Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

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 12/24. 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

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Fort Myers to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
5:45 pm - 10:12 pmRSW-MDW
5h 27m1 stop
Frontier Logo
6:15 am - 4:50 pmMDW-RSW
9h 35m1 stop
$150Frontier
Find Deal
lun., dic. 8 - lun., dic. 15
Frontier Logo
1:13 pm - 6:39 pmRSW-MDW
6h 26m1 stop
Frontier Logo
9:15 am - 8:33 pmMDW-RSW
10h 18m1 stop
$163Frontier
Find Deal
jue., nov. 6 - vie., nov. 14
Frontier Logo
1:13 pm - 6:39 pmRSW-MDW
6h 26m1 stop
Frontier Logo
5:20 am - 11:19 amMDW-RSW
4h 59m1 stop
$176Frontier
Find Deal
jue., oct. 30 - dom., nov. 2
Frontier Logo
1:13 pm - 10:03 pmRSW-MDW
9h 50m1 stop
Frontier Logo
9:15 am - 8:33 pmMDW-RSW
10h 18m1 stop
$179Frontier
Find Deal
jue., nov. 6 - jue., nov. 13
Southwest Logo
6:30 am - 8:25 amRSW-MDW
2h 55mnonstop
Southwest Logo
8:20 am - 12:10 pmMDW-RSW
2h 50mnonstop
$196Southwest
Find Deal
vie., dic. 5 - lun., dic. 8
Southwest Logo
6:50 am - 8:45 amRSW-MDW
2h 55mnonstop
Southwest Logo
6:15 pm - 10:10 pmMDW-RSW
2h 55mnonstop
$201Southwest
Find Deal
vie., nov. 14 - mar., nov. 18
Delta Logo
7:49 pm - 11:40 pmRSW-MDW
4h 51m1 stop
Delta Logo
6:00 am - 12:26 pmMDW-RSW
5h 26m1 stop
$217Delta
Find Deal
vie., nov. 14 - lun., nov. 17
Delta Logo
5:38 pm - 11:40 pmRSW-MDW
7h 02m1 stop
Delta Logo
5:34 pm - 12:37 amMDW-RSW
6h 03m1 stop
$222Delta
Find Deal
jue., nov. 13 - jue., nov. 27
Multiple Airlines Logo
6:00 am - 4:30 pmRSW-MDW
11h 30m2 stops
Multiple Airlines Logo
6:05 am - 3:14 pmMDW-RSW
8h 09m1 stop
$264Multiple Airlines
Find Deal
jue., nov. 20 - lun., nov. 24
Multiple Airlines Logo
1:13 pm - 6:39 pmRSW-MDW
6h 26m1 stop
Multiple Airlines Logo
6:15 am - 9:39 pmMDW-RSW
14h 24m2 stops
$275Multiple Airlines
Find Deal
jue., nov. 6 - lun., nov. 10

Frontier flights from Fort Myers to Chicago Midway Airport

Our best Frontier deals on Fort Myers to Chicago Midway Airport flight tickets
Frontier
Dec 8
RSW5:45 pmFort Myers SW Florida Intl
5h 27m
1 stop
MDW10:12 pmChicago Midway
Dec 15
MDW6:15 amChicago Midway
9h 35m
1 stop
RSW4:50 pmFort Myers SW Florida Intl
$150
Find similar
Frontier
Nov 6
RSW1:13 pmFort Myers SW Florida Intl
9h 50m
1 stop
MDW10:03 pmChicago Midway
Nov 9
MDW6:15 amChicago Midway
5h 03m
1 stop
RSW12:18 pmFort Myers SW Florida Intl
$163
Find similar
Frontier
Oct 30
RSW1:13 pmFort Myers SW Florida Intl
6h 26m
1 stop
MDW6:39 pmChicago Midway
Nov 2
MDW5:20 amChicago Midway
4h 59m
1 stop
RSW11:19 amFort Myers SW Florida Intl
$176
Find similar

Southwest flights from Fort Myers to Chicago Midway Airport

Our best Southwest deals on Fort Myers to Chicago Midway Airport flight tickets
Southwest
Dec 5
RSW6:30 amFort Myers SW Florida Intl
2h 55m
MDW8:25 amChicago Midway
Dec 8
MDW8:20 amChicago Midway
2h 50m
RSW12:10 pmFort Myers SW Florida Intl
$196
Find similar
Southwest
Nov 14
RSW6:50 amFort Myers SW Florida Intl
2h 55m
MDW8:45 amChicago Midway
Nov 18
MDW6:15 pmChicago Midway
2h 55m
RSW10:10 pmFort Myers SW Florida Intl
$201
Find similar
Southwest
Dec 5
RSW6:30 amFort Myers SW Florida Intl
2h 55m
MDW8:25 amChicago Midway
Dec 8
MDW6:40 amChicago Midway
7h 20m
1 stop
RSW3:00 pmFort Myers SW Florida Intl
$206
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 octubre 23, 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

lun. 12/8

5:45 pm-10:12 pm

1 stop5h 27m

Chicago Midway

lun. 12/15

6:15 am-4:50 pm

1 stop9h 35m

$150

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

jue. 11/6

1:13 pm-6:39 pm

1 stop6h 26m

Chicago Midway

vie. 11/14

9:15 am-8:33 pm

1 stop10h 18m

$163

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

jue. 10/30

1:13 pm-6:39 pm

1 stop6h 26m

Chicago Midway

dom. 11/2

5:20 am-11:19 am

1 stop4h 59m

$176

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

jue. 11/6

1:13 pm-10:03 pm

1 stop9h 50m

Chicago Midway

jue. 11/13

9:15 am-8:33 pm

1 stop10h 18m

$179

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

vie. 12/5

6:30 am-8:25 am

Nonstop2h 55m

Chicago Midway

lun. 12/8

8:20 am-12:10 pm

Nonstop2h 50m

$196

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

vie. 11/14

6:50 am-8:45 am

Nonstop2h 55m

Chicago Midway

mar. 11/18

6:15 pm-10:10 pm

Nonstop2h 55m

$201

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

vie. 11/14

7:49 pm-11:40 pm

1 stop4h 51m

Chicago Midway

lun. 11/17

6:00 am-12:26 pm

1 stop5h 26m

$217

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

jue. 11/13

5:38 pm-11:40 pm

1 stop7h 02m

Chicago Midway

jue. 11/27

5:34 pm-12:37 am

1 stop6h 03m

$222

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

jue. 11/20

6:00 am-4:30 pm

2 stops11h 30m

Chicago Midway

lun. 11/24

6:05 am-3:14 pm

1 stop8h 09m

$264

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

jue. 11/6

1:13 pm-6:39 pm

1 stop6h 26m

Chicago Midway

lun. 11/10

6:15 am-9:39 pm

2 stops14h 24m

$275

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 $376. 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 $436.

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?

You could potentially save up to 21% on your flight if you consider stops on a Fort Myers to Chicago Midway Airport flight.

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

$148

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 $148. The best round-trip flight deal from Fort Myers to Chicago Midway Airport found on momondo in the last 72 hours is $253.
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 $179Free CancellationRating
8.0
4,236 reviews
Search Southwest flights
DeltaPriceFrom $216Free CancellationRating
7.9
7,982 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 15 Southwest flights for this route in a normal week, average airfare is usually $379 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.

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.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
sáb. 11/22
sáb. 11/29
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago