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RSW - MDW

Find cheap flights from Fort Myers to Chicago Midway Airport from $75

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Fort Myers to Midway departing on 5/20. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
Mon 5/27
Mon 6/3

Search hundreds of travel sites at once for deals on flights to Chicago Midway Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Fort Myers to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Fort Myers to Chicago, as well as popular online travel agencies
In the last 7 days travelers have searched 43,623,357 times on KAYAK, and here is why:

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Cheap flight deals from Fort Myers to Midway (RSW-MDW)

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Fort Myers to Midway that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
3:44 pm - 11:59 pmRSW-MDW
9h 15m1 stop
6:00 am - 2:55 pmMDW-RSW
7h 55m1 stop
$179Frontier
Find Deal
Fri, May 17 - Wed, May 22
6:58 am - 1:35 pmRSW-MDW
7h 37m1 stop
1:21 pm - 9:04 pmMDW-RSW
6h 43m1 stop
$216Delta
Find Deal
Wed, May 15 - Wed, May 22
5:26 pm - 9:41 pmRSW-MDW
5h 15m1 stop
6:49 pm - 12:39 amMDW-RSW
4h 50m1 stop
$227Delta
Find Deal
Thu, Jul 11 - Tue, Jul 16
5:57 pm - 10:01 pmRSW-MDW
5h 04m1 stop
6:00 am - 2:05 pmMDW-RSW
7h 05m1 stop
$247Delta
Find Deal
Sat, May 11 - Sun, May 12
3:44 pm - 11:50 pmRSW-MDW
9h 06m1 stop
10:16 am - 9:41 pmMDW-RSW
10h 25m1 stop
$254Frontier
Find Deal
Mon, May 20 - Tue, May 28
10:16 pm - 10:09 amRSW-MDW
12h 53m1 stop
10:59 am - 9:16 pmMDW-RSW
9h 17m1 stop
$278Frontier
Find Deal
Wed, Sep 4 - Wed, Sep 25
5:45 am - 10:11 amRSW-MDW
5h 26m1 stop
3:45 pm - 10:17 pmMDW-RSW
5h 32m1 stop
$287Delta
Find Deal
Sat, May 11 - Sat, May 11
3:44 pm - 11:59 pmRSW-MDW
9h 15m1 stop
2:33 pm - 9:41 pmMDW-RSW
6h 08m1 stop
$288Frontier
Find Deal
Fri, May 17 - Sun, May 19
6:30 am - 12:40 pmRSW-MDW
7h 10m1 stop
9:32 am - 3:21 pmMDW-RSW
4h 49m1 stop
$298Delta
Find Deal
Thu, May 23 - Sun, May 26
5:57 pm - 10:01 pmRSW-MDW
5h 04m1 stop
1:21 pm - 9:04 pmMDW-RSW
6h 43m1 stop
$312Delta
Find Deal
Sat, May 18 - Mon, May 20

Flights from Fort Myers to Midway - Travel Insights & Trends

Get data-powered insights and trends into flights from Fort Myers to Midway to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from Fort Myers to Chicago Midway Airport?

The average price of all flights from Fort Myers to Chicago Midway Airport clicked on KAYAK for each day over the last 12 months.
If your flying dates are flexible, you should consider flying to Chicago Midway Airport on a Friday, as we generally find the cheapest rates on that day for this route. On the other hand, Monday is the most expensive day to fly from Fort Myers to Chicago Midway Airport. For your return ticket, we recommend flying on a Tuesday and avoiding Thursdays for the best deals.

What is the cheapest month to fly from Fort Myers to Chicago Midway Airport?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Fort Myers to Chicago Midway Airport, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.
The cheapest month for flights from Fort Myers to Chicago Midway Airport is May, where tickets cost $248 on average. On the other hand, the most expensive months are January and December, where the average cost of tickets is $577 and $505 respectively.

How far in advance should I book a flight from Fort Myers to Chicago Midway Airport?

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Fort Myers to Chicago Midway Airport, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price on the flight from Fort Myers to Chicago Midway Airport, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 23 days before departure.

Which airlines provide the cheapest flights from Fort Myers to Chicago Midway Airport?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
In the last 72 hours, the cheapest one-way ticket from Fort Myers to Chicago Midway Airport found on KAYAK was with Frontier for $75. Frontier proposed a round-trip connection from $179 and Delta from $216.

How many flights are there between Fort Myers and Chicago Midway Airport per day?

Each day, there are between 2 and 3 nonstop flights that take off from Fort Myers and land in Chicago Midway Airport, with an average flight time of 2h 53m. The most common departure time is 4:00 pm and most flights take off in the morning. Each week, there are 20 flights. The most frequent day of departure is Friday, when 15% of all weekly flights depart. The fewest flights depart on a Sunday.

What’s the earliest departure time from Fort Myers to Chicago Midway Airport?

Early birds can take the earliest flight from Fort Myers at 5:30 am and will be landing in Chicago Midway Airport at 7:25 am.

What’s the latest departure time from Fort Myers to Chicago Midway Airport?

If you prefer to fly at night, the latest flight from Fort Myers to Chicago Midway Airport jets off at 8:55 pm and lands at 10:50 pm.

Good to know

Low season

April

High season

July

Cheapest flight

$75
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly with an average 4% increase in price.
Flight from Fort Myers to Chicago Midway Airport

When to book flights from Fort Myers to Midway

Are your dates flexible? Find out the best times to travel from Fort Myers to Midway based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Fort Myers to Chicago Midway Airport flights

  • What is the cheapest flight from Fort Myers to Chicago Midway Airport?

    In the last 3 days, the lowest price for a flight from Fort Myers to Chicago Midway Airport was $75 for a one-way ticket and $179 for a round-trip.

  • Do I need a passport to fly between Fort Myers and Chicago Midway Airport?

    No, a passport isn't needed to fly from Fort Myers to Chicago Midway Airport. However, local authorities might ask for an official ID.

  • Which airports will I be using when flying from Fort Myers to Chicago Midway Airport?

    Fort Myers airport is called Fort Myers SW Florida Intl and the only airport in Chicago Midway Airport is Chicago Midway.

  • Which aircraft models fly most regularly from Fort Myers to Chicago Midway Airport?

    We unfortunately don’t have that data for this specific route.

  • On which days can I fly direct from Fort Myers to Chicago Midway Airport?

    There are nonstop flights from Fort Myers to Chicago Midway Airport on a daily basis.

  • How does KAYAK find such low prices on flights from Fort Myers to Chicago Midway Airport?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Fort Myers to Chicago Midway Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Fort Myers to Chicago Midway Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport from Fort Myers is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Fort Myers to Chicago Midway Airport?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago Midway Airport with an airline and back to Fort Myers with another airline. Booking your flights between Fort Myers and MDW can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Fort Myers to Chicago Midway Airport?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago Midway Airport from Fort Myers up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Prefer to fly non-stop from Fort Myers to Chicago Midway Airport?

Find which airlines fly direct from SW Florida Intl to Midway, which days they fly and book direct flights.

Nonstop departures

Fort Myers SW Florida Intl to Chicago Midway

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Nonstop returns

Chicago Midway to Fort Myers SW Florida Intl

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights
See more direct flights

Top 3 airlines serving from Fort Myers to Midway

 
See real verified KAYAK customer reviews for airlines flying from Fort Myers to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Fort Myers to Midway? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
DeltaOverall score based on 10951 reviews
8.2boarding
8.6crew
8.0entertainment
7.4food
7.9comfort
Airline reviews

I liked the ease of checking in, luggage check in, wheel chair assistance, boarding and flight.

10.0 ExcellentAnonymous, Apr 2024PNS - ATL
Read more about Delta reviews

I liked the ease of checking in, luggage check in, wheel chair assistance, boarding and flight.

I usually have a positive experience with Delta. Complimentary upgrades are always nice!

The main person that was coordinating everything was a short white/light skin Spanish man and he was very rude. It honestly made me feel like it was everyone’s First day at work. His announcements were very not reasonable and they did not make sense. The stewardess on the flight that made the announcements she didn’t even know what she was talking about she sounded inebriated. There were no snacks or drinks on our flight there wasn’t even much turbulence. This flight was not enjoyable nor was it what a Delta flight should be and just this past week I flew with Delta 3 times.

nothing Delta could do... the person sitting next to me was huge and overflowing into my seat

Crew was great! I need wheelchair assistance and they knew who I was and updated me that my chair was on its way and to just hang tight. There was some turbulence but the captain announced we would be going thru it and he handled the plane well. Landing was soft and his.

Aircraft very cramped. Check-in was great with an agent helping us. Food was almost non-existent. Pre-flight went well once I got the app reloaded on my phone since we don’t fly much anymore.

I like that it got us where we were going. Everything else needed work. It was 1/2 hour late and we took off an hour late. The plane had to be cleaned and the disabled loaded on board before we could take off which took forever and then we sat at the terminal FOREVER before we took off. The ride was so bumpy that they couldn’t serve drinks and snack but to about 1/2 the plane. Seriously we should have flown out of Fort Lauderdale. We probably would’ve gotten home several hours earlier.

Flight was on time, the staff was personable & professional, & the plane arrived on time.

Flight was great. DELTA did a fantastic job! FLL airport was chaotic!

You lost my luggage!!! How frustrating!!! Now they can’t find one of our bags!!!! I really don’t have time for this!!!

This flight is frequently delayed. The connections seemingly are more frequently delayed. I’ve missed connections as a result twice on the same route to charlotte then Charleston. Final destination arrival has been the next day, twice in a row. No pilots, no crew. Too many excuses. Unfortunately, my days with American are over.

Entertainment was okay not because anything was wrong but it is a short flight so having no wifi is annoying but understandable. Crew was outstanding as usual

Those seats were way too narrow. I had the middle seat, one person was a very skinny person and we still couldn’t avoid touching each other anytime one of us moved. The other person was larger and we were basically sitting in each others lap the entire flight. There was zero entertainment. The flight was long enough to justify tvs, but no. Gotta sit there in your infant seat and twiddle your thumbs.

Flight was fine. It took an unusually long time to have baggage delivered to the carousel in ORD.

Average - flew with Jet Blue internal and it was far more comfortable and better food and entertainment. Notable difference

The flight got canceled due to mechanical issues, and he to be rebooked and missed my appointments for that day

The flight was scheduled to depart DCA at 12:30 pm but was delayed twice on the ground so that we were finally scheduled to depart at around 4:00 pm. Once we boarded, it was announced that takeoff would be delayed again to fix a hydraulic problem which delayed our eventual takeoff until around 5:00 pm. Once we departed, it was a smooth flight back to ORD. We did not get any explanation about what caused the original significant delay. In my experience, this happens frequently with AA.

The only problem experienced was a ground stop in Chicago due to weather. But the crew handled everything professionally. They prioritized rebooking those passengers who had connecting flights and then deplaning the other passengers. When the hold was lifted, they efficiently re-boarded all the passengers so that we could depart before our departure limit expired.

Our second leg to Jackson WY was unable to land due to weather. We were flown back to Dallas after stopping in SLC. We were given hotel rooms and vouchers. We were told that we would be back on the same plane in the morning. Instead we were given a different flight with different seats. Not a good experience. No one knew what was going on.

Turn on the heat. Flight was way too cold from Arizona to Chicago.

The seat are terrible. Don’t even think of sleeping on a Spirit flight. The kids that run the plane aka flight attendants are pretty rude and straight forward. They get the job done but without class.

I had a death in my family and booked my flight on Spirit. My flight was cancelled the morning of my flight, no explanation, no help to rebook, nobody to talk to. The next available flight was 2days later !!!! Terrible airline, will NEVER fly with them again!

They took a horrible route with a lot of turbulence and I eneded up getting sick. Even if the flight takes longer. Don't put people life at risk just to get to the airport on time.

The seats were very uncomfortable. The crew was very polite and helpful.

Every thing was fine ,low price,easy on time ,clean, good staff, really no issues

the landing was terrible. the plane touched down and had take off. the plane flew around and landed a second time.i understand the weather might of been the problem. It was a scary experience and no explanation from the captain.

Had to board plan 2x due to lack of security check after 1st boarding

Miserable. The crew was rude, the flight was delayed 5 hours for mechanical reasons and then “weather” even though other planes were leaving.

They kept Changing the flight times. It was delayed several times and at one point it was supposed to depart at 3.40am! At which point we ended up staying overnight and booked long a separate United flight for early morning departure. The spirit flight then got moved up and left at 1.30 in the morning when it was supposed to leave at 9.40pm the night before.

Flight was delayed...not horribly late. Just before push back engine shut down for a quick replacement item that took about five minutes. After that, everything was smooth and the pilot was able to make up time in the air so that our arrival time was not too far off the original anticipated arrival time.

Book cheap flights from Fort Myers to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Fort Myers to Chicago found on KAYAK in the last 72 hours.
5/20Mon
1 stopFrontier
9h 06mRSW-MDW
$75
5/3Fri
1 stopFrontier
6h 55mRSW-MDW
$84
6/8Sat
1 stopFrontier
12h 18mRSW-MDW
$86
5/31Fri
1 stopFrontier
9h 15mRSW-MDW
$88
5/11Sat
1 stopDelta
5h 04mRSW-MDW
$108
7/11Thu
1 stopDelta
5h 15mRSW-MDW
$119
5/9Thu
1 stopFrontier
7h 23mRSW-MDW
$120
7/6Sat
nonstopSouthwest
2h 55mRSW-MDW
$170
7/6Sat
2 stopsSouthwest
7h 30mRSW-MDW
$333
5/23Thu
2 stopsWestJet
27h 10mRSW-MDW
$576

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Last minute flights from Fort Myers to Midway

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Fort Myers to Chicago that are departing in the next 10 days.
5/2Thu
multi-stopDelta
4h 35mRSW-MDW
5/6Mon
multi-stopDelta
6h 13mMDW-RSW
$298
4/30Tue
multi-stopFrontier
7h 26mRSW-MDW
5/17Fri
multi-stopFrontier
7h 54mMDW-RSW
$308
5/1Wed
multi-stopDelta
4h 30mRSW-MDW
5/14Tue
multi-stopDelta
6h 43mMDW-RSW
$331
5/1Wed
multi-stopDelta
4h 30mRSW-MDW
5/17Fri
multi-stopDelta
6h 43mMDW-RSW
$342
5/1Wed
multi-stopDelta
4h 30mRSW-MDW
5/13Mon
multi-stopDelta
4h 45mMDW-RSW
$362
5/2Thu
multi-stopFrontier
7h 23mRSW-MDW
5/19Sun
multi-stopFrontier
6h 08mMDW-RSW
$368
5/2Thu
multi-stopDelta
4h 45mRSW-MDW
5/15Wed
multi-stopDelta
4h 47mMDW-RSW
$421
5/2Thu
multi-stopDelta
4h 35mRSW-MDW
5/9Thu
multi-stopDelta
7h 05mMDW-RSW
$448
5/2Thu
multi-stopDelta
4h 50mRSW-MDW
5/13Mon
multi-stopDelta
4h 45mMDW-RSW
$452
5/2Thu
multi-stopDelta
4h 35mRSW-MDW
5/6Mon
multi-stopDelta
5h 03mMDW-RSW
$462

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Fort Myers - Chicago Midway Airport Flights

Departure:

Fort Myers (RSW)United States

Destination:

Chicago Midway Airport (MDW)United States

Return flight deals:

Chicago Midway Airport - Fort Myers

Cabin classes: