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Find cheap flights from Chicago Midway Airport to Fort Myers from $76

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 6/5. 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
Sun 6/2
Sun 6/9

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 43,693,958 times on KAYAK, and here is why:

Save 22% or moreCompare multiple travel sites with one search.

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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
6:00 am - 2:55 pmMDW-RSW
7h 55m1 stop
3:44 pm - 11:59 pmRSW-MDW
9h 15m1 stop
$152Frontier
Find Deal
Wed, May 29 - Fri, May 31
2:28 pm - 9:41 pmMDW-RSW
6h 13m1 stop
3:44 pm - 11:50 pmRSW-MDW
9h 06m1 stop
$164Frontier
Find Deal
Thu, May 16 - Mon, May 20
10:59 am - 9:16 pmMDW-RSW
9h 17m1 stop
10:16 pm - 10:09 amRSW-MDW
12h 53m1 stop
$175Frontier
Find Deal
Thu, Aug 8 - Thu, Sep 5
1:21 pm - 9:04 pmMDW-RSW
6h 43m1 stop
6:58 am - 1:35 pmRSW-MDW
7h 37m1 stop
$216Delta
Find Deal
Wed, May 15 - Wed, May 22
9:32 am - 3:21 pmMDW-RSW
4h 49m1 stop
5:27 pm - 9:46 pmRSW-MDW
5h 19m1 stop
$221Delta
Find Deal
Tue, Jun 4 - Sat, Jun 29
1:21 pm - 9:04 pmMDW-RSW
6h 43m1 stop
12:20 pm - 5:05 pmRSW-MDW
5h 45m1 stop
$232Delta
Find Deal
Wed, May 22 - Thu, Jul 4
3:45 pm - 10:17 pmMDW-RSW
5h 32m1 stop
5:55 pm - 10:01 pmRSW-MDW
5h 06m1 stop
$237Delta
Find Deal
Thu, May 30 - Mon, Jun 3
7:35 pm - 10:40 amMDW-RSW
14h 05m1 stop
12:20 pm - 6:55 pmRSW-MDW
7h 35m1 stop
$375Avelo Airlines
Find Deal
Fri, Jun 7 - Mon, Jun 10
7:35 pm - 6:27 pmMDW-RSW
21h 52m2 stops
12:20 pm - 6:55 pmRSW-MDW
7h 35m1 stop
Fri, Jun 7 - Mon, Jun 10
8:45 pm - 11:43 pmMDW-RSW
25h 58m3 stops
6:15 am - 9:14 amRSW-MDW
27h 59m2 stops
Mon, May 13 - Thu, May 16

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, Tuesday 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 Friday, 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 December and March, where the average cost of tickets is $422 and $421 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 53 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 $76. Frontier proposed a round-trip connection from $152 and Delta from $216.

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

Each day, there are between 2 and 3 nonstop flights that take off from Chicago Midway Airport and land in Fort Myers, with an average flight time of 2h 41m. The most common departure time is 6:00 am and most flights take off in the morning. Each week, there are 20 flights. The most frequent day of departure is Wednesday, when 15% 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

March

Cheapest flight

$76
Best time to beat the crowds with an average 54% drop in price.
Most popular time to fly with an average 54% increase in price.
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 $76 for a one-way ticket and $152 for a round-trip.

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

    No

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

    We unfortunately don’t have that data for this specific 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 $394 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

Top tips for finding a cheap flight from MDW 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 10848 reviews
7.9Comfort
8.0Entertainment
8.2Boarding
7.4Food
8.6Crew
Airline reviews

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.

10.0 ExcellentDonnel, Apr 2024ATL - EYW
Read more about Delta reviews

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.

Boarding super slow with people allowed to linger in aisles

There were choices for the snacks. Good choices and tasty lunch and breakfast as well.

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.

Plane was so old it had cigarette butt trays in the seat

Everything was good, hard to really comfortable on a flight that long.

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

The weight limit per bag was really low - 40 lbs - so we had to pay extra. Then, they said their carry on size was 14x18x8, and we measured our bag very carefully. It was within the limit, yet they said it was too big, so we ended up paying an extra $100 for that too!! So it wasn’t the cheap flight we thought it would be. Then, they moved up our initial flight to depart 3 hours earlier which meant we had to be out on the road by 7 am and then have a 6 hour layover and we got home at 2am. It was a grueling day. I won’t be flying with them again.

Overall it was a good experience. Stewards were very kind and professional. The departure and arrival times were as promised. Plane was clean.

Terrible as usual!!!! Very unprofessional and rude flight attendants! You get what you pay for! HORRIBLE

My experience was above excellent!!!! First the lady that pushed me in the wheelchair to the gate was outstanding!!! Then the ladies at the gate went over and beyond, by helping me fill out the immigration form! I would not have been able to get to Guatemala without their help!!! God bless them all! They were amazing 🙏❤️🙏

First....my trip was from Ft. Myers to Philly (not the other way around). Plane was clean, staff was friendly and flight was efficient with boarding and flight time. Thumbs up all around.

Early departure and arrival. Cabin very cold. Waited a while for luggage to come out

The no frills ticket price. The seats are very uncomfortable.

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.

Bought seats on the flight and they were supposed to be 2 and a jumpseat. Plane clearly changed and it was a regular 3 seat row. Asked for a refund and was denied. If I wanted to sit next to someone else I wouldn't have bought the seats..

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.
6/5Wed
1 stopFrontier
9h 40mMDW-RSW
$76
5/11Sat
1 stopFrontier
11h 06mMDW-RSW
$81
6/5Wed
1 stopFrontier
9h 40mMDW-RSW
$84
5/11Sat
1 stopFrontier
11h 06mMDW-RSW
$85
5/15Wed
1 stopDelta
7h 30mMDW-RSW
$108
6/19Wed
1 stopDelta
4h 46mMDW-RSW
$113
5/26Sun
1 stopDelta
4h 07mMDW-RSW
$124
5/26Sun
1 stopFrontier
6h 08mMDW-RSW
$129
5/8Wed
1 stopDelta
7h 30mMDW-RSW
$154
8/4Sun
3 stops
40h 34mMDW-RSW
$320

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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.
5/4Sat
multi-stopDelta
4h 41mMDW-RSW
5/7Tue
multi-stopDelta
5h 04mRSW-MDW
$456
5/4Sat
multi-stopDelta
6h 13mMDW-RSW
6/19Wed
multi-stopDelta
5h 32mRSW-MDW
$523
5/4Sat
multi-stopDelta
4h 31mMDW-RSW
5/7Tue
multi-stopDelta
5h 04mRSW-MDW
$546
5/7Tue
multi-stopDelta
4h 36mMDW-RSW
5/8Wed
multi-stopDelta
5h 37mRSW-MDW
$587
5/4Sat
multi-stopDelta
4h 31mMDW-RSW
5/6Mon
multi-stopDelta
5h 43mRSW-MDW
$657
5/4Sat
multi-stopFrontier
11h 06mMDW-RSW
5/7Tue
multi-stopFrontier
7h 26mRSW-MDW
$728
5/5Sun
multi-stopDelta
4h 58mMDW-RSW
5/9Thu
multi-stopDelta
7h 07mRSW-MDW
$742
5/5Sun
multi-stopDelta
4h 58mMDW-RSW
5/6Mon
multi-stopDelta
7h 59mRSW-MDW
$782
5/5Sun
multi-stopDelta
4h 58mMDW-RSW
5/5Sun
multi-stopDelta
5h 55mRSW-MDW
$846
5/6Mon
multi-stopDelta
5h 50mMDW-RSW
5/10Fri
multi-stopDelta
6h 06mRSW-MDW
$937

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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: