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$56+ Cheap flights from Chicago (CHI) to Fort Myers Beach, FL

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 3/8. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — RSW
févr. 25 — mars 41
mar. 2/25
mar. 3/4
1 adult, Economy
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The best prices from Chicago to Fort Myers Beach are usually found in January or May, booked 27 days in advance, depart on a Tuesday or Wednesday and return on a Thursday

Cheap flight deals from Chicago to Fort Myers Beach

Keep the following information in mind while searching for Chicago to Fort Myers Beach flight deals. Data was last updated février 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$110
(Kiwi.com)

One-way from

$56
(Frontier)

Popular in

March

Cheapest in

January

Average price

$293
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 Chicago (CHI) to Fort Myers Beach
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One-way flight from Chicago (CHI) to Fort Myers Beach
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Highest demand for flights based on searches. 8% potential increase in price ($25 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in February 2025
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Find flight deals from Chicago to Fort Myers Beach

Cheapest flights from Chicago to Fort Myers Beach
Explore the most affordable flight options available from Chicago to Fort Myers Beach. Find the lowest fares from popular airlines and budget airlines, with prices last updated on février 20, 2025.

This Kiwi.com deal was found by Cheapflights users on 2/20. 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.
mar. 3/117:49 pmORD - RSW
Nonstop3h 01mMultiple Airlines
lun. 3/174:28 pmRSW - ORD
Nonstop3h 19mMultiple Airlines
Deal found 2/20$110
This Cheapflightsfares deal was found by Cheapflights users on 2/20. 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.
mer. 2/2610:32 amORD - RSW
Nonstop3h 01mFrontier
mer. 3/53:53 pmRSW - ORD
Nonstop3h 20mFrontier
Deal found 2/20$113
This Kiwi.com deal was found by Cheapflights users on 2/20. 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.
lun. 3/37:00 amORD - RSW
Nonstop2h 53mSpirit Airlines
jeu. 3/64:28 pmRSW - ORD
Nonstop3h 19mSpirit Airlines
Deal found 2/20$117
This Frontier deal was found by Cheapflights users on 2/19. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dim. 4/68:00 amMDW - RSW
1 stop10h 51mFrontier
mar. 4/811:23 amRSW - MDW
1 stop9h 28mFrontier
Deal found 2/19$160
This Delta deal was found by Cheapflights users on 2/20. 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.
mar. 4/87:15 amORD - RSW
1 stop9h 17mDelta
mar. 4/156:00 pmRSW - ORD
1 stop6h 59mDelta
Deal found 2/20$217
This Delta deal was found by Cheapflights users on 2/20. 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.
mar. 4/812:48 pmMDW - RSW
1 stop4h 58mDelta
mar. 4/156:00 pmRSW - MDW
1 stop5h 26mDelta
Deal found 2/20$217
This JetBlue deal was found by Cheapflights users on 2/20. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer. 3/265:10 pmORD - RSW
1 stop6h 49mJetBlue
mar. 4/16:00 amRSW - ORD
1 stop7h 29mJetBlue
Deal found 2/20$220
This American Airlines deal was found by Cheapflights users on 2/20. 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.
mer. 4/237:07 pmORD - RSW
Nonstop2h 56mAmerican Airlines
dim. 4/276:05 amRSW - ORD
Nonstop3h 17mAmerican Airlines
Deal found 2/20$241
This Southwest deal was found by Cheapflights users on 2/20. 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.
mer. 5/71:05 pmMDW - RSW
Nonstop2h 45mSouthwest
mer. 5/76:40 pmRSW - MDW
1 stop5h 30mSouthwest
Deal found 2/20$243

Find flights from Chicago to Fort Myers Beach within your budget

Customize your flight search to find flights from Chicago to Fort Myers Beach 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 février 20, 2025.

Fly from

Chicago

Fly to

Fort Myers Beach

Route

Depart

Return

Price

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

mar. 3/11

7:49 pm-11:50 pm

Nonstop3h 01m

Fort Myers SW Florida Intl

lun. 3/17

4:28 pm-6:47 pm

Nonstop3h 19m

$110

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

lun. 3/3

10:22 am-2:23 pm

Nonstop3h 01m

Fort Myers SW Florida Intl

mar. 3/11

6:00 am-8:20 am

Nonstop3h 20m

$113

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

lun. 3/3

7:00 am-10:53 am

Nonstop2h 53m

Fort Myers SW Florida Intl

jeu. 3/6

4:28 pm-6:47 pm

Nonstop3h 19m

$117

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

dim. 4/6

8:00 am-7:51 pm

1 stop10h 51m

Fort Myers SW Florida Intl

jeu. 4/10

11:23 am-9:40 pm

1 stop11h 17m

$160

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

mar. 4/8

7:15 am-5:32 pm

1 stop9h 17m

Fort Myers SW Florida Intl

mar. 4/15

6:00 pm-11:59 pm

1 stop6h 59m

$217

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

mar. 4/8

12:48 pm-6:46 pm

1 stop4h 58m

Fort Myers SW Florida Intl

mar. 4/15

6:00 pm-10:26 pm

1 stop5h 26m

$217

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

mer. 3/26

5:10 pm-12:59 am

1 stop6h 49m

Fort Myers SW Florida Intl

mar. 4/1

6:00 am-12:29 pm

1 stop7h 29m

$220

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

mer. 4/23

7:07 pm-11:03 pm

Nonstop2h 56m

Fort Myers SW Florida Intl

dim. 4/27

6:05 am-8:22 am

Nonstop3h 17m

$241

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

mer. 5/7

1:05 pm-4:50 pm

Nonstop2h 45m

Fort Myers SW Florida Intl

mer. 5/7

6:40 pm-11:10 pm

1 stop5h 30m

$243

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

dim. 4/20

8:50 pm-12:59 am

Nonstop3h 09m

$58

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

Showing 1-10 of 22 results
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Best time to book a flight from Chicago to Fort Myers Beach

Have a flexible travel schedule? Discover the best time to fly to Fort Myers Beach from Chicago 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.

Travel insights for flights from Chicago to Fort Myers Beach

Get recent, data-driven insights about flights from Chicago to Fort Myers Beach including ideal travel times, pricing trends, and more.

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

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Fort Myers Beach. Price data was last updated on February 14, 2025.

Booking 27 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago to Fort Myers Beach. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

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

Currently, January is the cheapest month in which you can book a flight from Chicago to Fort Myers Beach (average of $205). Flying from Chicago to Fort Myers Beach in June is currently the most expensive (average of $297). 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 CHI to FM9?

Find hourly flight availability from Chicago to Fort Myers Beach. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated février 20, 2025.

When flying from Chicago to Fort Myers Beach, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

What is the cheapest day to fly from Chicago to Fort Myers Beach?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Fort Myers Beach. Price data was last updated on June 9, 2024.

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

Weekly flight availability from Chicago to Fort Myers Beach

Explore weekly flight availability from Chicago to Fort Myers Beach. 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 février 20, 2025.

The most flights from CHI to FM9 are scheduled on a Thursday (26 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (4 on average).

Rainfall in Fort Myers Beach by month

Plan your trip to Fort Myers Beach by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Fort Myers Beach ranges from 1.7 - 10.1 inches per month. June is typically the wettest month, when rainfall can reach 10.1 in. December is typically the driest time to visit Fort Myers Beach when rainfall is around 1.7 in.

Temperature in Fort Myers Beach by month

Plan your trip to Fort Myers Beach by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Fort Myers Beach, use this chart to help with planning. For those seeking warmer temperatures, August is the ideal time of year to visit, when temperatures reach an average of 84.2 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 64.4 F).

Reviews of airlines servicing Fort Myers Beach

Get insights into the airlines that provide service to Fort Myers Beach. 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 Fort Myers Beach. Reviews last updated février 20, 2025.
Read reviews from past customers who have flown Southwest, Delta and JetBlue from Chicago to Fort Myers Beach. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Crew

8.7

Food

7.1

Comfort

8.1

Boarding

8.2

Overall

8.1

Reviews

1 / 20

10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

Southwest
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Crew

8.7

Food

7.1

Comfort

8.1

Boarding

8.2

Overall

8.1

Reviews

1 / 20

10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

Delta
8.0
Very good
8,220 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Crew

8.7

Food

7.1

Comfort

8.1

Boarding

8.2

Overall

8.1

Reviews

1 / 20

10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

JetBlue
7.4
Good
3,070 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Crew

8.7

Food

7.1

Comfort

8.1

Boarding

8.2

Overall

8.1

Reviews

1 / 20

10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

United Airlines
7.4
Good
8,766 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Crew

8.7

Food

7.1

Comfort

8.1

Boarding

8.2

Overall

8.1

Reviews

1 / 20

10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Crew

8.7

Food

7.1

Comfort

8.1

Boarding

8.2

Overall

8.1

Reviews

1 / 20

10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

Related info for your journey

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

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

    To fly one-way, consider booking your trip with Frontier, which is currently one of the cheapest options available, starting at $56. Spirit Airlines flights start at $71 while deals on JetBlue start at $96 one-way.

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

    Consider Frontier (89%), Air New Zealand (88%) or Air Canada (85%) when booking your flight. These represent the most reliable airlines when flying from Chicago to Fort Myers Beach.

  • What are the cheapest flights from Chicago to Fort Myers Beach?

    On average you can expect to pay $747 for a flight from Chicago to Fort Myers Beach. The cheapest flight overall is $42 while the most popular route, (Chicago O'Hare Intl - Fort Myers SW Florida Intl) is currently priced at $77.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Chicago to Fort Myers Beach 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 Chicago to Fort Myers Beach?

    Currently, January is the cheapest month in which you can book a flight from Chicago to Fort Myers Beach (average of $205). Flying from Chicago to Fort Myers Beach in June is currently the most expensive (average of $297). 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 Chicago to Fort Myers Beach

See prices for flight routes from nearby airports that may be better suited for you.
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Top 8 airlines flying from Chicago to Fort Myers Beach

Discover the top 8 airlines that operate flights from Chicago to Fort Myers Beach. 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 février 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$37Average$119FlexibilityNo cancel feeOn-time62%
Allegiant AirCheapest$74Average$196FlexibilityNo cancel feeOn-time88%
Spirit AirlinesCheapest$74Average$191FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$95Average$383FlexibilityNo cancel feeOn-time69%
Sun Country AirCheapest$134Average$360FlexibilityNo cancel feeOn-time83%
American AirlinesCheapest$155Average$338FlexibilityNo cancel feeOn-time71%
DeltaCheapest$195Average$411FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$235Average$449FlexibilityNo cancel feeOn-time63%
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