$55+ Cheap flights from Chicago (CHI) to Fort Myers Beach, FL
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/27. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — RSW
Apr 26 — May 31
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Fort Myers Beach with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from Chicago to Fort Myers Beach are usually found in August or September, booked 87 days in advance, depart on a Tuesday or Wednesday and return on a Friday
Cheap flight deals from Chicago to Fort Myers Beach
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Best
Last-minute
One-way
Cheapest flights from Chicago to Fort Myers BeachExplore the most affordable flight options available from Chicago to Fort Myers Beach. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 27, 2026.
Explore the most affordable flight options available from Chicago to Fort Myers Beach. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 27, 2026.
This Kiwi.com deal was found by Cheapflights users on 3/22. 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.
Sat 5/99:00 am
ORD
- RSW
Nonstop3h 06m
Multiple Airlines
Sun 5/1011:42 am
RSW
- ORD
Nonstop3h 02m
Multiple Airlines
Deal found 3/22![Multiple Airlines logo]()
$122
This Kiwi.com deal was found by Cheapflights users on 3/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/127:42 pm
ORD
- RSW
Nonstop2h 48m
Multiple Airlines
Thu 4/1612:17 pm
RSW
- ORD
Nonstop3h 30m
Multiple Airlines
Deal found 3/26![Multiple Airlines logo]()
$125
This Kiwi.com deal was found by Cheapflights users on 3/24. 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.
Sat 4/258:35 am
ORD
- RSW
Nonstop3h 21m
Frontier
Sun 4/2610:32 am
RSW
- ORD
Nonstop3h 30m
Frontier
Deal found 3/24![Frontier logo]()
$127
This Frontier deal was found by Cheapflights users on 3/26. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/167:00 am
ORD
- RSW
Nonstop3h 21m
Frontier
Thu 4/2312:17 pm
RSW
- ORD
Nonstop3h 30m
Frontier
Deal found 3/26![Frontier logo]()
$128
This CheapOair deal was found by Cheapflights users on 3/25. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/116:50 am
ORD
- RSW
Nonstop2h 47m
Multiple Airlines
Sat 4/181:51 pm
RSW
- ORD
Nonstop3h 30m
Multiple Airlines
Deal found 3/25![Multiple Airlines logo]()
$129
This Cheapflightsfares deal was found by Cheapflights users on 3/24. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/87:00 am
ORD
- RSW
Nonstop2h 47m
Spirit Airlines
Mon 5/1111:42 am
RSW
- ORD
Nonstop3h 02m
Spirit Airlines
Deal found 3/24![Spirit Airlines logo]()
$130
This Kiwi.com deal was found by Cheapflights users on 3/25. 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 4/237:00 am
ORD
- RSW
Nonstop3h 21m
Frontier
Sat 5/21:51 pm
RSW
- ORD
Nonstop3h 30m
Frontier
Deal found 3/25![Frontier logo]()
$131
This Kiwi.com deal was found by Cheapflights users on 3/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/136:50 am
ORD
- RSW
Nonstop2h 47m
Multiple Airlines
Thu 4/1612:17 pm
RSW
- ORD
Nonstop3h 30m
Multiple Airlines
Deal found 3/27![Multiple Airlines logo]()
$132
This Frontier deal was found by Cheapflights users on 3/25. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/135:15 am
ORD
- RSW
1 stop11h 35m
Frontier
Sat 4/181:51 pm
RSW
- ORD
Nonstop3h 30m
Frontier
Deal found 3/25![Frontier logo]()
$133
This Kiwi.com deal was found by Cheapflights users on 3/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/77:42 pm
ORD
- RSW
Nonstop2h 48m
Multiple Airlines
Thu 4/1612:17 pm
RSW
- ORD
Nonstop3h 30m
Multiple Airlines
Deal found 3/26![Multiple Airlines logo]()
$134
This Kiwi.com deal was found by Cheapflights users on 3/24. 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.
Sat 5/99:00 am
ORD
- RSW
Nonstop3h 06m
Multiple Airlines
Fri 5/1511:42 am
RSW
- ORD
Nonstop3h 02m
Multiple Airlines
Deal found 3/24![Multiple Airlines logo]()
$135
This Super.com deal was found by Cheapflights users on 3/23. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/167:00 am
ORD
- RSW
Nonstop3h 21m
Frontier
Sat 4/181:51 pm
RSW
- ORD
Nonstop3h 30m
Frontier
Deal found 3/23![Frontier logo]()
$136
Best flights from Chicago to Fort Myers BeachDiscover carefully curated flight deals from Chicago to Fort Myers Beach that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 27, 2026.
Discover carefully curated flight deals from Chicago to Fort Myers Beach that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 27, 2026.
This United Airlines deal was found by Cheapflights users on 3/24. 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 5/1210:30 am
ORD
- RSW
Nonstop3h 07m
United Airlines
Wed 5/2012:30 pm
RSW
- ORD
Nonstop3h 20m
United Airlines
Deal found 3/24![United Airlines logo]()
$189
This Southwest deal was found by Cheapflights users on 3/23. 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.
Sat 4/253:40 pm
MDW
- RSW
Nonstop2h 45m
Southwest
Sat 5/26:30 pm
RSW
- MDW
1 stop5h 05m
Southwest
Deal found 3/23![Southwest logo]()
$207
This Delta deal was found by Cheapflights users on 3/25. 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 6/96:40 am
ORD
- RSW
1 stop7h 05m
Delta
Sat 6/138:30 am
RSW
- ORD
1 stop6h 44m
Delta
Deal found 3/25![Delta logo]()
$266
This Southwest deal was found by Cheapflights users on 3/26. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/276:55 pm
MDW
- RSW
Nonstop2h 45m
Southwest
Mon 5/116:20 am
RSW
- MDW
2 stops9h 35m
Southwest
Deal found 3/26![Southwest logo]()
$212
This Southwest deal was found by Cheapflights users on 3/24. 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.
Sat 4/181:55 pm
ORD
- RSW
2 stops6h 45m
Southwest
Wed 4/225:45 pm
RSW
- ORD
1 stop5h 10m
Southwest
Deal found 3/24![Southwest logo]()
$218
This Southwest deal was found by Cheapflights users on 3/24. 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.
Sat 4/251:55 pm
ORD
- RSW
1 stop5h 10m
Southwest
Sat 5/26:25 am
RSW
- ORD
2 stops10h 05m
Southwest
Deal found 3/24![Southwest logo]()
$222
This Delta deal was found by Cheapflights users on 3/22. 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 4/188:15 am
ORD
- RSW
1 stop4h 39m
Delta
Thu 4/237:56 pm
RSW
- ORD
1 stop5h 03m
Delta
Deal found 3/22![Delta logo]()
$277
This Southwest deal was found by Cheapflights users on 3/26. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2712:50 pm
MDW
- RSW
2 stops7h 40m
Southwest
Mon 6/16:20 am
RSW
- MDW
2 stops7h 50m
Southwest
Deal found 3/26![Southwest logo]()
$223
This Delta deal was found by Cheapflights users on 3/23. 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 5/78:42 am
ORD
- RSW
1 stop7h 18m
Delta
Sun 5/107:50 pm
RSW
- ORD
1 stop5h 09m
Delta
Deal found 3/23![Delta logo]()
$277
This Southwest deal was found by Cheapflights users on 3/23. 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 5/512:50 pm
MDW
- RSW
Nonstop2h 45m
Southwest
Fri 5/88:25 pm
RSW
- MDW
Nonstop2h 55m
Southwest
Deal found 3/23![Southwest logo]()
$223
This Southwest deal was found by Cheapflights users on 3/27. 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.
Sun 5/310:30 am
ORD
- RSW
Nonstop2h 55m
Southwest
Thu 5/73:15 pm
RSW
- ORD
Nonstop3h 15m
Southwest
Deal found 3/27![Southwest logo]()
$227
This Southwest deal was found by Cheapflights users on 3/23. 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 4/303:05 pm
ORD
- RSW
1 stop5h 55m
Southwest
Mon 5/48:50 pm
RSW
- ORD
2 stops17h 00m
Southwest
Deal found 3/23![Southwest logo]()
$228
This Southwest deal was found by Cheapflights users on 3/23. 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 4/1710:30 am
ORD
- RSW
Nonstop2h 55m
Southwest
Sat 4/256:25 am
RSW
- ORD
1 stop7h 45m
Southwest
Deal found 3/23![Southwest logo]()
$242
This Southwest deal was found by Cheapflights users on 3/25. 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.
Fri 4/247:50 am
MDW
- RSW
1 stop6h 15m
Southwest
Mon 4/276:00 pm
RSW
- MDW
1 stop7h 05m
Southwest
Deal found 3/25![Southwest logo]()
$247
This Southwest deal was found by Cheapflights users on 3/22. 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.
Sun 4/197:50 pm
MDW
- RSW
Nonstop2h 45m
Southwest
Sat 4/256:00 am
RSW
- MDW
Nonstop2h 55m
Southwest
Deal found 3/22![Southwest logo]()
$248
This Southwest deal was found by Cheapflights users on 3/26. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/152:40 pm
ORD
- RSW
1 stop4h 55m
Southwest
Sat 4/186:25 am
RSW
- ORD
2 stops10h 05m
Southwest
Deal found 3/26![Southwest logo]()
$250
This Southwest deal was found by Cheapflights users on 3/25. 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.
Fri 4/2412:50 pm
MDW
- RSW
2 stops7h 35m
Southwest
Fri 5/17:50 pm
RSW
- MDW
1 stop4h 40m
Southwest
Deal found 3/25![Southwest logo]()
$282
This Southwest deal was found by Cheapflights users on 3/23. 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 5/14:35 pm
MDW
- RSW
1 stop4h 15m
Southwest
Tue 5/510:30 am
RSW
- MDW
2 stops9h 55m
Southwest
Deal found 3/23![Southwest logo]()
$282
This Southwest deal was found by Cheapflights users on 3/22. 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 4/187:45 am
MDW
- RSW
1 stop7h 30m
Southwest
Mon 4/207:50 pm
RSW
- MDW
1 stop4h 40m
Southwest
Deal found 3/22![Southwest logo]()
$286
Last-minute flights from Chicago to Fort Myers BeachDiscover last-minute flight deals from Chicago to Fort Myers Beach. Data last updated March 27, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Fort Myers Beach. Data last updated March 27, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 3/23. 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 4/67:42 pm
ORD
- RSW
Nonstop2h 48m
Multiple Airlines
Thu 4/1612:17 pm
RSW
- ORD
Nonstop3h 30m
Multiple Airlines
Deal found 3/23![Multiple Airlines logo]()
$135
This Kiwi.com deal was found by Cheapflights users on 3/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/77:42 pm
ORD
- RSW
Nonstop2h 48m
Multiple Airlines
Sat 4/181:51 pm
RSW
- ORD
Nonstop3h 30m
Multiple Airlines
Deal found 3/26![Multiple Airlines logo]()
$134
This CheapOair deal was found by Cheapflights users on 3/25. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/116:50 am
ORD
- RSW
Nonstop2h 47m
Multiple Airlines
Sat 4/181:51 pm
RSW
- ORD
Nonstop3h 30m
Multiple Airlines
Deal found 3/25![Multiple Airlines logo]()
$129
This Kiwi.com deal was found by Cheapflights users on 3/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/127:42 pm
ORD
- RSW
Nonstop2h 48m
Multiple Airlines
Thu 4/1612:17 pm
RSW
- ORD
Nonstop3h 30m
Multiple Airlines
Deal found 3/26![Multiple Airlines logo]()
$125
This Frontier deal was found by Cheapflights users on 3/25. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/135:15 am
ORD
- RSW
1 stop11h 35m
Frontier
Sat 4/181:51 pm
RSW
- ORD
Nonstop3h 30m
Frontier
Deal found 3/25![Frontier logo]()
$133
This Expedia deal was found by Cheapflights users on 3/23. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/135:15 am
ORD
- RSW
1 stop11h 35m
Frontier
Thu 4/1612:17 pm
RSW
- ORD
Nonstop3h 30m
Frontier
Deal found 3/23![Frontier logo]()
$137
This Frontier deal was found by Cheapflights users on 3/26. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/167:00 am
ORD
- RSW
Nonstop3h 21m
Frontier
Thu 4/2312:17 pm
RSW
- ORD
Nonstop3h 30m
Frontier
Deal found 3/26![Frontier logo]()
$128
This Frontier deal was found by Cheapflights users on 3/26. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/167:00 am
ORD
- RSW
Nonstop3h 21m
Frontier
Thu 4/3012:17 pm
RSW
- ORD
Nonstop3h 30m
Frontier
Deal found 3/26![Frontier logo]()
$130
This Super.com deal was found by Cheapflights users on 3/23. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/167:00 am
ORD
- RSW
Nonstop3h 21m
Frontier
Sat 4/181:51 pm
RSW
- ORD
Nonstop3h 30m
Frontier
Deal found 3/23![Frontier logo]()
$136
This Kiwi.com deal was found by Cheapflights users on 3/25. 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 4/237:00 am
ORD
- RSW
Nonstop3h 21m
Frontier
Sat 5/21:51 pm
RSW
- ORD
Nonstop3h 30m
Frontier
Deal found 3/25![Frontier logo]()
$131
This Kiwi.com deal was found by Cheapflights users on 3/24. 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.
Sat 4/258:35 am
ORD
- RSW
Nonstop3h 21m
Frontier
Sun 4/2610:32 am
RSW
- ORD
Nonstop3h 30m
Frontier
Deal found 3/24![Frontier logo]()
$127
This Southwest deal was found by Cheapflights users on 3/26. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/277:25 am
MDW
- RSW
Nonstop2h 45m
Southwest
Mon 5/116:50 am
RSW
- MDW
Nonstop2h 55m
Southwest
Deal found 3/26![Southwest logo]()
$197
One-way flights from Chicago to Fort Myers BeachSearch for one-way flight options from Chicago to Fort Myers Beach. Find affordable one-way fares based on user searches. Data last updated March 27, 2026.
Search for one-way flight options from Chicago to Fort Myers Beach. Find affordable one-way fares based on user searches. Data last updated March 27, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 3/27. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/276:30 am
ORD
- RSW
Nonstop2h 47m
Spirit Airlines
Deal found 3/27![Spirit Airlines logo]()
$55
This Frontier deal was found by Cheapflights users on 3/23. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/197:00 am
ORD
- RSW
Nonstop3h 21m
Frontier
Deal found 3/23![Frontier logo]()
$57
This Kiwi.com deal was found by Cheapflights users on 3/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/237:00 am
ORD
- RSW
Nonstop3h 21m
Frontier
Deal found 3/26![Frontier logo]()
$58
This Cheapflightsfares deal was found by Cheapflights users on 3/25. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/47:00 am
ORD
- RSW
Nonstop2h 47m
Spirit Airlines
Deal found 3/25![Spirit Airlines logo]()
$65
This Cheapflightsfares deal was found by Cheapflights users on 3/25. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/147:42 pm
ORD
- RSW
Nonstop2h 48m
Spirit Airlines
Deal found 3/25![Spirit Airlines logo]()
$69
This Super.com deal was found by Cheapflights users on 3/24. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/307:00 am
ORD
- RSW
Nonstop3h 21m
Frontier
Deal found 3/24![Frontier logo]()
$72
This Southwest deal was found by Cheapflights users on 3/25. 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.
Tue 4/214:05 pm
MDW
- RSW
Nonstop2h 45m
Southwest
Deal found 3/25![Southwest logo]()
$95
This Southwest deal was found by Cheapflights users on 3/24. 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 4/207:25 am
MDW
- RSW
Nonstop2h 45m
Southwest
Deal found 3/24![Southwest logo]()
$99
This Southwest deal was found by Cheapflights users on 3/23. 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.
Sat 4/253:40 pm
MDW
- RSW
Nonstop2h 45m
Southwest
Deal found 3/23![Southwest logo]()
$100
This Super.com deal was found by Cheapflights users on 3/25. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/96:00 am
MDW
- RSW
1 stop11h 41m
Frontier
Deal found 3/25![Frontier logo]()
$104
This Southwest deal was found by Cheapflights users on 3/25. 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.
Wed 4/294:40 pm
MDW
- RSW
1 stop4h 30m
Southwest
Deal found 3/25![Southwest logo]()
$105
This Frontier deal was found by Cheapflights users on 3/27. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/116:40 am
MDW
- RSW
1 stop11h 06m
Frontier
Deal found 3/27![Frontier logo]()
$106
Find flight deals from Chicago to Fort Myers Beach
Keep the following information in mind while searching for Chicago to Fort Myers Beach flight deals. Data was last updated March 27, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $122 (Kiwi.com) |
One-way from | $57 (Frontier) |
Popular in | December |
Cheapest in | August |
Average price | $341 |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Fort Myers Beach that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated March 27, 2026.
Use the filters below to find and compare flights from Chicago to Fort Myers Beach that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoFort Myers
ORD - RSW
ORDRSW
Chicago O'Hare Intl
Tue 5/12
10:30 am-2:37 pm
Nonstop3h 07m
Fort Myers SW Florida Intl
Wed 5/20
12:30 pm-2:50 pm
Nonstop3h 20m
$189
ChicagoFort Myers
MDW - RSW
MDWRSW
Chicago Midway
Sat 4/25
3:40 pm-7:25 pm
Nonstop2h 45m
Fort Myers SW Florida Intl
Sat 5/2
6:30 pm-10:35 pm
1 stop5h 05m
$207
ChicagoFort Myers
MDW - RSW
MDWRSW
Chicago Midway
Mon 4/27
6:55 pm-10:40 pm
Nonstop2h 45m
Fort Myers SW Florida Intl
Mon 5/11
6:20 am-2:55 pm
2 stops9h 35m
$212
ChicagoFort Myers
ORD - RSW
ORDRSW
Chicago O'Hare Intl
Sat 4/18
1:55 pm-9:40 pm
2 stops6h 45m
Fort Myers SW Florida Intl
Wed 4/22
5:45 pm-9:55 pm
1 stop5h 10m
$218
ChicagoFort Myers
ORD - RSW
ORDRSW
Chicago O'Hare Intl
Sat 4/25
1:55 pm-8:05 pm
1 stop5h 10m
Fort Myers SW Florida Intl
Sat 5/2
6:25 am-3:30 pm
2 stops10h 05m
$222
ChicagoFort Myers
MDW - RSW
MDWRSW
Chicago Midway
Wed 5/27
12:50 pm-9:30 pm
2 stops7h 40m
Fort Myers SW Florida Intl
Mon 6/1
6:20 am-1:10 pm
2 stops7h 50m
$223
Quickest round-trip
ChicagoFort Myers
MDW - RSW
MDWRSW
Chicago Midway
Tue 5/5
12:50 pm-4:35 pm
Nonstop2h 45m
Fort Myers SW Florida Intl
Fri 5/8
8:25 pm-10:20 pm
Nonstop2h 55m
$223
ChicagoFort Myers
ORD - RSW
ORDRSW
Chicago O'Hare Intl
Sun 5/3
10:30 am-2:25 pm
Nonstop2h 55m
Fort Myers SW Florida Intl
Thu 5/7
3:15 pm-5:30 pm
Nonstop3h 15m
$227
ChicagoFort Myers
ORD - RSW
ORDRSW
Chicago O'Hare Intl
Thu 4/30
3:05 pm-10:00 pm
1 stop5h 55m
Fort Myers SW Florida Intl
Mon 5/4
8:50 pm-12:50 pm
2 stops17h 00m
$228
ChicagoFort Myers
ORD - RSW
ORDRSW
Chicago O'Hare Intl
Fri 4/17
10:30 am-2:25 pm
Nonstop2h 55m
Fort Myers SW Florida Intl
Sat 4/25
6:25 am-1:10 pm
1 stop7h 45m
$242
Showing 1-10 of 40 resultsSorted by cheapest first
Best time to book a flight from Chicago to Fort Myers Beach
Have a flexible travel schedule? Discover the best time to fly to Fort Myers Beach from Chicago with our price prediction graph.
MDW-RSW
ORD-RSW
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago to Fort Myers Beach
CHI-FM9
MDW-RSW
ORD-RSW
How far ahead should I book a flight from Chicago to Fort Myers Beach?
Use this chart to determine the optimal time to book a round-trip flight from Chicago to Fort Myers Beach. Price data was last updated on March 13, 2026.
Booking 87 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago to Fort Myers Beach. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
What is the cheapest month to book a flight from Chicago to Fort Myers Beach?
Currently, March is the cheapest month in which you can book a flight from Chicago to Fort Myers Beach (average of $37). Flying from Chicago to Fort Myers Beach in November is currently the most expensive (average of $133). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from CHI to FM9?
Find hourly flight availability from Chicago to Fort Myers Beach. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated March 27, 2026.
One of the essential ways to save on airfare from Chicago to Fort Myers Beach is to remain as flexible as possible. Flights that are in the evening tend to be the most expensive. A flight in the morning could potentially save you up to 20% on airfare.
What is the cheapest day to fly from Chicago to Fort Myers Beach?
Use this chart to determine the cheapest time to fly round-trip from Chicago to Fort Myers Beach. Price data was last updated on March 23, 2026.
Travelers seeking maximum savings on their Chicago to Fort Myers Beach flight should consider departing on Wednesday afternoons when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Weekly flight availability from Chicago to Fort Myers Beach
Explore weekly flight availability from Chicago to Fort Myers Beach. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated March 27, 2026.
The most flights from CHI to FM9 are scheduled on a Friday (35 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (9 on average).
How much does it cost to fly round-trip from Chicago to Fort Myers Beach?
Reviews of airlines servicing Fort Myers Beach
Get insights into the airlines that provide service to Fort Myers Beach. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Fort Myers Beach. Reviews last updated March 27, 2026.
Get a feel of what it's like to fly with Southwest,United Airlines, andAmerican Airlines from Chicago to Fort Myers Beach by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Overall
8.0
Boarding
8.1
Food
7.0
Crew
8.6
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Overall
8.0
Boarding
8.1
Food
7.0
Crew
8.6
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Overall
8.0
Boarding
8.1
Food
7.0
Crew
8.6
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Overall
8.0
Boarding
8.1
Food
7.0
Crew
8.6
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Overall
8.0
Boarding
8.1
Food
7.0
Crew
8.6
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Overall
8.0
Boarding
8.1
Food
7.0
Crew
8.6
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Related info for your journey
Find useful and relevant information for your journey from Chicago to Fort Myers Beach. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Chicago to Fort Myers Beach
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Complete your trip
Complete your trip to Fort Myers Beach by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Fort Myers Beach by cabin class
Find flights from Chicago to Fort Myers Beach, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Fort Myers Beach flights
Browse other Chicago and Fort Myers Beach flight options. Last updated on March 27, 2026.
Other flights from Chicago
Browse through other flights departing from Chicago. Flights are based on user searches made on Cheapflights and were last updated on March 27, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 8 airlines flying from Chicago to Fort Myers Beach
Discover the top 8 airlines that operate flights from Chicago to Fort Myers Beach. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated March 27, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$58 | Average$199 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$66 | Average$182 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$99 | Average$223 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$108 | Average$348 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$143 | Average$230 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$158 | Average$357 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$159 | Average$358 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$171 | Average$381 | FlexibilityNo cancel fee | On-time63% |