$150+ 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 1/11. Fares are subject to change and may not be available on all flights or dates of travel.
RSW — MDW
Dec 5 — Dec 121
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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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 November 5, 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 November 5, 2026.
This Southwest deal was found by Cheapflights users on 11/1. 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 11/249:45 pm -
Nonstop3h 00m
Fri 11/276:40 pm -
Nonstop2h 50m
Deal found 11/1![Southwest logo]()
$313
This Southwest deal was found by Cheapflights users on 11/2. 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 11/2310:50 am -
1 stop4h 20m
Tue 12/16:25 pm -
Nonstop2h 55m
Deal found 11/2![Southwest logo]()
$319
This Southwest deal was found by Cheapflights users on 11/2. 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 11/2310:50 am -
1 stop4h 20m
Thu 11/267:45 am -
1 stop6h 00m
Deal found 11/2![Southwest logo]()
$328
This Southwest deal was found by Cheapflights users on 11/2. 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 11/267:25 am -
Nonstop2h 55m
Fri 11/275:05 am -
Nonstop2h 45m
Deal found 11/2![Southwest logo]()
$332
This Delta deal was found by Cheapflights users on 11/4. 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.
Thu 12/36:00 am -
1 stop8h 01m
Mon 12/76:00 am -
1 stop4h 57m
Deal found 11/4![Delta logo]()
$333
This Southwest deal was found by Cheapflights users on 11/4. 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.
Thu 12/311:55 am -
1 stop6h 55m
Mon 12/76:25 pm -
Nonstop2h 55m
Deal found 11/4![Southwest logo]()
$342
This Southwest deal was found by Cheapflights users on 11/2. 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.
Fri 12/41:35 pm -
2 stops7h 20m
Sat 12/58:00 am -
2 stops8h 20m
Deal found 11/2![Southwest logo]()
$343
This Southwest deal was found by Cheapflights users on 11/3. 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 12/47:45 pm -
Nonstop3h 00m
Sun 12/67:45 am -
Nonstop2h 45m
Deal found 11/3![Southwest logo]()
$346
This Southwest deal was found by Cheapflights users on 11/2. 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 12/108:25 am -
2 stops7h 15m
Mon 12/217:55 pm -
Nonstop2h 50m
Deal found 11/2![Southwest logo]()
$347
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 November 5, 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 November 5, 2026.
This Southwest deal was found by Cheapflights users on 10/31. 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 11/239:05 pm -
Nonstop3h 00m
Tue 12/16:45 am -
Nonstop2h 45m
Deal found 10/31![Southwest logo]()
$313
This Delta deal was found by Cheapflights users on 11/4. 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.
Fri 2/2612:59 pm -
1 stop6h 04m
Sat 2/273:15 pm -
1 stop5h 16m
Deal found 11/4![Delta logo]()
$333
This Southwest deal was found by Cheapflights users on 11/3. 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 2/186:20 am -
Nonstop3h 00m
Mon 2/225:25 am -
Nonstop2h 50m
Deal found 11/3![Southwest logo]()
$313
This Southwest deal was found by Cheapflights users on 11/2. 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 12/56:50 am -
Nonstop2h 55m
Sat 12/53:35 pm -
Nonstop2h 45m
Deal found 11/2![Southwest logo]()
$313
This Delta deal was found by Cheapflights users on 11/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/227:00 am -
1 stop5h 59m
Sat 12/54:08 pm -
1 stop4h 29m
Deal found 11/1![Delta logo]()
$366
This Southwest deal was found by Cheapflights users on 10/31. 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 2/265:05 pm -
1 stop4h 30m
Mon 3/13:20 pm -
1 stop7h 35m
Deal found 10/31![Southwest logo]()
$328
This Southwest deal was found by Cheapflights users on 11/4. 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.
Thu 12/241:35 pm -
2 stops7h 10m
Fri 1/112:45 pm -
1 stop6h 05m
Deal found 11/4![Southwest logo]()
$357
This Southwest deal was found by Cheapflights users on 11/3. 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 12/411:50 am -
1 stop6h 20m
Sun 12/67:50 am -
1 stop7h 20m
Deal found 11/3![Southwest logo]()
$366
This Southwest deal was found by Cheapflights users on 10/31. 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 11/246:15 am -
1 stop7h 10m
Tue 12/11:15 pm -
2 stops6h 55m
Deal found 10/31![Southwest logo]()
$384
This Southwest deal was found by Cheapflights users on 11/2. 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.
Fri 12/117:25 am -
2 stops5h 55m
Sun 12/132:40 pm -
1 stop6h 15m
Deal found 11/2![Southwest logo]()
$390
This Southwest deal was found by Cheapflights users on 10/31. 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 11/198:25 am -
2 stops7h 15m
Fri 11/271:10 pm -
Nonstop2h 40m
Deal found 10/31![Southwest logo]()
$398
Last-minute flights from Fort Myers to MidwayDiscover last-minute flight deals from Fort Myers to Midway. Data last updated November 5, 2026 and is based on user searches.
Discover last-minute flight deals from Fort Myers to Midway. Data last updated November 5, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 11/2. 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 11/2310:50 am -
1 stop4h 20m
Tue 12/16:25 pm -
Nonstop2h 55m
Deal found 11/2![Southwest logo]()
$319
This Southwest deal was found by Cheapflights users on 11/2. 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 11/2310:50 am -
1 stop4h 20m
Thu 11/267:45 am -
1 stop6h 00m
Deal found 11/2![Southwest logo]()
$328
This Southwest deal was found by Cheapflights users on 11/1. 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 11/249:45 pm -
Nonstop3h 00m
Fri 11/276:40 pm -
Nonstop2h 50m
Deal found 11/1![Southwest logo]()
$313
This Southwest deal was found by Cheapflights users on 11/2. 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 11/267:25 am -
Nonstop2h 55m
Fri 11/275:05 am -
Nonstop2h 45m
Deal found 11/2![Southwest logo]()
$332
This Delta deal was found by Cheapflights users on 11/4. 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.
Thu 12/36:00 am -
1 stop8h 01m
Mon 12/76:00 am -
1 stop4h 57m
Deal found 11/4![Delta logo]()
$333
This Southwest deal was found by Cheapflights users on 11/4. 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.
Thu 12/311:55 am -
1 stop6h 55m
Mon 12/76:25 pm -
Nonstop2h 55m
Deal found 11/4![Southwest logo]()
$342
This Southwest deal was found by Cheapflights users on 11/2. 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.
Fri 12/41:35 pm -
2 stops7h 20m
Sat 12/58:00 am -
2 stops8h 20m
Deal found 11/2![Southwest logo]()
$343
This Southwest deal was found by Cheapflights users on 11/3. 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 12/47:45 pm -
Nonstop3h 00m
Sun 12/67:45 am -
Nonstop2h 45m
Deal found 11/3![Southwest logo]()
$346
This Southwest deal was found by Cheapflights users on 11/2. 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 12/108:25 am -
2 stops7h 15m
Mon 12/217:55 pm -
Nonstop2h 50m
Deal found 11/2![Southwest logo]()
$347
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 November 5, 2026.
Search for one-way flight options from Fort Myers to Midway. Find affordable one-way fares based on user searches. Data last updated November 5, 2026.
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/119:00 pm -
2 stops27h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![Frontier logo]()
$150
This Kiwi.com deal was found by Cheapflights users on 11/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/117:00 am -
2 stops13h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/4![Multiple Airlines logo]()
$152
This Southwest deal was found by Cheapflights users on 11/4. 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.
Fri 12/119:05 pm -
Nonstop3h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/4![Southwest logo]()
$157
This Kiwi.com deal was found by Cheapflights users on 11/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/107:00 am -
2 stops34h 26m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/4![Multiple Airlines logo]()
$158
This Kiwi.com deal was found by Cheapflights users on 11/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/47:00 am -
2 stops29h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/4![Multiple Airlines logo]()
$160
This Southwest deal was found by Cheapflights users on 11/2. 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 2/225:05 pm -
1 stop4h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Southwest logo]()
$162
This Kiwi.com deal was found by Cheapflights users on 11/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/167:00 am -
2 stops37h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/4![Multiple Airlines logo]()
$163
This Delta deal was found by Cheapflights users on 11/4. 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.
Wed 1/611:37 am -
1 stop6h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/4![Delta logo]()
$167
This Kiwi.com deal was found by Cheapflights users on 11/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/37:00 am -
2 stops34h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Multiple Airlines logo]()
$169
This Mytrip deal was found by Cheapflights users on 10/31. 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.
Fri 11/209:25 pm -
2 stops17h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/31![Frontier logo]()
$170
This Southwest deal was found by Cheapflights users on 11/4. 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.
Wed 1/67:20 am -
2 stops8h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/4![Southwest logo]()
$172
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 November 5, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $313 (Southwest) |
One-way from | $150 (Kiwi.com) |
Popular in | October |
Cheapest in | February |
Average price | $408 |
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 November 5, 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
Quickest round-trip
Fort MyersChicago
RSW Fort Myers SW Florida Intl - MDW Chicago Midway
RSWMDW
Fort Myers SW Florida Intl
Sat 12/12
6:50 am-8:45 am
Nonstop2h 55m
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
Mon 12/21
4:43 pm-10:22 pm
1 stop6h 39m
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
Thu 11/26
11:15 am-2:40 pm
1 stop4h 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
Mon 1/11
5:55 am-12:40 pm
1 stop7h 45m
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
7:20 am-2:50 pm
2 stops8h 30m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$172
Fort MyersChicago
RSW Fort Myers SW Florida Intl - MDW Chicago Midway
RSWMDW
Fort Myers SW Florida Intl
Tue 12/29
8:20 pm-12:20 am
1 stop5h 00m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$186
Fort MyersChicago
RSW Fort Myers SW Florida Intl - MDW Chicago Midway
RSWMDW
Fort Myers SW Florida Intl
Sun 1/10
7:10 am-9:05 am
Nonstop2h 55m
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
Sun 1/31
5:05 pm-8:35 pm
1 stop4h 30m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$195
Fort MyersChicago
RSW Fort Myers SW Florida Intl - MDW Chicago Midway
RSWMDW
Fort Myers SW Florida Intl
Mon 11/23
9:05 pm-11:05 pm
Nonstop3h 00m
Chicago Midway
Tue 12/1
6:45 am-10:30 am
Nonstop2h 45m
$313
Fort MyersChicago
RSW Fort Myers SW Florida Intl - MDW Chicago Midway
RSWMDW
Fort Myers SW Florida Intl
Thu 2/18
6:20 am-8:20 am
Nonstop3h 00m
Chicago Midway
Mon 2/22
5:25 am-9:15 am
Nonstop2h 50m
$313
Showing 1-10 of 19 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 November.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 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, February is the cheapest month in which you can book a flight from Fort Myers to Chicago Midway Airport (average of $249). Flying from Fort Myers to Chicago Midway Airport in October is currently the most expensive (average of $565). 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 November 5, 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.
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
Our travel experts
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 November 5, 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.
Entertainment
7.5
Boarding
8.1
Food
7.0
Overall
8.0
Crew
8.6
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Boarding
8.1
Food
7.0
Overall
8.0
Crew
8.6
Comfort
8.0
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
Merrillville
Lansing
Valparaiso
Hammond
Saint Joseph
Porter
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Alternative routes for Fort Myers to Midway
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Fort Myers and Midway flights
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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 November 5, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$248 | Average$371 | FlexibilityNo cancel fee | On-time63% |