Illinois

$113+ Cheap flights from Fort Myers (RSW) to Illinois

RSW — ORD
Dec 11 — Dec 181
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Cheap flight deals from Fort Myers to Illinois

Cheapest flights from Fort Myers to Illinois

Fri 11/206:07 pm -
Nonstop3h 18m
Sun 12/63:30 pm -
Nonstop3h 02m
Deal found 11/10$228
Sun 12/205:21 pm -
1 stop8h 05m
Thu 1/74:44 pm -
Nonstop3h 02m
Deal found 11/8$232
Sun 11/226:07 pm -
Nonstop3h 18m
Fri 11/271:16 pm -
Nonstop2h 56m
Deal found 11/7$233
Sat 11/215:48 pm -
1 stop8h 05m
Sun 12/63:30 pm -
Nonstop3h 02m
Deal found 11/10$234
Wed 12/239:57 pm -
Nonstop3h 21m
Thu 1/1410:10 pm -
1 stop11h 10m
Deal found 11/8$235
Fri 12/48:31 pm -
Nonstop3h 18m
Fri 12/119:29 pm -
1 stop12h 51m
Deal found 11/7$237
Fri 12/48:31 pm -
Nonstop3h 18m
Sun 12/63:30 pm -
Nonstop3h 02m
Deal found 11/7$238
Sat 11/215:48 pm -
1 stop8h 05m
Fri 12/43:30 pm -
Nonstop2h 56m
Deal found 11/9$239
Sun 12/68:31 pm -
Nonstop3h 21m
Sun 12/139:29 pm -
1 stop12h 51m
Deal found 11/6$240
Sat 11/216:07 pm -
Nonstop3h 18m
Thu 12/33:30 pm -
Nonstop2h 56m
Deal found 11/10$241
Fri 12/48:31 pm -
Nonstop3h 18m
Mon 12/73:30 pm -
Nonstop3h 02m
Deal found 11/7$242
Fri 11/206:07 pm -
Nonstop3h 18m
Mon 12/73:30 pm -
Nonstop3h 02m
Deal found 11/10$243

Find flight deals from Fort Myers to Illinois

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$230
(Trip.com)

One-way from

$113
(Trip.com)

Popular in

August

Cheapest in

January

Average price

$343
Provider with most accurate pricing for Fort Myers SW Florida Intl-Chicago (CHI) flight deals.
Provider most trusted by Cheapflights users for Fort Myers SW Florida Intl-Chicago (CHI) flights.
From Fort Myers SW Florida Intl to Illinois
One-way flight from Fort Myers SW Florida Intl to Illinois
Highest demand for flights based on searches. 13% potential increase in price ($49 potential increase over avg. RT price).
Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
Average for round-trip flights in November 2026

Cheapflights Fare Finder

 
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 Fort Myers SW Florida Intl - ORD Chicago O'Hare Intl

RSWORD

Fort Myers SW Florida Intl

Tue 12/29

9:00 am-10:33 am

1 stop26h 33m

Chicago O'Hare Intl

Wed 12/31

12:00 am-1:00 am

Nonstop0h 00m

$168

Fort MyersChicago

RSW Fort Myers SW Florida Intl - ORD Chicago O'Hare Intl

RSWORD

Fort Myers SW Florida Intl

Tue 12/1

8:44 pm-11:03 pm

Nonstop3h 19m

Chicago O'Hare Intl

Wed 12/31

12:00 am-1:00 am

Nonstop0h 00m

$168
Quickest round-trip

Fort MyersChicago

RSW Fort Myers SW Florida Intl - MDW Chicago Midway

RSWMDW

Fort Myers SW Florida Intl

Sat 12/19

7:20 am-9:15 am

Nonstop2h 55m

Chicago Midway

Wed 12/31

12:00 am-1:00 am

Nonstop0h 00m

$168

Fort MyersChicago

RSW Fort Myers SW Florida Intl - MDW Chicago Midway

RSWMDW

Fort Myers SW Florida Intl

Tue 12/22

6:39 am-12:10 pm

1 stop6h 31m

Chicago Midway

Wed 12/31

12:00 am-1:00 am

Nonstop0h 00m

$178

Fort MyersChicago

RSW Fort Myers SW Florida Intl - ORD Chicago O'Hare Intl

RSWORD

Fort Myers SW Florida Intl

Wed 1/6

8:15 am-4:03 pm

1 stop8h 48m

Chicago O'Hare Intl

Wed 12/31

12:00 am-1:00 am

Nonstop0h 00m

$178

Fort MyersChicago

RSW Fort Myers SW Florida Intl - MDW Chicago Midway

RSWMDW

Fort Myers SW Florida Intl

Tue 1/5

6:14 pm-10:17 pm

1 stop5h 03m

Chicago Midway

Wed 12/31

12:00 am-1:00 am

Nonstop0h 00m

$178

Fort MyersChicago

RSW Fort Myers SW Florida Intl - MDW Chicago Midway

RSWMDW

Fort Myers SW Florida Intl

Mon 12/21

6:55 am-8:55 am

Nonstop3h 00m

Chicago Midway

Wed 12/31

12:00 am-1:00 am

Nonstop0h 00m

$183

Fort MyersChicago

RSW Fort Myers SW Florida Intl - ORD Chicago O'Hare Intl

RSWORD

Fort Myers SW Florida Intl

Wed 4/7

12:15 pm-2:40 pm

Nonstop3h 25m

Chicago O'Hare Intl

Wed 12/31

12:00 am-1:00 am

Nonstop0h 00m

$188

Fort MyersChicago

RSW Fort Myers SW Florida Intl - MDW Chicago Midway

RSWMDW

Fort Myers SW Florida Intl

Thu 12/31

7:45 pm-9:45 pm

Nonstop3h 00m

Chicago Midway

Wed 12/31

12:00 am-1:00 am

Nonstop0h 00m

$188

Fort MyersChicago

RSW Fort Myers SW Florida Intl - ORD Chicago O'Hare Intl

RSWORD

Fort Myers SW Florida Intl

Thu 12/31

7:20 pm-9:45 pm

Nonstop3h 25m

Chicago O'Hare Intl

Wed 12/31

12:00 am-1:00 am

Nonstop0h 00m

$188

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/6

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

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, February is the cheapest month in which you can book a flight from Fort Myers to Illinois (average of $200). Flying from Fort Myers to Illinois in October is currently the most expensive (average of $376). 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?

It’s typically best to fly out from Fort Myers to Illinois in the evening. Doing so could potentially save you 27% on the flight price compared to flying at noon, which is usually more expensive.

Weekly flight availability from Fort Myers to Illinois

The most flights from RSW to USIL are scheduled on a Tuesday (24 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (11 on average).

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

Airfare is below average for this route at the moment.
Fort Myers to Illinois flights typically cost between $257 and $415 in January.
The cheapest round-trip price found within the last 5 days was $230 on Frontier (Jan 12-Feb 2).

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 43 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?

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

Reviews of airlines servicing Illinois

See what other customers who have flown with Southwest,United Airlines, andJetBlue 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.

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

Related info for your journey

  • 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 21m. 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 ($41), Southwest ($78), and American Airlines ($97).

  • What are the most popular routes 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: Porter Airlines (94%), SWISS (93%), Air Canada( 88%).

  • 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 $1,071, our data indicates the cheapest price to be $100. The most popular route (Fort Myers SW Florida Intl - Chicago O'Hare Intl), is priced around $230.

  • 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, February is the cheapest month in which you can book a flight from Fort Myers to Illinois (average of $200). Flying from Fort Myers to Illinois in October is currently the most expensive (average of $376). 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

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Alternative routes for Fort Myers to Illinois

Top 6 airlines flying from Fort Myers to Illinois

AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$47Average$174FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$179Average$372FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$195Average$407FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$199Average$359FlexibilityNo cancel feeOn-time63%
JetBlueCheapest$264Average$325FlexibilityNo cancel feeOn-time62%
DeltaCheapest$289Average$376FlexibilityNo cancel feeOn-timeN/A

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