RSW - MDW

$147 Find Cheap Flights from Fort Myers to Chicago Midway Airport - Compare and Save

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 1/23. 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

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Everything you should know

Cheapest round-trip
$275
Typical prices: $218-$374
Southwest
Thu 8/20Sat 8/22
RSW - MDW • Non-stop
Cheapest one-way
$147
Typical prices: $148-$273
Southwest
Sat 1/23
RSW - MDW • 1 stop
Nonstop flights
Every day
You can fly direct with Southwest. Average duration is 2h 49m
Direct flights
Direct flights
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Direct flights
Direct flights
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When to travel
October
Cheapest • 30% price drop
June
Most popular
Good to know
Good to know
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Good to know
Good to know
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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 20 - Sat, Aug 22
Southwest Logo
11:55 am - 1:45 pm
RSW
-
MDW
2h 50mnonstop
Southwest Logo
3:05 pm - 6:50 pm
MDW
-
RSW
2h 45mnonstop
$275Southwest
Wed, Aug 19 - Mon, Aug 24
Southwest Logo
7:10 am - 8:55 am
RSW
-
MDW
2h 45mnonstop
Southwest Logo
1:00 pm - 4:45 pm
MDW
-
RSW
2h 45mnonstop
$275Southwest
Wed, Sep 2 - Sat, Sep 5
Southwest Logo
5:40 pm - 7:30 pm
RSW
-
MDW
2h 50mnonstop
Southwest Logo
3:05 pm - 6:55 pm
MDW
-
RSW
2h 50mnonstop
$275Southwest
Mon, Aug 24 - Thu, Aug 27
Southwest Logo
11:55 am - 1:45 pm
RSW
-
MDW
2h 50mnonstop
Southwest Logo
6:15 pm - 10:00 pm
MDW
-
RSW
2h 45mnonstop
$275Southwest
Mon, Aug 17 - Wed, Aug 19
Southwest Logo
5:25 pm - 7:15 pm
RSW
-
MDW
2h 50mnonstop
Southwest Logo
8:50 am - 12:40 pm
MDW
-
RSW
2h 50mnonstop
$283Southwest
Thu, Aug 20 - Sat, Aug 22
Southwest Logo
11:55 am - 1:45 pm
RSW
-
MDW
2h 50mnonstop
Southwest Logo
11:00 am - 2:40 pm
MDW
-
RSW
2h 40mnonstop
$283Southwest
Tue, Aug 18 - Wed, Aug 19
Southwest Logo
7:10 am - 8:55 am
RSW
-
MDW
2h 45mnonstop
Southwest Logo
6:00 pm - 9:45 pm
MDW
-
RSW
2h 45mnonstop
$283Southwest
Mon, Oct 5 - Mon, Oct 5
Southwest Logo
6:40 am - 8:30 am
RSW
-
MDW
2h 50mnonstop
Southwest Logo
6:50 pm - 10:35 pm
MDW
-
RSW
2h 45mnonstop
$283Southwest
Tue, Aug 18 - Thu, Aug 20
Delta Logo
6:29 pm - 10:36 pm
RSW
-
MDW
5h 07m
1 stop
Delta Logo
6:05 am - 2:24 pm
MDW
-
RSW
7h 19m
1 stop
$295Delta
Thu, Aug 13 - Thu, Aug 20
Delta Logo
5:35 am - 11:51 am
RSW
-
MDW
7h 16m
1 stop
Delta Logo
12:46 pm - 9:18 pm
MDW
-
RSW
7h 32m
1 stop
$295Delta
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.

Flight prices are typical for this route right now.

Flights to Chicago Midway Airport from Fort Myers usually cost between $218 and $374 in August.
The lowest price found in the past 5 days was $275 on Southwest (Aug 19-Aug 24).

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 October, where tickets cost $255 (return) on average. On the other hand, the most expensive months are March and December, where the average cost of round-trip tickets is $504 and $494 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 season

February

Cheapest flight

$147
Best time to beat the crowds with an average 17% drop in price.
Most popular time to fly with an average 9% 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 $147 for a one-way ticket and $275 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 $236 or less one-way and $338 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

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)