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Cheap flights from Chicago Midway Airport to Fort Myers from $137

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Fort Myers departing on 5/28. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Chicago Midway Airport to Fort Myers

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
8:40 am - 12:30 pm
MDW
-
RSW
2h 50mnonstop
Southwest Logo
5:40 pm - 7:30 pm
RSW
-
MDW
2h 50mnonstop
$291Southwest
Wed, Sep 16 - Wed, Sep 23
Southwest Logo
6:55 pm - 10:40 pm
MDW
-
RSW
2h 45mnonstop
Southwest Logo
5:10 pm - 7:05 pm
RSW
-
MDW
2h 55mnonstop
$293Southwest
Tue, Jun 23 - Thu, Jul 30
Southwest Logo
6:55 pm - 10:40 pm
MDW
-
RSW
2h 45mnonstop
Southwest Logo
7:10 am - 9:00 am
RSW
-
MDW
2h 50mnonstop
$295Southwest
Tue, Jul 7 - Tue, Jul 14
Southwest Logo
3:10 pm - 9:10 pm
MDW
-
RSW
5h 00m
1 stop
Southwest Logo
7:10 am - 9:00 am
RSW
-
MDW
2h 50mnonstop
$301Southwest
Wed, Jun 10 - Tue, Jun 16
Southwest Logo
5:55 pm - 9:40 pm
MDW
-
RSW
2h 45mnonstop
Southwest Logo
6:00 am - 10:45 am
RSW
-
MDW
5h 45m
1 stop
$303Southwest
Sat, Jun 6 - Tue, Jun 9
Southwest Logo
1:00 pm - 4:45 pm
MDW
-
RSW
2h 45mnonstop
Southwest Logo
4:25 pm - 10:25 pm
RSW
-
MDW
7h 00m
1 stop
$305Southwest
Mon, Jun 1 - Sat, Jun 6
Southwest Logo
8:40 am - 5:00 pm
MDW
-
RSW
7h 20m
2 stops
Southwest Logo
5:40 pm - 7:30 pm
RSW
-
MDW
2h 50mnonstop
$306Southwest
Wed, Sep 16 - Wed, Sep 23
Southwest Logo
5:55 pm - 9:40 pm
MDW
-
RSW
2h 45mnonstop
Southwest Logo
7:35 am - 2:05 pm
RSW
-
MDW
7h 30m
2 stops
$308Southwest
Sat, Jun 6 - Wed, Jun 10
Southwest Logo
7:45 am - 5:50 pm
MDW
-
RSW
9h 05m
1 stop
Southwest Logo
7:10 am - 9:00 am
RSW
-
MDW
2h 50mnonstop
$309Southwest
Sat, Jun 13 - Tue, Jun 16
Southwest Logo
2:40 pm - 9:55 pm
MDW
-
RSW
6h 15m
2 stops
Southwest Logo
5:10 am - 7:00 am
RSW
-
MDW
2h 50mnonstop
$310Southwest
Thu, Jun 11 - Mon, Jun 15

Southwest flights from Chicago Midway Airport to Fort Myers

Our best Southwest deals on Chicago Midway Airport to Fort Myers flight tickets
Southwest
Sep 16
MDW8:40 amChicago Midway
2h 50m
RSW12:30 pmFort Myers SW Florida Intl
Sep 23
RSW5:40 pmFort Myers SW Florida Intl
2h 50m
MDW7:30 pmChicago Midway
$291
Southwest
Jun 23
MDW6:55 pmChicago Midway
2h 45m
RSW10:40 pmFort Myers SW Florida Intl
Jul 30
RSW5:10 pmFort Myers SW Florida Intl
2h 55m
MDW7:05 pmChicago Midway
$293
Southwest
Jul 7
MDW6:55 pmChicago Midway
2h 45m
RSW10:40 pmFort Myers SW Florida Intl
Jul 14
RSW7:10 amFort Myers SW Florida Intl
2h 50m
MDW9:00 amChicago Midway
$295

Delta flights from Chicago Midway Airport to Fort Myers

Our best Delta deals on Chicago Midway Airport to Fort Myers flight tickets
Delta
Jun 2
MDW6:23 amChicago Midway
7h 11m
1 stop
RSW2:34 pmFort Myers SW Florida Intl
Jun 10
RSW6:34 pmFort Myers SW Florida Intl
4h 43m
1 stop
MDW10:17 pmChicago Midway
$311
Delta
Jul 16
MDW6:00 amChicago Midway
5h 11m
1 stop
RSW12:11 pmFort Myers SW Florida Intl
Jul 25
RSW7:20 amFort Myers SW Florida Intl
6h 49m
1 stop
MDW1:09 pmChicago Midway
$315
Delta
May 30
MDW10:45 amChicago Midway
7h 10m
1 stop
RSW6:55 pmFort Myers SW Florida Intl
Jun 3
RSW3:45 pmFort Myers SW Florida Intl
6h 24m
1 stop
MDW9:09 pmChicago Midway
$332

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to Fort Myers that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated May 5, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Fort Myers that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Wed 9/16

8:40 am-12:30 pm

Nonstop2h 50m

Fort Myers SW Florida Intl

Wed 9/23

5:40 pm-7:30 pm

Nonstop2h 50m

$291

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Tue 6/23

6:55 pm-10:40 pm

Nonstop2h 45m

Fort Myers SW Florida Intl

Thu 7/30

5:10 pm-7:05 pm

Nonstop2h 55m

$293
Quickest round-trip

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Tue 7/7

6:55 pm-10:40 pm

Nonstop2h 45m

Fort Myers SW Florida Intl

Tue 7/14

7:10 am-9:00 am

Nonstop2h 50m

$295

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Wed 6/10

3:10 pm-9:10 pm

1 stop5h 00m

Fort Myers SW Florida Intl

Tue 6/16

7:10 am-9:00 am

Nonstop2h 50m

$301

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Sat 6/6

5:55 pm-9:40 pm

Nonstop2h 45m

Fort Myers SW Florida Intl

Tue 6/9

6:00 am-10:45 am

1 stop5h 45m

$303

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Mon 6/1

1:00 pm-4:45 pm

Nonstop2h 45m

Fort Myers SW Florida Intl

Sat 6/6

4:25 pm-10:25 pm

1 stop7h 00m

$305

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Wed 9/16

8:40 am-5:00 pm

2 stops7h 20m

Fort Myers SW Florida Intl

Wed 9/23

5:40 pm-7:30 pm

Nonstop2h 50m

$306

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Sat 6/6

5:55 pm-9:40 pm

Nonstop2h 45m

Fort Myers SW Florida Intl

Wed 6/10

7:35 am-2:05 pm

2 stops7h 30m

$308

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Sat 6/13

7:45 am-5:50 pm

1 stop9h 05m

Fort Myers SW Florida Intl

Tue 6/16

7:10 am-9:00 am

Nonstop2h 50m

$309

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Thu 6/11

2:40 pm-9:55 pm

2 stops6h 15m

Fort Myers SW Florida Intl

Mon 6/15

5:10 am-7:00 am

Nonstop2h 50m

$310

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Fort Myers from

How to get the cheapest flight ticket from Chicago Midway Airport to Fort Myers

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the typical price of a round-trip flight between Chicago Midway Airport and Fort Myers?

What is the cheapest month to fly to Fort Myers?

In general, September is the cheapest month to fly from Chicago Midway Airport to Fort Myers. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $171. If you are unable to visit Fort Myers during the month of September, then departing from Chicago Midway Airport during the month January is also very affordable. Most momondo users find prices during this month for around $261.

What is the cheapest day to depart on your flight to Fort Myers?

The cheapest day to depart from Chicago Midway Airport to Fort Myers is on a Wednesday when prices can be found for as low as $260. Flights from Chicago Midway Airport to Fort Myers on a Sunday will generally be more expensive and average around $300. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

What is the cheapest time of day to depart on your flight to Fort Myers?

The cheapest time of day to fly to Fort Myers is in the afternoon when flights can be purchased for as low as $270. Flights at noon are often more expensive with an average ticket price of $298.

What is the cheapest Chicago Midway to Fort Myers SW Florida Intl flight route?

Fly from Chicago Midway to Fort Myers SW Florida Intl for the best Chicago Midway - Fort Myers SW Florida Intl flight prices

How far in advance should I book a flight from Chicago Midway Airport to Fort Myers?

You are more likely to see cheaper flights to Fort Myers from Chicago Midway Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Fort Myers for around $350 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Fort Myers from Chicago Midway Airport for as low as $267 on momondo.

Can stopping save me money on Chicago Midway Airport to Fort Myers flights?

You could potentially save up to 10% on your flight if you consider stops on a Chicago Midway Airport to Fort Myers flight.

How have Chicago Midway Airport to Fort Myers flight prices changed over time?

As of May 2026, prices for Chicago Midway Airport to Fort Myers flights are approximately 23% cheaper when compared to flights at the same time last year.

When to book flights from Chicago Midway Airport to Fort Myers

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to Fort Myers according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago Midway Airport to Fort Myers (MDW to RSW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Fort Myers

Best Price Found

$190

Fastest flight time

2h 40m

Direct flights

Every day

Airports in Fort Myers

1 airport
The best one-way flight to Fort Myers from Chicago Midway Airport in the past 72 hours is $190. The best round-trip flight deal from Chicago Midway Airport to Fort Myers found on momondo in the last 72 hours is $315.
The fastest flight from Chicago Midway Airport to Fort Myers takes 2h 40m
Direct flights go from Chicago Midway Airport to Fort Myers every day.
There is 1 airport in Fort Myers. From Chicago Midway Airport there are direct flights to Fort Myers SW Florida Intl (RSW).
Search flight deals

Frequently asked questions about flying from Chicago Midway Airport to Fort Myers

  • How far is Chicago Midway to Fort Myers SW Florida Intl by plane?

    Fort Myers SW Florida Intl is 1097.4 mi away from Chicago Midway. Flights usually cover this in 2h 40m, depending on flying conditions and air traffic around both airports.

  • When did momondo last update prices for flights from Chicago Midway Airport to Fort Myers SW Florida Intl Airport?

    Prices for flights from Chicago Midway Airport to Fort Myers SW Florida Intl Airport refresh daily.

  • How many operators does momondo search for flights from Chicago Midway Airport to Fort Myers SW Florida Intl Airport?

  • How old do you have to be to fly from Chicago Midway Airport to Fort Myers SW Florida Intl Airport?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago Midway Airport to Fort Myers SW Florida Intl Airport.

  • What documentation or ID do you need to fly to Fort Myers SW Florida Intl Airport?

    The travel and health documents you'll need for your trip to Fort Myers SW Florida Intl Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Fort Myers SW Florida Intl Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Chicago Midway Airport to Fort Myers?

  • What is the most popular airline from Chicago Midway Airport to Fort Myers?

Best airlines flying from Chicago Midway Airport to Fort Myers

Compare and see reviews for airlines that fly from Chicago Midway Airport to Fort Myers with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $171Free CancellationRating
7.9
4,305 reviews
Search Southwest flights
DeltaPriceFrom $287Free CancellationRating
7.9
8,459 reviews
Search Delta flights

  • Southwest Flights From Chicago Midway Airport to Fort Myers

    Southwest operates around 14 flights from Chicago Midway Airport to Fort Myers every week. The average price of these flights found in the last 72 hours has been $348, but momondo users have found Southwest deals from Chicago Midway Airport to Fort Myers from as low as $171 round-trip. Southwest has been scored 7.9/10 in 4,305 reviews.

Traveling to a place near Fort Myers?

Book flights to Fort Myers if you plan to visit one of these locations
Fort Myers Beach
Sanibel
Cape Coral
Captiva
Estero
Boca Grande
North Fort Myers
Lehigh Acres

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Fort Myers?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Chicago to Fort Myers. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from Chicago to Fort Myers with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Fort Myers from Chicago with this policy.

How can momondo help me find flights from Chicago to Fort Myers?

momondo provides multiple filters to help you find the best flight to Fort Myers from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Chicago to Fort Myers right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Chicago to Fort Myers flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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