$142+ Cheap flights from Fort Myers (RSW) to Chicago (CHI)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/5. Fares are subject to change and may not be available on all flights or dates of travel.
RSW — CHI
Sep 5 — Sep 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 Chicago with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from Fort Myers SW Florida Intl to Chicago are usually found in January or February, booked 29 days in advance, depart on a Thursday or Friday and return on a Wednesday
Cheap flight deals from Fort Myers to Chicago
Cheapest
Best
Last-minute
One-way
Cheapest flights from Fort Myers to ChicagoExplore the most affordable flight options available from Fort Myers to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 6, 2026.
Explore the most affordable flight options available from Fort Myers to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 6, 2026.
This Frontier deal was found by Cheapflights users on 8/1. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/218:55 pm -
Nonstop4h 52m
Sat 11/282:08 pm -
Nonstop4h 52m
Deal found 8/1![Frontier logo]()
$276
This CheapOair deal was found by Cheapflights users on 8/1. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2212:45 pm -
1 stop6h 39m
Mon 10/262:15 pm -
1 stop8h 22m
Deal found 8/1![Multiple Airlines logo]()
$277
This Frontier deal was found by Cheapflights users on 8/2. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/310:52 am -
1 stop9h 20m
Thu 9/107:25 am -
1 stop8h 20m
Deal found 8/2![Frontier logo]()
$278
This Trip.com deal was found by Cheapflights users on 8/2. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/2612:45 pm -
1 stop6h 39m
Mon 11/302:08 pm -
Nonstop4h 52m
Deal found 8/2![Frontier logo]()
$281
This United Airlines deal was found by Cheapflights users on 8/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/54:40 pm -
Nonstop3h 19m
Sun 9/610:30 am -
Nonstop3h 06m
Deal found 8/3![United Airlines logo]()
$283
This Southwest deal was found by Cheapflights users on 8/3. 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.
Sat 9/57:10 am -
Nonstop2h 45m
Sun 9/66:25 pm -
Nonstop2h 45m
Deal found 8/3![Southwest logo]()
$283
This American Airlines deal was found by Cheapflights users on 8/3. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/56:07 am -
Nonstop3h 23m
Sun 9/67:05 pm -
Nonstop2h 57m
Deal found 8/3![American Airlines logo]()
$284
This CheapOair deal was found by Cheapflights users on 8/1. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/316:00 am -
1 stop8h 20m
Mon 11/22:15 pm -
1 stop8h 22m
Deal found 8/1![JetBlue logo]()
$285
This JetBlue deal was found by Cheapflights users on 8/4. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/161:40 pm -
1 stop9h 16m
Mon 10/191:00 pm -
1 stop6h 40m
Deal found 8/4![JetBlue logo]()
$287
This Kiwi.com deal was found by Cheapflights users on 8/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/310:52 am -
1 stop9h 20m
Tue 9/81:59 pm -
2 stops31h 14m
Deal found 8/1![Multiple Airlines logo]()
$289
This Mytrip deal was found by Cheapflights users on 8/5. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/3011:32 am -
1 stop6h 46m
Fri 10/27:17 pm -
1 stop13h 50m
Deal found 8/5![Avelo Airlines logo]()
$290
This JetBlue deal was found by Cheapflights users on 8/4. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/1411:05 am -
1 stop8h 56m
Fri 9/187:00 am -
1 stop6h 47m
Deal found 8/4![JetBlue logo]()
$291
Best flights from Fort Myers to ChicagoDiscover carefully curated flight deals from Fort Myers to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 6, 2026.
Discover carefully curated flight deals from Fort Myers to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 6, 2026.
This United Airlines deal was found by Cheapflights users on 8/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/24:40 pm -
Nonstop3h 19m
Sun 9/65:51 pm -
Nonstop3h 06m
Deal found 8/3![United Airlines logo]()
$294
This Southwest deal was found by Cheapflights users on 8/1. 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.
Fri 9/116:50 am -
Nonstop2h 50m
Mon 9/146:15 pm -
Nonstop2h 50m
Deal found 8/1![Southwest logo]()
$294
This Delta deal was found by Cheapflights users on 8/5. 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.
Wed 9/25:35 am -
1 stop7h 41m
Sat 9/56:30 pm -
1 stop5h 10m
Deal found 8/5![Delta logo]()
$321
This Southwest deal was found by Cheapflights users on 8/2. 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.
Wed 9/25:40 pm -
Nonstop2h 50m
Sat 9/59:20 am -
2 stops8h 35m
Deal found 8/2![Southwest logo]()
$309
This United Airlines deal was found by Cheapflights users on 8/1. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/36:50 am -
1 stop8h 55m
Wed 10/74:30 pm -
Nonstop3h 06m
Deal found 8/1![United Airlines logo]()
$311
This Delta deal was found by Cheapflights users on 8/5. 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 12/266:00 am -
1 stop7h 37m
Thu 12/319:30 am -
1 stop6h 48m
Deal found 8/5![Delta logo]()
$325
This United Airlines deal was found by Cheapflights users on 8/4. 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.
Tue 10/66:50 am -
1 stop8h 55m
Sat 10/244:30 pm -
Nonstop3h 06m
Deal found 8/4![United Airlines logo]()
$311
This Southwest deal was found by Cheapflights users on 8/4. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/186:50 am -
Nonstop2h 50m
Mon 9/216:15 pm -
Nonstop2h 50m
Deal found 8/4![Southwest logo]()
$324
This Delta deal was found by Cheapflights users on 8/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/221:19 pm -
1 stop6h 40m
Sat 8/296:40 am -
1 stop4h 33m
Deal found 8/1![Delta logo]()
$339
This United Airlines deal was found by Cheapflights users on 8/5. 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 9/212:27 pm -
Nonstop3h 14m
Thu 9/37:15 am -
Nonstop3h 06m
Deal found 8/5![United Airlines logo]()
$319
This Southwest deal was found by Cheapflights users on 8/5. 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.
Sat 11/77:05 am -
2 stops7h 20m
Mon 11/95:10 am -
1 stop5h 35m
Deal found 8/5![Southwest logo]()
$330
This United Airlines deal was found by Cheapflights users on 8/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/25:14 pm -
1 stop7h 12m
Wed 9/97:05 am -
1 stop8h 34m
Deal found 8/3![United Airlines logo]()
$325
This Southwest deal was found by Cheapflights users on 8/3. 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 9/21:20 pm -
1 stop7h 20m
Wed 9/912:35 pm -
2 stops6h 40m
Deal found 8/3![Southwest logo]()
$330
This United Airlines deal was found by Cheapflights users on 8/4. 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.
Thu 8/277:00 am -
1 stop6h 59m
Mon 8/315:51 pm -
Nonstop3h 06m
Deal found 8/4![United Airlines logo]()
$329
This Southwest deal was found by Cheapflights users on 8/6. 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 9/175:25 pm -
Nonstop2h 50m
Sun 9/209:00 am -
Nonstop2h 45m
Deal found 8/6![Southwest logo]()
$336
This United Airlines deal was found by Cheapflights users on 8/4. 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.
Fri 9/187:00 pm -
1 stop6h 28m
Mon 9/2110:30 am -
Nonstop3h 06m
Deal found 8/4![United Airlines logo]()
$334
This Southwest deal was found by Cheapflights users on 8/1. 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.
Wed 10/75:45 pm -
Nonstop2h 50m
Sun 10/118:15 am -
1 stop4h 30m
Deal found 8/1![Southwest logo]()
$346
This United Airlines deal was found by Cheapflights users on 8/2. 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.
Fri 11/611:42 am -
1 stop7h 28m
Mon 11/91:10 pm -
Nonstop3h 02m
Deal found 8/2![United Airlines logo]()
$334
This Southwest deal was found by Cheapflights users on 8/6. 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.
Fri 9/113:40 pm -
2 stops7h 20m
Sun 9/205:00 am -
1 stop5h 15m
Deal found 8/6![Southwest logo]()
$350
This Southwest deal was found by Cheapflights users on 8/2. 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 11/66:20 am -
2 stops8h 30m
Mon 11/912:50 pm -
2 stops8h 45m
Deal found 8/2![Southwest logo]()
$354
Last-minute flights from Fort Myers to ChicagoDiscover last-minute flight deals from Fort Myers to Chicago. Data last updated August 6, 2026 and is based on user searches.
Discover last-minute flight deals from Fort Myers to Chicago. Data last updated August 6, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 8/2. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/310:52 am -
1 stop9h 20m
Thu 9/107:25 am -
1 stop8h 20m
Deal found 8/2![Frontier logo]()
$278
This Kiwi.com deal was found by Cheapflights users on 8/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/310:52 am -
1 stop9h 20m
Tue 9/81:59 pm -
2 stops31h 14m
Deal found 8/1![Multiple Airlines logo]()
$289
This Southwest deal was found by Cheapflights users on 8/3. 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.
Thu 9/312:05 pm -
Nonstop2h 45m
Sun 9/66:25 pm -
Nonstop2h 45m
Deal found 8/3![Southwest logo]()
$294
This United Airlines deal was found by Cheapflights users on 8/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/54:40 pm -
Nonstop3h 19m
Sun 9/610:30 am -
Nonstop3h 06m
Deal found 8/3![United Airlines logo]()
$283
This Southwest deal was found by Cheapflights users on 8/3. 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.
Sat 9/57:10 am -
Nonstop2h 45m
Sun 9/66:25 pm -
Nonstop2h 45m
Deal found 8/3![Southwest logo]()
$283
This American Airlines deal was found by Cheapflights users on 8/3. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/56:07 am -
Nonstop3h 23m
Sun 9/67:05 pm -
Nonstop2h 57m
Deal found 8/3![American Airlines logo]()
$284
This American Airlines deal was found by Cheapflights users on 8/2. 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.
Sat 9/511:27 am -
Nonstop3h 23m
Tue 9/86:45 am -
Nonstop2h 52m
Deal found 8/2![American Airlines logo]()
$294
This American Airlines deal was found by Cheapflights users on 8/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1111:56 am -
Nonstop3h 19m
Mon 9/146:50 am -
Nonstop3h 01m
Deal found 8/1![American Airlines logo]()
$295
This JetBlue deal was found by Cheapflights users on 8/4. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/1411:05 am -
1 stop8h 56m
Fri 9/187:00 am -
1 stop6h 47m
Deal found 8/4![JetBlue logo]()
$291
This Kiwi.com deal was found by Cheapflights users on 8/2. 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 9/227:00 am -
2 stops12h 23m
Sun 9/277:25 am -
1 stop8h 20m
Deal found 8/2![Multiple Airlines logo]()
$287
This Mytrip deal was found by Cheapflights users on 8/4. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/2311:32 am -
1 stop6h 46m
Fri 9/257:17 pm -
1 stop13h 50m
Deal found 8/4![Avelo Airlines logo]()
$285
This Mytrip deal was found by Cheapflights users on 8/5. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/3011:32 am -
1 stop6h 46m
Fri 10/27:17 pm -
1 stop13h 50m
Deal found 8/5![Avelo Airlines logo]()
$290
One-way flights from Fort Myers to ChicagoSearch for one-way flight options from Fort Myers to Chicago. Find affordable one-way fares based on user searches. Data last updated August 6, 2026.
Search for one-way flight options from Fort Myers to Chicago. Find affordable one-way fares based on user searches. Data last updated August 6, 2026.
This United Airlines deal was found by Cheapflights users on 8/6. 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.
Sat 9/59:15 am -
Nonstop3h 14m
Deal found 8/6![United Airlines logo]()
$142
This Southwest deal was found by Cheapflights users on 8/3. 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.
Sat 9/57:10 am -
Nonstop2h 45m
Deal found 8/3![Southwest logo]()
$142
This Kiwi.com deal was found by Cheapflights users on 8/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/318:09 pm -
2 stops18h 27m
Deal found 8/3![Frontier logo]()
$143
This American Airlines deal was found by Cheapflights users on 8/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/64:39 pm -
Nonstop3h 31m
Deal found 8/1![American Airlines logo]()
$144
This Kiwi.com deal was found by Cheapflights users on 8/6. 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 9/27:00 am -
2 stops17h 08m
Deal found 8/6![Multiple Airlines logo]()
$145
This Kiwi.com deal was found by Cheapflights users on 8/2. 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.
Fri 10/1611:34 am -
2 stops9h 54m
Deal found 8/2![Frontier logo]()
$146
This Kiwi.com deal was found by Cheapflights users on 8/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/310:52 am -
1 stop9h 20m
Deal found 8/3![Frontier logo]()
$147
This JetBlue deal was found by Cheapflights users on 8/4. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/46:00 am -
1 stop8h 20m
Deal found 8/4![JetBlue logo]()
$148
This Kiwi.com deal was found by Cheapflights users on 8/2. 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.
Sat 8/2911:38 am -
2 stops21h 15m
Deal found 8/2![Frontier logo]()
$150
This Kiwi.com deal was found by Cheapflights users on 8/2. 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.
Fri 10/1612:45 pm -
2 stops24h 22m
Deal found 8/2![Frontier logo]()
$151
This Delta deal was found by Cheapflights users on 8/4. 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.
Sat 9/512:22 pm -
1 stop5h 37m
Deal found 8/4![Delta logo]()
$152
This American Airlines deal was found by Cheapflights users on 8/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/76:07 am -
Nonstop3h 23m
Deal found 8/1![American Airlines logo]()
$153
Find flight deals from Fort Myers to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Fort Myers (RSW) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated August 6, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $276 (Frontier) |
One-way from | $142 (United Airlines) |
Popular in | June |
Cheapest in | January |
Average price | $264 |
Cheapflights Fare Finder
Customize your flight search to find flights from Fort Myers to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 6, 2026.
Use the filters below to find and compare flights from Fort Myers to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Fort MyersChicago
RSW Fort Myers SW Florida Intl - ORD Chicago O'Hare Intl
RSWORD
Fort Myers SW Florida Intl
Wed 9/2
4:40 pm-6:59 pm
Nonstop3h 19m
Chicago O'Hare Intl
Sun 9/6
5:51 pm-9:57 pm
Nonstop3h 06m
$294
Fort MyersChicago
RSW Fort Myers SW Florida Intl - MDW Chicago Midway
RSWMDW
Fort Myers SW Florida Intl
Fri 9/11
6:50 am-8:40 am
Nonstop2h 50m
Chicago Midway
Mon 9/14
6:15 pm-10:05 pm
Nonstop2h 50m
$294
Fort MyersChicago
RSW Fort Myers SW Florida Intl - MDW Chicago Midway
RSWMDW
Fort Myers SW Florida Intl
Wed 9/2
5:40 pm-7:30 pm
Nonstop2h 50m
Chicago Midway
Sat 9/5
9:20 am-6:55 pm
2 stops8h 35m
$309
Fort MyersChicago
RSW Fort Myers SW Florida Intl - ORD Chicago O'Hare Intl
RSWORD
Fort Myers SW Florida Intl
Sat 10/3
6:50 am-2:45 pm
1 stop8h 55m
Chicago O'Hare Intl
Wed 10/7
4:30 pm-8:36 pm
Nonstop3h 06m
$311
Fort MyersChicago
RSW Fort Myers SW Florida Intl - ORD Chicago O'Hare Intl
RSWORD
Fort Myers SW Florida Intl
Tue 10/6
6:50 am-2:45 pm
1 stop8h 55m
Chicago O'Hare Intl
Sat 10/24
4:30 pm-8:36 pm
Nonstop3h 06m
$311
Fort MyersChicago
RSW Fort Myers SW Florida Intl - ORD Chicago O'Hare Intl
RSWORD
Fort Myers SW Florida Intl
Wed 9/2
12:27 pm-2:41 pm
Nonstop3h 14m
Chicago O'Hare Intl
Thu 9/3
7:15 am-11:21 am
Nonstop3h 06m
$319
Fort MyersChicago
RSW Fort Myers SW Florida Intl - ORD Chicago O'Hare Intl
RSWORD
Fort Myers SW Florida Intl
Wed 9/2
5:35 am-12:16 pm
1 stop7h 41m
Chicago O'Hare Intl
Sat 9/5
6:30 pm-12:40 am
1 stop5h 10m
$321
Fort MyersChicago
RSW Fort Myers SW Florida Intl - MDW Chicago Midway
RSWMDW
Fort Myers SW Florida Intl
Fri 9/18
6:50 am-8:40 am
Nonstop2h 50m
Chicago Midway
Mon 9/21
6:15 pm-10:05 pm
Nonstop2h 50m
$324
Fort MyersChicago
RSW Fort Myers SW Florida Intl - ORD Chicago O'Hare Intl
RSWORD
Fort Myers SW Florida Intl
Sat 12/26
6:00 am-12:37 pm
1 stop7h 37m
Chicago O'Hare Intl
Thu 12/31
9:30 am-5:18 pm
1 stop6h 48m
$325
Fort MyersChicago
RSW Fort Myers SW Florida Intl - ORD Chicago O'Hare Intl
RSWORD
Fort Myers SW Florida Intl
Wed 9/2
5:14 pm-11:26 pm
1 stop7h 12m
Chicago O'Hare Intl
Wed 9/9
7:05 am-4:39 pm
1 stop8h 34m
$325
Showing 1-10 of 50 resultsSorted by cheapest first
Compare providers for flights from Fort Myers to Chicago
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Fort Myers to Chicago in August.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*1 star | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy- | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star |
- Most accurate provider: When it comes to deals on Fort Myers-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Fort Myers-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Fort Myers-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Fort Myers-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Fort Myers-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Fort Myers to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Fort Myers with our price prediction graph.
RSW-CHI
RSW-ORD
RSW-MDW
RSW-RFD
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Fort Myers to Chicago
RSW-CHI
RSW-ORD
RSW-MDW
RSW-RFD
What is the cheapest month to book a flight from Fort Myers to Chicago?
Currently, January is the cheapest month in which you can book a flight from Fort Myers to Chicago (average of $192). Flying from Fort Myers to Chicago 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 CHI?
Find hourly flight availability from Fort Myers to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 6, 2026.
It’s typically best to fly out from Fort Myers to Chicago in the evening. Doing so could potentially save you 24% on the flight price compared to flying at noon, which is usually more expensive.
Weekly flight availability from Fort Myers to Chicago
Explore weekly flight availability from Fort Myers to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated August 6, 2026.
The most flights from RSW to CHI are scheduled on a Wednesday (18 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (6 on average).
How much does it cost to fly round-trip from Fort Myers to Chicago?
Airfare is typical for this route at the moment.
Fort Myers to Chicago flights typically cost between $189 and $317 in November.The cheapest round-trip price found within the last 5 days was $276 on Frontier (Nov 21-Nov 28).
How far ahead should I book a flight from Fort Myers to Chicago?
The price you pay for your flight from Fort Myers to Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 72 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
What is the cheapest day to fly from Fort Myers to Chicago?
Use this chart to determine the cheapest time to fly round-trip from Fort Myers to Chicago. Price data was last updated on August 1, 2026.
Travelers seeking maximum savings on their Fort Myers to Chicago flight should consider departing on Sunday evenings when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
The best insider tips for Fort Myers to Chicago flights
AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Fort Myers to Chicago trip
Our travel experts
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated August 6, 2026.
Get a feel of what it's like to fly with Southwest,United Airlines, andAmerican Airlines from Fort Myers to Chicago by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.6
Food
7.0
Overall
8.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Food
7.0
Overall
8.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Food
7.0
Overall
8.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Food
7.0
Overall
8.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Food
7.0
Overall
8.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Food
7.0
Overall
8.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
Find useful and relevant information for your journey from Fort Myers to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
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
Chicago flight routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights
Top destinations
Alternative routes for Fort Myers to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on August 6, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Fort Myers to Chicago by cabin class
Find flights from Fort Myers to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Fort Myers and Chicago flights
Browse other Fort Myers and Chicago flight options. Last updated on August 6, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Fort Myers to Chicago flights
Consider these flights traveling from Fort Myers to Chicago.
Top 5 airlines flying from Fort Myers to Chicago
Discover the top 5 airlines that operate flights from Fort Myers to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 6, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$43 | Average$98 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$105 | Average$284 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$159 | Average$316 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$167 | Average$306 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$183 | Average$351 | FlexibilityNo cancel fee | On-time63% |