$148+ Cheap flights from Chicago (CHI) to Fort Myers Beach, FL
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/15. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — RSW
Aug 15 — Aug 221
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 August or February, booked 63 days in advance, depart on a Wednesday or Saturday and return on a Thursday
Cheap flight deals from Chicago to Fort Myers Beach
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Best
Last-minute
One-way
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 July 16, 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 July 16, 2026.
This Frontier deal was found by Cheapflights users on 7/15. 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 12/410:52 am
ORD
- RSW
Nonstop3h 06m
Frontier
Sun 12/63:53 pm
RSW
- ORD
Nonstop3h 21m
Frontier
Deal found 7/15![Frontier logo]()
$260
This Priceline deal was found by Cheapflights users on 7/15. 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.
Fri 12/1110:52 am
ORD
- RSW
Nonstop3h 06m
Frontier
Mon 12/143:53 pm
RSW
- ORD
Nonstop3h 21m
Frontier
Deal found 7/15![Frontier logo]()
$268
This Kiwi.com deal was found by Cheapflights users on 7/12. 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 9/36:00 am
ORD
- RSW
1 stop29h 00m
Frontier
Sun 9/2012:45 pm
RSW
- ORD
1 stop24h 56m
Frontier
Deal found 7/12![Frontier logo]()
$272
This United Airlines deal was found by Cheapflights users on 7/14. 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 8/67:05 am
ORD
- RSW
Nonstop3h 09m
United Airlines
Mon 8/107:00 am
RSW
- ORD
Nonstop3h 23m
United Airlines
Deal found 7/14![United Airlines logo]()
$275
This Southwest deal was found by Cheapflights users on 7/13. 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 8/66:15 pm
MDW
- RSW
Nonstop2h 45m
Southwest
Mon 8/106:50 am
RSW
- MDW
Nonstop2h 50m
Southwest
Deal found 7/13![Southwest logo]()
$275
This American Airlines deal was found by Cheapflights users on 7/15. 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.
Sat 8/296:45 am
ORD
- RSW
Nonstop2h 52m
American Airlines
Sat 9/54:39 pm
RSW
- ORD
Nonstop3h 31m
American Airlines
Deal found 7/15![American Airlines logo]()
$276
This Kiwi.com deal was found by Cheapflights users on 7/11. 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 9/36:00 am
ORD
- RSW
1 stop29h 00m
Frontier
Sun 9/1312:45 pm
RSW
- ORD
1 stop24h 56m
Frontier
Deal found 7/11![Frontier logo]()
$279
This United Airlines deal was found by Cheapflights users on 7/12. 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.
Mon 10/124:30 pm
ORD
- RSW
Nonstop3h 06m
United Airlines
Sat 10/176:50 am
RSW
- ORD
1 stop8h 55m
United Airlines
Deal found 7/12![United Airlines logo]()
$281
This Southwest deal was found by Cheapflights users on 7/15. 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 10/174:10 pm
MDW
- RSW
Nonstop2h 45m
Southwest
Wed 10/211:55 pm
RSW
- MDW
1 stop4h 15m
Southwest
Deal found 7/15![Southwest logo]()
$281
This Kiwi.com deal was found by Cheapflights users on 7/11. 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 9/66:00 am
ORD
- RSW
1 stop29h 00m
Multiple Airlines
Tue 9/157:00 am
RSW
- ORD
2 stops17h 55m
Multiple Airlines
Deal found 7/11![Multiple Airlines logo]()
$284
This American Airlines deal was found by Cheapflights users on 7/11. 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.
Wed 11/186:50 pm
ORD
- RSW
Nonstop3h 02m
American Airlines
Tue 11/245:53 am
RSW
- ORD
Nonstop3h 28m
American Airlines
Deal found 7/11![American Airlines logo]()
$285
This Southwest deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/310:30 am
MDW
- RSW
1 stop6h 15m
Southwest
Mon 9/76:50 am
RSW
- MDW
Nonstop2h 50m
Southwest
Deal found 7/13![Southwest logo]()
$285
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 July 16, 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 July 16, 2026.
This United Airlines deal was found by Cheapflights users on 7/14. 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.
Sat 10/102:10 pm
ORD
- RSW
1 stop6h 47m
United Airlines
Tue 10/138:45 am
RSW
- ORD
Nonstop3h 14m
United Airlines
Deal found 7/14![United Airlines logo]()
$285
This Southwest deal was found by Cheapflights users on 7/15. 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 8/83:05 pm
MDW
- RSW
Nonstop2h 45m
Southwest
Mon 8/106:10 am
RSW
- MDW
1 stop10h 15m
Southwest
Deal found 7/15![Southwest logo]()
$291
This Delta deal was found by Cheapflights users on 7/15. 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 10/282:00 pm
ORD
- RSW
1 stop6h 19m
Delta
Mon 11/28:10 am
RSW
- ORD
1 stop7h 19m
Delta
Deal found 7/15![Delta logo]()
$295
This Sun Country Air deal was found by Cheapflights users on 7/14. 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.
Fri 10/96:39 pm
ORD
- RSW
1 stop23h 12m
Sun Country Air
Tue 10/134:14 pm
RSW
- ORD
1 stop27h 54m
Sun Country Air
Deal found 7/14![Sun Country Air logo]()
$415
This United Airlines deal was found by Cheapflights users on 7/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/69:02 am
ORD
- RSW
Nonstop3h 06m
United Airlines
Sat 10/176:50 am
RSW
- ORD
1 stop8h 55m
United Airlines
Deal found 7/16![United Airlines logo]()
$291
This Delta deal was found by Cheapflights users on 7/15. 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 9/241:50 pm
ORD
- RSW
1 stop6h 45m
Delta
Mon 9/286:24 pm
RSW
- ORD
1 stop6h 35m
Delta
Deal found 7/15![Delta logo]()
$295
This Southwest deal was found by Cheapflights users on 7/13. 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 10/95:50 pm
MDW
- RSW
1 stop5h 00m
Southwest
Sat 10/177:30 am
RSW
- MDW
Nonstop2h 50m
Southwest
Deal found 7/13![Southwest logo]()
$315
This Delta deal was found by Cheapflights users on 7/11. 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 8/1210:54 am
MDW
- RSW
1 stop7h 04m
Delta
Wed 8/195:35 am
RSW
- MDW
1 stop5h 24m
Delta
Deal found 7/11![Delta logo]()
$295
This United Airlines deal was found by Cheapflights users on 7/13. 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
ORD
- RSW
Nonstop3h 06m
United Airlines
Mon 10/2611:42 am
RSW
- ORD
1 stop7h 28m
United Airlines
Deal found 7/13![United Airlines logo]()
$315
This Southwest deal was found by Cheapflights users on 7/11. 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 9/46:15 pm
MDW
- RSW
Nonstop2h 45m
Southwest
Thu 9/105:05 pm
RSW
- MDW
2 stops6h 15m
Southwest
Deal found 7/11![Southwest logo]()
$320
This Delta deal was found by Cheapflights users on 7/13. 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 8/56:05 am
MDW
- RSW
1 stop5h 08m
Delta
Wed 8/125:35 am
RSW
- MDW
1 stop7h 16m
Delta
Deal found 7/13![Delta logo]()
$295
This United Airlines deal was found by Cheapflights users on 7/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/117:15 am
ORD
- RSW
Nonstop3h 06m
United Airlines
Sun 9/135:14 pm
RSW
- ORD
1 stop8h 45m
United Airlines
Deal found 7/16![United Airlines logo]()
$326
This Southwest deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/37:55 am
MDW
- RSW
2 stops6h 10m
Southwest
Mon 9/76:10 am
RSW
- MDW
1 stop7h 05m
Southwest
Deal found 7/14![Southwest logo]()
$330
This Delta deal was found by Cheapflights users on 7/11. 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 10/175:39 pm
ORD
- RSW
1 stop5h 52m
Delta
Thu 12/178:10 am
RSW
- ORD
1 stop7h 03m
Delta
Deal found 7/11![Delta logo]()
$305
This Delta deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/149:30 am
MDW
- RSW
1 stop6h 12m
Delta
Sat 11/215:40 pm
RSW
- MDW
1 stop5h 30m
Delta
Deal found 7/15![Delta logo]()
$315
This Southwest deal was found by Cheapflights users on 7/14. 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 8/131:00 pm
MDW
- RSW
Nonstop2h 45m
Southwest
Sun 8/167:20 am
RSW
- MDW
Nonstop2h 45m
Southwest
Deal found 7/14![Southwest logo]()
$356
This United Airlines deal was found by Cheapflights users on 7/15. 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.
Tue 8/44:26 pm
ORD
- RSW
Nonstop3h 08m
United Airlines
Sat 8/87:00 am
RSW
- ORD
Nonstop3h 23m
United Airlines
Deal found 7/15![United Airlines logo]()
$374
This Delta deal was found by Cheapflights users on 7/13. 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 10/233:40 pm
ORD
- RSW
1 stop6h 29m
Delta
Mon 10/266:32 pm
RSW
- ORD
1 stop6h 19m
Delta
Deal found 7/13![Delta logo]()
$325
This Southwest deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/225:05 am
MDW
- RSW
Nonstop2h 40m
Southwest
Sun 10/257:05 am
RSW
- MDW
Nonstop2h 50m
Southwest
Deal found 7/15![Southwest logo]()
$377
This Delta deal was found by Cheapflights users on 7/14. 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 10/243:40 pm
ORD
- RSW
1 stop6h 29m
Delta
Sun 10/257:50 am
RSW
- ORD
1 stop6h 11m
Delta
Deal found 7/14![Delta logo]()
$336
This Delta deal was found by Cheapflights users on 7/15. 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 8/2110:54 am
MDW
- RSW
1 stop7h 04m
Delta
Sun 8/235:35 am
RSW
- MDW
1 stop7h 16m
Delta
Deal found 7/15![Delta logo]()
$366
This Delta deal was found by Cheapflights users on 7/11. 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 12/45:25 pm
MDW
- RSW
1 stop6h 10m
Delta
Sun 12/65:35 am
RSW
- MDW
1 stop7h 21m
Delta
Deal found 7/11![Delta logo]()
$366
Last-minute flights from Chicago to Fort Myers BeachDiscover last-minute flight deals from Chicago to Fort Myers Beach. Data last updated July 16, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Fort Myers Beach. Data last updated July 16, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 7/12. 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 8/46:00 pm
MDW
- RSW
Nonstop2h 45m
Southwest
Tue 8/117:10 am
RSW
- MDW
Nonstop2h 45m
Southwest
Deal found 7/12![Southwest logo]()
$292
This Delta deal was found by Cheapflights users on 7/13. 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 8/46:05 am
MDW
- RSW
1 stop7h 19m
Delta
Sat 8/85:35 am
RSW
- MDW
1 stop5h 35m
Delta
Deal found 7/13![Delta logo]()
$295
This Southwest deal was found by Cheapflights users on 7/13. 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 8/412:35 pm
MDW
- RSW
2 stops6h 35m
Southwest
Sat 8/86:15 am
RSW
- MDW
1 stop4h 15m
Southwest
Deal found 7/13![Southwest logo]()
$300
This United Airlines deal was found by Cheapflights users on 7/14. 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 8/67:05 am
ORD
- RSW
Nonstop3h 09m
United Airlines
Thu 8/134:40 pm
RSW
- ORD
Nonstop3h 19m
United Airlines
Deal found 7/14![United Airlines logo]()
$275
This Southwest deal was found by Cheapflights users on 7/13. 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 8/66:15 pm
MDW
- RSW
Nonstop2h 45m
Southwest
Mon 8/106:50 am
RSW
- MDW
Nonstop2h 50m
Southwest
Deal found 7/13![Southwest logo]()
$275
This United Airlines deal was found by Cheapflights users on 7/13. 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 8/64:26 pm
ORD
- RSW
Nonstop3h 08m
United Airlines
Tue 8/115:14 pm
RSW
- ORD
1 stop8h 45m
United Airlines
Deal found 7/13![United Airlines logo]()
$285
This American Airlines deal was found by Cheapflights users on 7/13. 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.
Thu 8/67:05 pm
ORD
- RSW
Nonstop2h 57m
American Airlines
Mon 8/1011:04 am
RSW
- ORD
1 stop5h 56m
American Airlines
Deal found 7/13![American Airlines logo]()
$302
This Delta deal was found by Cheapflights users on 7/13. 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 8/1210:33 am
ORD
- RSW
1 stop5h 11m
Delta
Tue 8/183:30 pm
RSW
- ORD
1 stop6h 25m
Delta
Deal found 7/13![Delta logo]()
$295
This Southwest deal was found by Cheapflights users on 7/13. 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 8/205:30 am
MDW
- RSW
2 stops10h 00m
Southwest
Mon 8/243:40 pm
RSW
- MDW
2 stops7h 15m
Southwest
Deal found 7/13![Southwest logo]()
$305
This United Airlines deal was found by Cheapflights users on 7/13. 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 8/2110:30 am
ORD
- RSW
Nonstop3h 06m
United Airlines
Tue 8/2512:27 pm
RSW
- ORD
Nonstop3h 14m
United Airlines
Deal found 7/13![United Airlines logo]()
$305
This Kiwi.com deal was found by Cheapflights users on 7/13. 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 8/276:00 am
ORD
- RSW
1 stop29h 00m
Multiple Airlines
Mon 8/317:10 am
RSW
- ORD
2 stops16h 58m
Multiple Airlines
Deal found 7/13![Multiple Airlines logo]()
$298
This American Airlines deal was found by Cheapflights users on 7/15. 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.
Sat 8/296:45 am
ORD
- RSW
Nonstop2h 52m
American Airlines
Sat 9/54:39 pm
RSW
- ORD
Nonstop3h 31m
American Airlines
Deal found 7/15![American Airlines logo]()
$276
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 July 16, 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 July 16, 2026.
This United Airlines deal was found by Cheapflights users on 7/13. 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 12/27:45 am
ORD
- RSW
1 stop6h 59m
United Airlines
Deal found 7/13![United Airlines logo]()
$148
This Delta deal was found by Cheapflights users on 7/13. 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 8/65:10 pm
MDW
- RSW
1 stop6h 30m
Delta
Deal found 7/13![Delta logo]()
$148
This Kiwi.com deal was found by Cheapflights users on 7/14. 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 9/18:05 am
ORD
- RSW
2 stops36h 52m
Multiple Airlines
Deal found 7/14![Multiple Airlines logo]()
$149
This Kiwi.com deal was found by Cheapflights users on 7/12. 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 8/318:05 am
ORD
- RSW
3 stops36h 53m
Multiple Airlines
Deal found 7/12![Multiple Airlines logo]()
$150
This Kiwi.com deal was found by Cheapflights users on 7/11. 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 9/1012:03 pm
MDW
- RSW
2 stops34h 08m
Multiple Airlines
Deal found 7/11![Multiple Airlines logo]()
$151
This Kiwi.com deal was found by Cheapflights users on 7/15. 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 8/61:50 pm
ORD
- RSW
2 stops32h 18m
Multiple Airlines
Deal found 7/15![Multiple Airlines logo]()
$152
This Delta deal was found by Cheapflights users on 7/16. 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 9/128:05 am
ORD
- RSW
1 stop7h 29m
Delta
Deal found 7/16![Delta logo]()
$153
This Southwest deal was found by Cheapflights users on 7/13. 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 8/412:35 pm
MDW
- RSW
2 stops6h 35m
Southwest
Deal found 7/13![Southwest logo]()
$153
This Mytrip deal was found by Cheapflights users on 7/15. 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 8/217:08 pm
ORD
- RSW
1 stop13h 58m
Avelo Airlines
Deal found 7/15![Avelo Airlines logo]()
$155
This Kiwi.com deal was found by Cheapflights users on 7/13. 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 8/208:05 am
ORD
- RSW
2 stops26h 55m
Frontier
Deal found 7/13![Frontier logo]()
$157
This Kiwi.com deal was found by Cheapflights users on 7/12. 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 9/2812:03 pm
MDW
- RSW
2 stops46h 42m
Multiple Airlines
Deal found 7/12![Multiple Airlines logo]()
$157
This Delta deal was found by Cheapflights users on 7/14. 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 12/215:55 pm
ORD
- RSW
1 stop5h 40m
Delta
Deal found 7/14![Delta logo]()
$158
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 July 16, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $260 (Frontier) |
One-way from | $148 (United Airlines) |
Popular in | December |
Cheapest in | August |
Average price | $314 |
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 2,558,603 searches. Data last updated July 16, 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
ORD - RSW
ORDRSW
Chicago O'Hare Intl
Sat 10/10
2:10 pm-9:57 pm
1 stop6h 47m
Fort Myers SW Florida Intl
Tue 10/13
8:45 am-10:59 am
Nonstop3h 14m
$285
ChicagoFort Myers
MDW - RSW
MDWRSW
Chicago Midway
Sat 8/8
3:05 pm-6:50 pm
Nonstop2h 45m
Fort Myers SW Florida Intl
Mon 8/10
6:10 am-3:25 pm
1 stop10h 15m
$291
ChicagoFort Myers
ORD - RSW
ORDRSW
Chicago O'Hare Intl
Tue 10/6
9:02 am-1:08 pm
Nonstop3h 06m
Fort Myers SW Florida Intl
Sat 10/17
6:50 am-2:45 pm
1 stop8h 55m
$291
ChicagoFort Myers
ORD - RSW
ORDRSW
Chicago O'Hare Intl
Wed 10/28
2:00 pm-9:19 pm
1 stop6h 19m
Fort Myers SW Florida Intl
Mon 11/2
8:10 am-2:29 pm
1 stop7h 19m
$295
ChicagoFort Myers
ORD - RSW
ORDRSW
Chicago O'Hare Intl
Thu 9/24
1:50 pm-9:35 pm
1 stop6h 45m
Fort Myers SW Florida Intl
Mon 9/28
6:24 pm-11:59 pm
1 stop6h 35m
$295
ChicagoFort Myers
MDW - RSW
MDWRSW
Chicago Midway
Wed 8/12
10:54 am-6:58 pm
1 stop7h 04m
Fort Myers SW Florida Intl
Wed 8/19
5:35 am-9:59 am
1 stop5h 24m
$295
ChicagoFort Myers
MDW - RSW
MDWRSW
Chicago Midway
Wed 8/5
6:05 am-12:13 pm
1 stop5h 08m
Fort Myers SW Florida Intl
Wed 8/12
5:35 am-11:51 am
1 stop7h 16m
$295
ChicagoFort Myers
ORD - RSW
ORDRSW
Chicago O'Hare Intl
Sat 10/17
5:39 pm-12:31 am
1 stop5h 52m
Fort Myers SW Florida Intl
Thu 12/17
8:10 am-2:13 pm
1 stop7h 03m
$305
ChicagoFort Myers
MDW - RSW
MDWRSW
Chicago Midway
Fri 10/9
5:50 pm-11:50 pm
1 stop5h 00m
Fort Myers SW Florida Intl
Sat 10/17
7:30 am-9:20 am
Nonstop2h 50m
$315
ChicagoFort Myers
ORD - RSW
ORDRSW
Chicago O'Hare Intl
Fri 10/23
9:02 am-1:08 pm
Nonstop3h 06m
Fort Myers SW Florida Intl
Mon 10/26
11:42 am-6:10 pm
1 stop7h 28m
$315
Showing 1-10 of 44 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 July 16, 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 afternoon 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 July 16, 2026.
The most flights from CHI to FM9 are scheduled on a Thursday (20 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (11 on average).
How much does it cost to fly round-trip from Chicago to Fort Myers Beach?
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 July 11, 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 July 16, 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.
Boarding
8.1
Crew
8.6
Food
7.0
Entertainment
7.5
Overall
8.0
Comfort
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Boarding
8.1
Crew
8.6
Food
7.0
Entertainment
7.5
Overall
8.0
Comfort
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Boarding
8.1
Crew
8.6
Food
7.0
Entertainment
7.5
Overall
8.0
Comfort
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Boarding
8.1
Crew
8.6
Food
7.0
Entertainment
7.5
Overall
8.0
Comfort
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Boarding
8.1
Crew
8.6
Food
7.0
Entertainment
7.5
Overall
8.0
Comfort
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Boarding
8.1
Crew
8.6
Food
7.0
Entertainment
7.5
Overall
8.0
Comfort
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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Complete your trip
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Find flights from Chicago to Fort Myers Beach, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Fort Myers Beach flights
Browse other Chicago and Fort Myers Beach flight options. Last updated on July 16, 2026.
Other flights from Chicago
Browse through other flights departing from Chicago. Flights are based on user searches made on Cheapflights and were last updated on July 16, 2026.
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 2,558,603 searches. Data last updated July 16, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$66 | Average$180 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$99 | Average$216 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$130 | Average$357 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$144 | Average$294 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$160 | Average$373 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$162 | Average$361 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$197 | Average$395 | FlexibilityNo cancel fee | On-time63% |