RSW - MDW

$90 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 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

KAYAK searches 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
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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.

Recent round-trip flight deals from Fort Myers to Midway

KAYAK's recommended round-trip deals from the most popular airlines that fly from Fort Myers to Midway.
Discover the best prices for you by selecting your travel dates on KAYAK.
Choose your dates
Delta Logo
5:40 am - 12:03 pmRSW-MDW
7h 23m1 stop
Delta Logo
9:16 am - 4:49 pmMDW-RSW
6h 33m1 stop
$217Delta
Find Deal
Tue, Apr 29 - Wed, May 7
Southwest Logo
6:40 pm - 11:10 pmRSW-MDW
5h 30m1 stop
Southwest Logo
6:20 pm - 10:05 pmMDW-RSW
2h 45mnonstop
$223Southwest
Find Deal
Tue, Apr 29 - Wed, May 7
Delta Logo
5:37 pm - 9:27 pmRSW-MDW
4h 50m1 stop
Delta Logo
10:25 am - 5:50 pmMDW-RSW
6h 25m1 stop
$227Delta
Find Deal
Tue, May 27 - Sat, May 31
Frontier Logo
10:11 am - 5:28 pmRSW-MDW
8h 17m1 stop
Frontier Logo
12:15 pm - 9:23 pmMDW-RSW
8h 08m1 stop
$228Frontier
Find Deal
Fri, May 2 - Mon, May 5
Southwest Logo
5:10 am - 7:10 amRSW-MDW
3h 00mnonstop
Southwest Logo
6:25 am - 1:55 pmMDW-RSW
6h 30m1 stop
$237Southwest
Find Deal
Thu, May 15 - Wed, May 21
Southwest Logo
7:30 am - 11:55 amRSW-MDW
5h 25m1 stop
Southwest Logo
8:50 pm - 12:35 amMDW-RSW
2h 45mnonstop
$247Southwest
Find Deal
Fri, May 2 - Sun, May 4
Delta Logo
5:30 am - 9:40 amRSW-MDW
5h 10m1 stop
Delta Logo
1:55 pm - 11:13 pmMDW-RSW
8h 18m1 stop
$248Delta
Find Deal
Wed, May 7 - Wed, May 14
Southwest Logo
5:10 am - 7:10 amRSW-MDW
3h 00mnonstop
Southwest Logo
8:45 am - 12:35 pmMDW-RSW
2h 50mnonstop
$253Southwest
Find Deal
Thu, May 15 - Wed, May 21
Southwest Logo
7:15 am - 9:10 amRSW-MDW
2h 55mnonstop
Southwest Logo
6:20 pm - 10:05 pmMDW-RSW
2h 45mnonstop
$254Southwest
Find Deal
Wed, May 28 - Wed, May 28
Frontier Logo
6:16 pm - 11:21 pmRSW-MDW
6h 05m1 stop
Frontier Logo
6:00 am - 5:18 pmMDW-RSW
10h 18m1 stop
$440Frontier
Find Deal
Thu, Jul 17 - Sun, Jul 20

KAYAK's insights & trends for Fort Myers to Midway flights

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 round-trip flights from Fort Myers to Chicago Midway Airport clicked on KAYAK for each day over the last 12 months.
If you are looking for a flight deal from Fort Myers to Chicago Midway Airport, look for departures on Fridays and avoid leaving on a Monday, as it's usually the priciest day. When flying back from Chicago Midway Airport, Monday is the cheapest day to fly and Tuesday is the most expensive.

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 round-trip 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 February, where tickets cost $334 (return) on average. On the other hand, the most expensive months are January and July, where the average cost of round-trip tickets is $877 and $497 respectively.

Good to know

Low season

January

High season

November

Cheapest flight

$90
Best time to beat the crowds but there is an average 94% increase in price.
Most popular time to fly and prices are also 9% 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 $90 for a one-way ticket and $217 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 737-800 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 $424 and an overall rating of 8.0, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $437 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 $159 or less one-way and $401 or less round-trip.

Prefer to fly direct 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.

Direct 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

Direct 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.
8.0
SouthwestOverall score based on 4275 reviews
8.2Boarding
7.1Food
8.0Comfort
8.6Crew
7.6Entertainment
Airline reviews

WiFi on the flight was not working. Thus, entertainment options were limited.

8.0 ExcellentJames, Feb 2025SRQ - DEN
Read more Southwest reviews

WiFi on the flight was not working. Thus, entertainment options were limited.

Flight was awfully bumpy and landing was a bit jolting. I was in the restroom when snacks and drinks were served and was not asked if i wanted any. I had to ask for water finally.

Crew was great flight was great baggage claim was a failure. It took over 1 hour for bags to arrive. Poor communication poor effort when I spoke to the supervisor about the delay

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 Dekta Rep that checked us in was great. She's very personable, pleasant, and can tell she enjoys her job.

The young man who was our flight attendant in first class was lazy and did not do his job well at all. Never offered drinks upon boarding - actually I take that back... said "are you okay with water" as if I do not want to get you anything else, only passed the snacks around once, got my drink order wrong and then never offered a second round of drinks. He was the worst I have ever seen on Delta and we fly a lot.

Flight left early and arrived early. the whole trip was excellent.

Newer plane, relatively easy boarding, not a full flight and was told that we could not be moved up because of weight and balance issues. Otherwise, a very good experience.

Everything was great. Great service, excellent communication, and early arrival

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

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

Information on your arrival and departure airports

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