What is the cheapest airline that flies from Fort Myers SW Florida Intl to Chicago Midway?

Southwest and Delta are the most popular carriers operating from Fort Myers SW Florida Intl to Chicago Midway

How many flights depart from Fort Myers to Chicago Midway Airport on average per week?

As of September 2026, 4 flights take off from Fort Myers and land in Chicago Midway Airport each week. The most common flight departure day for this route is Tue, with 50% of weekly flights taking off on this day.

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?

There is 1 operator available for flights from Fort Myers SW Florida Intl Airport to Chicago Midway Airport as of September 2026.

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.

$146 Cheap Flights from Fort Myers to Chicago Midway Airport in 2026/27

Find the cheapest flights from Fort Myers to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

6:40 pm - 8:30 pmRSW Fort Myers SW Florida Intl-MDW Chicago Midway

2h 50mnonstop

5:05 am - 8:45 amMDW Chicago Midway-RSW Fort Myers SW Florida Intl

2h 40mnonstop

$283Southwest

Fri, Oct 23 - Mon, Oct 26

5:50 am - 12:45 pmRSW Fort Myers SW Florida Intl-MDW Chicago Midway

7h 55m2 stops Baltimore/Washington Columbus

1:15 pm - 9:10 pmMDW Chicago Midway-RSW Fort Myers SW Florida Intl

6h 55m2 stops Cincinnati Cinci./N. Kentucky Baltimore/Washington

$284Southwest

Thu, Oct 29 - Wed, Nov 4

7:40 am - 12:47 pmRSW Fort Myers SW Florida Intl-MDW Chicago Midway

6h 07m1 stop Detroit Metropolitan Wayne County

1:27 pm - 9:29 pmMDW Chicago Midway-RSW Fort Myers SW Florida Intl

7h 02m1 stop Detroit Metropolitan Wayne County

$285Delta

Fri, Oct 23 - Mon, Oct 26

6:20 am - 1:50 pmRSW Fort Myers SW Florida Intl-MDW Chicago Midway

8h 30m2 stops Baltimore/Washington Detroit Metropolitan Wayne County

12:45 pm - 7:45 pmMDW Chicago Midway-RSW Fort Myers SW Florida Intl

6h 00m1 stop Nashville Intl

$290Southwest

Fri, Dec 11 - Mon, Dec 14

8:00 pm - 12:10 amRSW Fort Myers SW Florida Intl-MDW Chicago Midway

5h 10m1 stop Nashville Intl

12:55 pm - 10:40 pmMDW Chicago Midway-RSW Fort Myers SW Florida Intl

8h 45m2 stops Charlotte Douglas Baltimore/Washington

$290Southwest

Fri, Nov 6 - Mon, Nov 9

6:50 pm - 11:15 pmRSW Fort Myers SW Florida Intl-MDW Chicago Midway

5h 25m1 stop Baltimore/Washington

1:20 pm - 10:05 pmMDW Chicago Midway-RSW Fort Myers SW Florida Intl

7h 45m2 stops Albany Intl Orlando

$290Southwest

Fri, Nov 6 - Mon, Nov 9

7:15 pm - 10:45 pmRSW Fort Myers SW Florida Intl-MDW Chicago Midway

4h 30m1 stop Lambert-St Louis

12:55 pm - 10:40 pmMDW Chicago Midway-RSW Fort Myers SW Florida Intl

8h 45m2 stops Charlotte Douglas Baltimore/Washington

$290Southwest

Fri, Nov 6 - Mon, Nov 9

2:15 pm - 6:37 pmRSW Fort Myers SW Florida Intl-MDW Chicago Midway

5h 22m1 stop Detroit Metropolitan Wayne County

10:35 am - 6:53 pmMDW Chicago Midway-RSW Fort Myers SW Florida Intl

7h 18m1 stop Atlanta Hartsfield-Jackson

$291Delta

Tue, Jan 26 - Tue, Feb 2

6:25 pm - 11:55 pmRSW Fort Myers SW Florida Intl-MDW Chicago Midway

6h 30m1 stop Nashville Intl

2:50 pm - 11:00 pmMDW Chicago Midway-RSW Fort Myers SW Florida Intl

7h 10m2 stops Detroit Metropolitan Wayne County Baltimore/Washington

$291Southwest

Fri, Oct 23 - Mon, Oct 26

6:00 am - 1:01 pmRSW Fort Myers SW Florida Intl-MDW Chicago Midway

8h 01m1 stop Detroit Metropolitan Wayne County

1:41 pm - 9:55 pmMDW Chicago Midway-RSW Fort Myers SW Florida Intl

7h 14m1 stop Detroit Metropolitan Wayne County

$291Delta

Thu, Dec 10 - Mon, Dec 14

Cheap last minute flights

Enter your travel dates to find the best prices.

7:10 am - 8:55 amRSW Fort Myers SW Florida Intl-MDW Chicago Midway

2h 45mnonstop

6:35 pm - 10:25 pmMDW Chicago Midway-RSW Fort Myers SW Florida Intl

2h 50mnonstop

$366Southwest

Wed, Sep 23 - Tue, Oct 6

7:10 am - 8:55 amRSW Fort Myers SW Florida Intl-MDW Chicago Midway

2h 45mnonstop

9:30 am - 5:05 pmMDW Chicago Midway-RSW Fort Myers SW Florida Intl

6h 35m1 stop Nashville Intl

$375Southwest

Wed, Sep 23 - Tue, Oct 6

7:20 am - 12:05 pmRSW Fort Myers SW Florida Intl-MDW Chicago Midway

5h 45m2 stops Orlando Atlanta Hartsfield-Jackson

6:35 pm - 10:25 pmMDW Chicago Midway-RSW Fort Myers SW Florida Intl

2h 50mnonstop

$381Southwest

Wed, Sep 23 - Tue, Oct 6

7:20 am - 12:05 pmRSW Fort Myers SW Florida Intl-MDW Chicago Midway

5h 45m2 stops Orlando Atlanta Hartsfield-Jackson

9:30 am - 5:05 pmMDW Chicago Midway-RSW Fort Myers SW Florida Intl

6h 35m1 stop Nashville Intl

$391Southwest

Wed, Sep 23 - Tue, Oct 6

7:20 am - 3:25 pmRSW Fort Myers SW Florida Intl-MDW Chicago Midway

9h 05m2 stops Orlando Atlanta Hartsfield-Jackson

7:55 am - 5:05 pmMDW Chicago Midway-RSW Fort Myers SW Florida Intl

8h 10m2 stops Buffalo Baltimore/Washington

$396Southwest

Wed, Sep 23 - Tue, Oct 6

7:10 am - 8:55 amRSW Fort Myers SW Florida Intl-MDW Chicago Midway

2h 45mnonstop

3:05 pm - 6:55 pmMDW Chicago Midway-RSW Fort Myers SW Florida Intl

2h 50mnonstop

$449Southwest

Tue, Sep 22 - Sat, Sep 26

3:15 pm - 5:10 pmRSW Fort Myers SW Florida Intl-MDW Chicago Midway

2h 55mnonstop

3:05 pm - 6:55 pmMDW Chicago Midway-RSW Fort Myers SW Florida Intl

2h 50mnonstop

$449Southwest

Sat, Sep 19 - Sat, Sep 26

5:40 pm - 7:30 pmRSW Fort Myers SW Florida Intl-MDW Chicago Midway

2h 50mnonstop

6:00 pm - 9:50 pmMDW Chicago Midway-RSW Fort Myers SW Florida Intl

2h 50mnonstop

$449Southwest

Wed, Sep 23 - Tue, Sep 29

6:19 pm - 10:44 pmRSW Fort Myers SW Florida Intl-MDW Chicago Midway

5h 25m1 stop Atlanta Hartsfield-Jackson

10:48 am - 4:45 pmMDW Chicago Midway-RSW Fort Myers SW Florida Intl

4h 57m1 stop Atlanta Hartsfield-Jackson

$469Delta

Sat, Sep 19 - Wed, Sep 23

6:19 pm - 10:44 pmRSW Fort Myers SW Florida Intl-MDW Chicago Midway

5h 25m1 stop Atlanta Hartsfield-Jackson

6:05 am - 1:30 pmMDW Chicago Midway-RSW Fort Myers SW Florida Intl

6h 25m1 stop Atlanta Hartsfield-Jackson

$469Delta

Wed, Sep 23 - Sat, Sep 26

Cheap direct flights

Enter your travel dates to find the best prices.

6:40 pm - 8:30 pmRSW Fort Myers SW Florida Intl-MDW Chicago Midway

2h 50mnonstop

5:05 am - 8:45 amMDW Chicago Midway-RSW Fort Myers SW Florida Intl

2h 40mnonstop

$283Southwest

Fri, Oct 23 - Mon, Oct 26

6:40 am - 8:30 amRSW Fort Myers SW Florida Intl-MDW Chicago Midway

2h 50mnonstop

6:50 pm - 10:40 pmMDW Chicago Midway-RSW Fort Myers SW Florida Intl

2h 50mnonstop

$298Southwest

Thu, Oct 15 - Mon, Oct 19

7:20 am - 9:15 amRSW Fort Myers SW Florida Intl-MDW Chicago Midway

2h 55mnonstop

6:45 am - 10:30 amMDW Chicago Midway-RSW Fort Myers SW Florida Intl

2h 45mnonstop

$302Southwest

Sat, Nov 21 - Tue, Dec 1

7:35 am - 9:25 amRSW Fort Myers SW Florida Intl-MDW Chicago Midway

2h 50mnonstop

6:45 am - 10:30 amMDW Chicago Midway-RSW Fort Myers SW Florida Intl

2h 45mnonstop

$302Southwest

Sat, Oct 31 - Wed, Nov 4

2:55 pm - 5:00 pmRSW Fort Myers SW Florida Intl-MDW Chicago Midway

3h 05mnonstop

7:55 pm - 11:40 pmMDW Chicago Midway-RSW Fort Myers SW Florida Intl

2h 45mnonstop

$302Southwest

Wed, Dec 9 - Mon, Dec 21

6:50 am - 8:45 amRSW Fort Myers SW Florida Intl-MDW Chicago Midway

2h 55mnonstop

5:05 am - 8:50 amMDW Chicago Midway-RSW Fort Myers SW Florida Intl

2h 45mnonstop

$313Southwest

Fri, Feb 12 - Mon, Feb 15

5:45 pm - 7:35 pmRSW Fort Myers SW Florida Intl-MDW Chicago Midway

2h 50mnonstop

1:00 pm - 4:45 pmMDW Chicago Midway-RSW Fort Myers SW Florida Intl

2h 45mnonstop

$313Southwest

Wed, Oct 21 - Sun, Oct 25

6:50 am - 8:45 amRSW Fort Myers SW Florida Intl-MDW Chicago Midway

2h 55mnonstop

6:40 pm - 10:30 pmMDW Chicago Midway-RSW Fort Myers SW Florida Intl

2h 50mnonstop

$313Southwest

Sat, Nov 7 - Sun, Nov 8

6:50 am - 8:45 amRSW Fort Myers SW Florida Intl-MDW Chicago Midway

2h 55mnonstop

5:05 am - 8:50 amMDW Chicago Midway-RSW Fort Myers SW Florida Intl

2h 45mnonstop

$313Southwest

Fri, Feb 12 - Mon, Feb 15

7:45 pm - 9:40 pmRSW Fort Myers SW Florida Intl-MDW Chicago Midway

2h 55mnonstop

7:55 pm - 11:40 pmMDW Chicago Midway-RSW Fort Myers SW Florida Intl

2h 45mnonstop

$317Southwest

Thu, Dec 10 - Mon, Dec 21

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Southwest flights from Fort Myers to Chicago Midway Airport

Our best Southwest deals on Fort Myers to Chicago Midway Airport flight tickets

Southwest

Oct 23

RSW6:40 pmFort Myers SW Florida Intl

2h 50m

MDW8:30 pmChicago Midway

Oct 26

MDW5:05 amChicago Midway

2h 40m

RSW8:45 amFort Myers SW Florida Intl

$283

Southwest

Oct 29

RSW5:50 amFort Myers SW Florida Intl

7h 55m

2 stops

MDW12:45 pmChicago Midway

Nov 4

MDW1:15 pmChicago Midway

6h 55m

2 stops

RSW9:10 pmFort Myers SW Florida Intl

$284

Southwest

Nov 6

RSW6:50 pmFort Myers SW Florida Intl

5h 25m

1 stop

MDW11:15 pmChicago Midway

Nov 9

MDW1:20 pmChicago Midway

7h 45m

2 stops

RSW10:05 pmFort Myers SW Florida Intl

$290

Delta flights from Fort Myers to Chicago Midway Airport

Our best Delta deals on Fort Myers to Chicago Midway Airport flight tickets

Delta

Oct 23

RSW7:40 amFort Myers SW Florida Intl

6h 07m

1 stop

MDW12:47 pmChicago Midway

Oct 26

MDW1:27 pmChicago Midway

7h 02m

1 stop

RSW9:29 pmFort Myers SW Florida Intl

$285

Delta

Oct 7

RSW12:31 pmFort Myers SW Florida Intl

6h 29m

1 stop

MDW6:00 pmChicago Midway

Oct 14

MDW9:29 amChicago Midway

6h 56m

1 stop

RSW5:25 pmFort Myers SW Florida Intl

$296

Delta

Oct 10

RSW2:15 pmFort Myers SW Florida Intl

4h 45m

1 stop

MDW6:00 pmChicago Midway

Oct 12

MDW1:27 pmChicago Midway

7h 02m

1 stop

RSW9:29 pmFort Myers SW Florida Intl

$309

momondo Fare Finder

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

Cheapest round-trip

Quickest round-trip

Fort MyersChicago

RSW Fort Myers SW Florida Intl - MDW Chicago Midway

RSWMDW

Fort Myers SW Florida Intl

Fri 10/23

6:40 pm-8:30 pm

Nonstop2h 50m

Chicago Midway

Mon 10/26

5:05 am-8:45 am

Nonstop2h 40m

$283

Fort MyersChicago

RSW Fort Myers SW Florida Intl - MDW Chicago Midway

RSWMDW

Fort Myers SW Florida Intl

Thu 10/29

5:50 am-12:45 pm

2 stops7h 55m

Chicago Midway

Wed 11/4

1:15 pm-9:10 pm

2 stops6h 55m

$284

Fort MyersChicago

RSW Fort Myers SW Florida Intl - MDW Chicago Midway

RSWMDW

Fort Myers SW Florida Intl

Fri 10/23

7:40 am-12:47 pm

1 stop6h 07m

Chicago Midway

Mon 10/26

1:27 pm-9:29 pm

1 stop7h 02m

$285

Fort MyersChicago

RSW Fort Myers SW Florida Intl - MDW Chicago Midway

RSWMDW

Fort Myers SW Florida Intl

Fri 12/11

6:20 am-1:50 pm

2 stops8h 30m

Chicago Midway

Mon 12/14

12:45 pm-7:45 pm

1 stop6h 00m

$290

Fort MyersChicago

RSW Fort Myers SW Florida Intl - MDW Chicago Midway

RSWMDW

Fort Myers SW Florida Intl

Fri 11/6

8:00 pm-12:10 am

1 stop5h 10m

Chicago Midway

Mon 11/9

12:55 pm-10:40 pm

2 stops8h 45m

$290

Fort MyersChicago

RSW Fort Myers SW Florida Intl - MDW Chicago Midway

RSWMDW

Fort Myers SW Florida Intl

Fri 11/6

6:50 pm-11:15 pm

1 stop5h 25m

Chicago Midway

Mon 11/9

1:20 pm-10:05 pm

2 stops7h 45m

$290

Fort MyersChicago

RSW Fort Myers SW Florida Intl - MDW Chicago Midway

RSWMDW

Fort Myers SW Florida Intl

Fri 11/6

7:15 pm-10:45 pm

1 stop4h 30m

Chicago Midway

Mon 11/9

12:55 pm-10:40 pm

2 stops8h 45m

$290

Fort MyersChicago

RSW Fort Myers SW Florida Intl - MDW Chicago Midway

RSWMDW

Fort Myers SW Florida Intl

Tue 1/26

2:15 pm-6:37 pm

1 stop5h 22m

Chicago Midway

Tue 2/2

10:35 am-6:53 pm

1 stop7h 18m

$291

Fort MyersChicago

RSW Fort Myers SW Florida Intl - MDW Chicago Midway

RSWMDW

Fort Myers SW Florida Intl

Fri 10/23

6:25 pm-11:55 pm

1 stop6h 30m

Chicago Midway

Mon 10/26

2:50 pm-11:00 pm

2 stops7h 10m

$291

Fort MyersChicago

RSW Fort Myers SW Florida Intl - MDW Chicago Midway

RSWMDW

Fort Myers SW Florida Intl

Thu 12/10

6:00 am-1:01 pm

1 stop8h 01m

Chicago Midway

Mon 12/14

1:41 pm-9:55 pm

1 stop7h 14m

$291

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

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

Prices

Airlines

Other information

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 $366.
The lowest price recently found on this route was $283.

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

The month of October is, on average, the cheapest month to fly to Chicago Midway Airport from Fort Myers, with most prices found around $297. If you are unable to visit Chicago Midway Airport during the month of October, then departing from Fort Myers during the month February is also very affordable. Most momondo users find prices during this month for around $302.

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

According to our data, Saturday is the cheapest day to fly to Chicago Midway Airport from Fort Myers. The lowest ticket price found for a Saturday departure recently was $404. 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?

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	$146
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 $146. The best round-trip flight deal from Fort Myers to Chicago Midway Airport found on momondo in the last 72 hours is $283.

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?
There is 1 operator available for flights from Fort Myers SW Florida Intl Airport to Chicago Midway Airport as of September 2026.
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?
momondo data reveals that the most frequently booked plane model on the route from Fort Myers to Chicago Midway Airport is Boeing 737 MAX 8, representing 22.59% of all bookings. The subsequent popular models are Boeing 737-800 at 12.08%, Boeing 737 MAX 9 at 11.38%, and Boeing 737-800 Passenger/BBJ2 (winglets) at 11.38%.
What is the most popular airline from Fort Myers to Chicago Midway Airport?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Fort Myers to Chicago Midway Airport is Southwest (100% of total bookings).

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
Southwest	PriceFrom $242	Free Cancellation	Rating 8.0 4,188 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 4 Southwest flights for this route in a normal week, average airfare is usually $356 round-trip - but some users have found much cheaper deals with momondo.

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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.

An easier way to manage your Chicago Midway Airport trip

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Cheap flights from Fort Myers to Chicago from $146

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 11/16. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Find the cheapest flights from Fort Myers to Chicago

Cheap round-trip flights

Cheap one-way flights

Cheap last minute flights

Cheap direct flights

Big names and deals

Big names and deals

Filter for what you want

Filter for what you want

Trusted and free

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Price Alerts

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Southwest flights from Fort Myers to Chicago Midway Airport

Our best Southwest deals on Fort Myers to Chicago Midway Airport flight tickets

Delta flights from Fort Myers to Chicago Midway Airport

Our best Delta deals on Fort Myers to Chicago Midway Airport flight tickets

momondo Fare Finder

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

See travel insights to Chicago from

How to get the cheapest flight ticket from Fort Myers to Chicago Midway Airport

What is the typical price of a round-trip flight between Fort Myers and Chicago Midway Airport?

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

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

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

What is the cheapest Fort Myers SW Florida Intl to Chicago Midway flight route?

What cabin class options are available on Fort Myers to Chicago Midway Airport flights?

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

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

What is the cheapest airline that flies from Fort Myers SW Florida Intl to Chicago Midway?

How many flights depart from Fort Myers to Chicago Midway Airport on average per week?

When to book flights from Fort Myers to Chicago Midway Airport

Cheap Fort Myers to Chicago Midway Airport (RSW to MDW) flight deals and tips

Best Price Found

Fastest flight time

Direct flights

Frequently asked questions about flying 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

Traveling to a place near Chicago?

Why use momondo?

An easier way to manage your Chicago Midway Airport trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to Chicago

Popular cities in the United States

Popular flights according to clicks in the last 7 days on momondo

Chicago Midway Airport flight routes

According to popular flight searches on momondo this year

Fly your favorite airline to Chicago

Airlines are sorted and displayed according to clicks in the past 7 days on momondo

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List of cabin classes available on flights landing in Chicago. Availability may vary depending on flight origin and airline.

Complete your trip to Chicago

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