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$66+ Cheap flights from Fort Myers (RSW) to Illinois

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/17. Fares are subject to change and may not be available on all flights or dates of travel.
RSW — ORD
Jan 29 — Feb 51
Thu 1/29
Thu 2/5
1 adult, Economy
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Cheap flight deals from Fort Myers to Illinois

Cheapest flights from Fort Myers to Illinois
Explore the most affordable flight options available from Fort Myers to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 30, 2025.

This Priceline deal was found by Cheapflights users on 12/29. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/306:15 amRSW - ORD
Nonstop3h 09mSpirit Airlines
Mon 2/27:21 pmORD - RSW
Nonstop3h 03mSpirit Airlines
Deal found 12/29$228
This Super.com deal was found by Cheapflights users on 12/29. 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.
Tue 12/309:55 pmRSW - ORD
Nonstop3h 01mSpirit Airlines
Tue 1/69:19 amORD - RSW
Nonstop3h 10mSpirit Airlines
Deal found 12/29$283
This Priceline deal was found by Cheapflights users on 12/28. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/299:55 pmRSW - ORD
Nonstop3h 01mSpirit Airlines
Mon 1/54:55 pmORD - RSW
Nonstop3h 05mSpirit Airlines
Deal found 12/28$285
This Kiwi.com deal was found by Cheapflights users on 12/27. 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.
Tue 12/309:55 pmRSW - ORD
Nonstop3h 01mSpirit Airlines
Sat 1/34:55 pmORD - RSW
Nonstop3h 05mSpirit Airlines
Deal found 12/27$292
This Kiwi.com deal was found by Cheapflights users on 12/28. 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 12/296:15 amRSW - ORD
Nonstop3h 09mSpirit Airlines
Wed 1/74:55 pmORD - RSW
Nonstop3h 05mSpirit Airlines
Deal found 12/28$302
This CheapOair deal was found by Cheapflights users on 12/28. 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.
Tue 12/306:15 amRSW - ORD
Nonstop3h 09mSpirit Airlines
Sun 1/44:55 pmORD - RSW
Nonstop3h 05mSpirit Airlines
Deal found 12/28$311
This Kiwi.com deal was found by Cheapflights users on 12/29. 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 12/306:15 amRSW - ORD
Nonstop3h 09mMultiple Airlines
Mon 2/28:43 pmORD - RSW
2 stops37h 03mMultiple Airlines
Deal found 12/29$328
This Kiwi.com deal was found by Cheapflights users on 12/27. 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.
Tue 12/306:15 amRSW - ORD
Nonstop3h 09mSpirit Airlines
Fri 1/24:55 pmORD - RSW
Nonstop3h 05mSpirit Airlines
Deal found 12/27$329
This Priceline deal was found by Cheapflights users on 12/29. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/309:55 pmRSW - ORD
Nonstop3h 01mMultiple Airlines
Tue 1/69:35 amORD - RSW
1 stop7h 55mMultiple Airlines
Deal found 12/29$342
This Super.com deal was found by Cheapflights users on 12/29. 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.
Wed 12/319:55 pmRSW - ORD
Nonstop3h 01mSpirit Airlines
Sun 1/44:55 pmORD - RSW
Nonstop3h 05mSpirit Airlines
Deal found 12/29$343
This American Airlines deal was found by Cheapflights users on 12/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/301:51 pmRSW - STL
1 stop6h 39mAmerican Airlines
Sat 1/36:02 amSTL - RSW
1 stop5h 55mAmerican Airlines
Deal found 12/28$351
This United Airlines deal was found by Cheapflights users on 12/29. 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 12/304:27 pmRSW - MLI
1 stop5h 54mUnited Airlines
Sun 1/46:30 amMLI - RSW
1 stop7h 14mUnited Airlines
Deal found 12/29$419

Find flight deals from Fort Myers to Illinois

Keep the following information in mind while searching for Fort Myers to Illinois flight deals. Data was last updated December 30, 2025.

Most accurate provider

Justfly.com
3 stars

Most trusted provider

Justfly.com
3 stars

Round-trip from

$85
(Priceline)

One-way from

$66
(Southwest)

Popular in

December

Cheapest in

September

Average price

$282
Provider with most accurate pricing for Fort Myers SW Florida Intl-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Fort Myers SW Florida Intl-Chicago (CHI) flights.
Search Deals
From Fort Myers SW Florida Intl to Illinois
Search Deals
One-way flight from Fort Myers SW Florida Intl to Illinois
Search Deals
Highest demand for flights based on searches. 1% potential increase in price ($3 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Fort Myers to Illinois that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 30, 2025.
Use the filters below to find and compare flights from Fort Myers to Illinois that are best for you.

Fly from

Fort Myers

Fly to

Illinois

Route

Depart

Return

Price

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Sat 1/17

12:20 pm-4:40 pm

1 stop5h 20m

Chicago Midway

Sun 1/18

5:45 pm-9:30 pm

Nonstop2h 45m

$163

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Thu 2/26

6:00 am-11:54 am

1 stop6h 54m

Chicago O'Hare Intl

Sat 2/28

12:59 pm-11:52 pm

1 stop9h 53m

$181

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Thu 1/22

7:25 am-9:20 am

Nonstop2h 55m

Chicago Midway

Mon 1/26

5:45 pm-9:30 pm

Nonstop2h 45m

$199

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Thu 1/15

2:35 pm-4:58 pm

Nonstop3h 23m

Chicago O'Hare Intl

Tue 1/20

10:39 am-2:53 pm

Nonstop3h 14m

$213

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Fri 1/16

8:00 pm-10:00 pm

Nonstop3h 00m

Chicago Midway

Sun 1/18

5:45 pm-9:30 pm

Nonstop2h 45m

$213

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Tue 1/27

7:25 am-9:20 am

Nonstop2h 55m

Chicago Midway

Tue 2/3

1:40 pm-5:25 pm

Nonstop2h 45m

$213

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Fri 2/6

6:02 pm-10:22 pm

1 stop5h 20m

Chicago Midway

Sun 2/8

1:26 pm-9:39 pm

1 stop7h 13m

$217

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Sat 1/31

10:10 am-7:36 pm

1 stop10h 26m

Chicago O'Hare Intl

Sun 2/1

9:15 am-6:30 pm

1 stop8h 15m

$217

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Thu 1/22

7:25 am-9:20 am

Nonstop2h 55m

Chicago Midway

Sat 1/24

6:05 pm-9:50 pm

Nonstop2h 45m

$218

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Thu 1/22

6:02 pm-10:22 pm

1 stop5h 20m

Chicago Midway

Mon 1/26

12:48 pm-6:42 pm

1 stop4h 54m

$219

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/28

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

Have a flexible travel schedule? Discover the best time to fly to Illinois from Fort Myers with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Fort Myers to Illinois

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

Currently, January is the cheapest month in which you can book a flight from Fort Myers to Illinois (average of $31). Flying from Fort Myers to Illinois in June is currently the most expensive (average of $115). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from RSW to IL?

Find hourly flight availability from Fort Myers to Illinois. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 30, 2025.

It’s typically best to fly out from Fort Myers to Illinois in the evening. Doing so could potentially save you 21% on the flight price compared to flying in the afternoon, which is usually more expensive.

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

Use this chart to determine the cheapest time to fly round-trip from Fort Myers to Illinois. Price data was last updated on December 27, 2025.

Travelers seeking maximum savings on their Fort Myers to Illinois flight should consider departing on Thursday evenings when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Fort Myers to Illinois

Explore weekly flight availability from Fort Myers to Illinois. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated December 30, 2025.

The most flights from RSW to USIL are scheduled on a Tuesday (28 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (16 on average).

Reviews of airlines servicing Illinois

Get insights into the airlines that provide service to Illinois. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Illinois. Reviews last updated December 30, 2025.
See what other customers who have flown with Southwest, United Airlines, and American Airlines from Fort Myers to Illinois have to say. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,251 reviews

Boarding

8.1

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Southwest
8.0
Very good
4,251 reviews
Southwest
8.0
Very good
4,251 reviews

Boarding

8.1

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
United Airlines
7.4
Good
9,124 reviews
Southwest
8.0
Very good
4,251 reviews

Boarding

8.1

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
American Airlines
7.2
Good
11,074 reviews
Southwest
8.0
Very good
4,251 reviews

Boarding

8.1

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Spirit Airlines
6.3
Okay
8,243 reviews
Southwest
8.0
Very good
4,251 reviews

Boarding

8.1

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Frontier
5.7
Fair
3,069 reviews
Southwest
8.0
Very good
4,251 reviews

Boarding

8.1

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Related info for your journey

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

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

    For a flight from Fort Myers to Illinois, you will be flying from SW Florida Intl. Fort Myers SW Florida Intl (RSW) is just 10.0 mi from the center of the city.

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

    Departing from Fort Myers to Illinois will take you 3h 23m. The distance between Fort Myers and Illinois is about 1122 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    The cheapest airlines for a one-way flight from Fort Myers to Illinois are Frontier ($29), Spirit Airlines ($40), and American Airlines ($79).

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

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

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

    Before booking your flight to Illinois from Fort Myers, check out the most reliable airlines to get you to your destination on time: United Airlines (82%), Spirit Airlines (81%), Emirates( 75%).

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

    Looking for the cheapest flight from Fort Myers to Illinois? While on average our users pay $441, our data indicates the cheapest price to be $55. The most popular route (Fort Myers SW Florida Intl - Chicago O'Hare Intl), is priced around $59.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Fort Myers to Illinois 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 Fort Myers to Illinois?

    Currently, January is the cheapest month in which you can book a flight from Fort Myers to Illinois (average of $31). Flying from Fort Myers to Illinois in June is currently the most expensive (average of $115). 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.

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Alternative routes for Fort Myers to Illinois

See prices for flight routes from nearby airports that may be better suited for you.
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Top 6 airlines flying from Fort Myers to Illinois

Discover the top 6 airlines that operate flights from Fort Myers to Illinois. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$46Average$134FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$61Average$157FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$158Average$336FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$158Average$303FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$179Average$373FlexibilityNo cancel feeOn-time63%
DeltaCheapest$216Average$397FlexibilityNo cancel feeOn-timeN/A

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