisely and lock in a direct flight from Fort Myers, FL (RSW-Southwest Florida Intl.) to Chicago, IL (MDW-Midway Intl.) with Southwest Airlines. This air carrier is the smart choice if you're looking to get to Chicago (and vicinity) as soon as practicable.

If I am not able to travel due to COVID-19, can I change my booking to a later date?

For more info about changing your flight to Chicago, IL (MDW-Midway Intl.), please visit our Customer Service Portal.

How long is the flight from Fort Myers, FL (RSW-Southwest Florida Intl.) to Chicago Airport?

If you're traveling from Fort Myers to Chicago, you can expect the journey to take about 3 hours and 12 minutes. If this is longer than you would have liked, why not take advantage of it? Read up on where you're headed, work on your itinerary and get as much shut-eye as possible before the adventure begins.

What is the flight distance from Fort Myers, FL (RSW-Southwest Florida Intl.) to Chicago Airport?

The flight distance from Fort Myers, FL (RSW-Southwest Florida Intl.) to Chicago, IL (MDW-Midway Intl.) is 1,118 mi. Remember to bring along some reading material or a few podcasts to make your flight fly by.

What airlines fly from Fort Myers, FL (RSW-Southwest Florida Intl.) to Chicago Airport?

Want to fly nonstop from Fort Myers, FL (RSW-Southwest Florida Intl.) to Chicago, IL (MDW-Midway Intl.)? No problem. Southwest Airlines (WN) offers 144 flights per month and is the top choice for many savvy travelers.

What is the best day to buy a plane ticket?

This just in! Airfares offered on Tuesdays tend to be the cheapest, according to flight demand on Travelocity in 2019. Wednesday and Friday prices are also good, but you may want to prepare your budget if booking on a Monday, as data shows the start of the week is when prices are generally at their highest.

What are the cheapest days to fly?

Frequent travelers may already know this, but earlier in the week can be the cheapest time to fly. In 2019, flights departing on a Tuesday were generally the cheapest of the week, whereas you may pay a premium for weekend flights when demand is usually high. On average, tickets were most expensive for Saturday departures, so if you need to fly out on a weekend, you might look for deals ahead of time.

How far in advance can you book a flight?

Trying to figure out how early you should book your flight? It's possible to start comparing international airfares on Travelocity up to 12 months in advance. However, it does depend on the carrier as not all airlines release their prices that far out. According to our 2019 flight demand trends, last minute planners can still bag a bargain with some of the cheapest fares appearing 1-2 weeks prior to their travel dates.

How can I save money on airline tickets?

We'll let you in on a secret...You can save big on flights if you mix and match your airlines and fare types. In fact, travelers who booked flights on Travelocity in 2019 saved nearly 50% when their return flights consisted of two different airlines or fare types.

*According to flight demand on Travelocity.com from January to December 2019. Savings are subject to change based on departure location, date and destination.

Southwest Florida Intl. to Midway Intl. Flight FAQ

Traveling FromSouthwest Florida Intl.
Traveling ToMidway Intl.
Shortest Flight Time0 hours 45 mins
Earliest Departure Time7:15AM CDT
Latest Departure Time4:45PM CDT
Lowest Flight Price$158

Fort Myers to Chicago Carriers and Route Information

Flight path for flights from Southwest Florida International Airport to Chicago Midway International Airport.


Distance:
1,113.00 miles


*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.