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Midway

$72+ Cheap flights from Fort Myers (RSW) to Midway (MDW)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/28. Fares are subject to change and may not be available on all flights or dates of travel.
RSW — MDW
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
1 adult, Economy
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Cheap flight deals from Fort Myers to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Fort Myers (RSW) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated August 14, 2025.

Round-trip from

$143
(Mytrip)

One-way from

$72
(Booking.com)

Popular in

January

Cheapest in

August

Average price

$208
From Fort Myers SW Florida Intl to Chicago Midway
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One-way flight from Fort Myers SW Florida Intl to Chicago Midway
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Highest demand for flights based on searches. 25% potential increase in price ($140 potential increase over avg. RT price).
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Cheapest flight prices on average. 11% potential price decrease ($43 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Find flight deals from Fort Myers to Midway

Cheapest flights from Fort Myers to Midway
Explore the most affordable flight options available from Fort Myers to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 14, 2025.

This Mytrip deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/117:24 pmRSW - MDW
1 stop4h 56mFrontier
Sun 9/146:20 amMDW - RSW
1 stop11h 09mFrontier
Deal found 8/14$143
This Booking.com deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/187:24 pmRSW - MDW
1 stop4h 56mFrontier
Sun 9/216:20 amMDW - RSW
1 stop11h 09mFrontier
Deal found 8/14$144
This Priceline deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/1712:27 pmRSW - MDW
1 stop6h 00mFrontier
Sun 10/196:20 amMDW - RSW
1 stop4h 56mFrontier
Deal found 8/14$148
This Frontier deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/231:01 pmRSW - MDW
1 stop11h 24mFrontier
Fri 10/319:15 amMDW - RSW
1 stop10h 18mFrontier
Deal found 8/14$157
This Southwest deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/236:40 amRSW - MDW
Nonstop2h 50mSouthwest
Tue 10/2812:15 pmMDW - RSW
Nonstop2h 40mSouthwest
Deal found 8/14$158
This Southwest deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/125:40 pmRSW - MDW
Nonstop2h 50mSouthwest
Mon 9/157:00 pmMDW - RSW
Nonstop2h 45mSouthwest
Deal found 8/12$159
This FlightHub deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/47:24 pmRSW - MDW
1 stop21h 36mFrontier
Sun 9/78:06 amMDW - RSW
1 stop23h 52mFrontier
Deal found 8/14$164
This Southwest deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/125:40 pmRSW - MDW
Nonstop2h 50mSouthwest
Fri 9/197:00 pmMDW - RSW
Nonstop2h 45mSouthwest
Deal found 8/13$171
This Southwest deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/309:15 amRSW - MDW
Nonstop2h 50mSouthwest
Fri 10/37:15 pmMDW - RSW
Nonstop2h 40mSouthwest
Deal found 8/13$183
This Frontier deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/261:01 pmRSW - MDW
1 stop11h 24mFrontier
Thu 10/309:15 amMDW - RSW
1 stop10h 18mFrontier
Deal found 8/14$184
This Southwest deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/116:50 amRSW - MDW
Nonstop2h 50mSouthwest
Sun 9/149:15 amMDW - RSW
Nonstop2h 45mSouthwest
Deal found 8/14$186
This Southwest deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/41:20 pmRSW - MDW
Nonstop2h 55mSouthwest
Mon 9/87:00 pmMDW - RSW
Nonstop2h 45mSouthwest
Deal found 8/14$189

Cheapflights Fare Finder

 
Customize your flight search to find flights from Fort Myers to Midway 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, Cheapflights users made 2,558,603 searches. Data last updated August 14, 2025.
Use the filters below to find and compare flights from Fort Myers to Chicago Midway Airport that are best for you.

Fly from

Fort Myers

Fly to

Midway

Route

Depart

Return

Price

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Thu 9/11

7:24 pm-11:20 pm

1 stop4h 56m

Chicago Midway

Sun 9/14

6:20 am-6:29 pm

1 stop11h 09m

$143

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Thu 9/25

7:24 pm-11:20 pm

1 stop4h 56m

Chicago Midway

Sun 9/28

6:20 am-6:29 pm

1 stop11h 09m

$144

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Thu 11/6

1:13 pm-6:39 pm

1 stop6h 26m

Chicago Midway

Sun 11/9

6:20 am-12:18 pm

1 stop4h 58m

$144

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Thu 9/18

7:24 pm-11:20 pm

1 stop4h 56m

Chicago Midway

Sun 9/21

6:20 am-6:29 pm

1 stop11h 09m

$144

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Fri 10/17

12:27 pm-5:27 pm

1 stop6h 00m

Chicago Midway

Sun 10/19

6:20 am-12:16 pm

1 stop4h 56m

$148

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Thu 10/23

1:01 pm-11:25 pm

1 stop11h 24m

Chicago Midway

Fri 10/31

9:15 am-8:33 pm

1 stop10h 18m

$157

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Thu 10/23

1:01 pm-11:25 pm

1 stop11h 24m

Chicago Midway

Sun 10/26

8:25 am-9:21 pm

1 stop11h 56m

$157

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Thu 10/23

1:01 pm-11:25 pm

1 stop11h 24m

Chicago Midway

Thu 10/30

9:15 am-8:33 pm

1 stop10h 18m

$157

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Thu 10/23

6:40 am-8:30 am

Nonstop2h 50m

Chicago Midway

Tue 10/28

12:15 pm-3:55 pm

Nonstop2h 40m

$158

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Fri 10/24

12:10 pm-2:05 pm

Nonstop2h 55m

Chicago Midway

Mon 10/27

5:15 am-8:55 am

Nonstop2h 40m

$159

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/14

Showing 1-10 of 23 results
1
2
3

The best insider tips for Fort Myers to Chicago Midway Airport flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
Cheapflights partnered with top experts to bring you the best recommendations for your Fort Myers to Chicago Midway Airport trip
Airports
RSW

During peak tourist seasons, plan an extra 20 minutes for check-in at RSW due to smaller airline ticket counters.

Read more about RSWby Matt Meltzer
MDW

The Orange Line train is a convenient and cheap way to reach downtown Chicago from MDW, taking less than 30 minutes.

Read more about MDWby Ramsey Qubein
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on MDW

Ramsey Qubein

Ramsey Qubein

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more
Matt Meltzer

Matt Meltzer

Expert on RSW

Matt Meltzer

Matt Meltzer

Matt Meltzer has been a travel writer for over a decade, covering U.S. domestic locations and hotels for Thrillist, Fifty Grande, Matador Network, Conde Nast Traveler, and other top publications. He's won multiple travel journalism awards from the Society of American Travel Writers and North American Travel Journalists Association, and currently resides in South Florida.

Read more

Best time to book a flight from Fort Myers to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Fort Myers with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Fort Myers to Chicago Midway Airport

What is the cheapest month to book a flight from Fort Myers to Chicago Midway Airport?

Currently, April is the cheapest month in which you can book a flight from Fort Myers to Chicago Midway Airport (average of $160). Flying from Fort Myers to Chicago Midway Airport in November is currently the most expensive (average of $249). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from RSW to MDW?

Find hourly flight availability from Fort Myers to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 14, 2025.

One of the essential ways to save on airfare from Fort Myers to Chicago Midway Airport is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the afternoon could potentially save you up to 13% on airfare.

What is the cheapest day to fly from Fort Myers to Chicago Midway Airport?

Use this chart to determine the cheapest time to fly round-trip from Fort Myers to Midway. Price data was last updated on August 10, 2025.

Travelers seeking maximum savings on their Fort Myers to Chicago Midway Airport flight should consider departing on Friday afternoons when fares are most often at their lowest. Tuesday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated August 14, 2025.
Get a feel of what it's like to fly with Southwest and Delta from Fort Myers to Chicago Midway Airport by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,244 reviews

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Southwest
8.0
Very good
4,244 reviews
Southwest
8.0
Very good
4,244 reviews

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Delta
8.0
Very good
7,980 reviews
Southwest
8.0
Very good
4,244 reviews

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Related info for your journey

Find useful and relevant information for your journey from Fort Myers to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Fort Myers to Chicago Midway?

    If you book a flight to Chicago Midway from Fort Myers, you will be flying from SW Florida Intl, which is the city’s only airport. Fort Myers SW Florida Intl (RSW) is located 10.0 mi from the center of Fort Myers. There is 1 flight from SW Florida Intl to Chicago Midway per day from 2 different airlines.

  • What are the cheapest airlines flying from Fort Myers to Chicago Midway Airport round-trip?

    Flying on Southwest is currently your cheapest option to Chicago Midway Airport, with prices starting at $183. Another option worth looking into is Delta, starting at $216 round trip. You may be able to fly from Fort Myers to Chicago Midway Airport for 55% less than the average price by searching for these airlines.

  • What are the cheapest flights from Fort Myers to Chicago Midway Airport?

    On average you can expect to pay $231 for a flight from Fort Myers to Chicago Midway Airport. The cheapest flight overall is $92 while the most popular route, (Fort Myers SW Florida Intl - Chicago Midway) is currently priced at $158.

  • Can I find deals for flights from Fort Myers to Midway that include hotel bookings?

    Yes. In addition to deals on Fort Myers to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Fort Myers to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Fort Myers to Midway.

  • Can I find deals for business class flights from Fort Myers to Midway?

    Yes. Cheapflights offers flight deals from Fort Myers to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Fort Myers to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Fort Myers to Chicago Midway Airport (average of $160). Flying from Fort Myers to Chicago Midway Airport in November is currently the most expensive (average of $249). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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Top 2 airlines flying from Fort Myers to Midway

Discover the top 2 airlines that operate flights from Fort Myers to Midway. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$183Average$386FlexibilityNo cancel feeOn-time63%
DeltaCheapest$216Average$386FlexibilityNo cancel feeOn-timeN/A

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