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Fort Myers

$129+ 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 9/5. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — RSW
7월 9 — 7월 161
목 7/9
목 7/16
1 adult, Economy
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Cheap 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 6월 9, 2026.

This Southwest deal was found by Cheapflights users on 6/8. 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.
목 9/105:15 am
MDW
-
RSW
2 stops10h 15m
Southwest
월 9/146:50 am
RSW
-
MDW
Nonstop2h 50m
Southwest
Deal found 6/8$259
This Delta deal was found by Cheapflights users on 6/7. 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.
수 8/125:09 pm
MLI
-
RSW
1 stop6h 31m
Delta
화 8/185:35 am
RSW
-
MLI
1 stop5h 50m
Delta
Deal found 6/7$261
This American Airlines deal was found by Cheapflights users on 6/8. 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.
화 9/226:18 am
PIA
-
RSW
1 stop6h 46m
American Airlines
토 10/311:14 am
RSW
-
PIA
1 stop5h 57m
American Airlines
Deal found 6/8$261
This Southwest deal was found by Cheapflights users on 6/7. 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.
토 8/112:00 pm
MDW
-
RSW
1 stop6h 10m
Southwest
수 8/51:10 pm
RSW
-
MDW
1 stop7h 20m
Southwest
Deal found 6/7$262
This Southwest deal was found by Cheapflights users on 6/7. 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.
수 11/1111:45 am
MDW
-
RSW
1 stop6h 10m
Southwest
월 11/167:10 am
RSW
-
MDW
1 stop5h 15m
Southwest
Deal found 6/7$264
This Southwest deal was found by Cheapflights users on 6/7. 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.
목 9/171:00 pm
MDW
-
RSW
2 stops6h 55m
Southwest
월 9/216:50 am
RSW
-
MDW
Nonstop2h 50m
Southwest
Deal found 6/7$268
This Delta deal was found by Cheapflights users on 6/4. 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.
토 9/195:10 pm
MLI
-
RSW
1 stop6h 22m
Delta
수 9/236:35 pm
RSW
-
MLI
1 stop4h 49m
Delta
Deal found 6/4$271
This Southwest deal was found by Cheapflights users on 6/8. 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.
수 11/48:00 am
MDW
-
RSW
1 stop4h 55m
Southwest
월 11/96:20 am
RSW
-
MDW
2 stops8h 30m
Southwest
Deal found 6/8$280
This United Airlines deal was found by Cheapflights users on 6/8. 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.
월 8/246:30 am
ORD
-
RSW
1 stop8h 25m
United Airlines
목 8/2712:27 pm
RSW
-
ORD
Nonstop3h 14m
United Airlines
Deal found 6/8$285
This Delta deal was found by Cheapflights users on 6/8. 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.
금 7/316:35 am
ORD
-
RSW
1 stop4h 36m
Delta
화 8/43:30 pm
RSW
-
ORD
1 stop6h 25m
Delta
Deal found 6/8$286
This Delta deal was found by Cheapflights users on 6/8. 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.
월 8/176:05 am
MDW
-
RSW
1 stop7h 19m
Delta
금 8/216:29 pm
RSW
-
MDW
1 stop5h 07m
Delta
Deal found 6/8$286
This Southwest deal was found by Cheapflights users on 6/8. 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.
월 8/179:00 am
MDW
-
RSW
Nonstop2h 45m
Southwest
금 8/216:25 pm
RSW
-
MDW
1 stop4h 30m
Southwest
Deal found 6/8$287

Find 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 6월 9, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$259
(Southwest)

One-way from

$129
(Kiwi.com)

Popular in

December

Cheapest in

August

Average price

$331
Provider with most accurate pricing for Chicago (CHI)-Fort Myers SW Florida Intl flight deals.
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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. 12% potential increase in price ($41 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in June 2026
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 6월 9, 2026.
Use the filters below to find and compare flights from Illinois to Fort Myers that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

월 7/27

10:35 am-2:44 pm

Nonstop3h 09m

Fort Myers SW Florida Intl

토 8/1

7:00 am-9:23 am

Nonstop3h 23m

$295
Quickest round-trip

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

목 9/17

6:15 pm-10:00 pm

Nonstop2h 45m

Fort Myers SW Florida Intl

월 9/21

6:50 am-8:40 am

Nonstop2h 50m

$315

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

화 7/14

6:55 pm-10:45 pm

Nonstop2h 50m

Fort Myers SW Florida Intl

금 7/17

5:10 am-7:00 am

Nonstop2h 50m

$315

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

수 9/2

8:48 am-5:23 pm

1 stop7h 35m

Fort Myers SW Florida Intl

월 9/7

5:35 am-10:13 am

1 stop5h 38m

$325

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

토 10/3

4:30 pm-12:32 am

1 stop7h 02m

Fort Myers SW Florida Intl

수 10/7

6:30 pm-10:10 pm

1 stop4h 40m

$325

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

화 7/7

11:25 am-9:15 pm

2 stops8h 50m

Fort Myers SW Florida Intl

화 7/14

6:10 am-12:15 pm

2 stops7h 05m

$325

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

목 9/10

11:25 am-5:45 pm

1 stop5h 20m

Fort Myers SW Florida Intl

목 9/17

6:50 am-8:40 am

Nonstop2h 50m

$325

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

화 9/8

8:15 am-1:45 pm

1 stop4h 30m

Fort Myers SW Florida Intl

금 9/11

5:25 pm-7:15 pm

Nonstop2h 50m

$325

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

화 7/21

4:26 pm-8:34 pm

Nonstop3h 08m

Fort Myers SW Florida Intl

일 7/26

7:00 am-9:23 am

Nonstop3h 23m

$326

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

화 7/21

6:55 pm-10:45 pm

Nonstop2h 50m

Fort Myers SW Florida Intl

일 7/26

5:10 pm-7:05 pm

Nonstop2h 55m

$326

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/9

Showing 1-10 of 60 resultsSorted by cheapest first
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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, September is the cheapest month in which you can book a flight from Illinois to Fort Myers (average of $39). Flying from Illinois to Fort Myers in August is currently the most expensive (average of $493). 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 6월 9, 2026.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 6% on flights from Illinois to Fort Myers by exploring options for tickets at noon.

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 6월 9, 2026.

The most flights from USIL to RSW are scheduled on a Sunday (17 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (5 on average).

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

How far ahead should I book a flight from Illinois to Fort Myers?

The best time to book flights from Illinois to Fort Myers is 86 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

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 June 8, 2026.

Travelers seeking maximum savings on their Illinois to Fort Myers flight should consider departing on Monday evenings 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.

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 45m. 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 Frontier, with whom users have recently found tickets for as low as $29. However, be on the lookout for offers from JetBlue and American 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 (88%), United Airlines (85%), Air Canada (83%).

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

    On average you can expect to pay $298 for a flight from Illinois to Fort Myers. The cheapest flight overall is $114 while the most popular route, (Chicago O'Hare Intl - Fort Myers SW Florida Intl) is currently priced at $189.

  • 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, September is the cheapest month in which you can book a flight from Illinois to Fort Myers (average of $39). Flying from Illinois to Fort Myers in August is currently the most expensive (average of $493). 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
North Fort Myers
Lehigh Acres
Estero
Sanibel

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Top 6 airlines flying from Illinois to Fort Myers

Discover the top 6 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 6월 9, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$66Average$180FlexibilityNo cancel feeOn-time62%
DeltaCheapest$130Average$370FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$144Average$268FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$158Average$380FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$161Average$352FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$171Average$365FlexibilityNo cancel feeOn-time63%

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