$142+ Cheap flights from Fort Myers (RSW) to Chicago (CHI)
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 9/17. Fares are subject to change and may not be available on all flights or dates of travel.
RSW — CHI
Sep 26 — Oct 31
Round-trip
1 adult, Economy
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Find cheap flights from Fort Myers to Chicago 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 Fort Myers SW Florida Intl to Chicago are usually found in January or February, booked 29 days in advance, depart on a Thursday or Friday and return on a Wednesday
Cheap flight deals from Fort Myers to Chicago
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Cheapest flights from Fort Myers to ChicagoExplore the most affordable flight options available from Fort Myers to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 27, 2026.
Explore the most affordable flight options available from Fort Myers to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 27, 2026.
This CheapOair deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” 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 10/2212:45 pm -
1 stop10h 54m
Sat 10/311:00 pm -
1 stop9h 59m
Deal found 8/23![Multiple Airlines logo]()
$281
This Super.com deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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.
Wed 11/258:55 pm -
Nonstop4h 52m
Mon 11/302:08 pm -
Nonstop4h 52m
Deal found 8/26![Frontier logo]()
$282
This United Airlines deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 10/224:34 pm -
Nonstop3h 19m
Tue 10/2712:59 pm -
Nonstop3h 02m
Deal found 8/26![United Airlines logo]()
$283
This Southwest deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 9/245:25 pm -
Nonstop2h 50m
Mon 9/286:15 pm -
Nonstop2h 50m
Deal found 8/27![Southwest logo]()
$283
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/126:02 am -
Nonstop3h 27m
Mon 9/146:50 am -
Nonstop3h 01m
Deal found 8/22![American Airlines logo]()
$284
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/266:50 am -
1 stop8h 55m
Wed 9/307:05 am -
Nonstop3h 06m
Deal found 8/22![United Airlines logo]()
$289
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/161:40 pm -
1 stop9h 16m
Sat 10/312:15 pm -
1 stop8h 22m
Deal found 8/22![JetBlue logo]()
$291
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2212:17 pm -
Nonstop3h 14m
Mon 10/266:55 am -
1 stop8h 00m
Deal found 8/22![United Airlines logo]()
$293
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.
Sat 9/127:30 am -
1 stop6h 35m
Mon 9/146:15 pm -
Nonstop2h 50m
Deal found 8/22![Southwest logo]()
$293
This Southwest deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” 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 9/237:10 am -
Nonstop2h 45m
Sat 9/2610:55 am -
Nonstop2h 40m
Deal found 8/23![Southwest logo]()
$294
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/136:00 am -
1 stop8h 20m
Mon 11/162:15 pm -
1 stop8h 22m
Deal found 8/22![JetBlue logo]()
$295
This CheapOair deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” 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.
Mon 11/238:55 pm -
Nonstop4h 52m
Sat 11/2810:00 am -
1 stop23h 26m
Deal found 8/23![Multiple Airlines logo]()
$297
Best flights from Fort Myers to ChicagoDiscover carefully curated flight deals from Fort Myers to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 27, 2026.
Discover carefully curated flight deals from Fort Myers to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 27, 2026.
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.
Thu 10/222:15 pm -
1 stop7h 15m
Mon 10/263:40 pm -
1 stop7h 41m
Deal found 8/22![Delta logo]()
$303
This United Airlines deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 10/98:45 am -
Nonstop3h 14m
Sat 10/102:10 pm -
1 stop6h 47m
Deal found 8/24![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.
Thu 9/246:50 am -
Nonstop2h 50m
Sun 9/276:55 pm -
Nonstop2h 50m
Deal found 8/21![Southwest logo]()
$325
This Sun Country Air deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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.
Tue 11/247:53 pm -
1 stop14h 58m
Sat 11/2810:00 am -
1 stop23h 26m
Deal found 8/25![Sun Country Air logo]()
$335
This Delta deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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 10/317:40 am -
1 stop6h 19m
Mon 11/21:55 pm -
1 stop6h 34m
Deal found 8/25![Delta logo]()
$303
This Southwest deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/174:50 pm -
1 stop5h 00m
Tue 1/51:15 pm -
2 stops6h 50m
Deal found 8/25![Southwest logo]()
$330
This Delta deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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 9/262:45 pm -
1 stop5h 11m
Tue 9/291:51 pm -
1 stop4h 43m
Deal found 8/25![Delta logo]()
$303
This United Airlines deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 10/22:14 pm -
Nonstop3h 10m
Sun 10/1110:51 am -
Nonstop3h 06m
Deal found 8/26![United Airlines logo]()
$353
This Delta deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1710:54 am -
1 stop4h 55m
Thu 1/75:55 pm -
1 stop5h 40m
Deal found 8/24![Delta logo]()
$303
This Southwest deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” 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 11/64:35 pm -
Nonstop2h 55m
Sun 11/87:45 am -
Nonstop2h 45m
Deal found 8/23![Southwest logo]()
$343
This Sun Country Air deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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.
Tue 12/221:50 pm -
1 stop21h 18m
Wed 12/3011:40 am -
1 stop21h 53m
Deal found 8/25![Sun Country Air logo]()
$385
This Delta deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/172:09 pm -
1 stop4h 52m
Tue 1/55:25 pm -
1 stop4h 43m
Deal found 8/24![Delta logo]()
$303
This United Airlines deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/2312:27 pm -
Nonstop3h 14m
Wed 9/307:05 am -
Nonstop3h 06m
Deal found 8/23![United Airlines logo]()
$373
This Southwest deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” 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 10/26:25 pm -
1 stop6h 30m
Sun 10/48:10 am -
Nonstop2h 45m
Deal found 8/23![Southwest logo]()
$353
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 9/166:19 pm -
1 stop5h 25m
Sat 9/194:30 pm -
1 stop7h 05m
Deal found 8/21![Delta logo]()
$303
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 11/1310:50 am -
1 stop4h 20m
Sun 11/155:10 am -
1 stop5h 35m
Deal found 8/22![Southwest logo]()
$358
This Delta deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 10/141:12 pm -
1 stop6h 59m
Fri 10/236:30 am -
1 stop7h 36m
Deal found 8/26![Delta logo]()
$321
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.
Sat 10/107:30 am -
Nonstop2h 50m
Sun 10/118:10 am -
Nonstop2h 45m
Deal found 8/22![Southwest logo]()
$365
This Delta deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 12/152:09 pm -
1 stop4h 52m
Fri 1/85:25 pm -
1 stop4h 43m
Deal found 8/24![Delta logo]()
$321
This Delta deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/172:09 pm -
1 stop4h 52m
Fri 1/89:30 am -
1 stop4h 36m
Deal found 8/24![Delta logo]()
$321
This Delta deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/137:59 pm -
1 stop4h 53m
Thu 1/75:55 pm -
1 stop5h 40m
Deal found 8/24![Delta logo]()
$345
Last-minute flights from Fort Myers to ChicagoDiscover last-minute flight deals from Fort Myers to Chicago. Data last updated August 27, 2026 and is based on user searches.
Discover last-minute flight deals from Fort Myers to Chicago. Data last updated August 27, 2026 and is based on user searches.
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/126:02 am -
Nonstop3h 27m
Mon 9/146:50 am -
Nonstop3h 01m
Deal found 8/22![American Airlines logo]()
$284
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.
Sat 9/127:30 am -
1 stop6h 35m
Mon 9/146:15 pm -
Nonstop2h 50m
Deal found 8/22![Southwest logo]()
$293
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 9/126:19 pm -
1 stop6h 40m
Mon 9/146:40 am -
1 stop4h 26m
Deal found 8/22![Delta logo]()
$304
This Southwest deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 9/167:10 am -
Nonstop2h 45m
Thu 9/176:15 pm -
Nonstop2h 50m
Deal found 8/24![Southwest logo]()
$301
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 9/166:19 pm -
1 stop5h 25m
Sat 9/194:30 pm -
1 stop7h 05m
Deal found 8/21![Delta logo]()
$303
This Southwest deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 9/227:10 am -
Nonstop2h 45m
Tue 9/296:00 pm -
Nonstop2h 50m
Deal found 8/24![Southwest logo]()
$283
This Delta deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 9/226:19 pm -
1 stop6h 40m
Tue 9/2911:17 am -
1 stop4h 57m
Deal found 8/24![Delta logo]()
$303
This Southwest deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” 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 9/237:10 am -
Nonstop2h 45m
Sat 9/2610:55 am -
Nonstop2h 40m
Deal found 8/23![Southwest logo]()
$294
This American Airlines deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 9/246:02 am -
Nonstop3h 27m
Wed 9/307:07 pm -
Nonstop3h 02m
Deal found 8/26![American Airlines logo]()
$283
This United Airlines deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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 9/254:34 pm -
Nonstop3h 19m
Wed 9/309:02 am -
Nonstop3h 06m
Deal found 8/25![United Airlines logo]()
$301
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/266:50 am -
1 stop8h 55m
Wed 9/307:05 am -
Nonstop3h 06m
Deal found 8/22![United Airlines logo]()
$289
This Southwest deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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 9/286:10 am -
1 stop10h 20m
Sat 10/34:10 pm -
Nonstop2h 45m
Deal found 8/25![Southwest logo]()
$299
One-way flights from Fort Myers to ChicagoSearch for one-way flight options from Fort Myers to Chicago. Find affordable one-way fares based on user searches. Data last updated August 27, 2026.
Search for one-way flight options from Fort Myers to Chicago. Find affordable one-way fares based on user searches. Data last updated August 27, 2026.
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/179:15 am -
Nonstop3h 14m
Deal found 8/22![United Airlines logo]()
$142
This Southwest deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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 9/215:25 pm -
Nonstop2h 50m
Deal found 8/25![Southwest logo]()
$142
This Kiwi.com deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/208:55 pm -
Nonstop4h 52m
Deal found 8/23![Frontier logo]()
$143
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/216:00 am -
1 stop6h 47m
Deal found 8/22![JetBlue logo]()
$144
This Mytrip deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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.
Mon 9/2811:52 am -
1 stop7h 21m
Deal found 8/25![Avelo Airlines logo]()
$146
This United Airlines deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 9/266:50 am -
1 stop8h 55m
Deal found 8/26![United Airlines logo]()
$147
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.
Wed 10/211:55 pm -
1 stop4h 15m
Deal found 8/22![Southwest logo]()
$147
This Kiwi.com deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/112:46 pm -
1 stop25h 44m
Deal found 8/24![Frontier logo]()
$148
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.
Thu 9/176:19 pm -
1 stop6h 40m
Deal found 8/22![Delta logo]()
$152
This Delta deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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 9/226:19 pm -
1 stop5h 25m
Deal found 8/25![Delta logo]()
$152
This American Airlines deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/247:26 pm -
Nonstop3h 29m
Deal found 8/25![American Airlines logo]()
$153
This Southwest deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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 10/247:30 am -
Nonstop2h 50m
Deal found 8/25![Southwest logo]()
$153
Find flight deals from Fort Myers to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Fort Myers (RSW) to Chicago (CHI). 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 27, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $281 (CheapOair) |
One-way from | $142 (United Airlines) |
Popular in | July |
Cheapest in | January |
Average price | $321 |
Cheapflights Fare Finder
Customize your flight search to find flights from Fort Myers to Chicago 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 27, 2026.
Use the filters below to find and compare flights from Fort Myers to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Fort MyersChicago
RSW Fort Myers SW Florida Intl - ORD Chicago O'Hare Intl
RSWORD
Fort Myers SW Florida Intl
Thu 10/22
2:15 pm-8:30 pm
1 stop7h 15m
Chicago O'Hare Intl
Mon 10/26
3:40 pm-12:21 am
1 stop7h 41m
$303
Fort MyersChicago
RSW Fort Myers SW Florida Intl - ORD Chicago O'Hare Intl
RSWORD
Fort Myers SW Florida Intl
Sat 10/31
7:40 am-12:59 pm
1 stop6h 19m
Chicago O'Hare Intl
Mon 11/2
1:55 pm-9:29 pm
1 stop6h 34m
$303
Fort MyersChicago
RSW Fort Myers SW Florida Intl - ORD Chicago O'Hare Intl
RSWORD
Fort Myers SW Florida Intl
Sat 9/26
2:45 pm-6:56 pm
1 stop5h 11m
Chicago O'Hare Intl
Tue 9/29
1:51 pm-7:34 pm
1 stop4h 43m
$303
Fort MyersChicago
RSW Fort Myers SW Florida Intl - ORD Chicago O'Hare Intl
RSWORD
Fort Myers SW Florida Intl
Thu 12/17
10:54 am-2:49 pm
1 stop4h 55m
Chicago O'Hare Intl
Thu 1/7
5:55 pm-12:35 am
1 stop5h 40m
$303
Fort MyersChicago
RSW Fort Myers SW Florida Intl - MDW Chicago Midway
RSWMDW
Fort Myers SW Florida Intl
Thu 12/17
2:09 pm-6:01 pm
1 stop4h 52m
Chicago Midway
Tue 1/5
5:25 pm-11:08 pm
1 stop4h 43m
$303
Fort MyersChicago
RSW Fort Myers SW Florida Intl - MDW Chicago Midway
RSWMDW
Fort Myers SW Florida Intl
Wed 9/16
6:19 pm-10:44 pm
1 stop5h 25m
Chicago Midway
Sat 9/19
4:30 pm-12:35 am
1 stop7h 05m
$303
Fort MyersChicago
RSW Fort Myers SW Florida Intl - ORD Chicago O'Hare Intl
RSWORD
Fort Myers SW Florida Intl
Fri 10/9
8:45 am-10:59 am
Nonstop3h 14m
Chicago O'Hare Intl
Sat 10/10
2:10 pm-9:57 pm
1 stop6h 47m
$311
Fort MyersChicago
RSW Fort Myers SW Florida Intl - ORD Chicago O'Hare Intl
RSWORD
Fort Myers SW Florida Intl
Wed 10/14
1:12 pm-7:11 pm
1 stop6h 59m
Chicago O'Hare Intl
Fri 10/23
6:30 am-3:06 pm
1 stop7h 36m
$321
Fort MyersChicago
RSW Fort Myers SW Florida Intl - MDW Chicago Midway
RSWMDW
Fort Myers SW Florida Intl
Tue 12/15
2:09 pm-6:01 pm
1 stop4h 52m
Chicago Midway
Fri 1/8
5:25 pm-11:08 pm
1 stop4h 43m
$321
Fort MyersChicago
RSW Fort Myers SW Florida Intl - MDW Chicago Midway
RSWMDW
Fort Myers SW Florida Intl
Thu 12/17
2:09 pm-6:01 pm
1 stop4h 52m
Chicago Midway
Fri 1/8
9:30 am-3:06 pm
1 stop4h 36m
$321
Showing 1-10 of 50 resultsSorted by cheapest first
Compare providers for flights from Fort Myers to Chicago
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Fort Myers to Chicago in August.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*1 star | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy- | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star |
- Most accurate provider: When it comes to deals on Fort Myers-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Fort Myers-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Fort Myers-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Fort Myers-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Fort Myers-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Fort Myers to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Fort Myers with our price prediction graph.
RSW-CHI
RSW-ORD
RSW-MDW
RSW-RFD
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Fort Myers to Chicago
RSW-CHI
RSW-ORD
RSW-MDW
RSW-RFD
What is the cheapest month to book a flight from Fort Myers to Chicago?
Currently, February is the cheapest month in which you can book a flight from Fort Myers to Chicago (average of $193). Flying from Fort Myers to Chicago in July is currently the most expensive (average of $363). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from RSW to CHI?
Find hourly flight availability from Fort Myers to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 27, 2026.
It’s typically best to fly out from Fort Myers to Chicago in the evening. Doing so could potentially save you 24% on the flight price compared to flying at noon, which is usually more expensive.
Weekly flight availability from Fort Myers to Chicago
Explore weekly flight availability from Fort Myers to Chicago. 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 27, 2026.
The most flights from RSW to CHI are scheduled on a Tuesday (19 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 Fort Myers to Chicago?
Airfare is typical for this route at the moment.
Fort Myers to Chicago flights typically cost between $263 and $346 in October.The cheapest round-trip price found within the last 5 days was $281 on Multiple Airlines (Oct 22-Oct 31).
How far ahead should I book a flight from Fort Myers to Chicago?
The price you pay for your flight from Fort Myers to Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 31 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
What is the cheapest day to fly from Fort Myers to Chicago?
Use this chart to determine the cheapest time to fly round-trip from Fort Myers to Chicago. Price data was last updated on August 22, 2026.
Travelers seeking maximum savings on their Fort Myers to Chicago flight should consider departing on Sunday evenings when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
The best insider tips for Fort Myers to Chicago flights
AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Fort Myers to Chicago trip
Our travel experts
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated August 27, 2026.
Get a feel of what it's like to fly with Southwest,United Airlines, andAmerican Airlines from Fort Myers to Chicago 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
Entertainment
7.5
Comfort
8.0
Food
7.0
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Crew
8.6
Entertainment
7.5
Comfort
8.0
Food
7.0
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Crew
8.6
Entertainment
7.5
Comfort
8.0
Food
7.0
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Crew
8.6
Entertainment
7.5
Comfort
8.0
Food
7.0
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Crew
8.6
Entertainment
7.5
Comfort
8.0
Food
7.0
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Crew
8.6
Entertainment
7.5
Comfort
8.0
Food
7.0
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
Find useful and relevant information for your journey from Fort Myers to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
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Other flights to Chicago
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Top 5 airlines flying from Fort Myers to Chicago
Discover the top 5 airlines that operate flights from Fort Myers to Chicago. 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 27, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$43 | Average$98 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$105 | Average$284 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$159 | Average$326 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$174 | Average$310 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$199 | Average$355 | FlexibilityNo cancel fee | On-time63% |