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$75+ Cheap flights from Chicago (CHI) to Fort Myers (RSW)

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 5/19. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — RSW
May 6 — May 131
Tue 5/6
Tue 5/13
1 adult, Economy
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Find cheap flights from Chicago to Fort Myers with Cheapflights

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Cheapflights Tip: The best prices from Chicago to Fort Myers SW Florida Intl are usually found in January or August, booked 49 days in advance, depart on a Tuesday or Wednesday and return on a Thursday

Cheap flight deals from Chicago to Fort Myers

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Fort Myers (RSW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated May 1, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$152
(Cheapflightsfares)

One-way from

$75
(FlightHub)

Popular in

March

Cheapest in

January

Average price

$253
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 SW Florida Intl
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One-way flight from Chicago (CHI) to Fort Myers SW Florida Intl
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($34 potential increase over avg. RT price).
Search Deals
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 May 2025
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Find flight deals from Chicago to Fort Myers

Cheapest flights from Chicago to Fort Myers
Explore the most affordable flight options available from Chicago to Fort Myers. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 1, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 4/30. 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 5/3012:26 pmORD - RSW
Nonstop2h 47mSpirit Airlines
Sun 6/19:15 amRSW - ORD
Nonstop3h 16mSpirit Airlines
Deal found 4/30$152
This Mytrip deal was found by Cheapflights users on 4/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/57:48 pmORD - RSW
1 stop15h 13mMultiple Airlines
Sun 6/89:15 amRSW - ORD
Nonstop3h 16mMultiple Airlines
Deal found 4/30$181
This American Airlines deal was found by Cheapflights users on 4/30. 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 6/286:55 amORD - RSW
Nonstop2h 47mAmerican Airlines
Sat 7/54:26 pmRSW - ORD
Nonstop3h 15mAmerican Airlines
Deal found 4/30$188
This Southwest deal was found by Cheapflights users on 4/30. 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.
Tue 6/177:50 pmMDW - RSW
Nonstop2h 45mSouthwest
Tue 6/246:30 amRSW - MDW
Nonstop2h 50mSouthwest
Deal found 4/30$197
This United Airlines deal was found by Cheapflights users on 4/29. 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.
Wed 5/217:10 amORD - RSW
Nonstop3h 05mUnited Airlines
Sun 5/2512:14 pmRSW - ORD
Nonstop3h 13mUnited Airlines
Deal found 4/29$201
This Delta deal was found by Cheapflights users on 4/30. 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.
Tue 6/36:24 amORD - RSW
1 stop6h 19mDelta
Tue 6/1012:54 pmRSW - ORD
1 stop6h 55mDelta
Deal found 4/30$217
This Delta deal was found by Cheapflights users on 4/30. 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.
Wed 6/46:00 amMDW - RSW
1 stop5h 22mDelta
Wed 6/185:49 pmRSW - MDW
1 stop4h 56mDelta
Deal found 4/30$217
This JetBlue deal was found by Cheapflights users on 4/30. 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.
Wed 5/710:50 amORD - RSW
1 stop8h 13mJetBlue
Wed 5/287:00 amRSW - ORD
1 stop9h 04mJetBlue
Deal found 4/30$238
This Frontier deal was found by Cheapflights users on 4/30. 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.
Fri 5/912:15 pmMDW - RSW
1 stop8h 08mFrontier
Mon 5/1210:11 amRSW - MDW
1 stop8h 17mFrontier
Deal found 4/30$258
This Southwest deal was found by Cheapflights users on 4/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/131:30 pmORD - RSW
1 stop6h 05mSouthwest
Sat 9/207:10 amRSW - ORD
1 stop4h 35mSouthwest
Deal found 4/29$263
This Sun Country Air deal was found by Cheapflights users on 4/30. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/98:05 pmORD - RSW
1 stop17h 19mSun Country Air
Thu 5/2912:35 pmRSW - ORD
1 stop7h 34mSun Country Air
Deal found 4/30$265
This Frontier deal was found by Cheapflights users on 4/30. 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.
Mon 5/512:58 pmORD - RSW
1 stop7h 25mFrontier
Mon 5/1910:11 amRSW - ORD
1 stop9h 18mFrontier
Deal found 4/30$280

Cheapflights Fare Finder

Customize your flight search to find flights from Chicago to Fort Myers 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 1, 2025.
Use the filters below to find and compare flights from Chicago to Fort Myers that are best for you.

Fly from

Chicago

Fly to

Fort Myers

Route

Depart

Return

Price

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Fri 5/30

12:26 pm-4:13 pm

Nonstop2h 47m

Fort Myers SW Florida Intl

Sun 6/1

9:15 am-11:31 am

Nonstop3h 16m

$152

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Thu 6/5

7:48 pm-12:01 pm

1 stop15h 13m

Fort Myers SW Florida Intl

Sun 6/8

9:15 am-11:31 am

Nonstop3h 16m

$181

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Sat 6/28

6:55 am-10:42 am

Nonstop2h 47m

Fort Myers SW Florida Intl

Sat 7/5

4:26 pm-6:41 pm

Nonstop3h 15m

$188

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Tue 6/17

7:50 pm-11:35 pm

Nonstop2h 45m

Fort Myers SW Florida Intl

Tue 6/24

6:30 am-8:20 am

Nonstop2h 50m

$197

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Wed 5/21

7:10 am-11:15 am

Nonstop3h 05m

Fort Myers SW Florida Intl

Sun 5/25

12:14 pm-2:27 pm

Nonstop3h 13m

$201

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Tue 6/3

6:24 am-1:43 pm

1 stop6h 19m

Fort Myers SW Florida Intl

Tue 6/10

12:54 pm-6:49 pm

1 stop6h 55m

$217

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Wed 6/4

4:15 pm-11:37 pm

1 stop6h 22m

Fort Myers SW Florida Intl

Wed 6/11

5:49 pm-9:45 pm

1 stop4h 56m

$217

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Wed 5/7

10:50 am-8:03 pm

1 stop8h 13m

Fort Myers SW Florida Intl

Wed 5/28

7:00 am-3:04 pm

1 stop9h 04m

$238

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Fri 5/9

12:15 pm-9:23 pm

1 stop8h 08m

Fort Myers SW Florida Intl

Mon 5/12

10:11 am-5:28 pm

1 stop8h 17m

$258

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Fri 5/9

8:05 pm-2:24 pm

1 stop17h 19m

Fort Myers SW Florida Intl

Thu 5/29

12:35 pm-7:09 pm

1 stop7h 34m

$265

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

Showing 1-10 of 26 results
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Compare providers for flights from Chicago to Fort Myers

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Fort Myers in May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy3 starsTrust Score*2 stars
PricelinePrice Accuracy2 starsTrust Score*3 stars
Kiwi.comPrice Accuracy3 starsTrust Score*3 stars
FareScanPrice Accuracy-Trust Score*3 stars
CheapfaremartPrice Accuracy-Trust Score*1 star
JustAirTicketPrice Accuracy-Trust Score*3 stars
Justfly.comPrice Accuracy3 starsTrust Score*2 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago-Fort Myers flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Fort Myers flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Fort Myers flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Fort Myers flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Fort Myers flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Chicago to Fort Myers

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

Cheapflights Insights

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

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

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Fort Myers. Price data was last updated on April 25, 2025.

The best time to book flights from Chicago to Fort Myers is 49 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

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

Currently, January is the cheapest month in which you can book a flight from Chicago to Fort Myers (average of $205). Flying from Chicago to Fort Myers 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 RSW?

Find hourly flight availability from Chicago to Fort Myers. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 1, 2025.

A simple way to save on the total cost of your ticket is to fly from Chicago to Fort Myers in the morning. If you’re flexible enough to do this you can expect to save up to 16% on your trip compared to booking a flight at noon.

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

Use this chart to determine the cheapest time to fly round-trip from Chicago to Fort Myers. Price data was last updated on March 30, 2025.

Travelers seeking maximum savings on their Chicago to Fort Myers 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

Explore weekly flight availability from Chicago to Fort Myers. 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 1, 2025.

The most flights from CHI to RSW are scheduled on a Wednesday (22 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (6 on average).

Rainfall in Fort Myers by month

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

In terms of precipitation, rainfall in Fort Myers 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 when rainfall is around 1.7 in.

Temperature in Fort Myers by month

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

If weather is an important factor for your trip to Fort Myers, 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

Get insights into the airlines that provide service to Fort Myers. 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. Reviews last updated May 1, 2025.
Get a feel of what it's like to fly with Southwest, Delta and United Airlines from Chicago to Fort Myers by reading reviews from past customers. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,294 reviews

Overall

8.0

Comfort

8.0

Boarding

8.2

Food

7.1

Crew

8.6

Entertainment

7.6

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
8.0
Very good
4,294 reviews
Southwest
8.0
Very good
4,294 reviews

Overall

8.0

Comfort

8.0

Boarding

8.2

Food

7.1

Crew

8.6

Entertainment

7.6

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
7,934 reviews
Southwest
8.0
Very good
4,294 reviews

Overall

8.0

Comfort

8.0

Boarding

8.2

Food

7.1

Crew

8.6

Entertainment

7.6

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
8,696 reviews
Southwest
8.0
Very good
4,294 reviews

Overall

8.0

Comfort

8.0

Boarding

8.2

Food

7.1

Crew

8.6

Entertainment

7.6

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
7.3
Good
2,924 reviews
Southwest
8.0
Very good
4,294 reviews

Overall

8.0

Comfort

8.0

Boarding

8.2

Food

7.1

Crew

8.6

Entertainment

7.6

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
8.0
Very good
4,294 reviews

Overall

8.0

Comfort

8.0

Boarding

8.2

Food

7.1

Crew

8.6

Entertainment

7.6

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. 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 into for flights to Fort Myers from Chicago?

    Located just 10.0 mi from the city center, Fort Myers SW Florida Intl is the airport most travelers will use when flying to Fort Myers from Chicago. Booking flights from Chicago to SW Florida Intl (RSW) should be relatively easy as there are 13 daily inbound flights from Chicago from 7 different airlines.

  • What are the cheapest airlines flying from Chicago to Fort Myers round-trip?

    Flying on Spirit Airlines is currently your cheapest option to Fort Myers, with prices starting at $152. Additional round-trip tickets that might be worth considering are offered by American Airlines and Southwest, with the lowest prices starting at $188 and $197, respectively. These flights start at 48% lower than the current average price 3 months from now.

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

    The cheapest airlines for a one-way flight from Chicago to Fort Myers are Spirit Airlines ($75), American Airlines ($90), and Southwest ($90).

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

    No one likes to see their flight delayed. When booking a flight from Chicago to Fort Myers consider choosing Finnair (100%), Air New Zealand (89%) or Air Canada (85%) as they are the most reliable in getting you off to your destination on time.

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

    While on average a flight from Chicago to Fort Myers is generally $500, our data shows the cheapest flight currently is $60. When looking at the most popular route, (Chicago O'Hare Intl - Fort Myers SW Florida Intl), you can expect to pay $131 for that flight.

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

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

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

    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.

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

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

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

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Sanibel
North Fort Myers
Estero
Lehigh Acres

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Alternative routes for Chicago to Fort Myers

See prices for flight routes from nearby airports that may be better suited for you.
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Top 7 airlines flying from Chicago to Fort Myers

Discover the top 7 airlines that operate flights from Chicago to Fort Myers. 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 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$54Average$135FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$83Average$253FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$95Average$368FlexibilityNo cancel feeOn-time69%
Sun Country AirCheapest$134Average$348FlexibilityNo cancel feeOn-time83%
American AirlinesCheapest$174Average$320FlexibilityNo cancel feeOn-time71%
DeltaCheapest$216Average$372FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$235Average$478FlexibilityNo cancel feeOn-time63%

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