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Cheap flights from Fort Myers to Chicago from $79

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 5/9. 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
0 bags

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Find the cheapest flights from Fort Myers to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
7:36 pm - 10:19 pm
RSW
-
MDW
27h 43m
1 stop
Frontier Logo
6:00 am - 5:50 pm
MDW
-
RSW
10h 50m
1 stop
$208Frontier
Thu, Apr 9 - Mon, Apr 13
Southwest Logo
7:00 am - 8:55 am
RSW
-
MDW
2h 55mnonstop
Southwest Logo
8:00 am - 3:20 pm
MDW
-
RSW
6h 20m
1 stop
$212Southwest
Wed, May 6 - Wed, May 13
Frontier Logo
3:43 pm - 10:19 pm
RSW
-
MDW
7h 36m
1 stop
Frontier Logo
6:00 am - 6:41 pm
MDW
-
RSW
11h 41m
1 stop
$215Frontier
Fri, Mar 27 - Thu, Apr 9
Southwest Logo
7:00 am - 8:55 am
RSW
-
MDW
2h 55mnonstop
Southwest Logo
12:50 pm - 4:35 pm
MDW
-
RSW
2h 45mnonstop
$216Southwest
Wed, May 6 - Wed, May 13
Delta Logo
5:30 am - 9:56 am
RSW
-
MDW
5h 26m
1 stop
Delta Logo
10:41 am - 4:23 pm
MDW
-
RSW
4h 42m
1 stop
$217Delta
Tue, Apr 21 - Tue, Apr 28
Delta Logo
8:00 am - 12:43 pm
RSW
-
MDW
5h 43m
1 stop
Delta Logo
6:23 am - 12:20 pm
MDW
-
RSW
4h 57m
1 stop
$218Delta
Wed, May 6 - Sun, May 10
Frontier Logo
3:43 pm - 10:19 pm
RSW
-
MDW
7h 36m
1 stop
Frontier Logo
6:00 am - 6:01 pm
MDW
-
RSW
11h 01m
1 stop
$219Frontier
Mon, Mar 30 - Mon, Apr 6
Southwest Logo
6:20 am - 12:05 pm
RSW
-
MDW
6h 45m
1 stop
Southwest Logo
4:05 pm - 7:50 pm
MDW
-
RSW
2h 45mnonstop
$224Southwest
Thu, Apr 16 - Tue, Apr 21
Southwest Logo
6:45 pm - 10:15 pm
RSW
-
MDW
4h 30m
1 stop
Southwest Logo
12:50 pm - 9:30 pm
MDW
-
RSW
7h 40m
2 stops
$227Southwest
Wed, May 6 - Wed, May 13
Southwest Logo
9:20 am - 3:45 pm
RSW
-
MDW
7h 25m
2 stops
Southwest Logo
12:50 pm - 9:30 pm
MDW
-
RSW
7h 40m
2 stops
$232Southwest
Wed, May 6 - Wed, May 13

Frontier flights from Fort Myers to Chicago Midway Airport

Our best Frontier deals on Fort Myers to Chicago Midway Airport flight tickets
Frontier
Apr 9
RSW7:36 pmFort Myers SW Florida Intl
27h 43m
1 stop
MDW10:19 pmChicago Midway
Apr 13
MDW6:00 amChicago Midway
10h 50m
1 stop
RSW5:50 pmFort Myers SW Florida Intl
$208
Frontier
Mar 27
RSW3:43 pmFort Myers SW Florida Intl
7h 36m
1 stop
MDW10:19 pmChicago Midway
Apr 9
MDW6:00 amChicago Midway
11h 41m
1 stop
RSW6:41 pmFort Myers SW Florida Intl
$215
Frontier
Mar 30
RSW3:43 pmFort Myers SW Florida Intl
7h 36m
1 stop
MDW10:19 pmChicago Midway
Apr 6
MDW6:00 amChicago Midway
11h 01m
1 stop
RSW6:01 pmFort Myers SW Florida Intl
$219

Delta flights from Fort Myers to Chicago Midway Airport

Our best Delta deals on Fort Myers to Chicago Midway Airport flight tickets
Delta
Apr 21
RSW5:30 amFort Myers SW Florida Intl
5h 26m
1 stop
MDW9:56 amChicago Midway
Apr 28
MDW10:41 amChicago Midway
4h 42m
1 stop
RSW4:23 pmFort Myers SW Florida Intl
$217
Delta
May 6
RSW8:00 amFort Myers SW Florida Intl
5h 43m
1 stop
MDW12:43 pmChicago Midway
May 10
MDW6:23 amChicago Midway
4h 57m
1 stop
RSW12:20 pmFort Myers SW Florida Intl
$218
Delta
Mar 25
RSW6:00 amFort Myers SW Florida Intl
7h 29m
1 stop
MDW12:29 pmChicago Midway
Mar 30
MDW6:07 pmChicago Midway
5h 29m
1 stop
RSW12:36 amFort Myers SW Florida Intl
$237

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 February 26, 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

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Thu 4/9

7:36 pm-10:19 pm

1 stop27h 43m

Chicago Midway

Mon 4/13

6:00 am-5:50 pm

1 stop10h 50m

$208

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Wed 5/6

7:00 am-8:55 am

Nonstop2h 55m

Chicago Midway

Wed 5/13

8:00 am-3:20 pm

1 stop6h 20m

$212

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Fri 3/27

3:43 pm-10:19 pm

1 stop7h 36m

Chicago Midway

Thu 4/9

6:00 am-6:41 pm

1 stop11h 41m

$215

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Wed 5/6

7:00 am-8:55 am

Nonstop2h 55m

Chicago Midway

Wed 5/13

12:50 pm-4:35 pm

Nonstop2h 45m

$216

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Tue 4/21

5:30 am-9:56 am

1 stop5h 26m

Chicago Midway

Tue 4/28

10:41 am-4:23 pm

1 stop4h 42m

$217

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Wed 5/6

8:00 am-12:43 pm

1 stop5h 43m

Chicago Midway

Sun 5/10

6:23 am-12:20 pm

1 stop4h 57m

$218

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Mon 3/30

3:43 pm-10:19 pm

1 stop7h 36m

Chicago Midway

Mon 4/6

6:00 am-6:01 pm

1 stop11h 01m

$219

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Thu 4/16

6:20 am-12:05 pm

1 stop6h 45m

Chicago Midway

Tue 4/21

4:05 pm-7:50 pm

Nonstop2h 45m

$224

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Wed 5/6

6:45 pm-10:15 pm

1 stop4h 30m

Chicago Midway

Wed 5/13

12:50 pm-9:30 pm

2 stops7h 40m

$227

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Wed 5/6

9:20 am-3:45 pm

2 stops7h 25m

Chicago Midway

Wed 5/13

12:50 pm-9:30 pm

2 stops7h 40m

$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 October is also very affordable. Most momondo users find prices during this month for around $282.

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

According to our data, Friday is the cheapest day to fly to Chicago Midway Airport from Fort Myers. The lowest ticket price found for a Friday departure recently was $360. 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 morning is the least expensive time of day to depart. momondo users have found prices as low as $378 when looking at flights departing in the morning. Try not to purchase tickets at noon because they tend to be around $472. 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?

As of February 2026, prices for Fort Myers to Chicago Midway Airport flights are approximately 5% cheaper 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

$218

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 $218. The best round-trip flight deal from Fort Myers to Chicago Midway Airport found on momondo in the last 72 hours is $340.
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 $170Free CancellationRating
8.0
4,299 reviews
Search Southwest flights
DeltaPriceFrom $216Free CancellationRating
7.9
8,237 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 $170 round-trip. Over the 22 Southwest flights for this route in a normal week, average airfare is usually $364 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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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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