$139+ Cheap flights from Chicago (CHI) to Fort Myers (RSW)
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 9/16. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — RSW
Sep 21 — Sep 281
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Fort Myers 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 SW Florida Intl are usually found in February or January, booked 63 days in advance, depart on a Wednesday or Tuesday and return on a Thursday
Cheap flight deals from Chicago to Fort Myers
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Cheapest flights from Chicago to Fort MyersExplore the most affordable flight options available from Chicago to Fort Myers. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 22, 2026.
Explore the most affordable flight options available from Chicago to Fort Myers. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 22, 2026.
This Expedia deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1010:52 am -
Nonstop3h 06m
Mon 12/143:53 pm -
Nonstop3h 21m
Deal found 8/17![Frontier logo]()
$240
This Priceline deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/272:08 pm -
Nonstop4h 52m
Fri 12/45:58 pm -
Nonstop3h 21m
Deal found 8/17![Frontier logo]()
$245
This Frontier deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier 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 10/812:45 pm -
1 stop10h 54m
Deal found 8/17![Frontier logo]()
$259
This Super.com deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” 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
Sun 12/63:53 pm -
Nonstop3h 21m
Deal found 8/21![Frontier logo]()
$260
This Super.com deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1110:52 am -
Nonstop3h 06m
Mon 12/143:53 pm -
Nonstop3h 21m
Deal found 8/17![Frontier logo]()
$263
This Priceline deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/202:08 pm -
Nonstop4h 52m
Sun 12/63:53 pm -
Nonstop3h 21m
Deal found 8/19![Frontier logo]()
$265
This Kiwi.com deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/107:25 am -
1 stop27h 26m
Tue 9/157:00 am -
2 stops12h 23m
Deal found 8/17![Multiple Airlines logo]()
$272
This Priceline deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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
Wed 10/216:00 am -
1 stop6h 47m
Deal found 8/19![Multiple Airlines logo]()
$273
This CheapOair deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/107:25 am -
1 stop8h 20m
Mon 9/1411:05 am -
1 stop8h 56m
Deal found 8/17![Multiple Airlines logo]()
$276
This Priceline deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/247:25 am -
1 stop8h 20m
Sat 10/310:45 am -
1 stop9h 16m
Deal found 8/17![Multiple Airlines logo]()
$277
This Expedia deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/1310:52 am -
Nonstop3h 06m
Sat 12/196:05 am -
1 stop11h 42m
Deal found 8/17![Multiple Airlines logo]()
$280
This Southwest deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/171:00 pm -
Nonstop2h 45m
Mon 9/216:50 am -
Nonstop2h 50m
Deal found 8/19![Southwest logo]()
$283
Best flights from Chicago to Fort MyersDiscover carefully curated flight deals from Chicago to Fort Myers that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 22, 2026.
Discover carefully curated flight deals from Chicago to Fort Myers that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 22, 2026.
This United Airlines deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/107:15 am -
Nonstop3h 06m
Mon 9/144:41 pm -
Nonstop3h 19m
Deal found 8/20![United Airlines logo]()
$283
This Southwest deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/156:00 pm -
Nonstop2h 50m
Tue 9/227:10 am -
Nonstop2h 45m
Deal found 8/20![Southwest logo]()
$283
This Delta deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/151:55 pm -
1 stop6h 34m
Tue 11/1710:52 am -
1 stop4h 46m
Deal found 8/17![Delta logo]()
$303
This Southwest deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/15:05 am -
Nonstop2h 40m
Mon 10/56:40 am -
Nonstop2h 50m
Deal found 8/18![Southwest logo]()
$283
This United Airlines deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/157:15 am -
Nonstop3h 06m
Mon 9/215:14 pm -
1 stop7h 13m
Deal found 8/18![United Airlines logo]()
$293
This Delta deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/279:30 am -
1 stop5h 23m
Mon 2/17:49 pm -
1 stop5h 01m
Deal found 8/21![Delta logo]()
$303
This Delta deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/38:05 am -
1 stop4h 27m
Mon 12/214:51 pm -
1 stop5h 19m
Deal found 8/20![Delta logo]()
$303
This United Airlines deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/2812:59 pm -
Nonstop3h 02m
Wed 12/21:47 pm -
1 stop7h 23m
Deal found 8/20![United Airlines logo]()
$304
This Southwest deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/112:45 pm -
1 stop6h 30m
Wed 10/217:20 am -
2 stops8h 20m
Deal found 8/19![Southwest logo]()
$308
This Delta deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” 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 9/193:40 pm -
1 stop4h 54m
Tue 9/225:30 am -
1 stop4h 55m
Deal found 8/22![Delta logo]()
$303
This United Airlines deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” 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 9/143:45 pm -
Nonstop3h 06m
Fri 9/187:00 pm -
1 stop6h 28m
Deal found 8/21![United Airlines logo]()
$311
This Southwest deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” 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 9/3010:10 am -
2 stops8h 45m
Sat 10/36:40 am -
2 stops8h 15m
Deal found 8/21![Southwest logo]()
$313
This Delta deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/285:30 am -
1 stop5h 36m
Sat 10/32:45 pm -
1 stop7h 11m
Deal found 8/17![Delta logo]()
$303
This United Airlines deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” 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 10/2310:51 am -
Nonstop3h 06m
Fri 11/132:15 pm -
Nonstop3h 19m
Deal found 8/21![United Airlines logo]()
$319
This Southwest deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/38:10 am -
2 stops11h 25m
Fri 10/91:45 pm -
1 stop6h 30m
Deal found 8/20![Southwest logo]()
$332
This Delta deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” 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 1/307:10 am -
1 stop5h 43m
Wed 2/34:15 pm -
1 stop5h 22m
Deal found 8/21![Delta logo]()
$303
This United Airlines deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/186:30 am -
1 stop8h 25m
Fri 9/2512:17 pm -
Nonstop3h 14m
Deal found 8/19![United Airlines logo]()
$329
This Delta deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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 8/19![Delta logo]()
$303
This Southwest deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2212:45 pm -
1 stop9h 10m
Sun 10/257:05 am -
Nonstop2h 50m
Deal found 8/20![Southwest logo]()
$341
This Southwest deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/243:10 pm -
2 stops5h 55m
Sat 9/267:20 am -
2 stops6h 50m
Deal found 8/20![Southwest logo]()
$343
This Delta deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/511:28 am -
1 stop4h 26m
Sat 12/194:51 pm -
1 stop6h 19m
Deal found 8/20![Delta logo]()
$334
This Southwest deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” 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 10/306:50 pm -
Nonstop2h 45m
Sun 11/19:05 pm -
Nonstop2h 55m
Deal found 8/22![Southwest logo]()
$343
This Delta deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/149:29 am -
1 stop6h 56m
Sun 10/255:30 am -
1 stop5h 33m
Deal found 8/19![Delta logo]()
$345
Last-minute flights from Chicago to Fort MyersDiscover last-minute flight deals from Chicago to Fort Myers. Data last updated August 22, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Fort Myers. Data last updated August 22, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/107:25 am -
1 stop27h 26m
Tue 9/157:00 am -
2 stops12h 23m
Deal found 8/17![Multiple Airlines logo]()
$272
This CheapOair deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/107:25 am -
1 stop8h 20m
Mon 9/1411:05 am -
1 stop8h 56m
Deal found 8/17![Multiple Airlines logo]()
$276
This United Airlines deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/103:45 pm -
Nonstop3h 06m
Sat 9/194:41 pm -
Nonstop3h 19m
Deal found 8/18![United Airlines logo]()
$283
This American Airlines deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/107:07 pm -
Nonstop3h 02m
Mon 9/146:02 am -
Nonstop3h 27m
Deal found 8/19![American Airlines logo]()
$284
This JetBlue deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/117:00 am -
1 stop6h 47m
Mon 9/1411:05 am -
1 stop8h 56m
Deal found 8/17![JetBlue logo]()
$291
This Southwest deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/171:00 pm -
Nonstop2h 45m
Mon 9/216:50 am -
Nonstop2h 50m
Deal found 8/19![Southwest logo]()
$283
This JetBlue deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/197:00 am -
1 stop6h 46m
Wed 10/146:00 am -
1 stop6h 47m
Deal found 8/21![JetBlue logo]()
$287
This United Airlines deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/197:15 am -
Nonstop3h 06m
Sat 9/266:50 am -
1 stop8h 55m
Deal found 8/17![United Airlines logo]()
$289
This Priceline deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/247:25 am -
1 stop8h 20m
Sat 10/310:45 am -
1 stop9h 16m
Deal found 8/17![Multiple Airlines logo]()
$277
This CheapOair deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair 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 10/111:05 am -
1 stop8h 56m
Deal found 8/19![Multiple Airlines logo]()
$282
This Mytrip deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/257:17 pm -
1 stop13h 50m
Mon 9/2811:52 am -
1 stop7h 21m
Deal found 8/17![Avelo Airlines logo]()
$273
This Southwest deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/289:00 am -
Nonstop2h 45m
Tue 10/61:55 pm -
1 stop4h 15m
Deal found 8/20![Southwest logo]()
$289
One-way flights from Chicago to Fort MyersSearch for one-way flight options from Chicago to Fort Myers. Find affordable one-way fares based on user searches. Data last updated August 22, 2026.
Search for one-way flight options from Chicago to Fort Myers. Find affordable one-way fares based on user searches. Data last updated August 22, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/166:25 am -
2 stops14h 48m
Deal found 8/17![Multiple Airlines logo]()
$139
This United Airlines deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/217:15 am -
Nonstop3h 06m
Deal found 8/18![United Airlines logo]()
$142
This Southwest deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/106:15 pm -
Nonstop2h 50m
Deal found 8/18![Southwest logo]()
$142
This Billigflug deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Billigflug is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/196:50 am -
Nonstop3h 01m
Deal found 8/18![Alaska Airlines logo]()
$143
This JetBlue deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/227:05 am -
1 stop7h 12m
Deal found 8/18![JetBlue logo]()
$144
This Kiwi.com deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/177:25 am -
1 stop27h 26m
Deal found 8/18![Frontier logo]()
$145
This Kiwi.com deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/36:30 am -
2 stops28h 15m
Deal found 8/17![Multiple Airlines logo]()
$146
This JetBlue deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/172:15 pm -
1 stop8h 22m
Deal found 8/18![JetBlue logo]()
$148
This Kiwi.com deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/177:28 pm -
2 stops49h 45m
Deal found 8/17![Multiple Airlines logo]()
$149
This Kiwi.com deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/186:30 am -
2 stops14h 43m
Deal found 8/18![Multiple Airlines logo]()
$150
This Delta deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/198:05 am -
1 stop7h 28m
Deal found 8/18![Delta logo]()
$152
This Southwest deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/191:55 pm -
1 stop5h 25m
Deal found 8/18![Southwest logo]()
$152
Find flight deals from Chicago to Fort Myers
Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Fort Myers (RSW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated August 22, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $240 (Expedia) |
One-way from | $139 (Kiwi.com) |
Popular in | December |
Cheapest in | February |
Average price | $295 |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Fort Myers 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 August 22, 2026.
Use the filters below to find and compare flights from Chicago to Fort Myers that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoFort Myers
ORD Chicago O'Hare Intl - RSW Fort Myers SW Florida Intl
ORDRSW
Chicago O'Hare Intl
Thu 9/10
7:15 am-11:21 am
Nonstop3h 06m
Fort Myers SW Florida Intl
Mon 9/14
4:41 pm-7:00 pm
Nonstop3h 19m
$283
ChicagoFort Myers
MDW Chicago Midway - RSW Fort Myers SW Florida Intl
MDWRSW
Chicago Midway
Tue 9/15
6:00 pm-9:50 pm
Nonstop2h 50m
Fort Myers SW Florida Intl
Tue 9/22
7:10 am-8:55 am
Nonstop2h 45m
$283
Quickest round-trip
ChicagoFort Myers
MDW Chicago Midway - RSW Fort Myers SW Florida Intl
MDWRSW
Chicago Midway
Thu 10/1
5:05 am-8:45 am
Nonstop2h 40m
Fort Myers SW Florida Intl
Mon 10/5
6:40 am-8:30 am
Nonstop2h 50m
$283
ChicagoFort Myers
ORD Chicago O'Hare Intl - RSW Fort Myers SW Florida Intl
ORDRSW
Chicago O'Hare Intl
Tue 9/15
7:15 am-11:21 am
Nonstop3h 06m
Fort Myers SW Florida Intl
Mon 9/21
5:14 pm-11:27 pm
1 stop7h 13m
$293
ChicagoFort Myers
ORD Chicago O'Hare Intl - RSW Fort Myers SW Florida Intl
ORDRSW
Chicago O'Hare Intl
Thu 10/15
1:55 pm-9:29 pm
1 stop6h 34m
Fort Myers SW Florida Intl
Tue 11/17
10:52 am-2:38 pm
1 stop4h 46m
$303
ChicagoFort Myers
ORD Chicago O'Hare Intl - RSW Fort Myers SW Florida Intl
ORDRSW
Chicago O'Hare Intl
Wed 1/27
9:30 am-3:53 pm
1 stop5h 23m
Fort Myers SW Florida Intl
Mon 2/1
7:49 pm-11:50 pm
1 stop5h 01m
$303
ChicagoFort Myers
ORD Chicago O'Hare Intl - RSW Fort Myers SW Florida Intl
ORDRSW
Chicago O'Hare Intl
Tue 11/3
8:05 am-1:32 pm
1 stop4h 27m
Fort Myers SW Florida Intl
Mon 12/21
4:51 pm-9:10 pm
1 stop5h 19m
$303
ChicagoFort Myers
ORD Chicago O'Hare Intl - RSW Fort Myers SW Florida Intl
ORDRSW
Chicago O'Hare Intl
Sat 9/19
3:40 pm-9:34 pm
1 stop4h 54m
Fort Myers SW Florida Intl
Tue 9/22
5:30 am-9:25 am
1 stop4h 55m
$303
ChicagoFort Myers
ORD Chicago O'Hare Intl - RSW Fort Myers SW Florida Intl
ORDRSW
Chicago O'Hare Intl
Mon 9/28
5:30 am-12:06 pm
1 stop5h 36m
Fort Myers SW Florida Intl
Sat 10/3
2:45 pm-8:56 pm
1 stop7h 11m
$303
ChicagoFort Myers
ORD Chicago O'Hare Intl - RSW Fort Myers SW Florida Intl
ORDRSW
Chicago O'Hare Intl
Sat 1/30
7:10 am-1:53 pm
1 stop5h 43m
Fort Myers SW Florida Intl
Wed 2/3
4:15 pm-8:37 pm
1 stop5h 22m
$303
Showing 1-10 of 45 resultsSorted by cheapest first
Compare providers for flights from Chicago to Fort Myers
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Fort Myers in August.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy2 stars | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Chicago-Fort Myers flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Fort Myers flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Fort Myers flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago-Fort Myers flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Fort Myers flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Chicago to Fort Myers
Have a flexible travel schedule? Discover the best time to fly to Fort Myers from Chicago with our price prediction graph.
CHI-RSW
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
CHI-RSW
ORD-RSW
MDW-RSW
What is the cheapest month to book a flight from Chicago to Fort Myers?
Currently, January is the cheapest month in which you can book a flight from Chicago to Fort Myers (average of $225). Flying from Chicago to Fort Myers in June is currently the most expensive (average of $379). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from CHI to RSW?
Find hourly flight availability from Chicago to Fort Myers. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 22, 2026.
A simple way to save on the total cost of your ticket is to fly from Chicago to Fort Myers at noon. If you’re flexible enough to do this you can expect to save up to 15% on your trip compared to booking a flight in the evening.
Weekly flight availability from Chicago to Fort Myers
Explore weekly flight availability from Chicago to Fort Myers. 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 August 22, 2026.
The most flights from CHI to RSW are scheduled on a Friday (18 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (9 on average).
How much does it cost to fly round-trip from Chicago to Fort Myers?
Airfare is typical for this route at the moment.
Chicago to Fort Myers flights typically cost between $220 and $362 in December.The cheapest round-trip price found within the last 5 days was $240 on Frontier (Dec 10-Dec 14).
How often are flights from Chicago to Fort Myers delayed?
About 21% of weekly flights between Chicago and Fort Myers have experienced delays in the past year, with the average delay time being 148 minutes.
What is the most punctual flight time for Chicago to Fort Myers flights?
Historically, flights departing at night are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Thursday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Chicago to Fort Myers flights?
Over the last year, United Airlines have had the lowest number of delays on this route, with just 15% of flights being delayed.
How far ahead should I book a flight from Chicago to Fort Myers?
The best time to book flights from Chicago to Fort Myers is 34 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
What is the cheapest day to fly from Chicago to Fort Myers?
Use this chart to determine the cheapest time to fly round-trip from Chicago to Fort Myers. Price data was last updated on August 15, 2026.
Travelers seeking maximum savings on their Chicago to Fort Myers flight should consider departing on Wednesday evenings 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.
The best insider tips for Chicago to Fort Myers flights
AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Chicago to Fort Myers trip
Our travel experts
Reviews of airlines servicing Fort Myers
Get insights into the airlines that provide service to Fort Myers. 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. Reviews last updated August 22, 2026.
Read reviews from past customers who have flown Southwest,United Airlines, andAmerican Airlines from Chicago to Fort Myers. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.5
Boarding
8.1
Crew
8.6
Food
7.0
Comfort
8.0
Overall
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Entertainment
7.5
Boarding
8.1
Crew
8.6
Food
7.0
Comfort
8.0
Overall
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Entertainment
7.5
Boarding
8.1
Crew
8.6
Food
7.0
Comfort
8.0
Overall
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Entertainment
7.5
Boarding
8.1
Crew
8.6
Food
7.0
Comfort
8.0
Overall
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Entertainment
7.5
Boarding
8.1
Crew
8.6
Food
7.0
Comfort
8.0
Overall
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Entertainment
7.5
Boarding
8.1
Crew
8.6
Food
7.0
Comfort
8.0
Overall
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Related info for your journey
Find useful and relevant information for your journey from Chicago to Fort Myers. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Fort Myers?
Book flights to Fort Myers if you plan to visit one of these locationsNorth Fort Myers
Lehigh Acres
Sanibel
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Chicago and Fort Myers flights
Browse other Chicago and Fort Myers flight options. Last updated on August 22, 2026.
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Top 6 airlines flying from Chicago to Fort Myers
Discover the top 6 airlines that operate flights from Chicago to Fort Myers. 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 August 22, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$66 | Average$182 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$130 | Average$370 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$150 | Average$291 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$165 | Average$312 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$165 | Average$327 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$197 | Average$376 | FlexibilityNo cancel fee | On-time63% |