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Fort Myers

$74+ Cheap flights from Illinois to Fort Myers (RSW)

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 12/14. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — RSW
Dec 21 — Dec 281
Sun 12/21
Sun 12/28
1 adult, Economy
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Find flight deals from Illinois to Fort Myers

Cheapest flights from Illinois to Fort Myers
Explore the most affordable flight options available from Illinois to Fort Myers. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 21, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/19. Clicking the “Pick Dates” 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 12/148:15 amORD - RSW
Nonstop3h 05mMultiple Airlines
Tue 12/239:53 amRSW - ORD
2 stops13h 31mMultiple Airlines
Deal found 11/19$157
This Mytrip deal was found by Cheapflights users on 11/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/144:05 pmORD - RSW
1 stop16h 41mMultiple Airlines
Sat 12/209:55 pmRSW - ORD
Nonstop3h 01mMultiple Airlines
Deal found 11/20$158
This Super.com deal was found by Cheapflights users on 11/19. Clicking the “Pick Dates” 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 12/209:19 amORD - RSW
Nonstop3h 10mSpirit Airlines
Tue 12/239:55 pmRSW - ORD
Nonstop3h 01mSpirit Airlines
Deal found 11/19$159
This CheapOair deal was found by Cheapflights users on 11/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/199:19 amORD - RSW
Nonstop3h 10mSpirit Airlines
Sun 1/187:22 amRSW - ORD
Nonstop3h 12mSpirit Airlines
Deal found 11/20$160
This Kiwi.com deal was found by Cheapflights users on 11/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/143:20 pmORD - RSW
2 stops24h 30mMultiple Airlines
Fri 12/196:15 amRSW - ORD
Nonstop3h 09mMultiple Airlines
Deal found 11/20$162
This Kiwi.com deal was found by Cheapflights users on 11/18. Clicking the “Pick Dates” 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 12/118:15 amORD - RSW
Nonstop3h 05mMultiple Airlines
Mon 12/155:45 pmRSW - ORD
2 stops18h 23mMultiple Airlines
Deal found 11/18$163
This Expedia deal was found by Cheapflights users on 11/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/206:10 amORD - RSW
1 stop11h 33mFrontier
Mon 12/2211:13 amRSW - ORD
1 stop9h 53mFrontier
Deal found 11/20$164
This Kiwi.com deal was found by Cheapflights users on 11/19. Clicking the “Pick Dates” 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 12/226:00 amORD - RSW
2 stops25h 58mMultiple Airlines
Fri 12/266:15 amRSW - ORD
Nonstop3h 09mMultiple Airlines
Deal found 11/19$165
This Kiwi.com deal was found by Cheapflights users on 11/18. Clicking the “Pick Dates” 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 12/1212:15 pmORD - RSW
3 stops23h 06mMultiple Airlines
Sat 12/206:15 amRSW - ORD
Nonstop3h 09mMultiple Airlines
Deal found 11/18$166
This Kiwi.com deal was found by Cheapflights users on 11/19. Clicking the “Pick Dates” 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 12/78:15 amORD - RSW
Nonstop3h 05mMultiple Airlines
Fri 12/127:14 pmRSW - ORD
1 stop28h 10mMultiple Airlines
Deal found 11/19$167
This United Airlines deal was found by Cheapflights users on 11/19. Clicking the “Pick Dates” 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 12/177:25 amORD - RSW
Nonstop3h 01mUnited Airlines
Wed 12/2410:04 amRSW - ORD
Nonstop3h 15mUnited Airlines
Deal found 11/19$168
This Southwest deal was found by Cheapflights users on 11/19. Clicking the “Pick Dates” 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 12/176:15 pmMDW - RSW
Nonstop2h 55mSouthwest
Wed 12/245:35 pmRSW - MDW
Nonstop2h 55mSouthwest
Deal found 11/19$168

Cheap flight deals from Illinois to Fort Myers

Keep the following information in mind while searching for Illinois to Fort Myers flight deals. Data was last updated November 21, 2025.

Most accurate provider

Justfly.com
3 stars

Most trusted provider

Justfly.com
3 stars

Round-trip from

$155
(CheapOair)

One-way from

$74
(Southwest)

Popular in

March

Cheapest in

August

Average price

$341
Provider with most accurate pricing for Chicago (CHI)-Fort Myers SW Florida Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Fort Myers SW Florida Intl flights.
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From Illinois to Fort Myers SW Florida Intl
Search Deals
One-way flight from Illinois to Fort Myers SW Florida Intl
Search Deals
Highest demand for flights based on searches. 15% potential increase in price ($50 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Illinois to Fort Myers 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 November 21, 2025.
Use the filters below to find and compare flights from Illinois to Fort Myers that are best for you.

Fly from

Illinois

Fly to

Fort Myers

Route

Depart

Return

Price

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Sun 2/15

12:45 pm-4:48 pm

Nonstop3h 03m

Fort Myers SW Florida Intl

Wed 2/18

9:00 am-2:20 pm

1 stop6h 20m

$187

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Wed 12/17

8:20 am-12:10 pm

Nonstop2h 50m

Fort Myers SW Florida Intl

Wed 12/24

6:30 am-8:25 am

Nonstop2h 55m

$190

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Tue 2/24

5:00 am-11:35 am

1 stop5h 35m

Fort Myers SW Florida Intl

Tue 3/3

6:50 am-1:55 pm

2 stops8h 05m

$194

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Sun 1/11

8:45 am-6:30 pm

1 stop8h 45m

Fort Myers SW Florida Intl

Mon 1/12

10:15 am-7:45 pm

1 stop10h 30m

$197

SpringfieldFort Myers

SPI - RSW

SPIRSW

Springfield Capital

Wed 1/28

3:25 pm-10:03 pm

1 stop5h 38m

Fort Myers SW Florida Intl

Mon 2/2

7:05 am-2:18 pm

2 stops8h 13m

$204

SpringfieldFort Myers

SPI - RSW

SPIRSW

Springfield Capital

Mon 1/26

2:48 pm-10:03 pm

1 stop6h 15m

Fort Myers SW Florida Intl

Sat 1/31

11:10 am-10:09 pm

2 stops11h 59m

$204

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Sat 2/7

11:00 am-5:05 pm

1 stop5h 05m

Fort Myers SW Florida Intl

Sat 2/14

5:00 am-7:00 am

Nonstop3h 00m

$213

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Sun 2/15

6:00 am-9:55 am

Nonstop2h 55m

Fort Myers SW Florida Intl

Wed 2/18

12:20 pm-6:50 pm

1 stop7h 30m

$213

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Thu 1/22

5:30 am-11:55 am

1 stop5h 25m

Fort Myers SW Florida Intl

Sun 1/25

6:00 am-1:18 pm

1 stop8h 18m

$217

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Fri 2/6

5:30 am-2:00 pm

1 stop7h 30m

Fort Myers SW Florida Intl

Sat 2/14

6:00 am-1:21 pm

1 stop8h 21m

$217

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/21

Showing 1-10 of 60 results
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Best time to book a flight from Illinois to Fort Myers

Have a flexible travel schedule? Discover the best time to fly to Fort Myers from Illinois with our price prediction graph.
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 Illinois to Fort Myers

What is the cheapest month to book a flight from Illinois to Fort Myers?

Currently, March is the cheapest month in which you can book a flight from Illinois to Fort Myers (average of $43). Flying from Illinois to Fort Myers in November is currently the most expensive (average of $112). 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 IL to RSW?

Find hourly flight availability from Illinois to Fort Myers. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 21, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 28% on flights from Illinois to Fort Myers by exploring options for tickets in the evening.

What is the cheapest day to fly from Illinois to Fort Myers?

Use this chart to determine the cheapest time to fly round-trip from Illinois to Fort Myers. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Illinois to Fort Myers flight should consider departing on Wednesday mornings 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 Illinois to Fort Myers

Explore weekly flight availability from Illinois to Fort Myers. 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 November 21, 2025.

The most flights from USIL to RSW are scheduled on a Thursday (22 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (8 on average).

How much does it cost to fly round-trip from Illinois to Fort Myers?

Related info for your journey

Find useful and relevant information for your journey from Illinois to Fort Myers. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Fort Myers from Illinois?

    If you book a flight to Fort Myers from Illinois, you will be flying to SW Florida Intl, which is the city’s only airport. Fort Myers SW Florida Intl (RSW) is located 10.0 mi from the center of Fort Myers.

  • How long is the flight from Illinois to Fort Myers?

    Departing from Illinois to Fort Myers will take you 2h 50m. Airlines will cover a distance of 1106 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines to fly from Illinois to Fort Myers one-way?

    The cheapest airline one-way is Southwest, with whom users have recently found tickets for as low as $79. However, be on the lookout for offers from American Airlines and United Airlines, as they are both options that can get you from Illinois to Fort Myers for a low price.

  • What are the most popular routes from Illinois to Fort Myers?

    Most travelers choose Chicago O'Hare Intl - Fort Myers SW Florida Intl, Chicago Midway - Fort Myers SW Florida Intl or Lambert-St Louis - Fort Myers SW Florida Intl when deciding on the best route from Illinois to Fort Myers.

  • What are the most reliable airlines from Illinois to Fort Myers?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Illinois to Fort Myers on time: Air New Zealand (91%), Air Canada (89%), United Airlines (85%).

  • What are the cheapest flights from Illinois to Fort Myers?

    On average you can expect to pay $617 for a flight from Illinois to Fort Myers. The cheapest flight overall is $75 while the most popular route, (Chicago O'Hare Intl - Fort Myers SW Florida Intl) is currently priced at $58.

  • Can I find deals for flights from Illinois to Fort Myers that include hotel bookings?

    Yes. In addition to deals on Illinois to Fort Myers flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Illinois to Fort Myers?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Illinois to Fort Myers.

  • Can I find deals for business class flights from Illinois to Fort Myers?

    Yes. Cheapflights offers flight deals from Illinois to Fort Myers by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Illinois to Fort Myers?

    Currently, March is the cheapest month in which you can book a flight from Illinois to Fort Myers (average of $43). Flying from Illinois to Fort Myers in November is currently the most expensive (average of $112). 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.

See more FAQs

Traveling to a place near Fort Myers?

Book flights to Fort Myers if you plan to visit one of these locations
Sanibel
North Fort Myers
Estero
Lehigh Acres

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Alternative routes for Illinois to Fort Myers

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Top 8 airlines flying from Illinois to Fort Myers

Discover the top 8 airlines that operate flights from Illinois to Fort Myers. 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 November 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$54Average$130FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$85Average$292FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$95Average$217FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$156Average$376FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$166Average$362FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$172Average$425FlexibilityNo cancel feeOn-time63%
DeltaCheapest$178Average$409FlexibilityNo cancel feeOn-timeN/A
Allegiant AirCheapest$180Average$198FlexibilityNo cancel feeOn-time88%

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