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$90+ 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 7/4. Fares are subject to change and may not be available on all flights or dates of travel.
RSW — MDW
5月 5 — 5月 121
月 5/5
月 5/12
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 4月 30, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$208
(Southwest)

One-way from

$90
(Southwest)

Popular in

January

Cheapest in

June

Average price

$400
Provider with most accurate pricing for Fort Myers SW Florida Intl-Chicago Midway flight deals.
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Provider most trusted by Cheapflights users for Fort Myers SW Florida Intl-Chicago Midway flights.
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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. 21% potential increase in price ($118 potential increase over avg. RT price).
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Cheapest flight prices on average. 10% potential price decrease ($40 potential savings vs. average RT price).
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Average for round-trip flights in April 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 4月 30, 2025.

This Southwest deal was found by Cheapflights users on 4/28. 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.
土 5/245:50 pmRSW - MDW
Nonstop3h 00mSouthwest
火 5/278:45 amMDW - RSW
Nonstop2h 50mSouthwest
Deal found 4/28$208
This Delta deal was found by Cheapflights users on 4/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
木 5/298:00 amRSW - MDW
1 stop5h 28mDelta
火 6/36:00 amMDW - RSW
1 stop5h 22mDelta
Deal found 4/29$237
This CheapOair deal was found by Cheapflights users on 4/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
金 5/1610:11 amRSW - MDW
1 stop8h 17mFrontier
月 5/1912:15 pmMDW - RSW
1 stop8h 08mFrontier
Deal found 4/28$261
This Mytrip deal was found by Cheapflights users on 4/28. 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.
木 5/17:00 amRSW - MDW
3 stops25h 45mMultiple Airlines
月 5/58:35 amMDW - RSW
2 stops29h 53mMultiple Airlines
Deal found 4/28$724

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 4月 30, 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

土 5/31

5:30 am-9:40 am

1 stop5h 10m

Chicago Midway

火 6/3

1:55 pm-11:13 pm

1 stop8h 18m

$217

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

木 5/22

5:10 am-7:10 am

Nonstop3h 00m

Chicago Midway

日 5/25

7:20 pm-11:05 pm

Nonstop2h 45m

$221

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

金 5/16

10:11 am-5:28 pm

1 stop8h 17m

Chicago Midway

月 5/19

12:15 pm-9:23 pm

1 stop8h 08m

$270

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

金 7/4

4:20 pm-6:15 pm

Nonstop2h 55m

$90

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

土 5/31

5:30 am-9:40 am

1 stop5h 10m

$109

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

月 5/5

10:11 am-5:28 pm

1 stop8h 17m

$160

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

木 5/29

8:00 am-6:10 pm

2 stops35h 10m

$183

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

Compare providers for flights from Fort Myers to Midway

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Fort Myers to Midway in April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy2 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Fort Myers-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Fort Myers-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Fort Myers-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Fort Myers-Chicago Midway Airport flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Fort Myers-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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 4月 30, 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 4% on airfare.

Rainfall in Midway by month

Plan your trip to Midway by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

Plan your trip to Midway by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 4月 30, 2025.
Read through reviews of airlines operating flights from Fort Myers to Chicago, such as Southwest, Delta and Frontier. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,295 reviews

Boarding

8.2

Crew

8.6

Entertainment

7.6

Food

7.1

Overall

8.0

Comfort

8.0

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
4,295 reviews
Southwest
8.0
Very good
4,295 reviews

Boarding

8.2

Crew

8.6

Entertainment

7.6

Food

7.1

Overall

8.0

Comfort

8.0

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
7,929 reviews
Southwest
8.0
Very good
4,295 reviews

Boarding

8.2

Crew

8.6

Entertainment

7.6

Food

7.1

Overall

8.0

Comfort

8.0

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.
Frontier
6.0
Okay
3,284 reviews
Southwest
8.0
Very good
4,295 reviews

Boarding

8.2

Crew

8.6

Entertainment

7.6

Food

7.1

Overall

8.0

Comfort

8.0

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 are 2 flights 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 $208. Additional round-trip tickets that might be worth considering are offered by Delta and Frontier, with the lowest prices starting at $237 and $261, respectively. You may be able to fly from Fort Myers to Chicago Midway Airport for 52% less than the average price by searching for these airlines.

  • What are the cheapest airlines to fly from Fort Myers to Chicago Midway Airport one-way?

    $90 is the cheapest one-way deal found within the past few days, from Southwest. You may also be able to find cheap deals on Delta and Frontier, with prices starting from $109 and $160, respectively.

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

    On average you can expect to pay $276 for a flight from Fort Myers to Chicago Midway Airport. The cheapest flight overall is $89 while the most popular route, (Fort Myers SW Florida Intl - Chicago Midway) is currently priced at $208.

  • 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 Fort Myers?

Book flights to Fort Myers if you plan to visit one of these locations
Merrillville
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
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 4月 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$216Average$431FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$227Average$405FlexibilityNo cancel feeOn-time63%

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