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MDW - RSW

$93 Find cheap flights from Chicago Midway Airport to Fort Myers

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to Fort Myers departing on 8/28. 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
Thu 6/27
Thu 7/4

Search hundreds of travel sites at once for deals on flights to Fort Myers

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Fort Myers, 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 Chicago to Fort Myers, as well as popular online travel agencies
In the last 7 days travelers have searched 42,816,550 times on KAYAK, and here is why:

Save 21% or moreCompare multiple travel sites with one search.

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Filter your dealsChoose cabin class, free Wi-Fi and more.

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

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to Fort Myers 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
10:59 am - 9:16 pmMDW-RSW
9h 17m1 stop
10:16 pm - 10:09 amRSW-MDW
12h 53m1 stop
$156Frontier
Find Deal
Tue, Sep 10 - Wed, Sep 11
8:48 am - 6:32 pmMDW-RSW
8h 44m1 stop
10:29 am - 4:03 pmRSW-MDW
6h 34m1 stop
$198Frontier
Find Deal
Sat, Aug 3 - Sat, Aug 10
9:33 am - 4:39 pmMDW-RSW
6h 06m1 stop
6:49 am - 11:44 amRSW-MDW
5h 55m1 stop
$216Delta
Find Deal
Tue, Aug 13 - Sat, Aug 17
6:00 am - 1:49 pmMDW-RSW
6h 49m1 stop
5:42 am - 9:26 amRSW-MDW
4h 44m1 stop
$226Delta
Find Deal
Sat, Aug 17 - Sun, Aug 25
6:00 am - 1:49 pmMDW-RSW
6h 49m1 stop
5:45 am - 11:44 amRSW-MDW
6h 59m1 stop
$236Delta
Find Deal
Sat, Aug 17 - Mon, Aug 26
9:33 am - 4:37 pmMDW-RSW
6h 04m1 stop
12:26 pm - 5:04 pmRSW-MDW
5h 38m1 stop
$250Delta
Find Deal
Tue, Jul 16 - Tue, Jul 23
9:33 am - 4:37 pmMDW-RSW
6h 04m1 stop
12:26 pm - 5:04 pmRSW-MDW
5h 38m1 stop
$268Delta
Find Deal
Wed, Jul 17 - Wed, Jul 24
10:59 am - 9:16 pmMDW-RSW
9h 17m1 stop
10:16 pm - 10:09 amRSW-MDW
12h 53m1 stop
$287Frontier
Find Deal
Tue, Sep 10 - Tue, Sep 17
6:55 pm - 12:44 amMDW-RSW
4h 49m1 stop
5:45 am - 11:44 amRSW-MDW
6h 59m1 stop
$298Delta
Find Deal
Fri, Aug 23 - Mon, Aug 26
1:10 pm - 9:19 pmMDW-RSW
7h 09m1 stop
5:45 pm - 9:44 pmRSW-MDW
4h 59m1 stop
$300Delta
Find Deal
Tue, Oct 22 - Tue, Nov 12

Flights from Midway to Fort Myers - Travel Insights & Trends

Get data-powered insights and trends into flights from Midway to Fort Myers 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 Chicago Midway Airport to Fort Myers?

The average price of all flights from Chicago Midway Airport to Fort Myers clicked on KAYAK for each day over the last 12 months.
For Chicago Midway Airport to Fort Myers, Monday is the cheapest day to fly on average and Thursday is the most expensive. Flying from Fort Myers back to Chicago Midway Airport, the best deals are generally found on Saturday, with Monday being the most expensive.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Chicago Midway Airport to Fort Myers, 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 Chicago Midway Airport to Fort Myers is September, where tickets cost $178 on average. On the other hand, the most expensive months are March and December, where the average cost of tickets is $404 and $366 respectively.

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

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Chicago Midway Airport to Fort Myers, 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 Chicago Midway Airport to Fort Myers, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 27 days before departure.

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

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 Chicago Midway Airport to Fort Myers found on KAYAK was with Frontier for $93. Frontier proposed a round-trip connection from $156 and Delta from $216.

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

Each day, there are between 1 and 3 nonstop flights that take off from Chicago Midway Airport and land in Fort Myers, with an average flight time of 2h 45m. The most common departure time is 7:00 pm and most flights take off in the morning. Each week, there are 19 flights. The most frequent day of departure is Friday, when 16% of all weekly flights depart. The fewest flights depart on a Sunday.

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

Early birds can take the earliest flight from Chicago Midway Airport at 6:00 am and will be landing in Fort Myers at 9:45 am.

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

If you prefer to fly at night, the latest flight from Chicago Midway Airport to Fort Myers jets off at 8:10 pm and lands at 11:55 pm.

Good to know

Low season

October

High season

April

Cheapest flight

$93
Best time to beat the crowds with an average 3% drop in price.
Most popular time to fly and prices are also 0% lower on average.
Flight from Chicago Midway Airport to Fort Myers

When to book flights from Midway to Fort Myers

Are your dates flexible? Find out the best times to travel from Midway to Fort Myers 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 Chicago Midway Airport to Fort Myers flights

  • Southwest Airlines, the only provider with direct flights from Chicago Midway Airport to Fort Myers, has an Inflight Entertainment Portal featuring free movies, TV series, a flight tracker, texting, and live TV. It also has in-seat power with USB-A and USB-C ports to charge your device onboard.

    Chicago Midway International Airport (MDW) is ADA-compliant. Travelers with reduced mobility flying through the airport can access several services and amenities, including wheelchair assistance, dedicated lanes, elevators, accessible restrooms, and accessible parking spaces. For wheelchair help, contact your airline at least 48 hours before your trip or when making a reservation.

  • How do I get to downtown Fort Myers from Southwest Florida International Airport (RSW)?

    Public bus Route 50, run by LeeTran, provides connections to Daniels Parkway and U.S. 41, where you can connect to other routes. The journey time is around 1h 4 min, including a layover time of around 17 minutes. Different rental companies are available onsite in the Ground Transportation area. You can also opt for a taxi or hotel shuttle.

  • What airlines have eco-friendly flights from Chicago Midway Airport to Fort Myers?

    For sustainable flights from Chicago Midway Airport to Fort Myers, you can book Southwest Airlines, which has a direct flight with reduced carbon emissions. It emits 6% less CO₂ than a typical flight on this route. The airline has adopted several sustainable practices in its operations to lower greenhouse gas emissions.

  • Which airline offers unaccompanied minor service on flights from Chicago Midway Airport to Fort Myers?

    If you have a minor flying alone, consider booking Southwest Airlines, which offers an unaccompanied minor service on its direct flights at a fee. This service is mandatory for children aged 5 to 11. Your child will be escorted to the flight by a Southwest Airlines employee, receive the necessary assistance onboard, and be escorted to the person picking them up upon arrival.

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

    In the last 3 days, the lowest price for a flight from Chicago Midway Airport to Fort Myers was $93 for a one-way ticket and $156 for a round-trip.

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

    No

  • Which airlines offer Wi-Fi service onboard planes from Chicago Midway Airport to Fort Myers?

    American Airlines, and Alaska Airlines offer inflight Wi-Fi service on the Chicago Midway Airport to Fort Myers flight route.

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

    The Boeing 737-800 is the aircraft model that flies most regularly on the Chicago Midway Airport to Fort Myers flight route.

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

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

  • Which is the best airline for flights from Chicago to Fort Myers, Delta or Frontier?

    The two airlines most popular with KAYAK users for flights from Chicago to Fort Myers are Delta and Frontier. With an average price for the route of $403 and an overall rating of 8.0, Delta is the most popular choice. Frontier is also a great choice for the route, with an average price of $530 and an overall rating of 6.2.

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

    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 Chicago Midway Airport to Fort Myers.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Fort Myers from Chicago Midway Airport 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 Chicago Midway Airport to Fort Myers?

    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 Fort Myers with an airline and back to Chicago Midway Airport with another airline. Booking your flights between Chicago Midway Airport and RSW 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 Chicago Midway Airport to Fort Myers?

    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 Fort Myers from Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

KAYAK’s top tips for finding a cheap flight from Chicago Midway Airport to Fort Myers

  • Which other cities can I fly to from Melbourne?
  • From Melbourne, you can extend your trip to domestic destinations like Sydney, Brisbane, Perth, Canberra, Adelaide, Gold Coast, Cairns, and Hobart or international destinations like Singapore, Auckland, Hong Kong, Dubai, Los Angeles, London, Tokyo, and Bangkok. Melbourne Tullamarine Airport (MEL) serves several domestic and international airlines with flights to these destinations.
  • The Chicago Midway Airport (MDW) to Fort Myers (RSW) flight route features several direct and connecting flights. Popular layover cities for one-stop flights on this route include Philadelphia (PHL), Atlanta (ATL), Pittsburgh (PIT), Orlando (MCO), Nashville (BNA), and Washington D.C. (WAS). The layover city depends on the flight route.
  • Southwest Airlines and Delta Airlines have no maximum carry-on weight limit on their direct flights from Chicago Midway Airport to Fort Myers. You can bring one hand baggage and one personal item not exceeding certain dimensions onboard. The hand baggage must fit in the overhead compartment, while the personal item should fit beneath the seat in front of you.
  • For Business Class flights from Chicago Midway Airport to Fort Myers, you can book Delta Airlines, which has this travel option on its one-stop flights. Delta Airlines offers several benefits on its Business Class flights, including spacious seating, access to Delta Sky Club lounges, premium dining, priority check-in and boarding, and special baggage allowance.
See more tips

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

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

Nonstop departures

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

Nonstop returns

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
See more direct flights

Top 4 airlines serving from Midway to Fort Myers

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Fort Myers. 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 Midway to Fort Myers? 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 10502 reviews
7.4Food
8.2Boarding
8.6Crew
8.0Entertainment
7.9Comfort
Airline reviews

Awful. Flight was continuously getting delayed and gates kept changing without any reason. Flight was delayed for more then 3 hours

2.0 MediocreNairan, May 2024JFK - FLL
Read more about Delta reviews

Awful. Flight was continuously getting delayed and gates kept changing without any reason. Flight was delayed for more then 3 hours

5-hour delay due to storms in Tanoa and airspace restricted by Miami traffic controllers.

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

Horrible. This was not first class. This was a connecting flight whi h was late. My original flight never came. I hated the fact that delta gave me a connecting flight from New York to Orlando Florida. No meals and the television screens were not working. There wasn't even any power to charge your phones. This is NOT FIRST CLASS DELTA!!! Do better next time!

They did a fine job. Can't wait to use Delta in the future.

Seat back monitors and outlets were dead and not working.

The experience was good and the flight departed on time and landed early

The flight was delayed but we got to our final destination.

public website still broken for years randomly blocking browsers with privacy options active after loading a page maybe once. check-in on laptop was almost impossible but eventually randomly worked. had to print pass at airport since couldn't get back in to load digital pass on mobile firefox or chrome. red eye flight so smooth onboarding, plenty of room to spread out, easy offboarding. onboard wifi instructions mention vpn can cause problems connecting but fails to also mention private dns. no printed or built in menu list, seems weird to require personal device to point at qr code link for menu which does not even allow direct ordering. people with health condition risk related dietary restrictions trying to avoid for example cholesterol and sugar are left guessing what they can order either way without nutritional info highlights (cranberry juice was minute maid cocktail with as much suger as typical can of soda). tap to pay wasn't working and always seems sketchy to manually enter card info. good movie variety, so limited tv was okay.

Horrible. Flight ORD to CGH was okay, but Paris was a nightmare. Old planes, delays, involuntary downgrades, broken planes, terrible communication. CGH to CPT was my worst flight ever.

There was no screens on board AND the WiFi didn’t work. My seat was broken and couldn’t recline so I couldn’t even sleep. The flight attendants didn’t offer anything to make it more comfortable. It was such an old cramped plane, when the person in front of me reclined I couldn’t even open my tray table. All the United ads talk about guaranteeing everyone gets a screen!

I’ve had a couple flights this week on United that were delayed by an hour or more

Great! The plane was decently sized and comfortable. The staff was nice and there was great in flight entertainment

Last minute gate change nearly caused us to miss our flight. Change was not announced or displayed in the main board at the old gate. Terrible communication. When we landed we had to wait 20 minutes because there was another plane at the assigned gate. Not the crew’s fault, but adding 20 minutes to a 45 minute flight sucked.

delay several times and wait extra long to board. no entertainment service because there are problem for some rows. always encounter some delays for the last flight of the day.

The flight experience was very good! Especially the United Club!

I was not able to buy food in the flight. They refer to include your Credit card in the APP, and if you are not from USA (i have a credit card form Canada) it is not possible

The flight from Ottawa to Chicago took a lot longer due to DC in Ottawa. We got to Chicago and went to our gate to catch our flight. We only had nine minutes I found that very stressful.

Good boarding. Crew started quick with drinks and food. They came around several times for trash which I really liked. Other than turbulence due to storms in the area, flight was great.

The control panel for the seat back screen did not work at all after takeoff.

Flight expected to leave at 6:40 pm ended leaving at 8:00 am the following day. I slept in a cold airport. Never again Spirit for me…

This was the return leg of my journey with Spirit Airlines. Despite its reputation, I found no issues as it got me from point A to B safely and without delay, especially with no mechanical delays, which is fantastic in my book! The staff, from ground crew to cabin crew, were all pleasant and hassle-free. The flight was smooth from takeoff to landing. I have absolutely no complaints about this no-frills airline!

It was the worst ever, i will be filing a lawsuit to get a refund. Our flight was delayed 4 hours so we would miss our connecting flight, we were not rebooked to our destination the same day, we were not offered any options to get home on the same day despite being clear that we absolutely cannot get stranded at night due to family, we were forced to book our own flights on a different airline to get home, and spririt is refusing a refund because our flight wasn't cancelled, only delayed. oh yeah, and they lost our luggage on the first part of the trip and you cannot get a hold of customer service when anything goes wrong, on hold for 30+ minutes. and their app breaks so you can't use that either.

My flight was cancelled!!! I had to spend 200.00 on another flight!!

Horrible. Delays, no customer support and fake promises and everything. i am suffering to help as due to connecting flight getting missed no support on ground and customer support window is closed and we are sitting o ground without anything

Terrible… missed our flight due to ridiculously long time to go thru baggage check-in!

Everything was really good but the seats are not very comfortable.

Spirit canceled the flight in March and never notified me!

Pretty good. Would’ve been excellent if we would have left on time and the crew wasn’t late.

Spirit airline tries to screw you at every opportunity. Spirit wanted 65$ for an extra pound in the suitcase Made me open the suitcase at the counter to remove 1 pound. Staff very cold and rude Will never fly spirit again and will recommend same to family and friends

I fly Frontier because it’s affordable. I understand that the seats are tight and not the most comfortable…but that’s part of it. The problem with this flight was that there was a group of travelers directly behind me at the back of the plane who were ridiculously loud and obnoxious the entire flight. I’m pretty sure they were drunk and I could periodically smell an odd odor that I believe was one of them using a smokeless vape pen. The stewards had to remind them to keep quiet during the pre-flight instruction, but that was it. They never said another thing to them for the rest of the flight. It was a miserable.

Six hour delay. Poor customer service. No voucher. Bad communication. Missed important appointments.

I purchased a carry on bag online…was supposed to cost $72 but after a whole slew of bs charges, the total was over $175.00. Because of these hidden charges, I will not even consider flying Frontier ever again. It’s just not worth the hassle. I’m scratching this company off my list forever.

Flight delayed 3 times, resulting in late arrival, rental car place gave car away resulting in increased BS charges because I was late. Frontier blows.

It was impossible to change a carry-on for a checked bag after the initial selection. The flight was delayed 14 hours "to allow for a late arriving aircraft." The seats were shockingly uncomfortable. This was only the second time I've seen seats that didn't recline in an airline. The first was in an East Bloc airline before the fall if the Iron Curtain.

Was just ok with over selling I guess. A lot of people in a short space and when we finally arrive i20 minutes, waiting to get out from the plain because we were waiting authorization for out boarding? Something like that.

First time flying Frontier, I am not sure the Ala Carte menu of options is for me.

I liked getting off the plane. Everything else was well below standards. Not even offering a bag of peanuts for free for a 4 hours flight is ridiculous.

There was no wifi, there was no usb charger on the planes Frontier lowered the weight limit on suitcases from 50 to 40 pounds Frontier now charges for a seat...really? If i don't pay for a basic seat, do i stand the whole flight? Frontier now charges for the carry on, just like for the checked suitcase The bundle pricing is way over priced.

They changed my flight and did not want to accommodate me or try to help me in any way. They do not care about their customers.

Book cheap flights from Chicago to Fort Myers

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Chicago to Fort Myers found on KAYAK in the last 72 hours.
8/28Wed
1 stopFrontier
9h 17mMDW-RSW
$93
6/8Sat
1 stopFrontier
8h 40mMDW-RSW
$98
6/5Wed
1 stopFrontier
9h 40mMDW-RSW
$104
6/19Wed
1 stopFrontier
9h 40mMDW-RSW
$106
6/25Tue
1 stopDelta
7h 50mMDW-RSW
$108
6/25Tue
1 stopDelta
7h 50mMDW-RSW
$160
6/21Fri
1 stopAvelo Airlines
14h 00mMDW-RSW
$246
6/10Mon
3 stops
30h 38mMDW-RSW
$339
6/17Mon
3 stops
30h 38mMDW-RSW
$341
6/26Wed
2 stopsWestJet
24h 08mMDW-RSW
$698

Search by stops

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Last minute flights from Midway to Fort Myers

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 Chicago to Fort Myers that are departing in the next 10 days.
5/30Thu
multi-stopFrontier
6h 13mMDW-RSW
6/8Sat
multi-stopFrontier
12h 17mRSW-MDW
$237
5/31Fri
multi-stopFrontier
7h 54mMDW-RSW
6/8Sat
multi-stopFrontier
12h 17mRSW-MDW
$247
6/1Sat
multi-stopDelta
6h 47mMDW-RSW
6/5Wed
multi-stopDelta
7h 10mRSW-MDW
$411
6/1Sat
multi-stopDelta
4h 49mMDW-RSW
6/4Tue
multi-stopDelta
7h 05mRSW-MDW
$451
5/31Fri
multi-stopAvelo Airlines
15h 25mMDW-RSW
6/6Thu
multi-stopAvelo Airlines
24h 10mRSW-MDW
$506
5/31Fri
multi-stop
29h 19mMDW-RSW
6/6Thu
multi-stop
24h 10mRSW-MDW
$581
5/31Fri
multi-stopAvelo Airlines
15h 25mMDW-RSW
6/7Fri
multi-stopAvelo Airlines
7h 35mRSW-MDW
$588
5/31Fri
multi-stop
29h 19mMDW-RSW
6/7Fri
multi-stop
7h 35mRSW-MDW
$663
6/1Sat
multi-stopWestJet
16h 40mMDW-RSW
6/6Thu
multi-stopWestJet
27h 19mRSW-MDW
$1,276
6/1Sat
multi-stopWestJet
16h 40mMDW-RSW
6/6Thu
multi-stopWestJet
27h 19mRSW-MDW
$1,294

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Chicago Midway Airport - Fort Myers Flights

Departure:

Chicago Midway Airport (MDW)United States

Destination:

Fort Myers (RSW)United States

Return flight deals:

Fort Myers - Chicago Midway Airport

Cabin classes:

$378