$104+ 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 5/16. Fares are subject to change and may not be available on all flights or dates of travel.
RSW — ORD
Jun 5 — Jun 121
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 May 6, 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 May 6, 2026.
This Super.com deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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 5/92:01 pm
RSW
- ORD
Nonstop3h 21m
Frontier
Sat 5/169:00 am
ORD
- RSW
Nonstop3h 06m
Frontier
Deal found 5/4![Frontier logo]()
$191
This American Airlines deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/156:21 pm
RSW
- PIA
1 stop6h 19m
American Airlines
Wed 7/299:50 am
PIA
- RSW
1 stop5h 44m
American Airlines
Deal found 5/6![American Airlines logo]()
$261
This American Airlines deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 6/1712:47 pm
RSW
- ORD
Nonstop3h 22m
American Airlines
Tue 6/308:04 am
ORD
- RSW
Nonstop2h 53m
American Airlines
Deal found 5/5![American Airlines logo]()
$291
This Southwest deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/27:00 am
RSW
- MDW
Nonstop2h 55m
Southwest
Tue 6/96:55 pm
MDW
- RSW
Nonstop2h 45m
Southwest
Deal found 5/6![Southwest logo]()
$291
This American Airlines deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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 6/311:34 am
RSW
- ORD
Nonstop3h 19m
American Airlines
Mon 6/86:48 am
ORD
- RSW
Nonstop2h 53m
American Airlines
Deal found 5/4![American Airlines logo]()
$293
This Southwest deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/24:35 pm
RSW
- MDW
Nonstop3h 00m
Southwest
Sat 6/65:05 am
MDW
- RSW
Nonstop2h 40m
Southwest
Deal found 5/6![Southwest logo]()
$293
This United Airlines deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/47:00 am
RSW
- ORD
Nonstop3h 23m
United Airlines
Thu 6/117:16 am
ORD
- RSW
Nonstop3h 08m
United Airlines
Deal found 5/5![United Airlines logo]()
$295
This Southwest deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/45:10 am
RSW
- MDW
Nonstop2h 50m
Southwest
Mon 6/82:50 pm
MDW
- RSW
Nonstop2h 50m
Southwest
Deal found 5/6![Southwest logo]()
$295
This American Airlines deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 6/45:19 pm
RSW
- ORD
Nonstop3h 26m
American Airlines
Mon 6/86:48 am
ORD
- RSW
Nonstop2h 53m
American Airlines
Deal found 5/5![American Airlines logo]()
$296
This American Airlines deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 6/175:19 pm
RSW
- ORD
Nonstop3h 26m
American Airlines
Wed 7/16:29 am
ORD
- RSW
1 stop7h 37m
American Airlines
Deal found 5/5![American Airlines logo]()
$301
This Southwest deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” 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 6/104:40 pm
RSW
- MDW
1 stop7h 30m
Southwest
Wed 6/176:55 pm
MDW
- RSW
Nonstop2h 45m
Southwest
Deal found 5/3![Southwest logo]()
$301
This Southwest deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/306:00 am
RSW
- MDW
1 stop7h 25m
Southwest
Mon 7/136:55 pm
MDW
- RSW
Nonstop2h 45m
Southwest
Deal found 5/6![Southwest logo]()
$303
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 May 6, 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 May 6, 2026.
This United Airlines deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/14:39 pm
RSW
- ORD
Nonstop3h 21m
United Airlines
Wed 7/84:26 pm
ORD
- RSW
Nonstop3h 08m
United Airlines
Deal found 5/5![United Airlines logo]()
$291
This Southwest deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/27:00 am
RSW
- MDW
Nonstop2h 55m
Southwest
Tue 6/96:55 pm
MDW
- RSW
Nonstop2h 45m
Southwest
Deal found 5/5![Southwest logo]()
$291
This Delta deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/175:37 am
RSW
- ORD
1 stop7h 59m
Delta
Wed 7/16:35 am
ORD
- RSW
1 stop6h 58m
Delta
Deal found 5/4![Delta logo]()
$311
This American Airlines deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 6/26:00 am
RSW
- EVV
1 stop6h 56m
American Airlines
Tue 6/912:46 pm
EVV
- RSW
1 stop6h 44m
American Airlines
Deal found 5/6![American Airlines logo]()
$383
This Southwest deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/216:25 pm
RSW
- MDW
Nonstop2h 50m
Southwest
Sat 7/255:55 pm
MDW
- RSW
Nonstop2h 45m
Southwest
Deal found 5/6![Southwest logo]()
$293
This United Airlines deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” 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 6/84:39 pm
RSW
- ORD
Nonstop3h 21m
United Airlines
Mon 6/154:26 pm
ORD
- RSW
Nonstop3h 08m
United Airlines
Deal found 5/2![United Airlines logo]()
$295
This Kiwi.com deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 6/38:24 am
RSW
- RFD
1 stop28h 59m
Multiple Airlines
Mon 6/87:53 pm
RFD
- RSW
2 stops25h 05m
Multiple Airlines
Deal found 5/6![Multiple Airlines logo]()
$602
This Delta deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/225:35 am
RSW
- MDW
1 stop7h 21m
Delta
Wed 8/510:54 am
MDW
- RSW
1 stop4h 50m
Delta
Deal found 5/6![Delta logo]()
$311
This United Airlines deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 9/312:30 pm
RSW
- ORD
Nonstop3h 12m
United Airlines
Sat 9/1210:35 am
ORD
- RSW
Nonstop3h 06m
United Airlines
Deal found 5/6![United Airlines logo]()
$295
This Southwest deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/135:10 am
RSW
- MDW
Nonstop2h 50m
Southwest
Mon 7/276:55 pm
MDW
- RSW
Nonstop2h 45m
Southwest
Deal found 5/1![Southwest logo]()
$295
This Delta deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 7/278:00 pm
RSW
- ORD
1 stop4h 53m
Delta
Sat 8/86:40 am
ORD
- RSW
1 stop4h 33m
Delta
Deal found 5/5![Delta logo]()
$315
This United Airlines deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 6/211:59 am
RSW
- ORD
1 stop6h 03m
United Airlines
Tue 6/94:26 pm
ORD
- RSW
Nonstop3h 08m
United Airlines
Deal found 5/5![United Airlines logo]()
$301
This Southwest deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” 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 7/105:10 pm
RSW
- MDW
Nonstop2h 55m
Southwest
Mon 7/132:50 pm
MDW
- RSW
Nonstop2h 50m
Southwest
Deal found 5/2![Southwest logo]()
$315
This American Airlines deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 5/223:57 pm
RSW
- BMI
2 stops9h 02m
American Airlines
Tue 5/265:00 am
BMI
- RSW
2 stops9h 06m
American Airlines
Deal found 5/6![American Airlines logo]()
$405
This Delta deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” 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 9/185:35 am
RSW
- MLI
1 stop5h 51m
Delta
Sun 9/205:55 am
MLI
- RSW
1 stop5h 02m
Delta
Deal found 5/3![Delta logo]()
$339
This United Airlines deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/312:59 pm
RSW
- ORD
1 stop6h 45m
United Airlines
Wed 6/102:05 pm
ORD
- RSW
1 stop6h 54m
United Airlines
Deal found 5/4![United Airlines logo]()
$311
This Southwest deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/307:10 am
RSW
- MDW
Nonstop2h 50m
Southwest
Mon 7/66:55 pm
MDW
- RSW
Nonstop2h 45m
Southwest
Deal found 5/6![Southwest logo]()
$322
This American Airlines deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” 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.
Mon 6/13:57 pm
RSW
- PIA
2 stops9h 02m
American Airlines
Sun 6/79:51 am
PIA
- RSW
1 stop5h 56m
American Airlines
Deal found 5/2![American Airlines logo]()
$412
This Delta deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/65:23 am
RSW
- ORD
1 stop5h 46m
Delta
Sun 8/96:25 am
ORD
- RSW
1 stop6h 34m
Delta
Deal found 5/5![Delta logo]()
$346
This United Airlines deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” 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 5/306:02 am
RSW
- ORD
1 stop7h 04m
United Airlines
Sat 6/64:26 pm
ORD
- RSW
Nonstop3h 08m
United Airlines
Deal found 5/2![United Airlines logo]()
$324
This Southwest deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” 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 7/245:10 am
RSW
- MDW
Nonstop2h 50m
Southwest
Mon 7/2710:00 am
MDW
- RSW
1 stop5h 05m
Southwest
Deal found 5/2![Southwest logo]()
$325
This Delta deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/305:35 am
RSW
- ORD
1 stop5h 35m
Delta
Sun 8/26:35 am
ORD
- RSW
1 stop4h 36m
Delta
Deal found 5/4![Delta logo]()
$346
This Southwest deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” 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 5/306:25 am
RSW
- MDW
2 stops8h 30m
Southwest
Sat 6/65:55 pm
MDW
- RSW
Nonstop2h 45m
Southwest
Deal found 5/2![Southwest logo]()
$329
This Delta deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” 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 9/263:06 pm
RSW
- ORD
1 stop7h 39m
Delta
Sun 9/276:00 am
ORD
- RSW
1 stop6h 18m
Delta
Deal found 5/3![Delta logo]()
$346
This KAYAK deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/263:57 pm
RSW
- STL
2 stops8h 57m
American Airlines
Fri 5/295:21 am
STL
- RSW
2 stops8h 45m
American Airlines
Deal found 5/1![American Airlines logo]()
$482
This Southwest deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” 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 5/275:45 pm
RSW
- ORD
1 stop5h 10m
Southwest
Fri 5/2910:30 am
ORD
- RSW
Nonstop2h 55m
Southwest
Deal found 5/3![Southwest logo]()
$330
This Kiwi.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 7/18:24 am
RSW
- RFD
1 stop29h 00m
Multiple Airlines
Thu 10/229:30 am
RFD
- RSW
2 stops11h 17m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$618
This United Airlines deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” 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 8/37:00 am
RSW
- PIA
1 stop7h 57m
United Airlines
Sat 8/81:13 pm
PIA
- RSW
1 stop6h 21m
United Airlines
Deal found 5/2![United Airlines logo]()
$390
This Southwest deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/84:45 pm
RSW
- MDW
1 stop4h 55m
Southwest
Mon 6/1510:00 am
MDW
- RSW
1 stop5h 05m
Southwest
Deal found 5/2![Southwest logo]()
$335
This Delta deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 5/225:35 am
RSW
- BMI
1 stop6h 48m
Delta
Tue 5/264:14 pm
BMI
- RSW
1 stop7h 13m
Delta
Deal found 5/6![Delta logo]()
$369
Last-minute flights from Fort Myers to IllinoisDiscover last-minute flight deals from Fort Myers to Illinois. Data last updated May 6, 2026 and is based on user searches.
Discover last-minute flight deals from Fort Myers to Illinois. Data last updated May 6, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 5/95:46 pm
RSW
- MLI
1 stop5h 35m
Delta
Wed 5/135:56 am
MLI
- RSW
1 stop7h 44m
Delta
Deal found 5/5![Delta logo]()
$347
This CheapOair deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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 5/116:42 pm
RSW
- ORD
1 stop26h 50m
Frontier
Fri 5/159:37 pm
ORD
- RSW
1 stop18h 02m
Frontier
Deal found 5/4![Frontier logo]()
$321
This CheapOair deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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.
Sat 5/162:01 pm
RSW
- ORD
Nonstop3h 21m
Multiple Airlines
Mon 6/18:06 pm
ORD
- RSW
1 stop13h 32m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$304
This CheapOair deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” 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.
Sat 5/162:01 pm
RSW
- ORD
Nonstop3h 21m
Multiple Airlines
Tue 5/199:49 am
ORD
- RSW
1 stop7h 04m
Multiple Airlines
Deal found 5/3![Multiple Airlines logo]()
$307
This Southwest deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/27:00 am
RSW
- MDW
Nonstop2h 55m
Southwest
Tue 6/96:55 pm
MDW
- RSW
Nonstop2h 45m
Southwest
Deal found 5/6![Southwest logo]()
$291
This Southwest deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/24:35 pm
RSW
- MDW
Nonstop3h 00m
Southwest
Sat 6/65:05 am
MDW
- RSW
Nonstop2h 40m
Southwest
Deal found 5/6![Southwest logo]()
$293
This Southwest deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/45:10 am
RSW
- MDW
Nonstop2h 50m
Southwest
Mon 6/82:50 pm
MDW
- RSW
Nonstop2h 50m
Southwest
Deal found 5/6![Southwest logo]()
$295
This Southwest deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” 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 6/107:10 am
RSW
- MDW
Nonstop2h 50m
Southwest
Wed 6/176:55 pm
MDW
- RSW
Nonstop2h 45m
Southwest
Deal found 5/3![Southwest logo]()
$312
This Delta deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/165:37 am
RSW
- MDW
1 stop7h 28m
Delta
Tue 6/306:00 am
MDW
- RSW
1 stop7h 33m
Delta
Deal found 5/6![Delta logo]()
$311
This Southwest deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/256:15 am
RSW
- MDW
2 stops8h 10m
Southwest
Mon 6/296:55 pm
MDW
- RSW
Nonstop2h 45m
Southwest
Deal found 5/5![Southwest logo]()
$310
This Southwest deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/306:00 am
RSW
- MDW
1 stop7h 25m
Southwest
Mon 7/136:55 pm
MDW
- RSW
Nonstop2h 45m
Southwest
Deal found 5/6![Southwest logo]()
$303
This Delta deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/303:41 pm
RSW
- MDW
1 stop7h 36m
Delta
Sat 7/49:17 am
MDW
- RSW
1 stop7h 10m
Delta
Deal found 5/6![Delta logo]()
$313
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 May 6, 2026.
Search for one-way flight options from Fort Myers to Illinois. Find affordable one-way fares based on user searches. Data last updated May 6, 2026.
This Super.com deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” 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 5/162:01 pm
RSW
- ORD
Nonstop3h 21m
Frontier
Deal found 5/3![Frontier logo]()
$104
This Super.com deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” 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.
Mon 5/186:42 pm
RSW
- ORD
1 stop26h 50m
Frontier
Deal found 5/2![Frontier logo]()
$130
This Kiwi.com deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 6/267:00 am
RSW
- STL
2 stops26h 52m
Multiple Airlines
Deal found 5/6![Multiple Airlines logo]()
$131
This Kiwi.com deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/48:00 am
RSW
- STL
2 stops10h 37m
Multiple Airlines
Deal found 5/2![Multiple Airlines logo]()
$134
This Kiwi.com deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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 6/18:17 pm
RSW
- STL
2 stops22h 16m
Frontier
Deal found 5/4![Frontier logo]()
$136
This Kiwi.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 7/307:00 am
RSW
- STL
2 stops11h 37m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$137
This Kiwi.com deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 7/167:45 am
RSW
- STL
2 stops10h 52m
Multiple Airlines
Deal found 5/6![Multiple Airlines logo]()
$140
This Kiwi.com deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/2811:08 am
RSW
- STL
2 stops22h 49m
Frontier
Deal found 5/6![Frontier logo]()
$142
This Kiwi.com deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” 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 6/11:19 pm
RSW
- MDW
2 stops22h 53m
Frontier
Deal found 5/2![Frontier logo]()
$142
This Kiwi.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/38:09 pm
RSW
- STL
2 stops22h 28m
Frontier
Deal found 5/5![Frontier logo]()
$145
This United Airlines deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 6/237:00 am
RSW
- ORD
Nonstop3h 23m
United Airlines
Deal found 5/5![United Airlines logo]()
$146
This Southwest deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/27:00 am
RSW
- MDW
Nonstop2h 55m
Southwest
Deal found 5/6![Southwest logo]()
$146
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 May 6, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $191 (Super.com) |
One-way from | $104 (Super.com) |
Popular in | December |
Cheapest in | September |
Average price | $267 |
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 May 6, 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 MyersChicago
RSW - ORD
RSWORD
Fort Myers SW Florida Intl
Wed 7/1
4:39 pm-7:00 pm
Nonstop3h 21m
Chicago O'Hare Intl
Wed 7/8
4:26 pm-8:34 pm
Nonstop3h 08m
$291
Fort MyersChicago
RSW - MDW
RSWMDW
Fort Myers SW Florida Intl
Tue 6/2
7:00 am-8:55 am
Nonstop2h 55m
Chicago Midway
Tue 6/9
6:55 pm-10:40 pm
Nonstop2h 45m
$291
Quickest round-trip
Fort MyersChicago
RSW - MDW
RSWMDW
Fort Myers SW Florida Intl
Tue 7/21
6:25 pm-8:15 pm
Nonstop2h 50m
Chicago Midway
Sat 7/25
5:55 pm-9:40 pm
Nonstop2h 45m
$293
Fort MyersChicago
RSW - ORD
RSWORD
Fort Myers SW Florida Intl
Mon 6/8
4:39 pm-7:00 pm
Nonstop3h 21m
Chicago O'Hare Intl
Mon 6/15
4:26 pm-8:34 pm
Nonstop3h 08m
$295
Fort MyersChicago
RSW - ORD
RSWORD
Fort Myers SW Florida Intl
Thu 9/3
12:30 pm-2:42 pm
Nonstop3h 12m
Chicago O'Hare Intl
Sat 9/12
10:35 am-2:41 pm
Nonstop3h 06m
$295
Fort MyersChicago
RSW - MDW
RSWMDW
Fort Myers SW Florida Intl
Mon 7/13
5:10 am-7:00 am
Nonstop2h 50m
Chicago Midway
Mon 7/27
6:55 pm-10:40 pm
Nonstop2h 45m
$295
Fort MyersChicago
RSW - ORD
RSWORD
Fort Myers SW Florida Intl
Tue 6/2
11:59 am-5:02 pm
1 stop6h 03m
Chicago O'Hare Intl
Tue 6/9
4:26 pm-8:34 pm
Nonstop3h 08m
$301
Fort MyersChicago
RSW - ORD
RSWORD
Fort Myers SW Florida Intl
Wed 6/17
5:37 am-12:36 pm
1 stop7h 59m
Chicago O'Hare Intl
Wed 7/1
6:35 am-2:33 pm
1 stop6h 58m
$311
Fort MyersChicago
RSW - MDW
RSWMDW
Fort Myers SW Florida Intl
Wed 7/22
5:35 am-11:56 am
1 stop7h 21m
Chicago Midway
Wed 8/5
10:54 am-4:44 pm
1 stop4h 50m
$311
Fort MyersChicago
RSW - ORD
RSWORD
Fort Myers SW Florida Intl
Wed 6/3
12:59 pm-6:44 pm
1 stop6h 45m
Chicago O'Hare Intl
Wed 6/10
2:05 pm-9:59 pm
1 stop6h 54m
$311
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-ORD
RSW-PIA
RSW-MDW
RSW-MLI
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 Illinois
RSW-USIL
RSW-ORD
RSW-PIA
RSW-MDW
RSW-MLI
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 month to book a flight from Fort Myers to Illinois?
Currently, September is the cheapest month in which you can book a flight from Fort Myers to Illinois (average of $30). Flying from Fort Myers to Illinois in April is currently the most expensive (average of $77). 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 May 6, 2026.
It’s typically best to fly out from Fort Myers to Illinois in the evening. Doing so could potentially save you 38% on the flight price compared to flying in the afternoon, which is usually more expensive.
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 May 2, 2026.
Travelers seeking maximum savings on their Fort Myers to Illinois flight should consider departing on Thursday 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.
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 May 6, 2026.
The most flights from RSW to USIL are scheduled on a Monday (20 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (16 on average).
How much does it cost to fly round-trip from Fort Myers to Illinois?
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 May 6, 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.
Comfort
8.0
Food
7.0
Overall
7.9
Boarding
8.1
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Food
7.0
Overall
7.9
Boarding
8.1
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Food
7.0
Overall
7.9
Boarding
8.1
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Food
7.0
Overall
7.9
Boarding
8.1
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Food
7.0
Overall
7.9
Boarding
8.1
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Food
7.0
Overall
7.9
Boarding
8.1
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
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 May 6, 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 May 6, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$43 | Average$98 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$58 | Average$144 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$154 | Average$292 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$157 | Average$355 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$159 | Average$352 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$273 | Average$441 | FlexibilityNo cancel fee | On-timeN/A |