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Cheap flights from Fort Myers to Chicago from $145

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Fort Myers to Chicago departing on 6/5. 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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Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
7:00 am - 8:55 am
RSW
-
MDW
2h 55mnonstop
Southwest Logo
4:05 pm - 7:50 pm
MDW
-
RSW
2h 45mnonstop
$291Southwest
Tue, Jun 2 - Wed, Jun 3
Southwest Logo
5:10 am - 7:00 am
RSW
-
MDW
2h 50mnonstop
Southwest Logo
6:55 pm - 10:40 pm
MDW
-
RSW
2h 45mnonstop
$293Southwest
Thu, Jun 18 - Tue, Jun 23
Southwest Logo
5:10 am - 7:00 am
RSW
-
MDW
2h 50mnonstop
Southwest Logo
5:05 am - 8:45 am
MDW
-
RSW
2h 40mnonstop
$295Southwest
Thu, Jun 11 - Sat, Jun 20
Southwest Logo
10:30 am - 4:15 pm
RSW
-
MDW
6h 45m
1 stop
Southwest Logo
4:05 pm - 7:50 pm
MDW
-
RSW
2h 45mnonstop
$301Southwest
Tue, Jun 2 - Wed, Jun 3
Southwest Logo
5:10 am - 7:00 am
RSW
-
MDW
2h 50mnonstop
Southwest Logo
2:35 pm - 10:35 pm
MDW
-
RSW
7h 00m
1 stop
$303Southwest
Thu, Jun 18 - Tue, Jun 23
Southwest Logo
5:10 am - 7:00 am
RSW
-
MDW
2h 50mnonstop
Southwest Logo
5:00 am - 1:15 pm
MDW
-
RSW
7h 15m
1 stop
$305Southwest
Thu, Jun 11 - Sat, Jun 20
Southwest Logo
11:55 am - 2:00 pm
RSW
-
MDW
3h 05mnonstop
Southwest Logo
12:50 pm - 9:30 pm
MDW
-
RSW
7h 40m
2 stops
$306Southwest
Tue, Jun 2 - Wed, Jun 3
Southwest Logo
5:10 am - 7:00 am
RSW
-
MDW
2h 50mnonstop
Southwest Logo
8:20 am - 4:40 pm
MDW
-
RSW
7h 20m
2 stops
$308Southwest
Thu, Jun 18 - Tue, Jun 23
Southwest Logo
5:10 pm - 7:05 pm
RSW
-
MDW
2h 55mnonstop
Southwest Logo
1:00 pm - 9:55 pm
MDW
-
RSW
7h 55m
2 stops
$310Southwest
Thu, Jun 25 - Mon, Jun 29
Delta Logo
3:50 pm - 10:17 pm
RSW
-
MDW
7h 27m
1 stop
Delta Logo
9:17 am - 5:27 pm
MDW
-
RSW
7h 10m
1 stop
$311Delta
Tue, Jun 16 - Tue, Jun 30

Delta flights from Fort Myers to Chicago Midway Airport

Our best Delta deals on Fort Myers to Chicago Midway Airport flight tickets
Delta
Jun 16
RSW5:37 amFort Myers SW Florida Intl
7h 28m
1 stop
MDW12:05 pmChicago Midway
Jun 30
MDW6:00 amChicago Midway
7h 33m
1 stop
RSW2:33 pmFort Myers SW Florida Intl
$311
Delta
Jun 16
RSW6:34 pmFort Myers SW Florida Intl
4h 43m
1 stop
MDW10:17 pmChicago Midway
Jun 25
MDW12:50 pmChicago Midway
7h 22m
1 stop
RSW9:12 pmFort Myers SW Florida Intl
$323
Delta
Jun 25
RSW6:34 pmFort Myers SW Florida Intl
4h 43m
1 stop
MDW10:17 pmChicago Midway
Jun 29
MDW1:49 pmChicago Midway
8h 33m
1 stop
RSW11:22 pmFort Myers SW Florida Intl
$325

Southwest flights from Fort Myers to Chicago Midway Airport

Our best Southwest deals on Fort Myers to Chicago Midway Airport flight tickets
Southwest
Jun 2
RSW7:00 amFort Myers SW Florida Intl
2h 55m
MDW8:55 amChicago Midway
Jun 3
MDW4:05 pmChicago Midway
2h 45m
RSW7:50 pmFort Myers SW Florida Intl
$291
Southwest
Jun 18
RSW5:10 amFort Myers SW Florida Intl
2h 50m
MDW7:00 amChicago Midway
Jun 23
MDW6:55 pmChicago Midway
2h 45m
RSW10:40 pmFort Myers SW Florida Intl
$293
Southwest
Jun 11
RSW5:10 amFort Myers SW Florida Intl
2h 50m
MDW7:00 amChicago Midway
Jun 15
MDW6:55 pmChicago Midway
2h 45m
RSW10:40 pmFort Myers SW Florida Intl
$295

momondo Fare Finder

 
Customize your flight search to find flights from Fort Myers to Chicago Midway Airport 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 11, 2026.
Use the filters below to find and compare flights from Fort Myers to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Tue 6/2

7:00 am-8:55 am

Nonstop2h 55m

Chicago Midway

Wed 6/3

4:05 pm-7:50 pm

Nonstop2h 45m

$291

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Thu 6/18

5:10 am-7:00 am

Nonstop2h 50m

Chicago Midway

Tue 6/23

6:55 pm-10:40 pm

Nonstop2h 45m

$293
Quickest round-trip

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Thu 6/11

5:10 am-7:00 am

Nonstop2h 50m

Chicago Midway

Sat 6/20

5:05 am-8:45 am

Nonstop2h 40m

$295

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Tue 6/2

10:30 am-4:15 pm

1 stop6h 45m

Chicago Midway

Wed 6/3

4:05 pm-7:50 pm

Nonstop2h 45m

$301

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Thu 6/18

5:10 am-7:00 am

Nonstop2h 50m

Chicago Midway

Tue 6/23

2:35 pm-10:35 pm

1 stop7h 00m

$303

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Thu 6/11

5:10 am-7:00 am

Nonstop2h 50m

Chicago Midway

Sat 6/20

5:00 am-1:15 pm

1 stop7h 15m

$305

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Tue 6/2

11:55 am-2:00 pm

Nonstop3h 05m

Chicago Midway

Wed 6/3

12:50 pm-9:30 pm

2 stops7h 40m

$306

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Thu 6/18

5:10 am-7:00 am

Nonstop2h 50m

Chicago Midway

Tue 6/23

8:20 am-4:40 pm

2 stops7h 20m

$308

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Thu 6/25

5:10 pm-7:05 pm

Nonstop2h 55m

Chicago Midway

Mon 6/29

1:00 pm-9:55 pm

2 stops7h 55m

$310

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Tue 6/16

3:50 pm-10:17 pm

1 stop7h 27m

Chicago Midway

Tue 6/30

9:17 am-5:27 pm

1 stop7h 10m

$311

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 Chicago from

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

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 Fort Myers and Chicago Midway Airport?

What is the cheapest month to fly to Chicago Midway Airport?

The month of August is, on average, the cheapest month to fly to Chicago Midway Airport from Fort Myers, with most prices found around $208. If you are unable to visit Chicago Midway Airport during the month of August, then departing from Fort Myers during the month October is also very affordable. Most momondo users find prices during this month for around $255.

What is the cheapest day to depart on your flight to Chicago Midway Airport?

According to our data, Thursday is the cheapest day to fly to Chicago Midway Airport from Fort Myers. The lowest ticket price found for a Thursday departure recently was $351. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Sunday is the most expensive day to depart from Fort Myers because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $454.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from Fort Myers in the evening is the least expensive time of day to depart. momondo users have found prices as low as $306 when looking at flights departing in the evening. Try not to purchase tickets in the afternoon because they tend to be around $426. Of course, these prices can vary depending on the time of year and what airport you fly to.

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

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

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

You could potentially save up to 5% on your flight if you consider stops on a Fort Myers to Chicago Midway Airport flight.

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

When to book flights from Fort Myers to Chicago Midway Airport

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

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

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

Best Price Found

$219

Fastest flight time

2h 45m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Fort Myers in the past 72 hours is $219. The best round-trip flight deal from Fort Myers to Chicago Midway Airport found on momondo in the last 72 hours is $346.
The fastest flight from Fort Myers to Chicago Midway Airport takes 2h 45m
Direct flights go from Fort Myers to Chicago Midway Airport every day.
Search flight deals

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

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

    A flight from Fort Myers SW Florida Intl to Chicago Midway will travel around 1097.4 mi. Typically, this will take 2h 45m by plane in normal conditions.

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

    Prices for flights from Fort Myers SW Florida Intl Airport to Chicago Midway Airport were last updated today.

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

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

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Fort Myers SW Florida Intl Airport to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The travel and health documents required for your trip to Chicago Midway Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago Midway Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

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

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

Best airlines flying from Fort Myers to Chicago Midway Airport

Compare and see reviews for airlines that fly from Fort Myers to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $159Free CancellationRating
8.0
4,298 reviews
Search Southwest flights

  • Southwest Flights From Fort Myers to Chicago Midway Airport

    Southwest flight deals from Fort Myers to Chicago Midway Airport start from $159 round-trip. Over the 18 Southwest flights for this route in a normal week, average airfare is usually $357 round-trip - but some users have found much cheaper deals with momondo.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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Hammond
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Benton Harbor
Portage
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Munster
Schererville
Crown Point
Monticello
Chesterton
Porter
Griffith
Saint John

Why use momondo?

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

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Fort Myers.

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

Yes. momondo allows you to filter the results for Fort Myers to Chicago flights to just show those with flexible booking policies.

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

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

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

Of course. momondo tracks the price of Fort Myers to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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