$143+ Cheap flights from Chicago (CHI) to Fort Myers Beach, FL
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 11/27. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — RSW
Oct 5 — Oct 121
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Fort Myers Beach 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 to Fort Myers Beach are usually found in January or February, booked 63 days in advance, depart on a Wednesday or Tuesday and return on a Thursday
Cheap flight deals from Chicago to Fort Myers Beach
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Cheapest flights from Chicago to Fort Myers BeachExplore the most affordable flight options available from Chicago to Fort Myers Beach. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 5, 2026.
Explore the most affordable flight options available from Chicago to Fort Myers Beach. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 5, 2026.
This Frontier deal was found by Cheapflights users on 8/31. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/212:08 pm -
Nonstop4h 52m
Mon 11/238:55 pm -
Nonstop4h 52m
Deal found 8/31![Frontier logo]()
$243
This Frontier deal was found by Cheapflights users on 8/31. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/292:08 pm -
Nonstop4h 52m
Sun 12/63:53 pm -
Nonstop3h 21m
Deal found 8/31![Frontier logo]()
$248
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/310:52 am -
Nonstop3h 06m
Sun 12/63:53 pm -
Nonstop3h 21m
Deal found 9/2![Frontier logo]()
$253
This Kiwi.com deal was found by Cheapflights users on 8/31. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/1310:52 am -
Nonstop3h 06m
Mon 12/213:53 pm -
Nonstop3h 21m
Deal found 8/31![Frontier logo]()
$255
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/1410:52 am -
Nonstop3h 06m
Fri 12/2512:11 pm -
1 stop7h 34m
Deal found 9/1![Multiple Airlines logo]()
$256
This Frontier deal was found by Cheapflights users on 8/31. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/1310:52 am -
Nonstop3h 06m
Sat 12/193:53 pm -
Nonstop3h 21m
Deal found 8/31![Frontier logo]()
$258
This Frontier deal was found by Cheapflights users on 8/31. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/209:30 pm -
1 stop10h 33m
Thu 12/33:53 pm -
Nonstop3h 21m
Deal found 8/31![Frontier logo]()
$259
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.
Sun 11/222:08 pm -
Nonstop4h 52m
Mon 11/236:52 pm -
Nonstop3h 18m
Deal found 9/2![Frontier logo]()
$262
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/232:08 pm -
Nonstop4h 52m
Wed 11/258:55 pm -
Nonstop4h 52m
Deal found 9/2![Frontier logo]()
$263
This Frontier deal was found by Cheapflights users on 8/31. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/209:30 pm -
1 stop10h 33m
Mon 11/238:55 pm -
Nonstop4h 52m
Deal found 8/31![Frontier logo]()
$264
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/310:52 am -
Nonstop3h 06m
Mon 12/73:53 pm -
Nonstop3h 21m
Deal found 9/2![Frontier logo]()
$268
This Super.com deal was found by Cheapflights users on 8/31. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/202:08 pm -
Nonstop4h 52m
Sun 11/228:55 pm -
Nonstop4h 52m
Deal found 8/31![Frontier logo]()
$271
Best flights from Chicago to Fort Myers BeachDiscover carefully curated flight deals from Chicago to Fort Myers Beach that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 5, 2026.
Discover carefully curated flight deals from Chicago to Fort Myers Beach that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 5, 2026.
This United Airlines deal was found by Cheapflights users on 8/31. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/307:05 am -
Nonstop3h 06m
Wed 10/78:45 am -
Nonstop3h 14m
Deal found 8/31![United Airlines logo]()
$297
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/510:32 am -
1 stop7h 25m
Sat 12/1212:48 pm -
1 stop8h 27m
Deal found 9/1![Delta logo]()
$317
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 11/1212:00 pm -
1 stop6h 20m
Wed 11/188:25 am -
2 stops7h 15m
Deal found 9/3![Southwest logo]()
$322
This Sun Country Air deal was found by Cheapflights users on 8/31. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/207:50 pm -
1 stop12h 52m
Fri 12/258:15 am -
1 stop11h 30m
Deal found 8/31![Sun Country Air logo]()
$375
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/2311:30 am -
1 stop4h 52m
Sat 2/136:00 am -
1 stop7h 37m
Deal found 9/1![Delta logo]()
$317
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/232:10 pm -
1 stop6h 47m
Mon 10/266:41 pm -
Nonstop3h 19m
Deal found 9/3![United Airlines logo]()
$318
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 10/277:55 am -
2 stops8h 10m
Tue 12/81:35 pm -
2 stops7h 10m
Deal found 9/2![Southwest logo]()
$338
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.
Sat 10/311:27 pm -
1 stop4h 53m
Sat 11/75:30 am -
1 stop6h 07m
Deal found 9/2![Delta logo]()
$317
This United Airlines deal was found by Cheapflights users on 8/31. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/212:10 pm -
1 stop6h 47m
Wed 10/282:21 pm -
Nonstop3h 21m
Deal found 8/31![United Airlines logo]()
$335
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 12/26:45 am -
Nonstop2h 45m
Sun 12/65:40 am -
1 stop4h 25m
Deal found 9/2![Southwest logo]()
$352
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.
Wed 11/45:05 pm -
1 stop6h 16m
Fri 11/66:30 pm -
1 stop6h 27m
Deal found 9/3![Delta logo]()
$328
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/239:02 am -
Nonstop3h 06m
Sun 10/256:41 pm -
Nonstop3h 19m
Deal found 9/1![United Airlines logo]()
$353
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 2/2711:10 am -
1 stop4h 48m
Sat 3/64:30 pm -
1 stop6h 50m
Deal found 9/3![Delta logo]()
$331
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 12/308:55 am -
1 stop7h 20m
Sat 1/307:35 am -
2 stops8h 10m
Deal found 9/1![Southwest logo]()
$367
This Delta deal was found by Cheapflights users on 8/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/85:27 am -
1 stop5h 40m
Mon 10/267:40 am -
1 stop6h 19m
Deal found 8/31![Delta logo]()
$345
This Southwest deal was found by Cheapflights users on 8/31. 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.
Sun 11/2212:00 pm -
1 stop6h 20m
Wed 12/21:35 pm -
2 stops7h 20m
Deal found 8/31![Southwest logo]()
$387
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 2/259:30 am -
1 stop5h 23m
Sat 3/65:40 pm -
1 stop5h 40m
Deal found 9/2![Delta logo]()
$372
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 12/1812:05 pm -
1 stop5h 55m
Tue 12/298:20 pm -
1 stop4h 55m
Deal found 9/3![Southwest logo]()
$423
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 2/255:25 pm -
1 stop6h 10m
Sat 3/64:30 pm -
1 stop6h 40m
Deal found 9/2![Delta logo]()
$372
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 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 11/148:04 am -
1 stop4h 28m
Sat 11/211:06 pm -
1 stop4h 59m
Deal found 9/4![Delta logo]()
$385
This Delta deal was found by Cheapflights users on 8/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/56:04 am -
1 stop6h 28m
Mon 11/96:00 am -
1 stop7h 51m
Deal found 8/31![Delta logo]()
$392
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.
Thu 10/81:27 pm -
1 stop7h 02m
Mon 10/127:40 am -
1 stop6h 07m
Deal found 9/3![Delta logo]()
$428
Last-minute flights from Chicago to Fort Myers BeachDiscover last-minute flight deals from Chicago to Fort Myers Beach. Data last updated September 5, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Fort Myers Beach. Data last updated September 5, 2026 and is based on user searches.
This Billigflug 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 Billigflug is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/247:07 pm -
Nonstop3h 02m
Mon 9/286:02 am -
Nonstop3h 27m
Deal found 9/2![Alaska Airlines logo]()
$298
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/247:25 am -
1 stop8h 20m
Thu 10/11:36 pm -
1 stop6h 07m
Deal found 9/4![Multiple Airlines logo]()
$301
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 Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/17:25 am -
1 stop8h 20m
Thu 10/2912:45 pm -
1 stop10h 58m
Deal found 9/4![Frontier logo]()
$258
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/17:05 am -
Nonstop3h 06m
Sat 10/34:34 pm -
Nonstop3h 19m
Deal found 9/1![United Airlines logo]()
$297
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/17:25 am -
1 stop8h 20m
Mon 10/512:46 pm -
2 stops24h 05m
Deal found 9/1![Frontier logo]()
$302
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/110:51 am -
Nonstop3h 06m
Mon 10/512:16 pm -
1 stop5h 49m
Deal found 9/3![United Airlines logo]()
$307
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/24:30 pm -
Nonstop3h 06m
Tue 10/68:45 am -
Nonstop3h 14m
Deal found 9/1![United Airlines logo]()
$308
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/710:51 am -
Nonstop3h 06m
Tue 10/206:50 am -
1 stop8h 55m
Deal found 9/2![United Airlines logo]()
$303
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 10/79:35 am -
1 stop7h 25m
Wed 10/145:45 pm -
Nonstop2h 50m
Deal found 9/2![Southwest logo]()
$307
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 9/2. 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 10/271:15 pm -
Nonstop2h 45m
Thu 11/54:35 pm -
Nonstop2h 55m
Deal found 9/2![Southwest logo]()
$297
One-way flights from Chicago to Fort Myers BeachSearch for one-way flight options from Chicago to Fort Myers Beach. Find affordable one-way fares based on user searches. Data last updated September 5, 2026.
Search for one-way flight options from Chicago to Fort Myers Beach. Find affordable one-way fares based on user searches. Data last updated September 5, 2026.
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/271:58 pm -
Nonstop2h 56m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Frontier logo]()
$143
This Super.com deal was found by Cheapflights users on 8/31. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/302:08 pm -
Nonstop4h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 8/31![Frontier logo]()
$146
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/147:05 am -
Nonstop3h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![United Airlines logo]()
$149
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 Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/107:25 am -
1 stop8h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Frontier logo]()
$150
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/137:25 am -
1 stop8h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Frontier logo]()
$151
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/207:00 am -
Nonstop2h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![American Airlines logo]()
$152
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/210:52 am -
Nonstop3h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Frontier logo]()
$153
This Super.com deal was found by Cheapflights users on 8/31. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/212:08 pm -
Nonstop4h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 8/31![Frontier logo]()
$157
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 United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/145:30 am -
1 stop6h 19m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![United Airlines logo]()
$159
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
Find flight deals from Chicago to Fort Myers Beach
Keep the following information in mind while searching for Chicago to Fort Myers Beach flight deals. Data was last updated September 5, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $243 (Frontier) |
One-way from | $143 (Kiwi.com) |
Popular in | December |
Cheapest in | January |
Average price | $321 |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Fort Myers Beach 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 5, 2026.
Use the filters below to find and compare flights from Chicago to Fort Myers Beach 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
ORD Chicago O'Hare Intl - RSW Fort Myers SW Florida Intl
ORDRSW
Chicago O'Hare Intl
Tue 11/3
1:23 pm-6:50 pm
1 stop4h 27m
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
6:04 am-12:07 pm
1 stop5h 03m
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 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
Sat 10/31
8:20 am-12:05 pm
Nonstop2h 45m
Fort Myers SW Florida Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$160
ChicagoFort Myers
MDW Chicago Midway - RSW Fort Myers SW Florida Intl
MDWRSW
Chicago Midway
Tue 11/10
8:45 am-12:35 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 1/5
8:05 am-6:00 pm
1 stop8h 55m
Fort Myers SW Florida Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$173
ChicagoFort Myers
ORD Chicago O'Hare Intl - RSW Fort Myers SW Florida Intl
ORDRSW
Chicago O'Hare Intl
Fri 9/25
9:02 am-1:08 pm
Nonstop3h 06m
Fort Myers SW Florida Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$177
Quickest round-trip
ChicagoFort Myers
MDW Chicago Midway - RSW Fort Myers SW Florida Intl
MDWRSW
Chicago Midway
Fri 10/2
5:05 am-8:45 am
Nonstop2h 40m
Fort Myers SW Florida Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$182
Showing 1-10 of 45 resultsSorted by cheapest first
Best time to book a flight from Chicago to Fort Myers Beach
Have a flexible travel schedule? Discover the best time to fly to Fort Myers Beach from Chicago with our price prediction graph.
ORD-RSW
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 to Fort Myers Beach
CHI-FM9
ORD-RSW
MDW-RSW
What is the cheapest time of day to fly from CHI to FM9?
Find hourly flight availability from Chicago to Fort Myers Beach. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 5, 2026.
One of the essential ways to save on airfare from Chicago to Fort Myers Beach is to remain as flexible as possible. Flights that are in the evening tend to be the most expensive. A flight in the morning could potentially save you up to 31% on airfare.
Weekly flight availability from Chicago to Fort Myers Beach
Explore weekly flight availability from Chicago to Fort Myers Beach. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated September 5, 2026.
The most flights from CHI to FM9 are scheduled on a Thursday (18 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (7 on average).
How much does it cost to fly round-trip from Chicago to Fort Myers Beach?
Airfare is below average for this route at the moment.
Chicago to Fort Myers Beach flights typically cost between $283 and $402 in November.The cheapest round-trip price found within the last 5 days was $243 on Frontier (Nov 21-Nov 23).
What is the cheapest day to fly from Chicago to Fort Myers Beach?
Use this chart to determine the cheapest time to fly round-trip from Chicago to Fort Myers Beach. Price data was last updated on August 29, 2026.
Travelers seeking maximum savings on their Chicago to Fort Myers Beach flight should consider departing on Wednesday afternoons when fares are most often at their lowest. Friday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing Fort Myers Beach
Get insights into the airlines that provide service to Fort Myers Beach. 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 Beach. Reviews last updated September 5, 2026.
Get a feel of what it's like to fly with Southwest,United Airlines, andAmerican Airlines from Chicago to Fort Myers Beach 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
Crew
8.6
Comfort
8.0
Overall
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Entertainment
7.5
Boarding
8.1
Food
7.0
Crew
8.6
Comfort
8.0
Overall
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Entertainment
7.5
Boarding
8.1
Food
7.0
Crew
8.6
Comfort
8.0
Overall
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Entertainment
7.5
Boarding
8.1
Food
7.0
Crew
8.6
Comfort
8.0
Overall
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Entertainment
7.5
Boarding
8.1
Food
7.0
Crew
8.6
Comfort
8.0
Overall
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Entertainment
7.5
Boarding
8.1
Food
7.0
Crew
8.6
Comfort
8.0
Overall
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Related info for your journey
Find useful and relevant information for your journey from Chicago to Fort Myers Beach. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Chicago and Fort Myers Beach flights
Browse other Chicago and Fort Myers Beach flight options. Last updated on September 5, 2026.
Other flights from Chicago
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Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 7 airlines flying from Chicago to Fort Myers Beach
Discover the top 7 airlines that operate flights from Chicago to Fort Myers Beach. 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 5, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$58 | Average$198 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$109 | Average$215 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$130 | Average$364 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$165 | Average$378 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$166 | Average$362 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$186 | Average$326 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$197 | Average$393 | FlexibilityNo cancel fee | On-time63% |