$106+ Cheap flights from Fort Myers (RSW) to Illinois
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 10/23. Fares are subject to change and may not be available on all flights or dates of travel.
RSW — ORD
Aug 24 — Aug 311
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Fort Myers to Illinois 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.Cheap flight deals from Fort Myers to Illinois
Cheapest
Best
Last-minute
One-way
Cheapest flights from Fort Myers to IllinoisExplore the most affordable flight options available from Fort Myers to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 25, 2026.
Explore the most affordable flight options available from Fort Myers to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 25, 2026.
This United Airlines deal was found by Cheapflights users on 7/20. 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 9/512:15 pm
RSW
- PIA
2 stops7h 48m
United Airlines
Wed 9/95:50 am
PIA
- RSW
1 stop7h 46m
United Airlines
Deal found 7/20![United Airlines logo]()
$266
This American Airlines deal was found by Cheapflights users on 7/23. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/1311:27 am
RSW
- ORD
Nonstop3h 23m
American Airlines
Mon 8/176:45 am
ORD
- RSW
Nonstop2h 52m
American Airlines
Deal found 7/23![American Airlines logo]()
$275
This Southwest deal was found by Cheapflights users on 7/23. 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 8/197:10 am
RSW
- MDW
Nonstop2h 45m
Southwest
Mon 8/241:00 pm
MDW
- RSW
Nonstop2h 45m
Southwest
Deal found 7/23![Southwest logo]()
$275
This CheapOair deal was found by Cheapflights users on 7/22. 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.
Thu 10/2212:45 pm
RSW
- ORD
1 stop6h 39m
Multiple Airlines
Mon 10/262:15 pm
ORD
- RSW
1 stop8h 22m
Multiple Airlines
Deal found 7/22![Multiple Airlines logo]()
$279
This American Airlines deal was found by Cheapflights users on 7/23. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/196:07 am
RSW
- ORD
Nonstop3h 23m
American Airlines
Wed 8/267:04 pm
ORD
- RSW
Nonstop2h 55m
American Airlines
Deal found 7/23![American Airlines logo]()
$281
This American Airlines deal was found by Cheapflights users on 7/25. 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.
Sat 8/154:39 pm
RSW
- ORD
Nonstop3h 31m
American Airlines
Mon 8/176:45 am
ORD
- RSW
Nonstop2h 52m
American Airlines
Deal found 7/25![American Airlines logo]()
$283
This Southwest deal was found by Cheapflights users on 7/24. 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 9/15:40 pm
RSW
- MDW
Nonstop2h 50m
Southwest
Sat 9/53:05 pm
MDW
- RSW
Nonstop2h 50m
Southwest
Deal found 7/24![Southwest logo]()
$283
This Southwest deal was found by Cheapflights users on 7/24. 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.
Sun 9/68:15 am
RSW
- MDW
Nonstop2h 45m
Southwest
Wed 9/96:00 pm
MDW
- RSW
Nonstop2h 50m
Southwest
Deal found 7/24![Southwest logo]()
$284
This United Airlines deal was found by Cheapflights users on 7/22. 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 8/135:14 pm
RSW
- ORD
1 stop7h 12m
United Airlines
Tue 8/187:15 am
ORD
- RSW
Nonstop3h 06m
United Airlines
Deal found 7/22![United Airlines logo]()
$285
This Southwest deal was found by Cheapflights users on 7/22. 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.
Thu 8/136:50 am
RSW
- MDW
Nonstop2h 50m
Southwest
Tue 8/1810:20 am
MDW
- RSW
1 stop6h 15m
Southwest
Deal found 7/22![Southwest logo]()
$285
This Frontier deal was found by Cheapflights users on 7/22. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/103:53 pm
RSW
- ORD
Nonstop3h 21m
Frontier
Sun 12/1310:52 am
ORD
- RSW
Nonstop3h 06m
Frontier
Deal found 7/22![Frontier logo]()
$286
This United Airlines deal was found by Cheapflights users on 7/24. 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.
Sat 9/266:50 am
RSW
- ORD
1 stop8h 55m
United Airlines
Mon 9/284:30 pm
ORD
- RSW
Nonstop3h 06m
United Airlines
Deal found 7/24![United Airlines logo]()
$289
Best flights from Fort Myers to IllinoisDiscover carefully curated flight deals from Fort Myers to Illinois that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 25, 2026.
Discover carefully curated flight deals from Fort Myers to Illinois that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 25, 2026.
This United Airlines deal was found by Cheapflights users on 7/20. 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 9/512:27 pm
RSW
- PIA
1 stop7h 36m
United Airlines
Wed 9/910:32 am
PIA
- RSW
1 stop8h 19m
United Airlines
Deal found 7/20![United Airlines logo]()
$279
This Southwest deal was found by Cheapflights users on 7/23. 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.
Tue 10/205:45 pm
RSW
- MDW
Nonstop2h 50m
Southwest
Sat 10/248:05 am
MDW
- RSW
1 stop7h 10m
Southwest
Deal found 7/23![Southwest logo]()
$285
This American Airlines deal was found by Cheapflights users on 7/22. 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.
Thu 8/2711:04 am
RSW
- PIA
2 stops8h 11m
American Airlines
Tue 9/16:34 am
PIA
- RSW
1 stop6h 34m
American Airlines
Deal found 7/22![American Airlines logo]()
$295
This Delta deal was found by Cheapflights users on 7/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/512:22 pm
RSW
- MDW
1 stop5h 37m
Delta
Thu 9/104:30 pm
MDW
- RSW
1 stop7h 05m
Delta
Deal found 7/23![Delta logo]()
$310
This Sun Country Air deal was found by Cheapflights users on 7/23. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/247:53 pm
RSW
- ORD
1 stop14h 58m
Sun Country Air
Sat 11/2810:00 am
ORD
- RSW
1 stop5h 58m
Sun Country Air
Deal found 7/23![Sun Country Air logo]()
$335
This JetBlue deal was found by Cheapflights users on 7/24. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1011:05 am
RSW
- ORD
1 stop8h 56m
JetBlue
Sat 9/127:00 am
ORD
- RSW
1 stop6h 46m
JetBlue
Deal found 7/24![JetBlue logo]()
$391
This Kiwi.com deal was found by Cheapflights users on 7/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/58:24 am
RSW
- RFD
1 stop29h 10m
Multiple Airlines
Sun 8/911:37 am
RFD
- RSW
2 stops22h 06m
Multiple Airlines
Deal found 7/20![Multiple Airlines logo]()
$561
This United Airlines deal was found by Cheapflights users on 7/24. 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.
Tue 9/19:15 am
RSW
- ORD
Nonstop3h 14m
United Airlines
Sat 9/57:15 am
ORD
- RSW
Nonstop3h 06m
United Airlines
Deal found 7/24![United Airlines logo]()
$283
This Southwest deal was found by Cheapflights users on 7/23. 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.
Thu 8/137:20 am
RSW
- MDW
2 stops6h 05m
Southwest
Mon 8/171:00 pm
MDW
- RSW
Nonstop2h 45m
Southwest
Deal found 7/23![Southwest logo]()
$290
This American Airlines deal was found by Cheapflights users on 7/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/26:02 am
RSW
- BMI
1 stop7h 47m
American Airlines
Sun 10/45:02 am
BMI
- RSW
1 stop4h 49m
American Airlines
Deal found 7/20![American Airlines logo]()
$319
This United Airlines deal was found by Cheapflights users on 7/24. 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.
Mon 8/174:40 pm
RSW
- ORD
Nonstop3h 19m
United Airlines
Wed 8/196:30 am
ORD
- RSW
1 stop8h 25m
United Airlines
Deal found 7/24![United Airlines logo]()
$293
This Southwest deal was found by Cheapflights users on 7/20. 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.
Wed 8/197:10 am
RSW
- MDW
Nonstop2h 45m
Southwest
Sat 8/223:05 pm
MDW
- RSW
Nonstop2h 45m
Southwest
Deal found 7/20![Southwest logo]()
$295
This Delta deal was found by Cheapflights users on 7/20. 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.
Thu 9/106:24 pm
RSW
- ORD
1 stop6h 35m
Delta
Thu 9/176:40 am
ORD
- RSW
1 stop6h 41m
Delta
Deal found 7/20![Delta logo]()
$325
This United Airlines deal was found by Cheapflights users on 7/24. 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.
Mon 8/2412:15 pm
RSW
- ORD
1 stop5h 44m
United Airlines
Mon 8/3110:30 am
ORD
- RSW
Nonstop3h 06m
United Airlines
Deal found 7/24![United Airlines logo]()
$293
This Southwest deal was found by Cheapflights users on 7/24. 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 9/17:20 am
RSW
- MDW
2 stops9h 30m
Southwest
Sat 9/53:05 pm
MDW
- RSW
Nonstop2h 50m
Southwest
Deal found 7/24![Southwest logo]()
$298
This Delta deal was found by Cheapflights users on 7/21. 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.
Fri 9/185:30 am
RSW
- BMI
1 stop6h 48m
Delta
Sun 9/204:32 pm
BMI
- RSW
1 stop7h 03m
Delta
Deal found 7/21![Delta logo]()
$329
This American Airlines deal was found by Cheapflights users on 7/23. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/43:02 pm
RSW
- BMI
2 stops9h 57m
American Airlines
Mon 9/75:00 am
BMI
- RSW
1 stop4h 37m
American Airlines
Deal found 7/23![American Airlines logo]()
$334
This United Airlines deal was found by Cheapflights users on 7/20. 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.
Wed 8/199:15 am
RSW
- ORD
Nonstop3h 14m
United Airlines
Sat 8/227:15 am
ORD
- RSW
Nonstop3h 06m
United Airlines
Deal found 7/20![United Airlines logo]()
$295
This Southwest deal was found by Cheapflights users on 7/22. 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.
Thu 8/137:20 am
RSW
- MDW
2 stops6h 05m
Southwest
Tue 8/1812:20 pm
MDW
- RSW
1 stop6h 30m
Southwest
Deal found 7/22![Southwest logo]()
$300
This Delta deal was found by Cheapflights users on 7/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/266:24 pm
RSW
- ORD
1 stop6h 35m
Delta
Sun 9/275:30 am
ORD
- RSW
1 stop5h 36m
Delta
Deal found 7/23![Delta logo]()
$341
This United Airlines deal was found by Cheapflights users on 7/24. 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.
Thu 9/1012:09 pm
RSW
- ORD
1 stop5h 20m
United Airlines
Sat 9/127:30 am
ORD
- RSW
1 stop7h 25m
United Airlines
Deal found 7/24![United Airlines logo]()
$303
This Southwest deal was found by Cheapflights users on 7/21. 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 8/264:15 pm
RSW
- STL
1 stop5h 55m
Southwest
Sat 8/294:15 pm
STL
- RSW
Nonstop2h 30m
Southwest
Deal found 7/21![Southwest logo]()
$307
This American Airlines deal was found by Cheapflights users on 7/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/43:59 pm
RSW
- BMI
2 stops9h 36m
American Airlines
Sat 8/85:00 am
BMI
- RSW
1 stop4h 37m
American Airlines
Deal found 7/20![American Airlines logo]()
$374
This Delta deal was found by Cheapflights users on 7/20. 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.
Thu 8/63:30 pm
RSW
- MLI
1 stop7h 49m
Delta
Mon 8/1011:08 am
MLI
- RSW
1 stop6h 50m
Delta
Deal found 7/20![Delta logo]()
$344
This Southwest deal was found by Cheapflights users on 7/24. 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.
Mon 8/246:25 pm
RSW
- MDW
1 stop4h 30m
Southwest
Mon 8/311:20 pm
MDW
- RSW
2 stops7h 40m
Southwest
Deal found 7/24![Southwest logo]()
$308
This Delta deal was found by Cheapflights users on 7/22. 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 8/2012:22 pm
RSW
- ORD
1 stop7h 07m
Delta
Sun 8/238:48 am
ORD
- RSW
1 stop7h 35m
Delta
Deal found 7/22![Delta logo]()
$346
This Southwest deal was found by Cheapflights users on 7/20. 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 8/106:50 am
RSW
- MDW
Nonstop2h 50m
Southwest
Sat 8/153:05 pm
MDW
- RSW
Nonstop2h 45m
Southwest
Deal found 7/20![Southwest logo]()
$309
This American Airlines deal was found by Cheapflights users on 7/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/315:24 pm
RSW
- PIA
1 stop7h 58m
American Airlines
Mon 8/34:22 pm
PIA
- RSW
1 stop5h 30m
American Airlines
Deal found 7/20![American Airlines logo]()
$414
This United Airlines deal was found by Cheapflights users on 7/24. 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.
Tue 8/114:40 pm
RSW
- ORD
Nonstop3h 19m
United Airlines
Sat 8/157:15 am
ORD
- RSW
Nonstop3h 06m
United Airlines
Deal found 7/24![United Airlines logo]()
$346
This Delta deal was found by Cheapflights users on 7/20. 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 8/45:35 am
RSW
- BMI
1 stop6h 52m
Delta
Sat 8/84:24 pm
BMI
- RSW
1 stop7h 16m
Delta
Deal found 7/20![Delta logo]()
$369
Last-minute flights from Fort Myers to IllinoisDiscover last-minute flight deals from Fort Myers to Illinois. Data last updated July 25, 2026 and is based on user searches.
Discover last-minute flight deals from Fort Myers to Illinois. Data last updated July 25, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 7/20. 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.
Thu 8/63:30 pm
RSW
- MLI
1 stop7h 49m
Delta
Mon 8/1011:08 am
MLI
- RSW
1 stop6h 50m
Delta
Deal found 7/20![Delta logo]()
$344
This Southwest deal was found by Cheapflights users on 7/20. 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 8/106:50 am
RSW
- MDW
Nonstop2h 50m
Southwest
Sat 8/153:05 pm
MDW
- RSW
Nonstop2h 45m
Southwest
Deal found 7/20![Southwest logo]()
$309
This Southwest deal was found by Cheapflights users on 7/22. 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.
Thu 8/136:50 am
RSW
- MDW
Nonstop2h 50m
Southwest
Mon 8/1710:30 am
MDW
- RSW
1 stop6h 15m
Southwest
Deal found 7/22![Southwest logo]()
$285
This Southwest deal was found by Cheapflights users on 7/25. 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 8/156:25 am
RSW
- MDW
1 stop5h 15m
Southwest
Mon 8/179:00 am
MDW
- RSW
Nonstop2h 45m
Southwest
Deal found 7/25![Southwest logo]()
$293
This Southwest deal was found by Cheapflights users on 7/24. 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.
Mon 8/175:25 pm
RSW
- MDW
Nonstop2h 50m
Southwest
Wed 8/198:50 am
MDW
- RSW
Nonstop2h 50m
Southwest
Deal found 7/24![Southwest logo]()
$283
This Southwest deal was found by Cheapflights users on 7/23. 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.
Tue 8/186:15 pm
RSW
- STL
Nonstop2h 35m
Southwest
Sat 8/224:15 pm
STL
- RSW
Nonstop2h 30m
Southwest
Deal found 7/23![Southwest logo]()
$297
This Southwest deal was found by Cheapflights users on 7/23. 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 8/197:10 am
RSW
- MDW
Nonstop2h 45m
Southwest
Mon 8/241:00 pm
MDW
- RSW
Nonstop2h 45m
Southwest
Deal found 7/23![Southwest logo]()
$275
This Delta deal was found by Cheapflights users on 7/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/196:46 am
RSW
- MDW
1 stop6h 05m
Delta
Tue 8/2512:46 pm
MDW
- RSW
1 stop5h 12m
Delta
Deal found 7/23![Delta logo]()
$295
This American Airlines deal was found by Cheapflights users on 7/22. 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.
Wed 8/196:07 am
RSW
- STL
1 stop7h 47m
American Airlines
Mon 8/243:25 pm
STL
- RSW
1 stop5h 28m
American Airlines
Deal found 7/22![American Airlines logo]()
$317
This Delta deal was found by Cheapflights users on 7/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/266:29 pm
RSW
- MDW
1 stop5h 07m
Delta
Mon 8/316:05 am
MDW
- RSW
1 stop5h 08m
Delta
Deal found 7/23![Delta logo]()
$310
This American Airlines deal was found by Cheapflights users on 7/22. 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.
Thu 8/274:39 pm
RSW
- PIA
1 stop8h 20m
American Airlines
Tue 9/16:34 am
PIA
- RSW
1 stop6h 34m
American Airlines
Deal found 7/22![American Airlines logo]()
$290
This American Airlines deal was found by Cheapflights users on 7/23. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2811:27 am
RSW
- PIA
1 stop7h 48m
American Airlines
Tue 9/16:34 am
PIA
- RSW
1 stop6h 34m
American Airlines
Deal found 7/23![American Airlines logo]()
$300
One-way flights from Fort Myers to IllinoisSearch for one-way flight options from Fort Myers to Illinois. Find affordable one-way fares based on user searches. Data last updated July 25, 2026.
Search for one-way flight options from Fort Myers to Illinois. Find affordable one-way fares based on user searches. Data last updated July 25, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/2312:45 pm
RSW
- STL
2 stops45h 55m
Frontier
Deal found 7/22![Frontier logo]()
$106
This Kiwi.com deal was found by Cheapflights users on 7/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/248:38 pm
RSW
- STL
2 stops38h 02m
Frontier
Deal found 7/22![Frontier logo]()
$111
This Kiwi.com deal was found by Cheapflights users on 7/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/2012:45 pm
RSW
- STL
2 stops21h 55m
Frontier
Deal found 7/20![Frontier logo]()
$113
This Kiwi.com deal was found by Cheapflights users on 7/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1712:45 pm
RSW
- STL
2 stops21h 55m
Frontier
Deal found 7/20![Frontier logo]()
$117
This Kiwi.com deal was found by Cheapflights users on 7/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/1912:45 pm
RSW
- STL
2 stops45h 55m
Frontier
Deal found 7/22![Frontier logo]()
$121
This Kiwi.com deal was found by Cheapflights users on 7/23. 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.
Mon 9/2112:45 pm
RSW
- STL
2 stops45h 55m
Frontier
Deal found 7/23![Frontier logo]()
$125
This Kiwi.com deal was found by Cheapflights users on 7/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/275:55 pm
RSW
- STL
2 stops24h 27m
Frontier
Deal found 7/25![Frontier logo]()
$127
This Delta deal was found by Cheapflights users on 7/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1512:31 pm
RSW
- ORD
1 stop6h 54m
Delta
Deal found 7/23![Delta logo]()
$148
This Delta deal was found by Cheapflights users on 7/22. 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.
Mon 8/176:29 pm
RSW
- MDW
1 stop5h 07m
Delta
Deal found 7/22![Delta logo]()
$148
This Frontier deal was found by Cheapflights users on 7/21. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1512:45 pm
RSW
- ORD
1 stop6h 39m
Frontier
Deal found 7/21![Frontier logo]()
$149
This JetBlue deal was found by Cheapflights users on 7/24. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/218:00 am
RSW
- ORD
1 stop10h 43m
JetBlue
Deal found 7/24![JetBlue logo]()
$150
This United Airlines deal was found by Cheapflights users on 7/25. 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.
Mon 8/2412:15 pm
RSW
- ORD
1 stop5h 44m
United Airlines
Deal found 7/25![United Airlines logo]()
$152
Find flight deals from Fort Myers to Illinois
Keep the following information in mind while searching for Fort Myers to Illinois flight deals. Data was last updated July 25, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $266 (United Airlines) |
One-way from | $106 (Kiwi.com) |
Popular in | June |
Cheapest in | January |
Average price | $326 |
Cheapflights Fare Finder
Customize your flight search to find flights from Fort Myers to Illinois that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 25, 2026.
Use the filters below to find and compare flights from Fort Myers to Illinois that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Fort MyersPeoria
RSW - PIA
RSWPIA
Fort Myers SW Florida Intl
Sat 9/5
12:27 pm-7:03 pm
1 stop7h 36m
Greater Peoria
Wed 9/9
10:32 am-7:51 pm
1 stop8h 19m
$279
Fort MyersChicago
RSW - ORD
RSWORD
Fort Myers SW Florida Intl
Tue 9/1
9:15 am-11:29 am
Nonstop3h 14m
Chicago O'Hare Intl
Sat 9/5
7:15 am-11:21 am
Nonstop3h 06m
$283
Fort MyersChicago
RSW - MDW
RSWMDW
Fort Myers SW Florida Intl
Tue 10/20
5:45 pm-7:35 pm
Nonstop2h 50m
Chicago Midway
Sat 10/24
8:05 am-4:15 pm
1 stop7h 10m
$285
Fort MyersChicago
RSW - MDW
RSWMDW
Fort Myers SW Florida Intl
Thu 8/13
7:20 am-12:25 pm
2 stops6h 05m
Chicago Midway
Mon 8/17
1:00 pm-4:45 pm
Nonstop2h 45m
$290
Fort MyersChicago
RSW - ORD
RSWORD
Fort Myers SW Florida Intl
Mon 8/17
4:40 pm-6:59 pm
Nonstop3h 19m
Chicago O'Hare Intl
Wed 8/19
6:30 am-3:55 pm
1 stop8h 25m
$293
Fort MyersChicago
RSW - ORD
RSWORD
Fort Myers SW Florida Intl
Mon 8/24
12:15 pm-4:59 pm
1 stop5h 44m
Chicago O'Hare Intl
Mon 8/31
10:30 am-2:36 pm
Nonstop3h 06m
$293
Fort MyersPeoria
RSW - PIA
RSWPIA
Fort Myers SW Florida Intl
Thu 8/27
11:04 am-6:15 pm
2 stops8h 11m
Greater Peoria
Tue 9/1
6:34 am-2:08 pm
1 stop6h 34m
$295
Quickest round-trip
Fort MyersChicago
RSW - MDW
RSWMDW
Fort Myers SW Florida Intl
Wed 8/19
7:10 am-8:55 am
Nonstop2h 45m
Chicago Midway
Sat 8/22
3:05 pm-6:50 pm
Nonstop2h 45m
$295
Fort MyersChicago
RSW - ORD
RSWORD
Fort Myers SW Florida Intl
Wed 8/19
9:15 am-11:29 am
Nonstop3h 14m
Chicago O'Hare Intl
Sat 8/22
7:15 am-11:21 am
Nonstop3h 06m
$295
Fort MyersChicago
RSW - MDW
RSWMDW
Fort Myers SW Florida Intl
Tue 9/1
7:20 am-3:50 pm
2 stops9h 30m
Chicago Midway
Sat 9/5
3:05 pm-6:55 pm
Nonstop2h 50m
$298
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Fort Myers to Illinois
Have a flexible travel schedule? Discover the best time to fly to Illinois from Fort Myers with our price prediction graph.
RSW-MDW
RSW-PIA
RSW-STL
RSW-MLI
RSW-ORD
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 Illinois
RSW-USIL
RSW-MDW
RSW-PIA
RSW-STL
RSW-MLI
What is the cheapest month to book a flight from Fort Myers to Illinois?
Currently, February is the cheapest month in which you can book a flight from Fort Myers to Illinois (average of $195). Flying from Fort Myers to Illinois in June is currently the most expensive (average of $356). 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 IL?
Find hourly flight availability from Fort Myers to Illinois. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 25, 2026.
It’s typically best to fly out from Fort Myers to Illinois in the evening. Doing so could potentially save you 23% on the flight price compared to flying at noon, which is usually more expensive.
Weekly flight availability from Fort Myers to Illinois
Explore weekly flight availability from Fort Myers to Illinois. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated July 25, 2026.
The most flights from RSW to USIL are scheduled on a Monday (17 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (13 on average).
How much does it cost to fly round-trip from Fort Myers to Illinois?
Airfare is typical for this route at the moment.
Fort Myers to Illinois flights typically cost between $248 and $369 in August.The cheapest round-trip price found within the last 5 days was $275 on American Airlines (Aug 13-Aug 17).
How far ahead should I book a flight from Fort Myers to Illinois?
To ensure you get the cheapest price possible for a flight from Fort Myers to Illinois, you should look to book at least 72 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
What is the cheapest day to fly from Fort Myers to Illinois?
Use this chart to determine the cheapest time to fly round-trip from Fort Myers to Illinois. Price data was last updated on July 18, 2026.
Travelers seeking maximum savings on their Fort Myers to Illinois 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.
Reviews of airlines servicing Illinois
Get insights into the airlines that provide service to Illinois. 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 Illinois. Reviews last updated July 25, 2026.
See what other customers who have flown with Southwest,United Airlines, andAmerican Airlines from Fort Myers to Illinois have to say. 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.
Overall
8.0
Comfort
8.0
Entertainment
7.5
Crew
8.6
Boarding
8.1
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
8.0
Comfort
8.0
Entertainment
7.5
Crew
8.6
Boarding
8.1
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
8.0
Comfort
8.0
Entertainment
7.5
Crew
8.6
Boarding
8.1
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
8.0
Comfort
8.0
Entertainment
7.5
Crew
8.6
Boarding
8.1
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
8.0
Comfort
8.0
Entertainment
7.5
Crew
8.6
Boarding
8.1
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
8.0
Comfort
8.0
Entertainment
7.5
Crew
8.6
Boarding
8.1
Food
7.0
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 Illinois. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights
Top destinations
Alternative routes for Fort Myers to Illinois
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Illinois by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Fort Myers to Illinois by cabin class
Find flights from Fort Myers to Illinois, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Fort Myers and Illinois flights
Browse other Fort Myers and Illinois flight options. Last updated on July 25, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Fort Myers to Illinois flights
Consider these flights traveling from Fort Myers to Illinois.
Top 6 airlines flying from Fort Myers to Illinois
Discover the top 6 airlines that operate flights from Fort Myers to Illinois. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 25, 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$158 | Average$427 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$159 | Average$315 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$183 | Average$347 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$273 | Average$441 | FlexibilityNo cancel fee | On-timeN/A |