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Cheap flights from Chicago Midway Airport to Fort Myers from $85

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 4/13. 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
4:05 pm - 7:50 pm
MDW
-
RSW
2h 45mnonstop
Southwest Logo
6:40 pm - 10:15 pm
RSW
-
MDW
4h 35m
1 stop
$199Southwest
Tue, Apr 21 - Tue, Apr 28
Southwest Logo
9:50 am - 5:10 pm
MDW
-
RSW
6h 20m
1 stop
Southwest Logo
6:00 am - 7:55 am
RSW
-
MDW
2h 55mnonstop
$204Southwest
Wed, Apr 22 - Sat, Apr 25
Southwest Logo
8:00 am - 3:20 pm
MDW
-
RSW
6h 20m
1 stop
Southwest Logo
6:40 pm - 10:15 pm
RSW
-
MDW
4h 35m
1 stop
$209Southwest
Tue, Apr 21 - Tue, Apr 28
Southwest Logo
4:05 pm - 7:50 pm
MDW
-
RSW
2h 45mnonstop
Southwest Logo
6:00 am - 7:55 am
RSW
-
MDW
2h 55mnonstop
$213Southwest
Wed, May 6 - Sat, May 9
Southwest Logo
12:50 pm - 9:30 pm
MDW
-
RSW
7h 40m
2 stops
Southwest Logo
6:05 am - 11:35 am
RSW
-
MDW
6h 30m
1 stop
$214Southwest
Tue, Apr 21 - Tue, Apr 28
Southwest Logo
7:50 am - 3:40 pm
MDW
-
RSW
6h 50m
2 stops
Southwest Logo
6:05 am - 11:35 am
RSW
-
MDW
6h 30m
1 stop
$215Southwest
Tue, Apr 21 - Tue, Apr 28
Southwest Logo
4:05 pm - 7:50 pm
MDW
-
RSW
2h 45mnonstop
Southwest Logo
6:25 am - 1:55 pm
RSW
-
MDW
8h 30m
2 stops
$218Southwest
Wed, May 6 - Sat, May 9
Southwest Logo
3:40 pm - 7:25 pm
MDW
-
RSW
2h 45mnonstop
Southwest Logo
6:00 pm - 12:05 am
RSW
-
MDW
7h 05m
1 stop
$224Southwest
Sat, Apr 25 - Thu, Apr 30
Southwest Logo
3:40 pm - 7:25 pm
MDW
-
RSW
2h 45mnonstop
Southwest Logo
6:00 am - 7:55 am
RSW
-
MDW
2h 55mnonstop
$227Southwest
Sat, May 2 - Sat, May 9
Southwest Logo
4:05 pm - 7:50 pm
MDW
-
RSW
2h 45mnonstop
Southwest Logo
6:00 am - 7:55 am
RSW
-
MDW
2h 55mnonstop
$228Southwest
Wed, Apr 22 - Sat, Apr 25

Southwest flights from Chicago Midway Airport to Fort Myers

Our best Southwest deals on Chicago Midway Airport to Fort Myers flight tickets
Southwest
Apr 21
MDW4:05 pmChicago Midway
2h 45m
RSW7:50 pmFort Myers SW Florida Intl
Apr 28
RSW6:40 pmFort Myers SW Florida Intl
4h 35m
1 stop
MDW10:15 pmChicago Midway
$199
Southwest
Apr 22
MDW9:50 amChicago Midway
6h 20m
1 stop
RSW5:10 pmFort Myers SW Florida Intl
Apr 25
RSW6:00 amFort Myers SW Florida Intl
2h 55m
MDW7:55 amChicago Midway
$204
Southwest
Apr 21
MDW8:00 amChicago Midway
6h 20m
1 stop
RSW3:20 pmFort Myers SW Florida Intl
Apr 28
RSW6:40 pmFort Myers SW Florida Intl
4h 35m
1 stop
MDW10:15 pmChicago Midway
$209

Frontier flights from Chicago Midway Airport to Fort Myers

Our best Frontier deals on Chicago Midway Airport to Fort Myers flight tickets
Frontier
Mar 25
MDW6:05 amChicago Midway
11h 27m
1 stop
RSW6:32 pmFort Myers SW Florida Intl
Mar 30
RSW3:43 pmFort Myers SW Florida Intl
7h 36m
1 stop
MDW10:19 pmChicago Midway
$260
Frontier
Mar 25
MDW6:05 amChicago Midway
11h 27m
1 stop
RSW6:32 pmFort Myers SW Florida Intl
Mar 27
RSW3:43 pmFort Myers SW Florida Intl
7h 36m
1 stop
MDW10:19 pmChicago Midway
$270
Frontier
Mar 25
MDW6:05 amChicago Midway
11h 27m
1 stop
RSW6:32 pmFort Myers SW Florida Intl
Mar 30
RSW3:43 pmFort Myers SW Florida Intl
7h 36m
1 stop
MDW10:19 pmChicago Midway
$281

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 March 23, 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

Tue 4/21

4:05 pm-7:50 pm

Nonstop2h 45m

Fort Myers SW Florida Intl

Tue 4/28

6:40 pm-10:15 pm

1 stop4h 35m

$199

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Wed 4/22

9:50 am-5:10 pm

1 stop6h 20m

Fort Myers SW Florida Intl

Sat 4/25

6:00 am-7:55 am

Nonstop2h 55m

$204

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Tue 4/21

8:00 am-3:20 pm

1 stop6h 20m

Fort Myers SW Florida Intl

Tue 4/28

6:40 pm-10:15 pm

1 stop4h 35m

$209
Quickest round-trip

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Wed 5/6

4:05 pm-7:50 pm

Nonstop2h 45m

Fort Myers SW Florida Intl

Sat 5/9

6:00 am-7:55 am

Nonstop2h 55m

$213

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Tue 4/21

12:50 pm-9:30 pm

2 stops7h 40m

Fort Myers SW Florida Intl

Tue 4/28

6:05 am-11:35 am

1 stop6h 30m

$214

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Tue 4/21

7:50 am-3:40 pm

2 stops6h 50m

Fort Myers SW Florida Intl

Tue 4/28

6:05 am-11:35 am

1 stop6h 30m

$215

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Wed 5/6

4:05 pm-7:50 pm

Nonstop2h 45m

Fort Myers SW Florida Intl

Sat 5/9

6:25 am-1:55 pm

2 stops8h 30m

$218

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Sat 4/25

3:40 pm-7:25 pm

Nonstop2h 45m

Fort Myers SW Florida Intl

Thu 4/30

6:00 pm-12:05 am

1 stop7h 05m

$224

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Sat 5/2

3:40 pm-7:25 pm

Nonstop2h 45m

Fort Myers SW Florida Intl

Sat 5/9

6:00 am-7:55 am

Nonstop2h 55m

$227

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Wed 4/22

4:05 pm-7:50 pm

Nonstop2h 45m

Fort Myers SW Florida Intl

Sat 4/25

6:00 am-7:55 am

Nonstop2h 55m

$228

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 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 Tuesday when prices can be found for as low as $248. Flights from Chicago Midway Airport to Fort Myers on a Sunday will generally be more expensive and average around $295. 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 $263. Flights at noon are often more expensive with an average ticket price of $288.

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 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 $343 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 $228 on momondo.

What cabin class options are available on Chicago Midway to Fort Myers SW Florida Intl flights?

There is only 1 cabin class available to choose from on Chicago Midway to Fort Myers SW Florida Intl flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

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

No. A direct flight is the cheapest option for a flight between Chicago Midway Airport to Fort Myers.

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

As of March 2026, prices for Chicago Midway Airport to Fort Myers flights are approximately 31% more expensive 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

$168

Fastest flight time

2h 45m

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 $168. The best round-trip flight deal from Chicago Midway Airport to Fort Myers found on momondo in the last 72 hours is $334.
The fastest flight from Chicago Midway Airport to Fort Myers takes 2h 45m
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

  • 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 45m, 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
8.0
4,324 reviews
Search Southwest flights
DeltaPriceFrom $216Free CancellationRating
7.9
8,318 reviews
Search Delta flights

  • Southwest Flights From Chicago Midway Airport to Fort Myers

    Southwest operates around 29 flights from Chicago Midway Airport to Fort Myers every week. The average price of these flights found in the last 72 hours has been $343, 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 8.0/10 in 4,324 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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