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Cheap flights from Fort Myers to Chicago from $149

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
6:40 am - 8:30 amRSW  Fort Myers SW Florida Intl-MDW Chicago Midway
2h 50mnonstop
Southwest Logo
6:55 pm - 10:40 pmMDW  Chicago Midway-RSW Fort Myers SW Florida Intl
2h 45mnonstop
$297Southwest
Thu, Oct 29 - Mon, Nov 2
Southwest Logo
6:40 am - 8:30 amRSW  Fort Myers SW Florida Intl-MDW Chicago Midway
2h 50mnonstop
Southwest Logo
6:25 pm - 10:15 pmMDW  Chicago Midway-RSW Fort Myers SW Florida Intl
2h 50mnonstop
$297Southwest
Thu, Oct 29 - Wed, Nov 11
Southwest Logo
6:35 am - 8:25 amRSW  Fort Myers SW Florida Intl-MDW Chicago Midway
2h 50mnonstop
Southwest Logo
6:45 am - 10:30 amMDW  Chicago Midway-RSW Fort Myers SW Florida Intl
2h 45mnonstop
$297Southwest
Tue, Oct 27 - Tue, Nov 3
Southwest Logo
4:35 pm - 6:30 pmRSW  Fort Myers SW Florida Intl-MDW Chicago Midway
2h 55mnonstop
Southwest Logo
6:55 pm - 10:40 pmMDW  Chicago Midway-RSW Fort Myers SW Florida Intl
2h 45mnonstop
$297Southwest
Thu, Nov 5 - Mon, Nov 9
Southwest Logo
6:40 pm - 8:30 pmRSW  Fort Myers SW Florida Intl-MDW Chicago Midway
2h 50mnonstop
Southwest Logo
4:10 pm - 7:55 pmMDW  Chicago Midway-RSW Fort Myers SW Florida Intl
2h 45mnonstop
$297Southwest
Thu, Oct 1 - Sat, Oct 3
Southwest Logo
6:50 am - 8:45 amRSW  Fort Myers SW Florida Intl-MDW Chicago Midway
2h 55mnonstop
Southwest Logo
3:35 pm - 7:20 pmMDW  Chicago Midway-RSW Fort Myers SW Florida Intl
2h 45mnonstop
$297Southwest
Sat, Dec 12 - Sat, Dec 12
Southwest Logo
7:10 am - 8:55 amRSW  Fort Myers SW Florida Intl-MDW Chicago Midway
2h 45mnonstop
Southwest Logo
6:00 pm - 9:50 pmMDW  Chicago Midway-RSW Fort Myers SW Florida Intl
2h 50mnonstop
$297Southwest
Sat, Sep 26 - Tue, Sep 29
Southwest Logo
5:25 pm - 7:15 pmRSW  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
$297Southwest
Thu, Sep 24 - Mon, Sep 28
Delta Logo
5:20 am - 10:29 amRSW  Fort Myers SW Florida Intl-MDW Chicago Midway
6h 09m1 stop Atlanta Hartsfield-Jackson
Delta Logo
1:41 pm - 9:55 pmMDW  Chicago Midway-RSW Fort Myers SW Florida Intl
7h 14m1 stop Detroit Metropolitan Wayne County
$317Delta
Thu, Dec 10 - Mon, Dec 14
Delta Logo
6:00 am - 12:51 pmRSW  Fort Myers SW Florida Intl-MDW Chicago Midway
7h 51m1 stop Detroit Metropolitan Wayne County
Delta Logo
5:14 pm - 12:42 amMDW  Chicago Midway-RSW Fort Myers SW Florida Intl
6h 28m1 stop Atlanta Hartsfield-Jackson
$317Delta
Mon, Nov 23 - Tue, Dec 1

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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 26
RSW6:00 amFort Myers SW Florida Intl
6h 25m
1 stop
MDW11:25 amChicago Midway
Nov 26
MDW4:13 pmChicago Midway
6h 21m
1 stop
RSW11:34 pmFort Myers SW Florida Intl
$317
Delta
Dec 10
RSW6:00 amFort Myers SW Florida Intl
8h 01m
1 stop
MDW1:01 pmChicago Midway
Dec 14
MDW1:41 pmChicago Midway
7h 14m
1 stop
RSW9:55 pmFort Myers SW Florida Intl
$337
Delta
Nov 24
RSW6:00 amFort Myers SW Florida Intl
7h 51m
1 stop
MDW12:51 pmChicago Midway
Nov 26
MDW4:13 pmChicago Midway
6h 21m
1 stop
RSW11:34 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
Oct 29
RSW6:40 pmFort Myers SW Florida Intl
2h 50m
MDW8:30 pmChicago Midway
Nov 10
MDW6:45 amChicago Midway
2h 45m
RSW10:30 amFort Myers SW Florida Intl
$297
Southwest
Oct 29
RSW2:25 pmFort Myers SW Florida Intl
6h 30m
1 stop
MDW7:55 pmChicago Midway
Nov 2
MDW5:05 amChicago Midway
2h 45m
RSW8:50 amFort Myers SW Florida Intl
$307
Southwest
Oct 2
RSW6:40 amFort Myers SW Florida Intl
2h 50m
MDW8:30 amChicago Midway
Oct 5
MDW5:05 amChicago Midway
2h 40m
RSW8:45 amFort Myers SW Florida Intl
$308

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

Return

Price

Cheapest round-trip
Quickest round-trip

Fort MyersChicago

RSW Fort Myers SW Florida Intl - MDW Chicago Midway

RSWMDW

Fort Myers SW Florida Intl

Thu 10/29

6:40 am-8:30 am

Nonstop2h 50m

Chicago Midway

Mon 11/2

6:55 pm-10:40 pm

Nonstop2h 45m

$297

Fort MyersChicago

RSW Fort Myers SW Florida Intl - MDW Chicago Midway

RSWMDW

Fort Myers SW Florida Intl

Thu 10/29

6:40 am-8:30 am

Nonstop2h 50m

Chicago Midway

Wed 11/11

6:25 pm-10:15 pm

Nonstop2h 50m

$297

Fort MyersChicago

RSW Fort Myers SW Florida Intl - MDW Chicago Midway

RSWMDW

Fort Myers SW Florida Intl

Tue 10/27

6:35 am-8:25 am

Nonstop2h 50m

Chicago Midway

Tue 11/3

6:45 am-10:30 am

Nonstop2h 45m

$297

Fort MyersChicago

RSW Fort Myers SW Florida Intl - MDW Chicago Midway

RSWMDW

Fort Myers SW Florida Intl

Thu 11/5

4:35 pm-6:30 pm

Nonstop2h 55m

Chicago Midway

Mon 11/9

6:55 pm-10:40 pm

Nonstop2h 45m

$297

Fort MyersChicago

RSW Fort Myers SW Florida Intl - MDW Chicago Midway

RSWMDW

Fort Myers SW Florida Intl

Thu 10/1

6:40 pm-8:30 pm

Nonstop2h 50m

Chicago Midway

Sat 10/3

4:10 pm-7:55 pm

Nonstop2h 45m

$297

Fort MyersChicago

RSW Fort Myers SW Florida Intl - MDW Chicago Midway

RSWMDW

Fort Myers SW Florida Intl

Sat 12/12

6:50 am-8:45 am

Nonstop2h 55m

Chicago Midway

Sat 12/12

3:35 pm-7:20 pm

Nonstop2h 45m

$297

Fort MyersChicago

RSW Fort Myers SW Florida Intl - MDW Chicago Midway

RSWMDW

Fort Myers SW Florida Intl

Sat 9/26

7:10 am-8:55 am

Nonstop2h 45m

Chicago Midway

Tue 9/29

6:00 pm-9:50 pm

Nonstop2h 50m

$297

Fort MyersChicago

RSW Fort Myers SW Florida Intl - MDW Chicago Midway

RSWMDW

Fort Myers SW Florida Intl

Thu 9/24

5:25 pm-7:15 pm

Nonstop2h 50m

Chicago Midway

Mon 9/28

6:15 pm-10:05 pm

Nonstop2h 50m

$297

Fort MyersChicago

RSW Fort Myers SW Florida Intl - MDW Chicago Midway

RSWMDW

Fort Myers SW Florida Intl

Thu 12/10

5:20 am-10:29 am

1 stop6h 09m

Chicago Midway

Mon 12/14

1:41 pm-9:55 pm

1 stop7h 14m

$317

Fort MyersChicago

RSW Fort Myers SW Florida Intl - MDW Chicago Midway

RSWMDW

Fort Myers SW Florida Intl

Mon 11/23

6:00 am-12:51 pm

1 stop7h 51m

Chicago Midway

Tue 12/1

5:14 pm-12:42 am

1 stop6h 28m

$317

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 typical for flights on this route.

Typical prices usually range from $283 to $357.
The lowest price recently found on this route was $297.

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 September is also very affordable. Most momondo users find prices during this month for around $305.

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 $393. 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, Monday 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 $465.

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.

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

$149

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 $149. The best round-trip flight deal from Fort Myers to Chicago Midway Airport found on momondo in the last 72 hours is $297.
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 $242Free CancellationRating
8.0
4,200 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 $242 round-trip. Over the 8 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
Merrillville
New Buffalo
Hammond
Portage
Benton Harbor
Lansing
Saint Joseph
Valparaiso
Schererville
Munster
Chesterton
Monticello
Porter
Crown Point
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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