RSW - MDW

$53 Find Cheap Flights from Fort Myers to Chicago Midway Airport

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 2/22. 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

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 46,646,933 times on KAYAK, and here is why:

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Cheap Flight Deals from Fort Myers to Chicago Midway Airport (RSW-MDW)

 
These are the cheapest deals for flights from Fort Myers to Midway currently on KAYAK along with options from the most popular airlines KAYAK users selected for this route. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Recent round-trip flight deals from Fort Myers to Midway

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Fort Myers to Midway.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
9:58 pm - 6:39 amRSW-MDW
9h 41m1 stop
9:59 pm - 8:20 amMDW-RSW
9h 21m1 stop
$142Frontier
Find Deal
Wed, Dec 25 - Mon, Dec 30
8:50 pm - 10:45 pmRSW-MDW
2h 55mnonstop
6:25 pm - 10:15 pmMDW-RSW
2h 50mnonstop
$170Southwest
Find Deal
Thu, Jan 16 - Sun, Jan 19
9:58 pm - 6:39 amRSW-MDW
9h 41m1 stop
9:59 pm - 8:20 amMDW-RSW
9h 21m1 stop
$208Frontier
Find Deal
Wed, Dec 18 - Mon, Dec 30
5:40 pm - 7:40 pmRSW-MDW
3h 00mnonstop
7:00 pm - 10:50 pmMDW-RSW
2h 50mnonstop
$210Southwest
Find Deal
Fri, Jan 10 - Sun, Jan 12
5:40 am - 10:12 amRSW-MDW
5h 32m1 stop
2:08 pm - 9:18 pmMDW-RSW
6h 10m1 stop
$216Delta
Find Deal
Thu, Feb 6 - Mon, Feb 10
7:00 am - 9:00 amRSW-MDW
3h 00mnonstop
4:20 pm - 11:25 pmMDW-RSW
6h 05m1 stop
$233Southwest
Find Deal
Fri, Jan 10 - Sun, Jan 12
11:54 am - 5:01 pmRSW-MDW
6h 07m1 stop
9:38 am - 5:04 pmMDW-RSW
6h 26m1 stop
$236Delta
Find Deal
Sat, Dec 7 - Sat, Dec 14
10:51 am - 5:51 pmRSW-MDW
8h 00m1 stop
6:31 pm - 11:36 amMDW-RSW
16h 05m1 stop
$314Avelo Airlines
Find Deal
Thu, Jan 2 - Sun, Jan 5
9:05 pm - 10:36 amRSW-MDW
14h 31m2 stops
1:26 pm - 11:02 amMDW-RSW
20h 36m2 stops
$652WestJet
Find Deal
Fri, Jan 10 - Sun, Jan 12
9:05 pm - 5:47 pmRSW-MDW
21h 42m2 stops
10:19 am - 11:02 amMDW-RSW
23h 43m3 stops
$658WestJet
Find Deal
Fri, Jan 10 - Sun, Jan 12

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 Wednesday, 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 Sunday and avoiding Wednesdays 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 January, where tickets cost $296 on average. On the other hand, the most expensive months are July and December, where the average cost of tickets is $497 and $466 respectively.

Good to know

Low season

January

High season

September

Cheapest flight

$53
Best time to beat the crowds with an average 23% drop in price.
Most popular time to fly and prices are also 3% lower on average.
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 $53 for a one-way ticket and $142 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 airlines offer Wi-Fi service onboard planes from Fort Myers to Chicago Midway Airport?

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

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

    The Boeing 737 MAX 8 is the aircraft model that flies most regularly on the Fort Myers to Chicago Midway Airport flight 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.

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

    The two airlines most popular with KAYAK users for flights from Fort Myers to Chicago are Southwest and Delta. With an average price for the route of $414 and an overall rating of 8.1, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $419 and an overall rating of 8.0.

  • 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

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

  • Looking for a cheap flight? 25% of our users found flights on this route for $215 or less one-way and $384 or less round-trip.

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

Find which airlines fly direct from Fort Myers SW Florida Intl Airport to Chicago Midway Airport, 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 airlines flying 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.
8.1
SouthwestOverall score based on 5005 reviews
8.7Crew
8.2Boarding
7.7Entertainment
8.1Comfort
7.2Food
Airline reviews

Planes are aged. The wifi is unreliable and on many fights, no-existent. The flight attendants were very good.

6.0 Goodjohn, Nov 2024TPA - BWI
Read more Southwest reviews

Planes are aged. The wifi is unreliable and on many fights, no-existent. The flight attendants were very good.

I had a wonderful flight, but the only thing that annoyed me was how crowded TSA was. I still believe airports and all planes work together to bunch everyone together to drive up cost.

Easy to book and to get check in and get on and off.

Everything worked well. Crew was as entertaining as is possible on a plane flight. Southwest still has good legroom:

I like that it was on time and the staff was friendly.

Glad flight made it out. So many delays due to hurricane. everyone did a great job.

The flight was delayed about 20 minutes, but this was an evening flight, so it comes as no surprise. This flight came a good 1.5 days ahead of hurricane Helene which was still far out in the gulf. However, the flight never removed the seated buckle light. The staff announced from the beginning that due to the bad weather (I suppose the hurricane a day and a half away) they would have to do an abbreviated service with water and a snack. I am fine with their water and snack offering, but this was one of the smoothest flights I've had in years. If Southwest believes a flight like this requires everyone to remain seated, then all of their flights should remain buckled for the entire flight. I cannot help but wonder if things like this are a sneaky way to cut back on expenses since the airline is currently under a lot of pressure to reduce costs.

The first leg of the trip was great. The second leg from BWI to RIC was late, which was more screenful and tiring that late in the evening.

No space for our carryon and needed to check at plane before boarding !

Chairs are not reclinable. Not ear phones for sale. Seats should be assigned to avoid confrontations. Flight attendants were AMAZING.

I sat in comfort plus. It was fine. Seats were comfortable. I got drinks and snacks.

Good and consistent Printer in lounge did not work for me :(

Great - This was the last flight before hurricane closures and did a quick turnaround to get the plane heading north. Much appreciated.

I liked the screens in the seat headrest with movies to watch. I didn’t like being forced to check my carryon bag and being told there wasn’t room for my bag - when there were 5 bins sitting empty on takeoff. I didn’t like the “I don’t give a fig” attitude of the flight attendants and the delta gate attendants when I asked why they decided to put me out. They gave me a 1800 number to call but I can’t get a live person on the phone. Customer service is non existent. My business must not be that important to them.

It was not in Delta's control, but when we landed, we ended up parking at the wrong gate, and so everyone was already ready to deplane and had their carryon bags, ready to leave. But we had to sit down and move to the proper gate. This process took over 30 minutes. Again, not Delta's fault - more so on the staff at JFK

It’s was good. There’s so much room for improvement though. Since the plane was small, there was no entertainment but for years now, the most jarring aspect of travel is the lack of tasty snacks.

5 hour delay. They blamed the weather but it was the computer issues they had been dealing with for days.

Love delta but the delays and long waits for updates was just too much this time.

Flight for canceled. Horrible experience.. had to rent a car to drive myself up here.

If I can, I always fly Delta. I’ve found their service to always be reliable and pleasant.

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.
2/22Sat
1 stopFrontier
8h 31mRSW-MDW
$53
2/15Sat
1 stopFrontier
8h 31mRSW-MDW
$73
1/14Tue
nonstopSouthwest
3h 00mRSW-MDW
$79
1/10Fri
nonstopSouthwest
3h 00mRSW-MDW
$85
1/8Wed
1 stopDelta
7h 06mRSW-MDW
$108
1/6Mon
1 stopAvelo Airlines
15h 05mRSW-MDW
$112
12/16Mon
1 stopDelta
8h 31mRSW-MDW
$128
12/25Wed
2 stops
15h 13mRSW-MDW
$134
2/8Sat
2 stops
20h 27mRSW-MDW
$164
1/2Thu
1 stopAvelo Airlines
8h 00mRSW-MDW
$194

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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.
11/26Tue
multi-stopFrontier
26h 59mRSW-MDW
12/4Wed
multi-stopFrontier
31h 41mMDW-RSW
$249
11/24Sun
multi-stopFrontier
26h 39mRSW-MDW
11/26Tue
multi-stopFrontier
9h 53mMDW-RSW
$294
11/26Tue
multi-stopDelta
6h 07mRSW-MDW
12/3Tue
multi-stopDelta
6h 33mMDW-RSW
$321
11/25Mon
multi-stopFrontier
19h 17mRSW-MDW
11/29Fri
multi-stopFrontier
10h 21mMDW-RSW
$328
11/26Tue
multi-stopDelta
6h 07mRSW-MDW
12/4Wed
multi-stopDelta
5h 27mMDW-RSW
$362
11/26Tue
nonstopSouthwest
2h 55mRSW-MDW
12/4Wed
nonstopSouthwest
2h 55mMDW-RSW
$420
11/26Tue
nonstopSouthwest
2h 55mRSW-MDW
12/3Tue
nonstopSouthwest
2h 45mMDW-RSW
$423
11/25Mon
multi-stop
14h 00mRSW-MDW
11/29Fri
multi-stop
23h 59mMDW-RSW
$553
11/25Mon
multi-stop
14h 00mRSW-MDW
11/30Sat
multi-stop
33h 49mMDW-RSW
$578
11/23Sat
multi-stopWestJet
17h 32mRSW-MDW
11/26Tue
multi-stopWestJet
20h 45mMDW-RSW
$1,208

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Everything you need to know for your flight from Fort Myers to Midway

Information on your arrival and departure airports

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