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Cheap flights from Fort Myers to Chicago from $80

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 12/5. 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.
Frontier Logo
3:52 pm - 10:43 pmRSW-MDW
7h 51m1 stop
Frontier Logo
8:04 pm - 8:33 amMDW-RSW
11h 29m1 stop
$144Frontier
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Fri, Nov 21 - Sun, Nov 23
Southwest Logo
6:30 am - 8:25 amRSW-MDW
2h 55mnonstop
Southwest Logo
8:20 am - 12:10 pmMDW-RSW
2h 50mnonstop
$157Southwest
Find Deal
Wed, Dec 3 - Wed, Dec 10
Southwest Logo
6:30 am - 8:25 amRSW-MDW
2h 55mnonstop
Southwest Logo
7:25 pm - 11:10 pmMDW-RSW
2h 45mnonstop
$158Southwest
Find Deal
Wed, Dec 3 - Sun, Dec 7
Southwest Logo
6:30 am - 8:25 amRSW-MDW
2h 55mnonstop
Southwest Logo
7:25 pm - 11:10 pmMDW-RSW
2h 45mnonstop
$159Southwest
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Thu, Dec 4 - Sun, Dec 7
Frontier Logo
11:58 am - 7:31 pmRSW-MDW
8h 33m1 stop
Frontier Logo
8:41 pm - 8:33 amMDW-RSW
10h 52m1 stop
$166Frontier
Find Deal
Thu, Nov 20 - Fri, Nov 21
Southwest Logo
6:30 am - 8:25 amRSW-MDW
2h 55mnonstop
Southwest Logo
6:15 pm - 10:10 pmMDW-RSW
2h 55mnonstop
$169Southwest
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Thu, Dec 4 - Mon, Dec 8
Frontier Logo
7:14 pm - 1:59 pmRSW-MDW
19h 45m1 stop
Frontier Logo
6:15 am - 6:19 pmMDW-RSW
11h 04m1 stop
$170Frontier
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Fri, Dec 5 - Fri, Dec 12
Frontier Logo
4:09 pm - 9:17 amRSW-MDW
18h 08m1 stop
Frontier Logo
7:23 pm - 6:19 pmMDW-RSW
21h 56m1 stop
$172Frontier
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Mon, Dec 1 - Thu, Dec 4
Delta Logo
7:49 pm - 11:47 pmRSW-MDW
4h 58m1 stop
Delta Logo
9:34 am - 4:51 pmMDW-RSW
6h 17m1 stop
$217Delta
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Fri, Dec 5 - Mon, Dec 8
Delta Logo
5:35 am - 9:05 amRSW-MDW
4h 30m1 stop
Delta Logo
6:45 am - 1:55 pmMDW-RSW
6h 10m1 stop
$232Delta
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Sun, Dec 21 - Wed, Jan 7

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
RSW6:30 amFort Myers SW Florida Intl
2h 55m
MDW8:25 amChicago Midway
Dec 10
MDW8:20 amChicago Midway
2h 50m
RSW12:10 pmFort Myers SW Florida Intl
$157
Find similar
Southwest
Dec 3
RSW6:30 amFort Myers SW Florida Intl
2h 55m
MDW8:25 amChicago Midway
Dec 7
MDW7:25 pmChicago Midway
2h 45m
RSW11:10 pmFort Myers SW Florida Intl
$158
Find similar
Southwest
Dec 4
RSW6:30 amFort Myers SW Florida Intl
2h 55m
MDW8:25 amChicago Midway
Dec 7
MDW7:25 pmChicago Midway
2h 45m
RSW11:10 pmFort Myers SW Florida Intl
$159
Find similar

Frontier flights from Fort Myers to Chicago Midway Airport

Our best Frontier deals on Fort Myers to Chicago Midway Airport flight tickets
Frontier
Nov 21
RSW3:52 pmFort Myers SW Florida Intl
7h 51m
1 stop
MDW10:43 pmChicago Midway
Nov 23
MDW8:04 pmChicago Midway
11h 29m
1 stop
RSW8:33 amFort Myers SW Florida Intl
$144
Find similar
Frontier
Nov 20
RSW11:58 amFort Myers SW Florida Intl
8h 33m
1 stop
MDW7:31 pmChicago Midway
Nov 21
MDW8:41 pmChicago Midway
10h 52m
1 stop
RSW8:33 amFort Myers SW Florida Intl
$166
Find similar
Frontier
Dec 5
RSW7:14 pmFort Myers SW Florida Intl
19h 45m
1 stop
MDW1:59 pmChicago Midway
Dec 12
MDW6:15 amChicago Midway
11h 04m
1 stop
RSW6:19 pmFort Myers SW Florida Intl
$170
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 November 6, 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

Fri 11/21

3:52 pm-10:43 pm

1 stop7h 51m

Chicago Midway

Sun 11/23

8:04 pm-8:33 am

1 stop11h 29m

$144

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Wed 12/3

6:30 am-8:25 am

Nonstop2h 55m

Chicago Midway

Wed 12/10

8:20 am-12:10 pm

Nonstop2h 50m

$157

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Wed 12/3

6:30 am-8:25 am

Nonstop2h 55m

Chicago Midway

Sun 12/7

7:25 pm-11:10 pm

Nonstop2h 45m

$158

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Thu 12/4

6:30 am-8:25 am

Nonstop2h 55m

Chicago Midway

Sun 12/7

7:25 pm-11:10 pm

Nonstop2h 45m

$159

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Thu 11/20

11:58 am-7:31 pm

1 stop8h 33m

Chicago Midway

Fri 11/21

8:41 pm-8:33 am

1 stop10h 52m

$166

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Thu 12/4

6:30 am-8:25 am

Nonstop2h 55m

Chicago Midway

Mon 12/8

6:15 pm-10:10 pm

Nonstop2h 55m

$169

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Fri 12/5

7:14 pm-1:59 pm

1 stop19h 45m

Chicago Midway

Fri 12/12

6:15 am-6:19 pm

1 stop11h 04m

$170

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Mon 12/1

4:09 pm-9:17 am

1 stop18h 08m

Chicago Midway

Thu 12/4

7:23 pm-6:19 pm

1 stop21h 56m

$172

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Fri 12/5

7:49 pm-11:47 pm

1 stop4h 58m

Chicago Midway

Mon 12/8

9:34 am-4:51 pm

1 stop6h 17m

$217

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Sun 12/21

5:35 am-9:05 am

1 stop4h 30m

Chicago Midway

Wed 1/7

6:45 am-1:55 pm

1 stop6h 10m

$232

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 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, 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 $370. 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 $427.

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 $377 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

$175

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 $175. The best round-trip flight deal from Fort Myers to Chicago Midway Airport found on momondo in the last 72 hours is $323.
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 55m 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 $179Free CancellationRating
8.0
4,241 reviews
Search Southwest flights
DeltaPriceFrom $216Free CancellationRating
7.9
8,001 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 $179 round-trip. Over the 22 Southwest flights for this route in a normal week, average airfare is usually $377 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
Portage
Lansing
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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