RSW - MDW

$125 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 8/8. 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
1 adult, Economy, 0 bags

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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$293
Typical prices: $304-$181
Southwest
Thu 8/6Sun 8/9
RSW - MDW • Non-stop
Cheapest one-way
$125
Typical prices: $89-$104
Delta
Sat 8/8
RSW - MDW • 1 stop
Top airlines
Southwest
Cheapest • from $293 (round-trip)
Southwest
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Every day
You can fly direct with Southwest. Average duration is 2h 50m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
When to travel
August
Cheapest • 35% price drop
June
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Midway!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights 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 for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Fort Myers to Midway

Thu, Aug 6 - Sun, Aug 9
Southwest Logo
6:50 am - 8:40 am
RSW
-
MDW
2h 50mnonstop
Southwest Logo
9:00 am - 12:45 pm
MDW
-
RSW
2h 45mnonstop
$293Southwest
Tue, Aug 4 - Tue, Aug 11
Southwest Logo
6:10 am - 11:50 am
RSW
-
MDW
6h 40m
1 stop
Southwest Logo
12:35 pm - 8:10 pm
MDW
-
RSW
6h 35m
2 stops
$294Southwest
Sat, Jul 11 - Tue, Jul 14
Southwest Logo
11:40 am - 1:30 pm
RSW
-
MDW
2h 50mnonstop
Southwest Logo
6:55 pm - 10:45 pm
MDW
-
RSW
2h 50mnonstop
$295Southwest
Tue, Jul 7 - Sat, Aug 1
Delta Logo
5:35 am - 10:05 am
RSW
-
MDW
5h 30m
1 stop
Delta Logo
6:00 am - 12:11 pm
MDW
-
RSW
5h 11m
1 stop
$296Delta
Sun, Aug 9 - Tue, Aug 11
Delta Logo
8:09 am - 11:51 am
RSW
-
MDW
4h 42m
1 stop
Delta Logo
12:46 pm - 6:58 pm
MDW
-
RSW
5h 12m
1 stop
$297Delta
Sat, Aug 29 - Mon, Sep 7
Southwest Logo
6:25 am - 1:05 pm
RSW
-
MDW
7h 40m
2 stops
Southwest Logo
8:15 am - 8:50 pm
MDW
-
RSW
11h 35m
1 stop
$298Southwest
Tue, Jul 28 - Tue, Jul 28
Southwest Logo
7:35 am - 2:00 pm
RSW
-
MDW
7h 25m
1 stop
Southwest Logo
3:00 pm - 10:05 pm
MDW
-
RSW
6h 05m
2 stops
$301Southwest
Fri, Sep 25 - Fri, Oct 16
Southwest Logo
6:50 am - 8:40 am
RSW
-
MDW
2h 50mnonstop
Southwest Logo
7:50 am - 11:30 am
MDW
-
RSW
2h 40mnonstop
$302Southwest
Sat, Aug 29 - Mon, Sep 7
Southwest Logo
7:20 am - 1:10 pm
RSW
-
MDW
6h 50m
2 stops
Southwest Logo
9:00 am - 12:45 pm
MDW
-
RSW
2h 45mnonstop
$303Southwest
Sat, Jul 11 - Tue, Jul 14
Southwest Logo
11:40 am - 1:30 pm
RSW
-
MDW
2h 50mnonstop
Southwest Logo
7:00 am - 5:45 pm
MDW
-
RSW
9h 45m
1 stop
$305Southwest
Booking Insights

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.

How much is a round-trip flight from Fort Myers to Chicago Midway Airport?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Fort Myers to Chicago Midway Airport departing in August.

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 Thursdays 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 Sunday 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 August, where tickets cost $228 (return) on average. On the other hand, the most expensive months are March and December, where the average cost of round-trip tickets is $500 and $470 respectively.

Can I save money by flying with a layover from Fort Myers to Chicago Midway Airport?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $305 on average.

Find deals

Good to know

Low seasonFebruary
Cheapest flight$125
Best time to beat the crowds with an average 24% drop in price.
Most popular time to fly with an average 19% 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 5 days, the lowest price for a flight from Fort Myers to Chicago Midway Airport was $125 for a one-way ticket and $293 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.

  • 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.

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 $196 or less one-way and $356 or less round-trip.

Prefer to fly direct from Fort Myers to Chicago Midway Airport?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Fort Myers SW Florida Intl to Chicago Midway.
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

Reviews of the top airline 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.
7.9
SouthwestOverall score based on 4235 reviews
8.1Boarding
8.0Comfort
7.0Food
8.6Crew
7.5Entertainment
Airline reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

2.0 MediocreMatthew, Jun 2026
CVG - MDW
Read more Southwest reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

Kayak could’ve posted the correct gate number. Almost missed my flight.

Slow boarding, limited food and drink portions. Bad delays and turbulence

The flight was smooth. The Southwest experience has degraded overall, but this one was okay.

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

Truly terrible. Will never willingly fly southwest again. Seats are worse than before they switched to assigned seating. One flight attendant was the opposite of helpful (rude, unhelpful, dismissive, and as my stranger seatmate said unprompted: a total prick). This caused me, 15 minutes into the flight, to book an alternate return flight home on a competing airline (first class 1.2k purchase instead of my existing planned flight) just so I would not have to ever be on that aircraft, with that terrible service person, with those horrific seats ever again.

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

For the first time in a long time, the Wi-Fi actually worked the entire flight! The flight crew was amazing as usual.

Great flight. I didn't get a drink because I was asleep whole on the flight.

Communication about the delayed flight was poor. We were told to move gates three times but that was bad information. We went from gate 128 to gate 126 and then to gate 123 and back to gate 126. Communication about the delay was bad. Ended up being 1 1/2 hour late getting home.

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

Information on your arrival and departure airports

Fort Myers (RSW)
Midway (MDW)