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$70+ 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 12/24. Fares are subject to change and may not be available on all flights or dates of travel.
RSW — ORD
Nov 22 — Nov 291
Sat 11/22
Sat 11/29
1 adult, Economy
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Cheap 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 October 23, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$118
(American Airlines)

One-way from

$70
(Kiwi.com)

Popular in

June

Cheapest in

September

Average price

$251
Provider with most accurate pricing for Fort Myers SW Florida Intl-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Fort Myers SW Florida Intl-Chicago (CHI) flights.
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From Fort Myers SW Florida Intl to Illinois
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One-way flight from Fort Myers SW Florida Intl to Illinois
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Highest demand for flights based on searches. 8% potential increase in price ($19 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Find 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 October 23, 2025.

This American Airlines deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/136:16 amRSW - ORD
Nonstop3h 19mAmerican Airlines
Mon 12/156:45 amORD - RSW
Nonstop2h 54mAmerican Airlines
Deal found 10/23$118
This Cheapflightsfares deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/610:59 amRSW - ORD
Nonstop3h 04mSpirit Airlines
Mon 11/104:42 pmORD - RSW
Nonstop2h 51mSpirit Airlines
Deal found 10/21$119
This Cheapflightsfares deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/610:59 amRSW - ORD
Nonstop3h 04mSpirit Airlines
Sun 11/92:11 pmORD - RSW
Nonstop2h 57mSpirit Airlines
Deal found 10/21$127
This Cheapflightsfares deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/141:39 pmRSW - ORD
Nonstop3h 08mSpirit Airlines
Mon 11/174:42 pmORD - RSW
Nonstop2h 51mSpirit Airlines
Deal found 10/22$130
This CheapOair deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/269:55 pmRSW - ORD
Nonstop3h 01mSpirit Airlines
Wed 12/314:55 pmORD - RSW
Nonstop3h 05mSpirit Airlines
Deal found 10/23$131
This American Airlines deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/146:16 amRSW - ORD
Nonstop3h 19mAmerican Airlines
Tue 12/1612:01 pmORD - RSW
Nonstop2h 55mAmerican Airlines
Deal found 10/23$132
This Trip.com deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/131:13 pmRSW - ORD
1 stop11h 58mMultiple Airlines
Thu 11/272:01 pmORD - RSW
Nonstop2h 57mMultiple Airlines
Deal found 10/22$136
This Priceline deal was found by Cheapflights users on 10/21. 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.
Thu 12/111:14 pmRSW - ORD
Nonstop3h 08mMultiple Airlines
Mon 12/156:11 amORD - RSW
1 stop9h 39mMultiple Airlines
Deal found 10/21$137
This Cheapflightsfares deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/71:39 pmRSW - ORD
Nonstop3h 08mSpirit Airlines
Sun 11/92:11 pmORD - RSW
Nonstop2h 57mSpirit Airlines
Deal found 10/23$138
This Cheapflightsfares deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/316:22 amRSW - ORD
Nonstop2h 54mSpirit Airlines
Sun 11/22:11 pmORD - RSW
Nonstop2h 57mSpirit Airlines
Deal found 10/22$143
This Trip.com deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/69:28 pmRSW - ORD
1 stop10h 58mMultiple Airlines
Mon 11/104:42 pmORD - RSW
Nonstop2h 51mMultiple Airlines
Deal found 10/22$144
This Priceline deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/85:45 pmRSW - MDW
1 stop5h 27mFrontier
Mon 12/156:15 amMDW - RSW
1 stop9h 35mFrontier
Deal found 10/23$150

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 October 23, 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 - ORD

RSWORD

Fort Myers SW Florida Intl

Wed 12/10

5:05 pm-10:56 pm

1 stop6h 51m

Chicago O'Hare Intl

Mon 12/15

9:20 am-1:26 pm

Nonstop3h 06m

$172

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Fri 11/21

9:31 am-11:34 am

Nonstop3h 03m

Chicago O'Hare Intl

Sun 11/30

2:01 pm-5:58 pm

Nonstop2h 57m

$185

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Fri 12/5

6:30 am-8:25 am

Nonstop2h 55m

Chicago Midway

Mon 12/8

8:20 am-12:10 pm

Nonstop2h 50m

$196

Fort MyersSt. Louis

RSW - STL

RSWSTL

Fort Myers SW Florida Intl

Fri 1/16

2:10 pm-8:39 pm

1 stop7h 29m

Lambert-St Louis

Mon 1/19

10:45 am-4:57 pm

1 stop5h 12m

$197

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Fri 11/14

6:50 am-8:45 am

Nonstop2h 55m

Chicago Midway

Sun 11/16

7:25 pm-11:10 pm

Nonstop2h 45m

$201

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Tue 12/9

3:14 pm-9:52 pm

1 stop7h 38m

Chicago O'Hare Intl

Tue 12/16

11:25 am-10:04 pm

1 stop9h 39m

$211

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Mon 12/8

6:00 am-8:46 am

2 stops27h 46m

Chicago Midway

Mon 12/15

6:15 am-4:50 pm

1 stop9h 35m

$211

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Tue 11/25

1:00 pm-7:50 pm

1 stop7h 50m

Chicago O'Hare Intl

Fri 11/28

1:47 pm-11:48 pm

1 stop9h 01m

$211

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Sat 12/6

7:50 am-9:45 am

Nonstop2h 55m

Chicago Midway

Sat 12/6

5:30 pm-9:15 pm

Nonstop2h 45m

$215

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Fri 12/5

4:12 pm-9:56 pm

1 stop6h 44m

Chicago O'Hare Intl

Sun 12/7

6:45 am-3:03 pm

1 stop7h 18m

$217

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/22

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 October 23, 2025.

It’s typically best to fly out from Fort Myers to Illinois in the evening. Doing so could potentially save you 15% on the flight price compared to flying in the morning, 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 16, 2024.

Travelers seeking maximum savings on their Fort Myers to Illinois flight should consider departing on Monday at noon when fares are most often at their lowest. Tuesday 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 October 23, 2025.

The most flights from RSW to USIL are scheduled on a Monday (17 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (2 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 October 23, 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
4,236 reviews

Entertainment

7.5

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

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
4,236 reviews
Southwest
8.0
Very good
4,236 reviews

Entertainment

7.5

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

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
8,995 reviews
Southwest
8.0
Very good
4,236 reviews

Entertainment

7.5

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

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
11,033 reviews
Southwest
8.0
Very good
4,236 reviews

Entertainment

7.5

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

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
8,104 reviews
Southwest
8.0
Very good
4,236 reviews

Entertainment

7.5

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

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
5.8
Fair
3,128 reviews
Southwest
8.0
Very good
4,236 reviews

Entertainment

7.5

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

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 2h 55m. The distance between Fort Myers and Illinois is about 1106 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 Southwest ($78), American Airlines ($85), and Delta ($99).

  • 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: Spirit Airlines (96%), United Airlines (92%), Air Canada( 89%).

  • 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 $654, our data indicates the cheapest price to be $78. The most popular route (Fort Myers SW Florida Intl - Chicago O'Hare Intl), is priced around $85.

  • 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

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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 October 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$46Average$129FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$68Average$156FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$159Average$341FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$159Average$308FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$179Average$379FlexibilityNo cancel feeOn-time63%
DeltaCheapest$216Average$414FlexibilityNo cancel feeOn-timeN/A

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