$83 Cheap Flights from Fort Myers to Chicago

Feel at ease with free flight cancellations within 24 hours of booking

Change your flight without a fee on select flights

Find The Best Dates To Fly from Southwest Florida Intl. to Midway Intl.

Amazing RSW to MDW Flight Deals

The cheapest flights to Midway Intl. found within the past 7 days were $183 round trip and $83 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

Courtyard by Marriott Chicago Magnificent Mile
Fairmont Chicago at Millennium Park Gold Experience
Springhill Suites by Marriott Chicago Downtown/ River North
Moxy Chicago Downtown
InterContinental Chicago Magnificent Mile, an IHG Hotel
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FAQs about flights from Southwest Florida Intl. Airport (RSW) to Midway Intl. Airport (MDW)

Can I catch a flight from Fort Myers, FL Airport (RSW-Southwest Florida Intl.) to Chicago, IL Airport (MDW-Midway Intl.) right now?

It's always prudent to find out about any quarantine requirements and travel advice reports in place in your destination. Ensure you visit the Covid-19 Travel Advisor for up-to-date info on catching a flight to Chicago, IL Airport (MDW-Midway Intl.) from Fort Myers, FL Airport (RSW-Southwest Florida Intl.).

Are there direct flights from RSW to Midway Intl. Airport (MDW)?

You can't fly direct from Fort Myers, FL Airport (RSW-Southwest Florida Intl.) to Midway Airport, but we have the next best thing. Delta, Aeromexico and KLM provide flights with just one stopover.

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 Midway Airport, please visit our Customer Service Portal.

How long is the flight from Southwest Florida Intl. Airport to MDW?

Getting from Southwest Florida Intl. Airport to Midway Airport is a breeze, with travel taking just 2 hours and 48 minutes on average. With such a short journey ahead of you, you'll hit the tarmac feeling as fresh as when you boarded and ready to enjoy the next part of your getaway.

What is the flight distance from Southwest Florida Intl. Airport to Chicago Airport?

You'll need to travel about 1,367 mi from Southwest Florida Intl. Airport to Midway Airport before you can officially begin your adventures. Pick out a beverage when the drink cart trundles by and settle in for one or two of your favorite podcasts. You'll have more than enough time!

What airlines fly from Southwest Florida Intl. Airport to Midway Intl. Airport (MDW)?

There are no airlines currently offering direct flights between Southwest Florida Intl. Airport and Midway Intl. Airport (MDW). Save time and avoid irritating stopovers by investigating the quickest routes well in advance.

What airlines have practices regarding COVID-19 in place and use social distancing?

From the moment you enter the departure terminal to when you leave the arrivals terminal, if you're flying with Southwest Airlines, Delta or Volaris you can be sure that COVID-19 measures and social distancing rules have been adhered to. Many airlines have introduced capped capacity flights and keeping the middle seat empty.

What is the best day to buy a plane ticket?

This just in! Airfares offered on Thursdays tend to be the cheapest, according to flight demand on Travelocity in 2020. Wednesday and Friday prices are also good, but you may want to prepare your budget if booking on a Sunday, as data shows the end 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 2020, flights departing on a Monday 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 2020 flight demand trends, last minute planners can still bag a bargain with some of the cheapest fares appearing 2 weeks to 2 months 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 2020 saved nearly 40% when their return flights consisted of two different airlines or fare types.

*According to flight demand on Travelocity.com from January to December 2020. Savings are subject to change based on departure location, date and destination.

 

Traveling From Southwest Florida Intl.
Traveling To Midway Intl.
Shortest Flight Time 0 hours 55 mins
Earliest Departure Time 1:35PM CST
Latest Departure Time 9:25PM CST
Lowest Flight Price $183

Route Info

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

Distance:
1,113.00 miles

Discover our best flights from Fort Myers RSW to Chicago MDW. 

With 19 airlines to choose from on Travelocity, you can easily find the best option for you. Use our filters to sort by price, compare airlines, and find the most convenient flight times. 

 

Find our best return flights from Fort Myers RSW to Chicago MDW at the right price  

Airfares to Chicago MDW from Fort Myers RSW currently cost between $183 and $272. It’s usually cheaper to book a round trip than two separate one-way flights. Prices and availability subject to change. Additional terms may apply. 

 

Book one-way flights from Fort Myers RSW to Chicago MDW 

If you want to be flexible about when you return, or keep your travel options open ended, a one-way flight could be just the ticket! You’ll find one-way airfares from Fort Myers RSW to Chicago MDW on Travelocity starting at $83. Prices and availability subject to change. Additional terms may apply. 

 

Get to Chicago MDW from Fort Myers RSW quicker with direct flights. 

Get to Chicago faster, without the hassle of changing planes and moving baggage, by booking a direct flight. Expect your direct flight to MDW from RSW to take around 0 hour(s) 55 min(s).  

 

Find our cheapest airfares for flights from Fort Myers RSW to Chicago MDW

Find cheap flight deals by using our search filters to sort results starting with the lowest price airfares to MDW from RSW. Our Price Match Promise means if you find a lower rate on Travelocity.com or on another US-based website within 24 hours of booking, we’ll credit or refund the difference.  

 

Get our best airfare deals for your flight from Fort Myers RSW to Chicago MDW today 

If you’re flexible about when you travel, January is usually the cheapest month to fly from Fort Myers RSW to Chicago MDW. If you need to be more specific, search by date and arrival and departure times.Then, compare prices across different airlines, and sort results by lowest price first. 

 

Book flexible airline tickets for flights to Chicago MDW from Fort Myers RSW 

Some airlines let you change your travel dates without charging a fee. Use our ‘no change fee’ filter to see which flights to MDW from RSW have this option.  

 

Travel with confidence when you book flights to Chicago MDW from Fort Myers RSW with Travelocity 

We’ve secured fantastic deals with all the main airline carriers and it’s easy to compare, choose, and book with Travelocity. With 24/7 customer service and our free 'App', we’ll always keep you moving. 

*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.