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Illinois

$129+ 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 10/19. Fares are subject to change and may not be available on all flights or dates of travel.
RSW — ORD
Jun 28 — Jul 51
Sun 6/28
Sun 7/5
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 May 29, 2026.

This United Airlines deal was found by Cheapflights users on 5/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/297:00 am
RSW
-
MLI
1 stop6h 37m
United Airlines
Sat 10/242:28 pm
MLI
-
RSW
1 stop5h 08m
United Airlines
Deal found 5/27$261
This Delta deal was found by Cheapflights users on 5/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/235:35 am
RSW
-
MLI
1 stop5h 37m
Delta
Sat 8/15:10 pm
MLI
-
RSW
1 stop6h 13m
Delta
Deal found 5/28$290
This United Airlines deal was found by Cheapflights users on 5/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/174:39 pm
RSW
-
ORD
Nonstop3h 21m
United Airlines
Tue 6/234:26 pm
ORD
-
RSW
Nonstop3h 08m
United Airlines
Deal found 5/27$291
This Southwest deal was found by Cheapflights users on 5/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/156:25 pm
RSW
-
MDW
Nonstop2h 50m
Southwest
Tue 7/216:55 pm
MDW
-
RSW
Nonstop2h 50m
Southwest
Deal found 5/28$291
This American Airlines deal was found by Cheapflights users on 5/28. 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.
Wed 9/211:36 am
RSW
-
ORD
Nonstop3h 23m
American Airlines
Thu 9/311:54 am
ORD
-
RSW
Nonstop2h 55m
American Airlines
Deal found 5/28$293
This Southwest deal was found by Cheapflights users on 5/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/25:10 am
RSW
-
MDW
Nonstop2h 50m
Southwest
Tue 7/76:55 pm
MDW
-
RSW
Nonstop2h 50m
Southwest
Deal found 5/28$293
This American Airlines deal was found by Cheapflights users on 5/24. 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 5/293:57 pm
RSW
-
MLI
2 stops8h 58m
American Airlines
Sat 10/244:29 pm
MLI
-
RSW
1 stop4h 36m
American Airlines
Deal found 5/24$295
This American Airlines deal was found by Cheapflights users on 5/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/116:27 am
RSW
-
ORD
Nonstop3h 18m
American Airlines
Mon 7/136:50 am
ORD
-
RSW
Nonstop2h 55m
American Airlines
Deal found 5/29$295
This Southwest deal was found by Cheapflights users on 5/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/297:10 am
RSW
-
MDW
Nonstop2h 45m
Southwest
Mon 9/79:00 am
MDW
-
RSW
Nonstop2h 45m
Southwest
Deal found 5/28$295
This American Airlines deal was found by Cheapflights users on 5/25. 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.
Thu 6/255:19 pm
RSW
-
ORD
Nonstop3h 26m
American Airlines
Mon 6/2912:35 pm
ORD
-
RSW
Nonstop2h 54m
American Airlines
Deal found 5/25$296
This Southwest deal was found by Cheapflights users on 5/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/217:20 am
RSW
-
MDW
2 stops6h 00m
Southwest
Thu 9/241:00 pm
MDW
-
RSW
2 stops6h 55m
Southwest
Deal found 5/28$298
This American Airlines deal was found by Cheapflights users on 5/25. 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.
Wed 6/2412:47 pm
RSW
-
ORD
Nonstop3h 22m
American Airlines
Wed 7/16:48 am
ORD
-
RSW
Nonstop2h 53m
American Airlines
Deal found 5/25$299

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 May 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$290
(Delta)

One-way from

$129
(Priceline)

Popular in

May

Cheapest in

August

Average price

$317
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. 18% potential increase in price ($55 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
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 May 29, 2026.
Use the filters below to find and compare flights from Fort Myers to Illinois that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Wed 7/15

4:39 pm-7:00 pm

Nonstop3h 21m

Chicago O'Hare Intl

Tue 7/21

7:05 am-11:14 am

Nonstop3h 09m

$291

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Wed 7/15

6:25 pm-8:15 pm

Nonstop2h 50m

Chicago Midway

Tue 7/21

6:55 pm-10:45 pm

Nonstop2h 50m

$291

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Wed 6/24

12:30 pm-2:55 pm

Nonstop3h 25m

Chicago O'Hare Intl

Thu 6/25

4:26 pm-8:34 pm

Nonstop3h 08m

$293
Quickest round-trip

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Thu 9/17

6:50 am-8:40 am

Nonstop2h 50m

Chicago Midway

Mon 9/21

9:00 am-12:45 pm

Nonstop2h 45m

$295

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Thu 8/6

12:28 pm-2:53 pm

Nonstop3h 25m

Chicago O'Hare Intl

Wed 8/12

10:30 am-2:36 pm

Nonstop3h 06m

$295

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Tue 6/30

4:40 pm-11:10 pm

1 stop7h 30m

Chicago Midway

Tue 7/7

6:55 pm-10:45 pm

Nonstop2h 50m

$301

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Thu 7/23

5:10 am-7:00 am

Nonstop2h 50m

Chicago Midway

Mon 7/27

10:00 am-4:05 pm

1 stop5h 05m

$305

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Fri 7/17

5:10 pm-7:05 pm

Nonstop2h 55m

Chicago Midway

Tue 7/21

6:55 pm-10:45 pm

Nonstop2h 50m

$313

Fort MyersMoline

RSW - MLI

RSWMLI

Fort Myers SW Florida Intl

Thu 7/23

5:35 am-10:12 am

1 stop5h 37m

Moline Quad-City

Thu 7/30

5:10 pm-12:23 am

1 stop6h 13m

$319

Fort MyersMoline

RSW - MLI

RSWMLI

Fort Myers SW Florida Intl

Fri 9/18

5:30 am-10:23 am

1 stop5h 53m

Moline Quad-City

Sun 9/20

6:00 am-12:07 pm

1 stop5h 07m

$319

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/27

Showing 1-10 of 60 resultsSorted by cheapest first
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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 $36). Flying from Fort Myers to Illinois in May is currently the most expensive (average of $89). 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 May 29, 2026.

It’s typically best to fly out from Fort Myers to Illinois in the evening. Doing so could potentially save you 37% on the flight price compared to flying in the afternoon, which is usually more expensive.

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 May 29, 2026.

The most flights from RSW to USIL are scheduled on a Friday (18 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (9 on average).

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

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

To ensure you get the cheapest price possible for a flight from Fort Myers to Illinois, you should look to book at least 72 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

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 May 23, 2026.

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.

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 May 29, 2026.
See what other customers who have flown with Southwest,United Airlines, andAmerican 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
4,264 reviews

Crew

8.6

Overall

8.0

Entertainment

7.5

Comfort

8.0

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,264 reviews
Southwest
8.0
Very good
4,264 reviews

Crew

8.6

Overall

8.0

Entertainment

7.5

Comfort

8.0

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
United Airlines
7.4
Good
9,764 reviews
Southwest
8.0
Very good
4,264 reviews

Crew

8.6

Overall

8.0

Entertainment

7.5

Comfort

8.0

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
American Airlines
7.1
Good
11,643 reviews
Southwest
8.0
Very good
4,264 reviews

Crew

8.6

Overall

8.0

Entertainment

7.5

Comfort

8.0

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Spirit Airlines
6.2
Okay
Southwest
8.0
Very good
4,264 reviews

Crew

8.6

Overall

8.0

Entertainment

7.5

Comfort

8.0

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Frontier
5.6
Fair
2,929 reviews
Southwest
8.0
Very good
4,264 reviews

Crew

8.6

Overall

8.0

Entertainment

7.5

Comfort

8.0

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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 50m. 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 Frontier ($41), Spirit Airlines ($43), and Southwest ($78).

  • 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: Finnair (90%), Air Canada (86%), United Airlines( 85%).

  • 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 $683, our data indicates the cheapest price to be $120. The most popular route (Fort Myers SW Florida Intl - Chicago O'Hare Intl), is priced around $291.

  • 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 $36). Flying from Fort Myers to Illinois in May is currently the most expensive (average of $89). 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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Top 7 airlines flying from Fort Myers to Illinois

Discover the top 7 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 May 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$43Average$98FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$58Average$144FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$105Average$277FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$157Average$296FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$157Average$374FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$170Average$346FlexibilityNo cancel feeOn-time63%
DeltaCheapest$273Average$441FlexibilityNo cancel feeOn-timeN/A

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