$149+ Cheap flights from Midway (MDW) to Fort Myers (RSW)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/5. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — RSW
Oct 6 — Oct 131
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Midway to Fort Myers with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from Chicago Midway to Fort Myers SW Florida Intl are usually found in January or September, booked 61 days in advance, depart on a Monday or Wednesday and return on a Thursday
Cheap flight deals from Midway to Fort Myers
Cheapest
Best
Last-minute
One-way
Cheapest flights from Midway to Fort MyersExplore the most affordable flight options available from Midway to Fort Myers. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 6, 2026.
Explore the most affordable flight options available from Midway to Fort Myers. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 6, 2026.
This Southwest deal was found by Cheapflights users on 9/1. 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 11/125:05 am -
Nonstop2h 45m
Mon 11/167:00 am -
Nonstop2h 55m
Deal found 9/1![Southwest logo]()
$297
This Southwest deal was found by Cheapflights users on 9/2. 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 10/206:35 pm -
Nonstop2h 50m
Wed 10/281:55 pm -
1 stop4h 15m
Deal found 9/2![Southwest logo]()
$303
This Southwest deal was found by Cheapflights users on 9/3. 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 11/126:40 pm -
Nonstop2h 45m
Wed 11/1811:50 am -
1 stop6h 20m
Deal found 9/3![Southwest logo]()
$307
This Southwest deal was found by Cheapflights users on 9/1. 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.
Sat 9/263:05 pm -
Nonstop2h 50m
Wed 9/307:10 am -
Nonstop2h 45m
Deal found 9/1![Southwest logo]()
$308
This Southwest deal was found by Cheapflights users on 9/2. 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.
Sat 11/73:35 pm -
Nonstop2h 45m
Sat 11/1410:55 am -
2 stops7h 25m
Deal found 9/2![Southwest logo]()
$312
This Southwest deal was found by Cheapflights users on 9/1. 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.
Sat 10/104:10 pm -
Nonstop2h 50m
Wed 10/141:55 pm -
1 stop4h 15m
Deal found 9/1![Southwest logo]()
$314
This Delta deal was found by Cheapflights users on 9/2. 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.
Wed 10/216:04 am -
1 stop5h 03m
Sat 10/246:30 pm -
1 stop5h 03m
Deal found 9/2![Delta logo]()
$317
This Southwest deal was found by Cheapflights users on 9/1. 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 10/912:45 pm -
1 stop6h 30m
Mon 10/126:40 am -
Nonstop2h 50m
Deal found 9/1![Southwest logo]()
$318
This Southwest deal was found by Cheapflights users on 9/1. 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.
Sat 10/104:10 pm -
Nonstop2h 50m
Tue 10/135:45 pm -
Nonstop2h 50m
Deal found 9/1![Southwest logo]()
$319
This Southwest deal was found by Cheapflights users on 9/2. 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 10/69:35 am -
1 stop7h 25m
Wed 10/147:20 am -
2 stops8h 20m
Deal found 9/2![Southwest logo]()
$322
This Southwest deal was found by Cheapflights users on 9/2. 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.
Mon 10/266:50 pm -
Nonstop2h 50m
Fri 10/309:20 am -
2 stops6h 35m
Deal found 9/2![Southwest logo]()
$323
This Southwest deal was found by Cheapflights users on 9/2. 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 9/249:00 am -
Nonstop2h 45m
Mon 9/286:10 am -
1 stop10h 20m
Deal found 9/2![Southwest logo]()
$324
Best flights from Midway to Fort MyersDiscover carefully curated flight deals from Midway to Fort Myers that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 6, 2026.
Discover carefully curated flight deals from Midway to Fort Myers that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 6, 2026.
This Delta deal was found by Cheapflights users on 9/3. 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.
Sat 10/311:27 pm -
1 stop4h 53m
Sat 11/75:30 am -
1 stop6h 07m
Deal found 9/3![Delta logo]()
$317
This Southwest deal was found by Cheapflights users on 9/1. 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.
Sat 10/104:10 pm -
Nonstop2h 50m
Tue 10/135:45 pm -
Nonstop2h 50m
Deal found 9/1![Southwest logo]()
$319
This Southwest deal was found by Cheapflights users on 9/5. 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 10/225:05 am -
Nonstop2h 40m
Wed 10/2812:25 pm -
Nonstop2h 50m
Deal found 9/5![Southwest logo]()
$325
This Southwest deal was found by Cheapflights users on 9/1. 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 10/912:45 pm -
1 stop6h 30m
Tue 10/135:45 pm -
Nonstop2h 50m
Deal found 9/1![Southwest logo]()
$329
This Delta deal was found by Cheapflights users on 9/4. 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.
Sat 11/149:30 am -
1 stop6h 48m
Sat 11/216:23 pm -
1 stop5h 31m
Deal found 9/4![Delta logo]()
$365
This Southwest deal was found by Cheapflights users on 9/4. 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.
Sat 10/244:10 pm -
Nonstop2h 50m
Tue 10/271:55 pm -
1 stop4h 15m
Deal found 9/4![Southwest logo]()
$331
This Delta deal was found by Cheapflights users on 9/2. 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.
Thu 12/31:02 pm -
1 stop4h 50m
Sun 12/66:00 am -
1 stop8h 01m
Deal found 9/2![Delta logo]()
$372
This Southwest deal was found by Cheapflights users on 9/1. 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.
Mon 10/195:05 am -
Nonstop2h 40m
Sun 11/16:20 am -
2 stops8h 30m
Deal found 9/1![Southwest logo]()
$357
This Southwest deal was found by Cheapflights users on 9/1. 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.
Wed 10/218:10 am -
1 stop7h 55m
Sun 10/258:40 pm -
1 stop4h 30m
Deal found 9/1![Southwest logo]()
$362
This Southwest deal was found by Cheapflights users on 9/5. 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.
Sun 10/188:10 am -
Nonstop2h 45m
Tue 10/208:35 am -
2 stops9h 20m
Deal found 9/5![Southwest logo]()
$371
This Southwest deal was found by Cheapflights users on 9/1. 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.
Wed 12/21:15 pm -
2 stops6h 50m
Sun 12/66:20 am -
2 stops8h 30m
Deal found 9/1![Southwest logo]()
$383
Last-minute flights from Midway to Fort MyersDiscover last-minute flight deals from Midway to Fort Myers. Data last updated September 6, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Fort Myers. Data last updated September 6, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 9/2. 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 9/249:00 am -
Nonstop2h 45m
Mon 9/286:10 am -
1 stop10h 20m
Deal found 9/2![Southwest logo]()
$324
This Southwest deal was found by Cheapflights users on 9/1. 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.
Sat 9/263:05 pm -
Nonstop2h 50m
Wed 9/307:10 am -
Nonstop2h 45m
Deal found 9/1![Southwest logo]()
$308
This Southwest deal was found by Cheapflights users on 9/2. 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 10/61:40 pm -
2 stops6h 35m
Thu 10/86:20 pm -
1 stop7h 05m
Deal found 9/2![Southwest logo]()
$322
This Southwest deal was found by Cheapflights users on 9/3. 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.
Wed 10/74:30 pm -
1 stop4h 45m
Thu 10/86:40 pm -
Nonstop2h 50m
Deal found 9/3![Southwest logo]()
$307
This Southwest deal was found by Cheapflights users on 9/1. 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 10/912:45 pm -
1 stop6h 30m
Mon 10/126:40 am -
Nonstop2h 50m
Deal found 9/1![Southwest logo]()
$318
This Southwest deal was found by Cheapflights users on 9/1. 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.
Sat 10/104:10 pm -
Nonstop2h 50m
Wed 10/141:55 pm -
1 stop4h 15m
Deal found 9/1![Southwest logo]()
$314
This Southwest deal was found by Cheapflights users on 9/1. 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.
Sat 10/104:10 pm -
Nonstop2h 50m
Tue 10/135:45 pm -
Nonstop2h 50m
Deal found 9/1![Southwest logo]()
$319
This Southwest deal was found by Cheapflights users on 9/2. 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 10/206:35 pm -
Nonstop2h 50m
Wed 10/285:45 pm -
Nonstop2h 50m
Deal found 9/2![Southwest logo]()
$297
This Delta deal was found by Cheapflights users on 9/2. 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.
Wed 10/216:04 am -
1 stop5h 03m
Sat 10/246:30 pm -
1 stop5h 03m
Deal found 9/2![Delta logo]()
$317
This Southwest deal was found by Cheapflights users on 9/2. 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.
Mon 10/266:50 pm -
Nonstop2h 50m
Fri 10/309:20 am -
2 stops6h 35m
Deal found 9/2![Southwest logo]()
$323
One-way flights from Midway to Fort MyersSearch for one-way flight options from Midway to Fort Myers. Find affordable one-way fares based on user searches. Data last updated September 6, 2026.
Search for one-way flight options from Midway to Fort Myers. Find affordable one-way fares based on user searches. Data last updated September 6, 2026.
This Southwest deal was found by Cheapflights users on 9/3. 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.
Mon 10/56:50 pm -
Nonstop2h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Southwest logo]()
$149
This Delta deal was found by Cheapflights users on 9/2. 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.
Tue 10/131:27 pm -
1 stop7h 02m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Delta logo]()
$158
This Southwest deal was found by Cheapflights users on 9/2. 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.
Wed 10/144:30 pm -
1 stop4h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Southwest logo]()
$159
This Southwest deal was found by Cheapflights users on 9/3. 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 10/25:05 am -
Nonstop2h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Southwest logo]()
$160
This Southwest deal was found by Cheapflights users on 9/1. 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 11/101:15 pm -
2 stops6h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/1![Southwest logo]()
$164
This Delta deal was found by Cheapflights users on 9/4. 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.
Tue 10/201:27 pm -
1 stop7h 02m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Delta logo]()
$169
This Kiwi.com deal was found by Cheapflights users on 9/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/126:42 pm -
2 stops24h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Frontier logo]()
$172
Find flight deals from Midway to Fort Myers
Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Fort Myers (RSW). 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 September 6, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $292 (Southwest) |
One-way from | $149 (Southwest) |
Popular in | March |
Cheapest in | January |
Average price | $295 |
Cheapflights Fare Finder
Customize your flight search to find flights from Midway to Fort Myers 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 7,457,451 searches. Data last updated September 6, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Fort Myers that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoFort Myers
MDW Chicago Midway - RSW Fort Myers SW Florida Intl
MDWRSW
Chicago Midway
Mon 10/5
6:50 pm-10:40 pm
Nonstop2h 50m
Fort Myers SW Florida Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$149
ChicagoFort Myers
MDW Chicago Midway - RSW Fort Myers SW Florida Intl
MDWRSW
Chicago Midway
Wed 11/18
10:10 am-6:40 pm
1 stop7h 30m
Fort Myers SW Florida Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$159
ChicagoFort Myers
MDW Chicago Midway - RSW Fort Myers SW Florida Intl
MDWRSW
Chicago Midway
Wed 10/14
4:30 pm-10:15 pm
1 stop4h 45m
Fort Myers SW Florida Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$159
ChicagoFort Myers
MDW Chicago Midway - RSW Fort Myers SW Florida Intl
MDWRSW
Chicago Midway
Thu 10/29
6:50 pm-10:40 pm
Nonstop2h 50m
Fort Myers SW Florida Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$163
ChicagoFort Myers
MDW Chicago Midway - RSW Fort Myers SW Florida Intl
MDWRSW
Chicago Midway
Tue 11/10
1:15 pm-9:05 pm
2 stops6h 50m
Fort Myers SW Florida Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$164
ChicagoFort Myers
MDW Chicago Midway - RSW Fort Myers SW Florida Intl
MDWRSW
Chicago Midway
Sat 9/26
7:45 am-3:40 pm
1 stop6h 55m
Fort Myers SW Florida Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$192
Quickest round-trip
ChicagoFort Myers
MDW Chicago Midway - RSW Fort Myers SW Florida Intl
MDWRSW
Chicago Midway
Mon 11/30
7:55 pm-11:40 pm
Nonstop2h 45m
Fort Myers SW Florida Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$193
ChicagoFort Myers
MDW Chicago Midway - RSW Fort Myers SW Florida Intl
MDWRSW
Chicago Midway
Sat 10/31
1:27 pm-7:20 pm
1 stop4h 53m
Fort Myers SW Florida Intl
Sat 11/7
5:30 am-10:37 am
1 stop6h 07m
$317
ChicagoFort Myers
MDW Chicago Midway - RSW Fort Myers SW Florida Intl
MDWRSW
Chicago Midway
Sat 10/10
4:10 pm-8:00 pm
Nonstop2h 50m
Fort Myers SW Florida Intl
Tue 10/13
5:45 pm-7:35 pm
Nonstop2h 50m
$319
ChicagoFort Myers
MDW Chicago Midway - RSW Fort Myers SW Florida Intl
MDWRSW
Chicago Midway
Thu 10/22
5:05 am-8:45 am
Nonstop2h 40m
Fort Myers SW Florida Intl
Wed 10/28
12:25 pm-2:15 pm
Nonstop2h 50m
$325
Showing 1-10 of 18 resultsSorted by cheapest first
Compare providers for flights from Midway to Fort Myers
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 Midway to Fort Myers in September.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Chicago Midway Airport-Fort Myers flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-Fort Myers flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Fort Myers flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago Midway Airport-Fort Myers flights, Cheapflights users trust FlightHub the most. FlightHub 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 Chicago Midway Airport-Fort Myers 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 Midway to Fort Myers
Have a flexible travel schedule? Discover the best time to fly to Fort Myers from Midway with our price prediction graph.
MDW-RSW
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 Chicago Midway Airport to Fort Myers
How far ahead should I book a flight from Chicago Midway Airport to Fort Myers?
The best time to book flights from Chicago Midway Airport to Fort Myers is 60 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
What is the cheapest month to book a flight from Chicago Midway Airport to Fort Myers?
Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Fort Myers (average of $264). Flying from Chicago Midway Airport to Fort Myers in March is currently the most expensive (average of $520). 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 MDW to RSW?
Find hourly flight availability from Midway to Fort Myers. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 6, 2026.
Unlike in the evening, when flights are generally more expensive, you can save up to 25% on flights from Chicago Midway Airport to Fort Myers by exploring options for tickets in the afternoon.
What is the cheapest day to fly from Chicago Midway Airport to Fort Myers?
Use this chart to determine the cheapest time to fly round-trip from Midway to Fort Myers. Price data was last updated on August 29, 2026.
Travelers seeking maximum savings on their Chicago Midway Airport to Fort Myers flight should consider departing on Wednesday at noon when fares are most often at their lowest. Wednesday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
The best insider tips for Chicago Midway Airport to Fort Myers flights
AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Chicago Midway Airport to Fort Myers trip
Our travel experts
Reviews of airlines servicing Fort Myers
Get insights into the airlines that provide service to Fort Myers. 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 Fort Myers. Reviews last updated September 6, 2026.
Read reviews from past customers who have flown Southwest and Delta from Chicago Midway Airport to Fort Myers. 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.
Entertainment
7.5
Crew
8.6
Overall
8.0
Boarding
8.1
Comfort
8.0
Food
7.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Entertainment
7.5
Crew
8.6
Overall
8.0
Boarding
8.1
Comfort
8.0
Food
7.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Entertainment
7.5
Crew
8.6
Overall
8.0
Boarding
8.1
Comfort
8.0
Food
7.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Related info for your journey
Find useful and relevant information for your journey from Midway to Fort Myers. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Fort Myers?
Book flights to Fort Myers if you plan to visit one of these locationsNorth Fort Myers
Lehigh Acres
Sanibel
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Other flight options
Other flights from Midway
Popular flights
Alternative routes for Midway to Fort Myers
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Fort Myers by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Midway to Fort Myers by cabin class
Find flights from Midway to Fort Myers, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Midway and Fort Myers flights
Browse other Midway and Fort Myers flight options. Last updated on September 6, 2026.
Other flights from Midway
Browse through other flights departing from Midway. Flights are based on user searches made on Cheapflights and were last updated on September 6, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 2 airlines flying from Midway to Fort Myers
Discover the top 2 airlines that operate flights from Midway to Fort Myers. 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 7,457,451 searches. Data last updated September 6, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$216 | Average$405 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$237 | Average$380 | FlexibilityNo cancel fee | On-time63% |