$146+ Cheap flights from Fort Myers (RSW) to Midway (MDW)
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 11/9. Fares are subject to change and may not be available on all flights or dates of travel.
RSW — MDW
Oct 21 — Oct 281
Round-trip
1 adult, Economy
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Find cheap flights from Fort Myers to Midway 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.Cheap flight deals from Fort Myers to Midway
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Best
Last-minute
One-way
Cheapest flights from Fort Myers to MidwayExplore 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 September 21, 2026.
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 September 21, 2026.
This Southwest deal was found by Cheapflights users on 9/17. 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 12/31:35 pm -
2 stops7h 10m
Mon 12/71:15 pm -
2 stops6h 50m
Deal found 9/17![Southwest logo]()
$280
This Southwest deal was found by Cheapflights users on 9/17. 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 11/64:35 pm -
Nonstop2h 55m
Mon 11/95:05 am -
Nonstop2h 45m
Deal found 9/17![Southwest logo]()
$281
This Southwest deal was found by Cheapflights users on 9/17. 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 11/42:55 pm -
Nonstop3h 05m
Sat 11/77:55 am -
Nonstop2h 50m
Deal found 9/17![Southwest logo]()
$282
This Delta deal was found by Cheapflights users on 9/16. 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.
Fri 10/237:40 am -
1 stop6h 07m
Mon 10/261:27 pm -
1 stop7h 02m
Deal found 9/16![Delta logo]()
$285
This Southwest deal was found by Cheapflights users on 9/17. 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 10/167:25 pm -
1 stop4h 45m
Tue 10/202:10 pm -
1 stop4h 35m
Deal found 9/17![Southwest logo]()
$286
This Southwest deal was found by Cheapflights users on 9/17. 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 12/41:35 pm -
2 stops7h 10m
Sat 12/510:25 am -
1 stop6h 15m
Deal found 9/17![Southwest logo]()
$291
This Southwest deal was found by Cheapflights users on 9/17. 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 10/177:30 am -
Nonstop2h 50m
Tue 10/203:25 pm -
1 stop5h 40m
Deal found 9/17![Southwest logo]()
$292
This Delta deal was found by Cheapflights users on 9/17. 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.
Fri 12/46:27 pm -
1 stop5h 28m
Mon 12/71:41 pm -
1 stop7h 14m
Deal found 9/17![Delta logo]()
$296
This Southwest deal was found by Cheapflights users on 9/17. 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 10/156:40 am -
Nonstop2h 50m
Mon 10/196:50 pm -
Nonstop2h 50m
Deal found 9/17![Southwest logo]()
$297
This Southwest deal was found by Cheapflights users on 9/17. 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 10/179:25 am -
1 stop6h 50m
Wed 10/219:35 am -
1 stop7h 25m
Deal found 9/17![Southwest logo]()
$302
Best flights from Fort Myers to MidwayDiscover carefully curated flight deals from Fort Myers to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 21, 2026.
Discover carefully curated flight deals from Fort Myers to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 21, 2026.
This Delta deal was found by Cheapflights users on 9/16. 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.
Fri 10/237:40 am -
1 stop6h 07m
Mon 10/261:27 pm -
1 stop7h 02m
Deal found 9/16![Delta logo]()
$285
This Southwest deal was found by Cheapflights users on 9/17. 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 12/47:45 pm -
Nonstop2h 55m
Mon 12/711:45 am -
1 stop6h 15m
Deal found 9/17![Southwest logo]()
$291
This Delta deal was found by Cheapflights users on 9/16. 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 11/186:00 am -
1 stop7h 51m
Fri 1/13:30 pm -
1 stop4h 40m
Deal found 9/16![Delta logo]()
$309
This Southwest deal was found by Cheapflights users on 9/17. 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 10/196:40 am -
Nonstop2h 50m
Wed 11/46:45 am -
Nonstop2h 45m
Deal found 9/17![Southwest logo]()
$313
This Southwest deal was found by Cheapflights users on 9/18. 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 10/156:40 pm -
Nonstop2h 50m
Mon 10/195:00 am -
1 stop5h 45m
Deal found 9/18![Southwest logo]()
$323
This Delta deal was found by Cheapflights users on 9/20. 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 11/185:30 am -
2 stops12h 09m
Thu 11/2612:05 pm -
1 stop7h 56m
Deal found 9/20![Delta logo]()
$344
This Southwest deal was found by Cheapflights users on 9/17. 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 11/187:10 am -
1 stop5h 10m
Mon 11/2312:45 pm -
2 stops8h 00m
Deal found 9/17![Southwest logo]()
$326
This Delta deal was found by Cheapflights users on 9/16. 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 11/125:30 am -
1 stop5h 54m
Sun 11/155:13 pm -
1 stop6h 27m
Deal found 9/16![Delta logo]()
$348
This Southwest deal was found by Cheapflights users on 9/16. 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 12/107:10 am -
2 stops8h 45m
Mon 12/217:55 pm -
Nonstop2h 45m
Deal found 9/16![Southwest logo]()
$332
This Southwest deal was found by Cheapflights users on 9/19. 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 11/126:20 am -
2 stops8h 30m
Mon 11/1611:45 am -
1 stop6h 15m
Deal found 9/19![Southwest logo]()
$338
This Southwest deal was found by Cheapflights users on 9/18. 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 11/26:20 am -
2 stops8h 30m
Wed 11/46:45 am -
Nonstop2h 45m
Deal found 9/18![Southwest logo]()
$344
This Southwest deal was found by Cheapflights users on 9/19. 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 10/177:30 am -
Nonstop2h 50m
Tue 10/203:25 pm -
1 stop5h 40m
Deal found 9/19![Southwest logo]()
$346
Last-minute flights from Fort Myers to MidwayDiscover last-minute flight deals from Fort Myers to Midway. Data last updated September 21, 2026 and is based on user searches.
Discover last-minute flight deals from Fort Myers to Midway. Data last updated September 21, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 9/17. 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 10/712:31 pm -
1 stop6h 29m
Wed 10/149:29 am -
1 stop6h 56m
Deal found 9/17![Delta logo]()
$296
This Delta deal was found by Cheapflights users on 9/16. 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 10/102:15 pm -
1 stop4h 45m
Mon 10/121:27 pm -
1 stop7h 02m
Deal found 9/16![Delta logo]()
$309
This Southwest deal was found by Cheapflights users on 9/16. 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 10/147:20 am -
2 stops8h 20m
Wed 10/211:05 pm -
2 stops5h 40m
Deal found 9/16![Southwest logo]()
$312
This Southwest deal was found by Cheapflights users on 9/17. 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 10/156:40 am -
Nonstop2h 50m
Mon 10/196:50 pm -
Nonstop2h 50m
Deal found 9/17![Southwest logo]()
$297
This Southwest deal was found by Cheapflights users on 9/17. 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 10/167:25 pm -
1 stop4h 45m
Tue 10/202:10 pm -
1 stop4h 35m
Deal found 9/17![Southwest logo]()
$286
This Southwest deal was found by Cheapflights users on 9/17. 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 10/166:40 pm -
Nonstop2h 50m
Mon 10/193:45 pm -
1 stop6h 15m
Deal found 9/17![Southwest logo]()
$291
This Southwest deal was found by Cheapflights users on 9/17. 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 10/177:30 am -
Nonstop2h 50m
Tue 10/203:25 pm -
1 stop5h 40m
Deal found 9/17![Southwest logo]()
$292
This Southwest deal was found by Cheapflights users on 9/17. 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 10/179:25 am -
1 stop6h 50m
Wed 10/219:35 am -
1 stop7h 25m
Deal found 9/17![Southwest logo]()
$302
This Southwest deal was found by Cheapflights users on 9/17. 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 10/2111:35 am -
1 stop5h 30m
Thu 10/228:00 am -
2 stops7h 10m
Deal found 9/17![Southwest logo]()
$307
This Delta deal was found by Cheapflights users on 9/16. 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.
Fri 10/237:40 am -
1 stop6h 07m
Mon 10/261:27 pm -
1 stop7h 02m
Deal found 9/16![Delta logo]()
$285
One-way flights from Fort Myers to MidwaySearch for one-way flight options from Fort Myers to Midway. Find affordable one-way fares based on user searches. Data last updated September 21, 2026.
Search for one-way flight options from Fort Myers to Midway. Find affordable one-way fares based on user searches. Data last updated September 21, 2026.
This Delta deal was found by Cheapflights users on 9/17. 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.
Mon 11/96:00 am -
1 stop7h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Delta logo]()
$146
This Kiwi.com deal was found by Cheapflights users on 9/20. 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.
Fri 10/169:04 pm -
2 stops27h 39m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Frontier logo]()
$147
This Delta deal was found by Cheapflights users on 9/16. 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.
Fri 10/1612:31 pm -
1 stop6h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Delta logo]()
$151
This Southwest deal was found by Cheapflights users on 9/17. 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 10/196:40 am -
Nonstop2h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Southwest logo]()
$157
This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
Wed 10/146:26 pm -
2 stops30h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Multiple Airlines logo]()
$158
This Kiwi.com deal was found by Cheapflights users on 9/19. 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.
Wed 10/211:11 pm -
2 stops35h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Frontier logo]()
$160
This Kiwi.com deal was found by Cheapflights users on 9/20. 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.
Tue 10/201:11 pm -
2 stops35h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Frontier logo]()
$161
This Kiwi.com deal was found by Cheapflights users on 9/19. 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.
Tue 11/101:12 pm -
2 stops35h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Frontier logo]()
$163
This Kiwi.com deal was found by Cheapflights users on 9/19. 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 10/229:04 pm -
2 stops27h 39m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Frontier logo]()
$165
This Southwest deal was found by Cheapflights users on 9/16. 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 11/249:45 pm -
Nonstop3h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Southwest logo]()
$166
This Southwest deal was found by Cheapflights users on 9/20. 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 10/208:35 am -
1 stop5h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Southwest logo]()
$167
Find 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 September 21, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $280 (Southwest) |
One-way from | $146 (Delta) |
Popular in | March |
Cheapest in | October |
Average price | $313 |
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 7,457,451 searches. Data last updated September 21, 2026.
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
Cheapest round-trip
Fort MyersChicago
RSW Fort Myers SW Florida Intl - MDW Chicago Midway
RSWMDW
Fort Myers SW Florida Intl
Mon 11/9
6:00 am-12:51 pm
1 stop7h 51m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$146
Quickest round-trip
Fort MyersChicago
RSW Fort Myers SW Florida Intl - MDW Chicago Midway
RSWMDW
Fort Myers SW Florida Intl
Tue 10/20
12:25 pm-2:15 pm
Nonstop2h 50m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$157
Fort MyersChicago
RSW Fort Myers SW Florida Intl - MDW Chicago Midway
RSWMDW
Fort Myers SW Florida Intl
Thu 11/26
8:15 am-2:55 pm
1 stop7h 40m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$167
Fort MyersChicago
RSW Fort Myers SW Florida Intl - MDW Chicago Midway
RSWMDW
Fort Myers SW Florida Intl
Wed 1/6
11:00 am-4:25 pm
1 stop6h 25m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$167
Fort MyersChicago
RSW Fort Myers SW Florida Intl - MDW Chicago Midway
RSWMDW
Fort Myers SW Florida Intl
Tue 1/5
12:15 pm-6:37 pm
1 stop7h 22m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$167
Fort MyersChicago
RSW Fort Myers SW Florida Intl - MDW Chicago Midway
RSWMDW
Fort Myers SW Florida Intl
Wed 3/17
1:00 pm-4:25 pm
1 stop4h 25m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$183
Fort MyersChicago
RSW Fort Myers SW Florida Intl - MDW Chicago Midway
RSWMDW
Fort Myers SW Florida Intl
Sat 3/20
6:00 am-12:33 pm
1 stop7h 33m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$183
Fort MyersChicago
RSW Fort Myers SW Florida Intl - MDW Chicago Midway
RSWMDW
Fort Myers SW Florida Intl
Fri 11/6
2:15 pm-6:00 pm
1 stop4h 45m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$190
Fort MyersChicago
RSW Fort Myers SW Florida Intl - MDW Chicago Midway
RSWMDW
Fort Myers SW Florida Intl
Mon 1/4
8:00 pm-12:05 am
1 stop5h 05m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$203
Fort MyersChicago
RSW Fort Myers SW Florida Intl - MDW Chicago Midway
RSWMDW
Fort Myers SW Florida Intl
Fri 3/19
8:00 am-12:33 pm
1 stop5h 33m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$203
Showing 1-10 of 23 resultsSorted by cheapest first
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 September.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- 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 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 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.
RSW-MDW
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, October is the cheapest month in which you can book a flight from Fort Myers to Chicago Midway Airport (average of $297). Flying from Fort Myers to Chicago Midway Airport in March is currently the most expensive (average of $504). 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 September 21, 2026.
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 evening could potentially save you up to 30% 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 September 12, 2026.
Travelers seeking maximum savings on their Fort Myers to Chicago Midway Airport flight should consider departing on Thursday evenings when fares are most often at their lowest. Sunday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
The best insider tips for Fort Myers to Chicago Midway Airport 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 Fort Myers to Chicago Midway Airport trip
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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 September 21, 2026.
Get a feel of what it's like to fly with Southwest 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.
Overall
8.0
Food
7.0
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
8.0
Food
7.0
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
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.
Traveling to a place near Chicago Midway Airport?
Book flights to Chicago Midway Airport if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
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Top airline flying from Fort Myers to Midway
Discover the top airline 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 7,457,451 searches. Data last updated September 21, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$242 | Average$356 | FlexibilityNo cancel fee | On-time63% |