$112+ 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 6/12. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — RSW
Jun 15 — Jun 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 September, booked 87 days in advance, depart on a Wednesday or Tuesday and return on a Friday
Cheap flight deals from Chicago to Fort Myers Beach
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Best
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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 May 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 May 16, 2026.
This United Airlines deal was found by Cheapflights users on 5/13. 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 6/2410:35 am
ORD
- RSW
Nonstop3h 09m
United Airlines
Wed 7/17:00 am
RSW
- ORD
Nonstop3h 23m
United Airlines
Deal found 5/13![United Airlines logo]()
$291
This Southwest deal was found by Cheapflights users on 5/12. 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 6/96:55 pm
MDW
- RSW
Nonstop2h 45m
Southwest
Tue 6/167:10 am
RSW
- MDW
Nonstop2h 50m
Southwest
Deal found 5/12![Southwest logo]()
$291
This American Airlines deal was found by Cheapflights users on 5/12. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/112:35 pm
ORD
- RSW
Nonstop2h 54m
American Airlines
Wed 7/85:24 pm
RSW
- ORD
Nonstop3h 30m
American Airlines
Deal found 5/12![American Airlines logo]()
$292
This United Airlines deal was found by Cheapflights users on 5/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/157:05 am
ORD
- RSW
Nonstop3h 09m
United Airlines
Sat 7/257:00 am
RSW
- ORD
Nonstop3h 23m
United Airlines
Deal found 5/11![United Airlines logo]()
$293
This Southwest deal was found by Cheapflights users on 5/12. 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 6/24:05 pm
MDW
- RSW
Nonstop2h 45m
Southwest
Thu 7/95:10 am
RSW
- MDW
Nonstop2h 50m
Southwest
Deal found 5/12![Southwest logo]()
$293
This American Airlines deal was found by Cheapflights users on 5/14. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/137:52 pm
ORD
- RSW
Nonstop2h 58m
American Airlines
Sat 6/206:15 am
RSW
- ORD
Nonstop3h 22m
American Airlines
Deal found 5/14![American Airlines logo]()
$294
This United Airlines deal was found by Cheapflights users on 5/13. 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.
Sat 6/274:26 pm
ORD
- RSW
Nonstop3h 08m
United Airlines
Sat 7/47:00 am
RSW
- ORD
Nonstop3h 23m
United Airlines
Deal found 5/13![United Airlines logo]()
$295
This Southwest deal was found by Cheapflights users on 5/12. 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.
Mon 6/156:55 pm
MDW
- RSW
Nonstop2h 45m
Southwest
Thu 6/185:10 am
RSW
- MDW
Nonstop2h 50m
Southwest
Deal found 5/12![Southwest logo]()
$295
This Kiwi.com deal was found by Cheapflights users on 5/13. 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.
Tue 8/111:50 pm
ORD
- RSW
2 stops19h 23m
Multiple Airlines
Thu 8/2011:43 am
RSW
- ORD
1 stop25h 40m
Multiple Airlines
Deal found 5/13![Multiple Airlines logo]()
$300
This United Airlines deal was found by Cheapflights users on 5/13. 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 6/244:26 pm
ORD
- RSW
Nonstop3h 08m
United Airlines
Tue 6/305:00 pm
RSW
- ORD
1 stop8h 45m
United Airlines
Deal found 5/13![United Airlines logo]()
$301
This United Airlines deal was found by Cheapflights users on 5/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/104:26 pm
ORD
- RSW
Nonstop3h 08m
United Airlines
Mon 6/155:00 pm
RSW
- ORD
1 stop8h 45m
United Airlines
Deal found 5/11![United Airlines logo]()
$303
This Southwest deal was found by Cheapflights users on 5/11. 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.
Tue 6/24:05 pm
MDW
- RSW
Nonstop2h 45m
Southwest
Mon 6/295:55 am
RSW
- MDW
1 stop5h 05m
Southwest
Deal found 5/11![Southwest logo]()
$303
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 May 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 May 16, 2026.
This Southwest deal was found by Cheapflights users on 5/14. 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.
Tue 6/96:55 pm
MDW
- RSW
Nonstop2h 45m
Southwest
Tue 6/167:10 am
RSW
- MDW
Nonstop2h 50m
Southwest
Deal found 5/14![Southwest logo]()
$291
This United Airlines deal was found by Cheapflights users on 5/14. 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.
Wed 7/1510:35 am
ORD
- RSW
Nonstop3h 09m
United Airlines
Mon 7/2012:59 pm
RSW
- ORD
1 stop6h 45m
United Airlines
Deal found 5/14![United Airlines logo]()
$303
This Delta deal was found by Cheapflights users on 5/13. 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 8/66:05 am
MDW
- RSW
1 stop5h 08m
Delta
Wed 8/125:23 am
RSW
- MDW
1 stop5h 36m
Delta
Deal found 5/13![Delta logo]()
$313
This Sun Country Air deal was found by Cheapflights users on 5/15. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/56:25 pm
ORD
- RSW
1 stop15h 25m
Sun Country Air
Mon 6/812:31 pm
RSW
- ORD
1 stop6h 38m
Sun Country Air
Deal found 5/15![Sun Country Air logo]()
$425
This Southwest deal was found by Cheapflights users on 5/15. 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.
Tue 6/166:55 pm
MDW
- RSW
Nonstop2h 45m
Southwest
Tue 6/236:25 pm
RSW
- MDW
Nonstop2h 50m
Southwest
Deal found 5/15![Southwest logo]()
$295
This United Airlines deal was found by Cheapflights users on 5/13. 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 7/297:05 am
ORD
- RSW
Nonstop3h 09m
United Airlines
Mon 8/312:59 pm
RSW
- ORD
1 stop6h 45m
United Airlines
Deal found 5/13![United Airlines logo]()
$303
This Delta deal was found by Cheapflights users on 5/13. 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 8/1110:54 am
MDW
- RSW
1 stop4h 50m
Delta
Sat 8/1511:05 am
RSW
- MDW
1 stop5h 33m
Delta
Deal found 5/13![Delta logo]()
$313
This Southwest deal was found by Cheapflights users on 5/15. 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.
Tue 7/216:55 pm
MDW
- RSW
Nonstop2h 45m
Southwest
Tue 7/287:10 am
RSW
- MDW
Nonstop2h 50m
Southwest
Deal found 5/15![Southwest logo]()
$295
This Delta deal was found by Cheapflights users on 5/11. 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.
Thu 7/211:30 am
ORD
- RSW
1 stop4h 57m
Delta
Mon 7/65:37 am
RSW
- ORD
1 stop5h 36m
Delta
Deal found 5/11![Delta logo]()
$315
This Southwest deal was found by Cheapflights users on 5/15. 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 8/209:00 am
MDW
- RSW
Nonstop2h 45m
Southwest
Mon 8/2411:55 am
RSW
- MDW
Nonstop2h 50m
Southwest
Deal found 5/15![Southwest logo]()
$295
This United Airlines deal was found by Cheapflights users on 5/14. 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.
Fri 7/314:26 pm
ORD
- RSW
Nonstop3h 08m
United Airlines
Sun 8/97:00 am
RSW
- ORD
Nonstop3h 23m
United Airlines
Deal found 5/14![United Airlines logo]()
$346
This Delta deal was found by Cheapflights users on 5/14. 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 7/49:17 am
MDW
- RSW
1 stop7h 10m
Delta
Mon 7/206:45 am
RSW
- MDW
1 stop6h 11m
Delta
Deal found 5/14![Delta logo]()
$315
This Southwest deal was found by Cheapflights users on 5/15. 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.
Mon 7/136:55 pm
MDW
- RSW
Nonstop2h 45m
Southwest
Wed 7/157:10 am
RSW
- MDW
Nonstop2h 50m
Southwest
Deal found 5/15![Southwest logo]()
$295
This Delta deal was found by Cheapflights users on 5/11. 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.
Mon 6/294:25 pm
MDW
- RSW
1 stop5h 45m
Delta
Sat 7/46:34 pm
RSW
- MDW
1 stop4h 43m
Delta
Deal found 5/11![Delta logo]()
$315
This Southwest deal was found by Cheapflights users on 5/15. 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.
Tue 7/286:55 pm
MDW
- RSW
Nonstop2h 45m
Southwest
Sat 8/112:45 pm
RSW
- MDW
1 stop6h 30m
Southwest
Deal found 5/15![Southwest logo]()
$305
This Delta deal was found by Cheapflights users on 5/15. 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.
Tue 6/304:25 pm
MDW
- RSW
1 stop7h 37m
Delta
Sat 7/46:34 pm
RSW
- MDW
1 stop4h 43m
Delta
Deal found 5/15![Delta logo]()
$315
This United Airlines deal was found by Cheapflights users on 5/12. 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.
Thu 10/297:45 am
ORD
- RSW
1 stop6h 59m
United Airlines
Wed 11/47:00 am
RSW
- ORD
2 stops8h 42m
United Airlines
Deal found 5/12![United Airlines logo]()
$408
This Delta deal was found by Cheapflights users on 5/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/16:22 pm
ORD
- RSW
1 stop5h 40m
Delta
Wed 7/85:35 am
RSW
- ORD
2 stops13h 54m
Delta
Deal found 5/12![Delta logo]()
$333
This Delta deal was found by Cheapflights users on 5/15. 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 10/21:15 pm
ORD
- RSW
1 stop7h 03m
Delta
Mon 10/53:06 pm
RSW
- ORD
1 stop7h 39m
Delta
Deal found 5/15![Delta logo]()
$335
This Delta deal was found by Cheapflights users on 5/11. 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.
Tue 6/306:35 am
ORD
- RSW
1 stop4h 39m
Delta
Sun 7/55:37 am
RSW
- ORD
1 stop7h 59m
Delta
Deal found 5/11![Delta logo]()
$344
This Delta deal was found by Cheapflights users on 5/14. 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.
Thu 8/63:31 pm
ORD
- RSW
1 stop4h 47m
Delta
Sun 8/95:23 am
RSW
- ORD
1 stop5h 46m
Delta
Deal found 5/14![Delta logo]()
$346
This Delta deal was found by Cheapflights users on 5/15. 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 6/105:30 am
ORD
- RSW
1 stop5h 44m
Delta
Sun 6/145:37 am
RSW
- ORD
1 stop5h 36m
Delta
Deal found 5/15![Delta logo]()
$354
This Delta deal was found by Cheapflights users on 5/11. 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 7/1510:30 am
ORD
- RSW
1 stop7h 02m
Delta
Fri 7/315:35 am
RSW
- ORD
1 stop5h 35m
Delta
Deal found 5/11![Delta logo]()
$365
Last-minute flights from Chicago to Fort Myers BeachDiscover last-minute flight deals from Chicago to Fort Myers Beach. Data last updated May 16, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Fort Myers Beach. Data last updated May 16, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 5/12. 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 6/24:05 pm
MDW
- RSW
Nonstop2h 45m
Southwest
Thu 7/95:10 am
RSW
- MDW
Nonstop2h 50m
Southwest
Deal found 5/12![Southwest logo]()
$293
This Southwest deal was found by Cheapflights users on 5/11. 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.
Tue 6/24:05 pm
MDW
- RSW
Nonstop2h 45m
Southwest
Mon 6/295:55 am
RSW
- MDW
1 stop5h 05m
Southwest
Deal found 5/11![Southwest logo]()
$303
This Southwest deal was found by Cheapflights users on 5/12. 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 6/96:55 pm
MDW
- RSW
Nonstop2h 45m
Southwest
Tue 6/167:10 am
RSW
- MDW
Nonstop2h 50m
Southwest
Deal found 5/12![Southwest logo]()
$291
This United Airlines deal was found by Cheapflights users on 5/13. 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 6/104:26 pm
ORD
- RSW
Nonstop3h 08m
United Airlines
Tue 6/167:00 am
RSW
- ORD
Nonstop3h 23m
United Airlines
Deal found 5/13![United Airlines logo]()
$291
This United Airlines deal was found by Cheapflights users on 5/12. 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.
Wed 6/106:30 am
ORD
- RSW
1 stop8h 22m
United Airlines
Sat 6/137:00 am
RSW
- ORD
Nonstop3h 23m
United Airlines
Deal found 5/12![United Airlines logo]()
$303
This American Airlines deal was found by Cheapflights users on 5/14. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/137:52 pm
ORD
- RSW
Nonstop2h 58m
American Airlines
Sat 6/206:15 am
RSW
- ORD
Nonstop3h 22m
American Airlines
Deal found 5/14![American Airlines logo]()
$294
This Southwest deal was found by Cheapflights users on 5/13. 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.
Mon 6/156:55 pm
MDW
- RSW
Nonstop2h 45m
Southwest
Thu 6/185:10 am
RSW
- MDW
Nonstop2h 50m
Southwest
Deal found 5/13![Southwest logo]()
$295
This Southwest deal was found by Cheapflights users on 5/14. 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 6/182:45 pm
MDW
- RSW
1 stop7h 40m
Southwest
Wed 6/2412:10 pm
RSW
- MDW
Nonstop2h 55m
Southwest
Deal found 5/14![Southwest logo]()
$309
This United Airlines deal was found by Cheapflights users on 5/13. 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 6/244:26 pm
ORD
- RSW
Nonstop3h 08m
United Airlines
Tue 6/305:00 pm
RSW
- ORD
1 stop8h 45m
United Airlines
Deal found 5/13![United Airlines logo]()
$301
This United Airlines deal was found by Cheapflights users on 5/12. 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.
Thu 6/254:26 pm
ORD
- RSW
Nonstop3h 08m
United Airlines
Wed 7/14:39 pm
RSW
- ORD
Nonstop3h 21m
United Airlines
Deal found 5/12![United Airlines logo]()
$293
This United Airlines deal was found by Cheapflights users on 5/13. 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.
Sat 6/274:26 pm
ORD
- RSW
Nonstop3h 08m
United Airlines
Sat 7/47:00 am
RSW
- ORD
Nonstop3h 23m
United Airlines
Deal found 5/13![United Airlines logo]()
$295
This United Airlines deal was found by Cheapflights users on 5/10. 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 6/277:05 am
ORD
- RSW
Nonstop3h 09m
United Airlines
Thu 7/212:59 pm
RSW
- ORD
1 stop6h 45m
United Airlines
Deal found 5/10![United Airlines logo]()
$305
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 May 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 May 16, 2026.
This Mytrip deal was found by Cheapflights users on 5/15. 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 6/127:07 pm
ORD
- RSW
1 stop14h 59m
Avelo Airlines
Deal found 5/15![Avelo Airlines logo]()
$112
This Mytrip deal was found by Cheapflights users on 5/15. 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.
Thu 6/46:35 pm
ORD
- RSW
1 stop14h 01m
Avelo Airlines
Deal found 5/15![Avelo Airlines logo]()
$114
This Kiwi.com deal was found by Cheapflights users on 5/14. 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 8/111:50 pm
ORD
- RSW
2 stops19h 23m
Frontier
Deal found 5/14![Frontier logo]()
$118
This Kiwi.com deal was found by Cheapflights users on 5/13. 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.
Tue 8/1112:11 pm
MDW
- RSW
2 stops21h 02m
Frontier
Deal found 5/13![Frontier logo]()
$118
This Kiwi.com deal was found by Cheapflights users on 5/15. 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.
Mon 8/106:00 am
MDW
- RSW
2 stops27h 13m
Frontier
Deal found 5/15![Frontier logo]()
$127
This Kiwi.com deal was found by Cheapflights users on 5/13. 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.
Tue 6/21:29 pm
ORD
- RSW
2 stops28h 53m
Frontier
Deal found 5/13![Frontier logo]()
$129
This Kiwi.com deal was found by Cheapflights users on 5/13. 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.
Sat 8/86:00 am
MDW
- RSW
2 stops27h 13m
Frontier
Deal found 5/13![Frontier logo]()
$131
This Kiwi.com deal was found by Cheapflights users on 5/14. 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.
Sat 7/111:50 pm
ORD
- RSW
2 stops19h 23m
Frontier
Deal found 5/14![Frontier logo]()
$135
This Kiwi.com deal was found by Cheapflights users on 5/14. 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.
Mon 7/66:00 am
MDW
- RSW
2 stops51h 13m
Frontier
Deal found 5/14![Frontier logo]()
$135
This Kiwi.com deal was found by Cheapflights users on 5/13. 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.
Tue 8/111:50 pm
ORD
- RSW
2 stops31h 07m
Multiple Airlines
Deal found 5/13![Multiple Airlines logo]()
$137
This Kiwi.com deal was found by Cheapflights users on 5/12. 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.
Tue 8/412:11 pm
MDW
- RSW
2 stops32h 46m
Multiple Airlines
Deal found 5/12![Multiple Airlines logo]()
$137
This Kiwi.com deal was found by Cheapflights users on 5/14. 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 7/76:00 am
MDW
- RSW
2 stops36h 14m
Frontier
Deal found 5/14![Frontier logo]()
$138
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 May 16, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $291 (United Airlines) |
One-way from | $112 (Mytrip) |
Popular in | December |
Cheapest in | August |
Average price | $326 |
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 May 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
Quickest round-trip
ChicagoFort Myers
MDW - RSW
MDWRSW
Chicago Midway
Tue 6/9
6:55 pm-10:40 pm
Nonstop2h 45m
Fort Myers SW Florida Intl
Tue 6/16
7:10 am-9:00 am
Nonstop2h 50m
$291
ChicagoFort Myers
MDW - RSW
MDWRSW
Chicago Midway
Tue 6/16
6:55 pm-10:40 pm
Nonstop2h 45m
Fort Myers SW Florida Intl
Tue 6/23
6:25 pm-8:15 pm
Nonstop2h 50m
$295
ChicagoFort Myers
MDW - RSW
MDWRSW
Chicago Midway
Tue 7/21
6:55 pm-10:40 pm
Nonstop2h 45m
Fort Myers SW Florida Intl
Tue 7/28
7:10 am-9:00 am
Nonstop2h 50m
$295
ChicagoFort Myers
MDW - RSW
MDWRSW
Chicago Midway
Thu 8/20
9:00 am-12:45 pm
Nonstop2h 45m
Fort Myers SW Florida Intl
Mon 8/24
11:55 am-1:45 pm
Nonstop2h 50m
$295
ChicagoFort Myers
MDW - RSW
MDWRSW
Chicago Midway
Mon 7/13
6:55 pm-10:40 pm
Nonstop2h 45m
Fort Myers SW Florida Intl
Wed 7/15
7:10 am-9:00 am
Nonstop2h 50m
$295
ChicagoFort Myers
ORD - RSW
ORDRSW
Chicago O'Hare Intl
Wed 7/15
10:35 am-2:44 pm
Nonstop3h 09m
Fort Myers SW Florida Intl
Mon 7/20
12:59 pm-6:44 pm
1 stop6h 45m
$303
ChicagoFort Myers
ORD - RSW
ORDRSW
Chicago O'Hare Intl
Wed 7/29
7:05 am-11:14 am
Nonstop3h 09m
Fort Myers SW Florida Intl
Mon 8/3
12:59 pm-6:44 pm
1 stop6h 45m
$303
ChicagoFort Myers
MDW - RSW
MDWRSW
Chicago Midway
Tue 7/28
6:55 pm-10:40 pm
Nonstop2h 45m
Fort Myers SW Florida Intl
Sat 8/1
12:45 pm-6:15 pm
1 stop6h 30m
$305
ChicagoFort Myers
MDW - RSW
MDWRSW
Chicago Midway
Thu 8/6
6:05 am-12:13 pm
1 stop5h 08m
Fort Myers SW Florida Intl
Wed 8/12
5:23 am-9:59 am
1 stop5h 36m
$313
ChicagoFort Myers
MDW - RSW
MDWRSW
Chicago Midway
Tue 8/11
10:54 am-4:44 pm
1 stop4h 50m
Fort Myers SW Florida Intl
Sat 8/15
11:05 am-3:38 pm
1 stop5h 33m
$313
Showing 1-10 of 46 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.
MDW-RSW
ORD-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
MDW-RSW
ORD-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 May 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 25% on airfare.
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 May 9, 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. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
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 May 16, 2026.
The most flights from CHI to FM9 are scheduled on a Friday (23 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (4 on average).
How much does it cost to fly round-trip from Chicago to Fort Myers Beach?
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 May 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.
Food
7.0
Overall
8.0
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Food
7.0
Overall
8.0
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Food
7.0
Overall
8.0
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Food
7.0
Overall
8.0
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Food
7.0
Overall
8.0
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Food
7.0
Overall
8.0
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Crew
8.6
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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Alternative routes for Chicago to Fort Myers Beach
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Complete your trip
Complete your trip to Fort Myers Beach by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Fort Myers Beach by cabin class
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 May 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 May 16, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 8 airlines flying from Chicago to Fort Myers Beach
Discover the top 8 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 May 16, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$58 | Average$197 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$66 | Average$187 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$99 | Average$218 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$130 | Average$358 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$144 | Average$230 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$157 | Average$361 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$160 | Average$360 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$171 | Average$386 | FlexibilityNo cancel fee | On-time63% |