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Cheap flights from Fort Myers to Chicago from $140

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 11/13. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Fort Myers to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
6:25 pm - 10:00 pmRSW  Fort Myers SW Florida Intl-MDW Chicago Midway
4h 35m1 stop Lambert-St Louis
Southwest Logo
3:10 pm - 10:05 pmMDW  Chicago Midway-RSW Fort Myers SW Florida Intl
5h 55m2 stops Lambert-St Louis Orlando
$275Southwest
Mon, Sep 21 - Mon, Sep 28
Southwest Logo
1:25 pm - 7:45 pmRSW  Fort Myers SW Florida Intl-MDW Chicago Midway
7h 20m1 stop Columbus
Southwest Logo
3:10 pm - 10:05 pmMDW  Chicago Midway-RSW Fort Myers SW Florida Intl
5h 55m2 stops Lambert-St Louis Orlando
$275Southwest
Thu, Sep 24 - Mon, Sep 28
Southwest Logo
12:05 pm - 1:50 pmRSW  Fort Myers SW Florida Intl-MDW Chicago Midway
2h 45mnonstop
Southwest Logo
11:15 am - 4:40 pmMDW  Chicago Midway-RSW Fort Myers SW Florida Intl
4h 25m1 stop Indianapolis
$276Southwest
Fri, Sep 4 - Sun, Sep 6
Southwest Logo
6:45 am - 11:50 amRSW  Fort Myers SW Florida Intl-MDW Chicago Midway
6h 05m2 stops Orlando Lambert-St Louis
Southwest Logo
11:45 am - 7:00 pmMDW  Chicago Midway-RSW Fort Myers SW Florida Intl
6h 15m1 stop Kansas City
$276Southwest
Thu, Nov 26 - Tue, Dec 1
Southwest Logo
6:50 am - 8:40 amRSW  Fort Myers SW Florida Intl-MDW Chicago Midway
2h 50mnonstop
Southwest Logo
6:15 pm - 10:05 pmMDW  Chicago Midway-RSW Fort Myers SW Florida Intl
2h 50mnonstop
$277Southwest
Fri, Sep 18 - Mon, Sep 21
Southwest Logo
6:50 am - 8:40 amRSW  Fort Myers SW Florida Intl-MDW Chicago Midway
2h 50mnonstop
Southwest Logo
6:15 pm - 10:05 pmMDW  Chicago Midway-RSW Fort Myers SW Florida Intl
2h 50mnonstop
$277Southwest
Mon, Sep 14 - Fri, Sep 18
Southwest Logo
6:50 am - 8:40 amRSW  Fort Myers SW Florida Intl-MDW Chicago Midway
2h 50mnonstop
Southwest Logo
6:15 pm - 10:05 pmMDW  Chicago Midway-RSW Fort Myers SW Florida Intl
2h 50mnonstop
$277Southwest
Fri, Sep 18 - Mon, Sep 21
Southwest Logo
4:15 pm - 8:45 pmRSW  Fort Myers SW Florida Intl-MDW Chicago Midway
5h 30m1 stop Baltimore/Washington
Southwest Logo
9:00 am - 12:45 pmMDW  Chicago Midway-RSW Fort Myers SW Florida Intl
2h 45mnonstop
$279Southwest
Wed, Sep 2 - Mon, Sep 7
Delta Logo
6:29 pm - 10:36 pmRSW  Fort Myers SW Florida Intl-MDW Chicago Midway
5h 07m1 stop Atlanta Hartsfield-Jackson
Delta Logo
10:56 am - 6:58 pmMDW  Chicago Midway-RSW Fort Myers SW Florida Intl
7h 02m1 stop Atlanta Hartsfield-Jackson
$286Delta
Fri, Sep 4 - Sun, Sep 6
Delta Logo
6:29 pm - 10:36 pmRSW  Fort Myers SW Florida Intl-MDW Chicago Midway
5h 07m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:05 am - 12:13 pmMDW  Chicago Midway-RSW Fort Myers SW Florida Intl
5h 08m1 stop Atlanta Hartsfield-Jackson
$286Delta
Fri, Sep 4 - Sun, Sep 6

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Southwest flights from Fort Myers to Chicago Midway Airport

Our best Southwest deals on Fort Myers to Chicago Midway Airport flight tickets
Southwest
Sep 21
RSW6:25 pmFort Myers SW Florida Intl
4h 35m
1 stop
MDW10:00 pmChicago Midway
Sep 28
MDW3:10 pmChicago Midway
5h 55m
2 stops
RSW10:05 pmFort Myers SW Florida Intl
$275
Southwest
Sep 4
RSW12:05 pmFort Myers SW Florida Intl
2h 45m
MDW1:50 pmChicago Midway
Sep 6
MDW11:15 amChicago Midway
4h 25m
1 stop
RSW4:40 pmFort Myers SW Florida Intl
$276
Southwest
Sep 18
RSW6:50 amFort Myers SW Florida Intl
2h 50m
MDW8:40 amChicago Midway
Sep 21
MDW6:15 pmChicago Midway
2h 50m
RSW10:05 pmFort Myers SW Florida Intl
$277

Delta flights from Fort Myers to Chicago Midway Airport

Our best Delta deals on Fort Myers to Chicago Midway Airport flight tickets
Delta
Sep 4
RSW6:29 pmFort Myers SW Florida Intl
5h 07m
1 stop
MDW10:36 pmChicago Midway
Sep 6
MDW6:05 amChicago Midway
5h 08m
1 stop
RSW12:13 pmFort Myers SW Florida Intl
$286
Delta
Nov 12
RSW5:30 amFort Myers SW Florida Intl
6h 03m
1 stop
MDW10:33 amChicago Midway
Nov 15
MDW5:09 pmChicago Midway
6h 31m
1 stop
RSW12:40 amFort Myers SW Florida Intl
$302
Delta
Sep 5
RSW12:22 pmFort Myers SW Florida Intl
5h 37m
1 stop
MDW4:59 pmChicago Midway
Sep 10
MDW4:30 pmChicago Midway
7h 05m
1 stop
RSW12:35 amFort Myers SW Florida Intl
$303

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 August 15, 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 Fort Myers SW Florida Intl - MDW Chicago Midway

RSWMDW

Fort Myers SW Florida Intl

Mon 9/21

6:25 pm-10:00 pm

1 stop4h 35m

Chicago Midway

Mon 9/28

3:10 pm-10:05 pm

2 stops5h 55m

$275

Fort MyersChicago

RSW Fort Myers SW Florida Intl - MDW Chicago Midway

RSWMDW

Fort Myers SW Florida Intl

Thu 9/24

1:25 pm-7:45 pm

1 stop7h 20m

Chicago Midway

Mon 9/28

3:10 pm-10:05 pm

2 stops5h 55m

$275

Fort MyersChicago

RSW Fort Myers SW Florida Intl - MDW Chicago Midway

RSWMDW

Fort Myers SW Florida Intl

Fri 9/4

12:05 pm-1:50 pm

Nonstop2h 45m

Chicago Midway

Sun 9/6

11:15 am-4:40 pm

1 stop4h 25m

$276

Fort MyersChicago

RSW Fort Myers SW Florida Intl - MDW Chicago Midway

RSWMDW

Fort Myers SW Florida Intl

Thu 11/26

6:45 am-11:50 am

2 stops6h 05m

Chicago Midway

Tue 12/1

11:45 am-7:00 pm

1 stop6h 15m

$276
Quickest round-trip

Fort MyersChicago

RSW Fort Myers SW Florida Intl - MDW Chicago Midway

RSWMDW

Fort Myers SW Florida Intl

Fri 9/18

6:50 am-8:40 am

Nonstop2h 50m

Chicago Midway

Mon 9/21

6:15 pm-10:05 pm

Nonstop2h 50m

$277

Fort MyersChicago

RSW Fort Myers SW Florida Intl - MDW Chicago Midway

RSWMDW

Fort Myers SW Florida Intl

Mon 9/14

6:50 am-8:40 am

Nonstop2h 50m

Chicago Midway

Fri 9/18

6:15 pm-10:05 pm

Nonstop2h 50m

$277

Fort MyersChicago

RSW Fort Myers SW Florida Intl - MDW Chicago Midway

RSWMDW

Fort Myers SW Florida Intl

Fri 9/18

6:50 am-8:40 am

Nonstop2h 50m

Chicago Midway

Mon 9/21

6:15 pm-10:05 pm

Nonstop2h 50m

$277

Fort MyersChicago

RSW Fort Myers SW Florida Intl - MDW Chicago Midway

RSWMDW

Fort Myers SW Florida Intl

Wed 9/2

4:15 pm-8:45 pm

1 stop5h 30m

Chicago Midway

Mon 9/7

9:00 am-12:45 pm

Nonstop2h 45m

$279

Fort MyersChicago

RSW Fort Myers SW Florida Intl - MDW Chicago Midway

RSWMDW

Fort Myers SW Florida Intl

Fri 9/4

6:29 pm-10:36 pm

1 stop5h 07m

Chicago Midway

Sun 9/6

10:56 am-6:58 pm

1 stop7h 02m

$286

Fort MyersChicago

RSW Fort Myers SW Florida Intl - MDW Chicago Midway

RSWMDW

Fort Myers SW Florida Intl

Fri 9/4

6:29 pm-10:36 pm

1 stop5h 07m

Chicago Midway

Sun 9/6

6:05 am-12:13 pm

1 stop5h 08m

$286

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?

Prices are currently low for flights on this route.

Typical prices usually range from $283 to $374.
The lowest price recently found on this route was $275.

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

The month of October is, on average, the cheapest month to fly to Chicago Midway Airport from Fort Myers, with most prices found around $255. If you are unable to visit Chicago Midway Airport during the month of October, then departing from Fort Myers during the month September is also very affordable. Most momondo users find prices during this month for around $293.

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 $386. 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 $318 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $504. 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

What cabin class options are available on Fort Myers to Chicago Midway Airport flights?

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

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

$241

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 $241. The best round-trip flight deal from Fort Myers to Chicago Midway Airport found on momondo in the last 72 hours is $352.
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 $188Free CancellationRating
8.0
4,219 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 $188 round-trip. Over the 9 Southwest flights for this route in a normal week, average airfare is usually $359 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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Benton Harbor
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Schererville
Munster
Chesterton
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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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