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Cheap flights from Fort Myers to Chicago from $127

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
7:45 pm - 9:45 pmRSW  Fort Myers SW Florida Intl-MDW Chicago Midway
3h 00mnonstop
Southwest Logo
6:25 pm - 10:20 pmMDW  Chicago Midway-RSW Fort Myers SW Florida Intl
2h 55mnonstop
$253Southwest
Thu, Dec 3 - Mon, Dec 7
Southwest Logo
7:45 pm - 9:45 pmRSW  Fort Myers SW Florida Intl-MDW Chicago Midway
3h 00mnonstop
Southwest Logo
6:25 pm - 10:20 pmMDW  Chicago Midway-RSW Fort Myers SW Florida Intl
2h 55mnonstop
$253Southwest
Thu, Dec 3 - Mon, Dec 7
Southwest Logo
9:05 pm - 11:05 pmRSW  Fort Myers SW Florida Intl-MDW Chicago Midway
3h 00mnonstop
Southwest Logo
11:35 am - 3:15 pmMDW  Chicago Midway-RSW Fort Myers SW Florida Intl
2h 40mnonstop
$253Southwest
Mon, Nov 23 - Sat, Dec 5
Southwest Logo
6:50 am - 8:45 amRSW  Fort Myers SW Florida Intl-MDW Chicago Midway
2h 55mnonstop
Southwest Logo
6:25 pm - 10:20 pmMDW  Chicago Midway-RSW Fort Myers SW Florida Intl
2h 55mnonstop
$253Southwest
Sat, Dec 5 - Tue, Dec 8
Southwest Logo
2:45 pm - 7:40 pmRSW  Fort Myers SW Florida Intl-MDW Chicago Midway
5h 55m1 stop Baltimore/Washington
Southwest Logo
6:45 am - 10:30 amMDW  Chicago Midway-RSW Fort Myers SW Florida Intl
2h 45mnonstop
$263Southwest
Sat, Dec 5 - Tue, Dec 8
Southwest Logo
9:45 pm - 11:45 pmRSW  Fort Myers SW Florida Intl-MDW Chicago Midway
3h 00mnonstop
Southwest Logo
10:05 am - 7:00 pmMDW  Chicago Midway-RSW Fort Myers SW Florida Intl
7h 55m1 stop Kansas City
$263Southwest
Tue, Nov 24 - Tue, Dec 1
Southwest Logo
8:00 pm - 12:10 amRSW  Fort Myers SW Florida Intl-MDW Chicago Midway
5h 10m1 stop Nashville Intl
Southwest Logo
3:35 pm - 7:20 pmMDW  Chicago Midway-RSW Fort Myers SW Florida Intl
2h 45mnonstop
$263Southwest
Mon, Nov 23 - Sat, Dec 5
Southwest Logo
6:05 am - 12:05 pmRSW  Fort Myers SW Florida Intl-MDW Chicago Midway
7h 00m1 stop Lambert-St Louis
Southwest Logo
6:25 pm - 10:20 pmMDW  Chicago Midway-RSW Fort Myers SW Florida Intl
2h 55mnonstop
$263Southwest
Tue, Dec 1 - Wed, Dec 2
Delta Logo
6:00 am - 11:25 amRSW  Fort Myers SW Florida Intl-MDW Chicago Midway
6h 25m1 stop Detroit Metropolitan Wayne County
Delta Logo
5:12 pm - 12:42 amMDW  Chicago Midway-RSW Fort Myers SW Florida Intl
6h 30m1 stop Atlanta Hartsfield-Jackson
$273Delta
Thu, Nov 26 - Thu, Dec 3
Delta Logo
5:20 am - 10:28 amRSW  Fort Myers SW Florida Intl-MDW Chicago Midway
6h 08m1 stop Atlanta Hartsfield-Jackson
Delta Logo
9:37 am - 5:22 pmMDW  Chicago Midway-RSW Fort Myers SW Florida Intl
6h 45m1 stop Detroit Metropolitan Wayne County
$273Delta
Thu, Dec 10 - Mon, Dec 14

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Delta flights from Fort Myers to Chicago Midway Airport

Our best Delta deals on Fort Myers to Chicago Midway Airport flight tickets
Delta
Nov 22
RSW5:30 amFort Myers SW Florida Intl
5h 54m
1 stop
MDW10:24 amChicago Midway
Dec 1
MDW5:12 pmChicago Midway
6h 30m
1 stop
RSW12:42 amFort Myers SW Florida Intl
$321
Delta
Jan 15
RSW1:17 pmFort Myers SW Florida Intl
5h 43m
1 stop
MDW6:00 pmChicago Midway
Jan 19
MDW6:00 amChicago Midway
6h 00m
1 stop
RSW1:00 pmFort Myers SW Florida Intl
$333
Delta
Nov 22
RSW5:30 amFort Myers SW Florida Intl
5h 54m
1 stop
MDW10:24 amChicago Midway
Nov 27
MDW12:05 pmChicago Midway
7h 56m
1 stop
RSW9:01 pmFort Myers SW Florida Intl
$341

Southwest flights from Fort Myers to Chicago Midway Airport

Our best Southwest deals on Fort Myers to Chicago Midway Airport flight tickets
Southwest
Dec 3
RSW7:45 pmFort Myers SW Florida Intl
3h 00m
MDW9:45 pmChicago Midway
Dec 7
MDW6:25 pmChicago Midway
2h 55m
RSW10:20 pmFort Myers SW Florida Intl
$253
Southwest
Dec 3
RSW11:55 amFort Myers SW Florida Intl
6h 55m
1 stop
MDW5:50 pmChicago Midway
Dec 7
MDW6:25 pmChicago Midway
2h 55m
RSW10:20 pmFort Myers SW Florida Intl
$263
Southwest
Dec 3
RSW1:35 pmFort Myers SW Florida Intl
7h 10m
2 stops
MDW7:45 pmChicago Midway
Dec 7
MDW6:45 amChicago Midway
2h 45m
RSW10:30 amFort Myers SW Florida Intl
$268

momondo Fare Finder

 
Use the filters below to find and compare flights from Fort Myers to Chicago Midway Airport that are best for you.

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Route

Depart

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Price

Cheapest round-trip

Fort MyersChicago

RSW Fort Myers SW Florida Intl - MDW Chicago Midway

RSWMDW

Fort Myers SW Florida Intl

Thu 12/3

7:45 pm-9:45 pm

Nonstop3h 00m

Chicago Midway

Mon 12/7

6:25 pm-10:20 pm

Nonstop2h 55m

$253

Fort MyersChicago

RSW Fort Myers SW Florida Intl - MDW Chicago Midway

RSWMDW

Fort Myers SW Florida Intl

Thu 12/3

7:45 pm-9:45 pm

Nonstop3h 00m

Chicago Midway

Mon 12/7

6:25 pm-10:20 pm

Nonstop2h 55m

$253
Quickest round-trip

Fort MyersChicago

RSW Fort Myers SW Florida Intl - MDW Chicago Midway

RSWMDW

Fort Myers SW Florida Intl

Mon 11/23

9:05 pm-11:05 pm

Nonstop3h 00m

Chicago Midway

Sat 12/5

11:35 am-3:15 pm

Nonstop2h 40m

$253

Fort MyersChicago

RSW Fort Myers SW Florida Intl - MDW Chicago Midway

RSWMDW

Fort Myers SW Florida Intl

Sat 12/5

6:50 am-8:45 am

Nonstop2h 55m

Chicago Midway

Tue 12/8

6:25 pm-10:20 pm

Nonstop2h 55m

$253

Fort MyersChicago

RSW Fort Myers SW Florida Intl - MDW Chicago Midway

RSWMDW

Fort Myers SW Florida Intl

Sat 12/5

2:45 pm-7:40 pm

1 stop5h 55m

Chicago Midway

Tue 12/8

6:45 am-10:30 am

Nonstop2h 45m

$263

Fort MyersChicago

RSW Fort Myers SW Florida Intl - MDW Chicago Midway

RSWMDW

Fort Myers SW Florida Intl

Tue 11/24

9:45 pm-11:45 pm

Nonstop3h 00m

Chicago Midway

Tue 12/1

10:05 am-7:00 pm

1 stop7h 55m

$263

Fort MyersChicago

RSW Fort Myers SW Florida Intl - MDW Chicago Midway

RSWMDW

Fort Myers SW Florida Intl

Mon 11/23

8:00 pm-12:10 am

1 stop5h 10m

Chicago Midway

Sat 12/5

3:35 pm-7:20 pm

Nonstop2h 45m

$263

Fort MyersChicago

RSW Fort Myers SW Florida Intl - MDW Chicago Midway

RSWMDW

Fort Myers SW Florida Intl

Tue 12/1

6:05 am-12:05 pm

1 stop7h 00m

Chicago Midway

Wed 12/2

6:25 pm-10:20 pm

Nonstop2h 55m

$263

Fort MyersChicago

RSW Fort Myers SW Florida Intl - MDW Chicago Midway

RSWMDW

Fort Myers SW Florida Intl

Thu 11/26

6:00 am-11:25 am

1 stop6h 25m

Chicago Midway

Thu 12/3

5:12 pm-12:42 am

1 stop6h 30m

$273

Fort MyersChicago

RSW Fort Myers SW Florida Intl - MDW Chicago Midway

RSWMDW

Fort Myers SW Florida Intl

Thu 12/10

5:20 am-10:28 am

1 stop6h 08m

Chicago Midway

Mon 12/14

9:37 am-5:22 pm

1 stop6h 45m

$273

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 $402 to $465.
The lowest price recently found on this route was $253.

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

The month of February is, on average, the cheapest month to fly to Chicago Midway Airport from Fort Myers, with most prices found around $302. If you are unable to visit Chicago Midway Airport during the month of February, then departing from Fort Myers during the month May is also very affordable. Most momondo users find prices during this month for around $324.

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 $381. 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 $474.

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 $349 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.

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

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

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

As of October 2026, prices for Fort Myers to Chicago Midway Airport flights are approximately 97% more expensive when compared to flights at the same time last year.

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

$127

Fastest flight time

2h 50m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Fort Myers in the past 72 hours is $127. The best round-trip flight deal from Fort Myers to Chicago Midway Airport found on momondo in the last 72 hours is $253.
The fastest flight from Fort Myers to Chicago Midway Airport takes 2h 50m
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 50m 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 $255Free CancellationRating
7.9
4,217 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 $255 round-trip. Over the 6 Southwest flights for this route in a normal week, average airfare is usually $369 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
Merrillville
New Buffalo
Hammond
Portage
Lansing
Saint Joseph
Benton Harbor
Valparaiso
Schererville
Munster
Chesterton
Monticello
Crown Point
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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