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Cheap flights from Fort Myers to Chicago from $72

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 9/25. 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 Fort Myers to Chicago

Cheap round-trip flights

Frontier Logo
1:01 pm - 8:21 pmRSW-MDW
8h 20m1 stop
Frontier Logo
6:20 am - 12:16 pmMDW-RSW
4h 56m1 stop
$143Frontier
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Sun, Oct 12 - Sun, Oct 19
Frontier Logo
1:01 pm - 8:21 pmRSW-MDW
8h 20m1 stop
Frontier Logo
6:20 am - 12:16 pmMDW-RSW
4h 56m1 stop
$144Frontier
Find Deal
Thu, Oct 16 - Sun, Oct 19
Frontier Logo
12:27 pm - 5:27 pmRSW-MDW
6h 00m1 stop
Frontier Logo
6:20 am - 12:16 pmMDW-RSW
4h 56m1 stop
$152Frontier
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Fri, Oct 17 - Sun, Oct 19
Southwest Logo
6:40 am - 8:30 amRSW-MDW
2h 50mnonstop
Southwest Logo
8:30 pm - 12:10 amMDW-RSW
2h 40mnonstop
$159Southwest
Find Deal
Fri, Oct 17 - Sun, Oct 19
Southwest Logo
6:05 am - 7:55 amRSW-MDW
2h 50mnonstop
Southwest Logo
12:50 pm - 4:30 pmMDW-RSW
2h 40mnonstop
$181Southwest
Find Deal
Wed, Oct 15 - Sat, Oct 18
Southwest Logo
5:55 pm - 11:25 pmRSW-MDW
6h 30m1 stop
Southwest Logo
8:30 pm - 12:10 amMDW-RSW
2h 40mnonstop
$191Southwest
Find Deal
Fri, Oct 17 - Sun, Oct 19
Southwest Logo
2:45 pm - 4:35 pmRSW-MDW
2h 50mnonstop
Southwest Logo
9:40 am - 8:10 pmMDW-RSW
9h 30m1 stop
$197Southwest
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Fri, Oct 31 - Sun, Nov 2
Delta Logo
8:05 am - 12:34 pmRSW-MDW
5h 29m1 stop
Delta Logo
9:34 am - 4:53 pmMDW-RSW
6h 19m1 stop
$217Delta
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Fri, Dec 5 - Sun, Dec 7
Delta Logo
7:49 pm - 11:32 pmRSW-MDW
4h 43m1 stop
Delta Logo
5:34 pm - 12:37 amMDW-RSW
6h 03m1 stop
$237Delta
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Mon, Nov 24 - Thu, Nov 27
Delta Logo
7:00 am - 11:48 amRSW-MDW
5h 48m1 stop
Delta Logo
11:00 am - 6:04 pmMDW-RSW
6h 04m1 stop
$249Delta
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Wed, Oct 1 - Sat, Oct 4

Southwest flights from Fort Myers to Chicago Midway Airport

Our best Southwest deals on Fort Myers to Chicago Midway Airport flight tickets
Southwest
Oct 17
RSW6:40 amFort Myers SW Florida Intl
2h 50m
MDW8:30 amChicago Midway
Oct 19
MDW8:30 pmChicago Midway
2h 40m
RSW12:10 amFort Myers SW Florida Intl
$159
Find similar
Southwest
Oct 15
RSW6:05 amFort Myers SW Florida Intl
2h 50m
MDW7:55 amChicago Midway
Oct 18
MDW12:50 pmChicago Midway
2h 40m
RSW4:30 pmFort Myers SW Florida Intl
$181
Find similar
Southwest
Oct 17
RSW5:55 pmFort Myers SW Florida Intl
6h 30m
1 stop
MDW11:25 pmChicago Midway
Oct 19
MDW8:30 pmChicago Midway
2h 40m
RSW12:10 amFort Myers SW Florida Intl
$191
Find similar

Delta flights from Fort Myers to Chicago Midway Airport

Our best Delta deals on Fort Myers to Chicago Midway Airport flight tickets
Delta
Dec 5
RSW8:05 amFort Myers SW Florida Intl
5h 29m
1 stop
MDW12:34 pmChicago Midway
Dec 7
MDW9:34 amChicago Midway
6h 19m
1 stop
RSW4:53 pmFort Myers SW Florida Intl
$217
Find similar
Delta
Nov 24
RSW7:49 pmFort Myers SW Florida Intl
4h 43m
1 stop
MDW11:32 pmChicago Midway
Nov 27
MDW5:34 pmChicago Midway
6h 03m
1 stop
RSW12:37 amFort Myers SW Florida Intl
$237
Find similar
Delta
Oct 1
RSW7:00 amFort Myers SW Florida Intl
5h 48m
1 stop
MDW11:48 amChicago Midway
Oct 4
MDW11:00 amChicago Midway
6h 04m
1 stop
RSW6:04 pmFort Myers SW Florida Intl
$249
Find similar

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 September 16, 2025.
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

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Sun 10/12

1:01 pm-8:21 pm

1 stop8h 20m

Chicago Midway

Sun 10/19

6:20 am-12:16 pm

1 stop4h 56m

$143

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Thu 10/16

1:01 pm-8:21 pm

1 stop8h 20m

Chicago Midway

Sun 10/19

6:20 am-12:16 pm

1 stop4h 56m

$144

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Fri 10/17

12:27 pm-5:27 pm

1 stop6h 00m

Chicago Midway

Sun 10/19

6:20 am-12:16 pm

1 stop4h 56m

$152

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Fri 10/17

6:40 am-8:30 am

Nonstop2h 50m

Chicago Midway

Sun 10/19

8:30 pm-12:10 am

Nonstop2h 40m

$159

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Wed 10/15

6:05 am-7:55 am

Nonstop2h 50m

Chicago Midway

Sat 10/18

12:50 pm-4:30 pm

Nonstop2h 40m

$181

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Fri 10/17

5:55 pm-11:25 pm

1 stop6h 30m

Chicago Midway

Sun 10/19

8:30 pm-12:10 am

Nonstop2h 40m

$191

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Fri 10/31

2:45 pm-4:35 pm

Nonstop2h 50m

Chicago Midway

Sun 11/2

9:40 am-8:10 pm

1 stop9h 30m

$197

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Fri 12/5

8:05 am-12:34 pm

1 stop5h 29m

Chicago Midway

Sun 12/7

9:34 am-4:53 pm

1 stop6h 19m

$217

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Mon 11/24

7:49 pm-11:32 pm

1 stop4h 43m

Chicago Midway

Thu 11/27

5:34 pm-12:37 am

1 stop6h 03m

$237

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Wed 10/1

7:00 am-11:48 am

1 stop5h 48m

Chicago Midway

Sat 10/4

11:00 am-6:04 pm

1 stop6h 04m

$249

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 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 $228. If you are unable to visit Chicago Midway Airport during the month of August, then departing from Fort Myers during the month July is also very affordable. Most momondo users find prices during this month for around $303.

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

According to our data, Wednesday is the cheapest day to fly to Chicago Midway Airport from Fort Myers. The lowest ticket price found for a Wednesday departure recently was $383. 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, Saturday 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 $456.

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 afternoon is the least expensive time of day to depart. momondo users have found prices as low as $385 when looking at flights departing in the afternoon. Try not to purchase tickets at noon because they tend to be around $442. 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 SW Florida Intl to Chicago Midway flights?

There is only 1 cabin class available to choose from on Fort Myers SW Florida Intl to Chicago Midway 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?

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

$154

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 $154. The best round-trip flight deal from Fort Myers to Chicago Midway Airport found on momondo in the last 72 hours is $263.
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

  • 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 $183Free CancellationRating
8.0
4,242 reviews
Search Southwest flights
DeltaPriceFrom $216Free CancellationRating
7.9
7,957 reviews
Search Delta flights

  • Southwest Flights From Fort Myers to Chicago Midway Airport

    Southwest flight deals from Fort Myers to Chicago Midway Airport start from $183 round-trip. Over the 13 Southwest flights for this route in a normal week, average airfare is usually $385 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
Benton Harbor
Saint Joseph
Lansing
Portage
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
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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