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$63+ 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 3/3. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — RSW
Dec 23 — Dec 301
Mon 12/23
Mon 12/30
1 adult, Economy
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The best prices from Chicago to Fort Myers SW Florida Intl are usually found in August or April, booked 27 days in advance, depart on a Tuesday or Wednesday and return on a Saturday

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 December 18, 2024.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$114
(Cheapflightsfares)

One-way from

$63
(Kiwi.com)

Popular in

March

Cheapest in

August

Average price

$405
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
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High demand for flights, 4% potential price rise
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Best time to find cheap flights, 3% potential price drop
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Average for round-trip flights in December 2024
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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 December 18, 2024.

This Cheapflightsfares deal was found by Cheapflights users on 12/16. 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 12/195:05 amORD - RSW
Nonstop3h 02mMultiple Airlines
Tue 1/710:45 pmRSW - ORD
Nonstop3h 02mMultiple Airlines
Deal found 12/16$144
This Cheapflightsfares deal was found by Cheapflights users on 12/16. 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 12/195:05 amORD - RSW
Nonstop3h 02mFrontier
Tue 12/249:32 pmRSW - ORD
Nonstop3h 25mFrontier
Deal found 12/16$184
This Cheapflightsfares deal was found by Cheapflights users on 12/17. 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 12/196:05 amORD - RSW
Nonstop2h 59mSpirit Airlines
Thu 12/2610:45 pmRSW - ORD
Nonstop3h 02mSpirit Airlines
Deal found 12/17$199
This Frontier deal was found by Cheapflights users on 12/18. 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 12/309:59 pmMDW - RSW
1 stop9h 21mFrontier
Sat 1/410:21 pmRSW - MDW
1 stop9h 18mFrontier
Deal found 12/18$281
This Delta deal was found by Cheapflights users on 12/17. 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 12/245:51 pmMDW - RSW
1 stop5h 31mDelta
Sat 1/115:40 amRSW - MDW
1 stop5h 32mDelta
Deal found 12/17$301
This JetBlue deal was found by Cheapflights users on 12/17. 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.
Tue 12/248:42 amORD - RSW
1 stop9h 15mJetBlue
Wed 1/810:40 amRSW - ORD
1 stop8h 19mJetBlue
Deal found 12/17$341
This Cheapflightsfares deal was found by Cheapflights users on 12/18. 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.
Tue 12/2410:00 amORD - RSW
1 stop8h 12mSun Country Air
Tue 12/319:45 amRSW - ORD
1 stop8h 53mSun Country Air
Deal found 12/18$343
This Delta deal was found by Cheapflights users on 12/17. 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 12/245:57 pmORD - RSW
1 stop5h 24mDelta
Tue 1/78:00 amRSW - ORD
1 stop5h 55mDelta
Deal found 12/17$347
This Southwest deal was found by Cheapflights users on 12/17. 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 12/245:45 amORD - RSW
2 stops15h 05mSouthwest
Tue 1/76:35 amRSW - ORD
2 stops11h 10mSouthwest
Deal found 12/17$411
This Southwest deal was found by Cheapflights users on 12/17. 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 12/242:50 pmMDW - RSW
1 stop5h 05mSouthwest
Tue 12/317:15 amRSW - MDW
Nonstop2h 55mSouthwest
Deal found 12/17$417
This Mytrip deal was found by Cheapflights users on 12/18. 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 12/266:51 pmMDW - RSW
1 stop15h 04mMultiple Airlines
Mon 12/306:56 pmRSW - MDW
1 stop14h 53mMultiple Airlines
Deal found 12/18$462
This Mytrip deal was found by Cheapflights users on 12/17. 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 12/196:51 pmMDW - RSW
1 stop15h 53mAvelo Airlines
Mon 12/236:56 pmRSW - MDW
1 stop14h 53mAvelo Airlines
Deal found 12/17$677

Find flights from Chicago to Fort Myers within your budget

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 December 18, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Fri 1/10

5:35 am-9:29 am

Nonstop2h 54m

Fort Myers SW Florida Intl

Sun 1/12

10:21 pm-12:46 am

Nonstop3h 25m

$117

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Thu 1/16

5:35 am-9:29 am

Nonstop2h 54m

Fort Myers SW Florida Intl

Sun 1/26

7:30 am-9:39 am

Nonstop3h 09m

$120

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Sat 2/1

10:00 am-2:01 pm

Nonstop3h 01m

Fort Myers SW Florida Intl

Sat 2/15

8:16 pm-10:36 pm

Nonstop3h 20m

$124

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Thu 1/2

7:34 am-9:39 pm

1 stop13h 05m

Fort Myers SW Florida Intl

Sat 1/4

10:21 pm-6:39 am

1 stop9h 18m

$152

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Sat 2/22

6:00 am-9:59 am

Nonstop2h 59m

Fort Myers SW Florida Intl

Wed 2/26

11:01 am-4:56 pm

1 stop6h 55m

$162

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Sun 2/16

8:15 pm-12:05 am

Nonstop2h 50m

Fort Myers SW Florida Intl

Thu 2/20

8:50 pm-10:45 pm

Nonstop2h 55m

$170

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Sun 1/19

8:05 am-12:02 pm

Nonstop2h 57m

Fort Myers SW Florida Intl

Thu 1/23

7:51 am-12:30 pm

1 stop5h 39m

$189

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Sat 1/11

9:55 am-9:58 pm

1 stop11h 03m

Fort Myers SW Florida Intl

Tue 1/14

12:00 pm-5:53 pm

1 stop6h 53m

$190

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Fri 1/31

11:05 am-5:05 pm

1 stop5h 00m

Fort Myers SW Florida Intl

Mon 2/3

11:51 am-5:47 pm

1 stop6h 56m

$216

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Wed 1/8

10:57 am-5:05 pm

1 stop5h 08m

Fort Myers SW Florida Intl

Wed 1/15

6:10 pm-10:20 pm

1 stop5h 10m

$216

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/17

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 December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy3 starsTrust Score*1 star
FareScanPrice Accuracy3 starsTrust Score*1 star
PricelinePrice Accuracy1 starTrust Score*3 stars
Kiwi.comPrice Accuracy3 starsTrust Score*3 stars
CheapOairPrice Accuracy2 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 FlightHub the most. FlightHub 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.

Travel insights for flights from Chicago to Fort Myers

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

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 December 13, 2024.

The best time to book flights from Chicago to Fort Myers is 27 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 March is currently the most expensive (average of $284). 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 December 18, 2024.

A simple way to save on the total cost of your ticket is to fly from Chicago to Fort Myers in the evening. If you’re flexible enough to do this you can expect to save up to 28% 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 December 16, 2024.

Travelers seeking maximum savings on their Chicago to Fort Myers flight should consider departing on Monday evenings when fares are most often at their lowest. Sunday at noon 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 December 18, 2024.

The most flights from CHI to RSW are scheduled on a Wednesday (21 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (2 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 December 18, 2024.
Get a feel of what it's like to fly with Frontier, Delta and American 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
8.1
Very good
4,848 reviews

Crew

8.7

Entertainment

7.7

Boarding

8.2

Comfort

8.1

Food

7.2

Overall

8.1

Reviews

1 / 10

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
4,848 reviews
Southwest
8.1
Very good
4,848 reviews

Crew

8.7

Entertainment

7.7

Boarding

8.2

Comfort

8.1

Food

7.2

Overall

8.1

Reviews

1 / 10

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
8,604 reviews
Southwest
8.1
Very good
4,848 reviews

Crew

8.7

Entertainment

7.7

Boarding

8.2

Comfort

8.1

Food

7.2

Overall

8.1

Reviews

1 / 10

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.

Avelo Airlines
7.5
Good
74 reviews
Southwest
8.1
Very good
4,848 reviews

Crew

8.7

Entertainment

7.7

Boarding

8.2

Comfort

8.1

Food

7.2

Overall

8.1

Reviews

1 / 10

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
3,279 reviews
Southwest
8.1
Very good
4,848 reviews

Crew

8.7

Entertainment

7.7

Boarding

8.2

Comfort

8.1

Food

7.2

Overall

8.1

Reviews

1 / 10

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
9,059 reviews
Southwest
8.1
Very good
4,848 reviews

Crew

8.7

Entertainment

7.7

Boarding

8.2

Comfort

8.1

Food

7.2

Overall

8.1

Reviews

1 / 10

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 9 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 $114. Additional round-trip tickets that might be worth considering are offered by Frontier and United Airlines, with the lowest prices starting at $132 and $162, respectively. These flights start at 61% 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 Frontier ($63), Southwest ($79), and Spirit Airlines ($82).

  • 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 Air New Zealand (93%), Air Canada (91%) or Spirit Airlines (89%) 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 $735, our data shows the cheapest flight currently is $56. When looking at the most popular route, (Chicago O'Hare Intl - Fort Myers SW Florida Intl), you can expect to pay $68 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 March is currently the most expensive (average of $284). 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

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 December 18, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$59Average$172FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$65Average$233FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$95Average$361FlexibilityNo cancel feeOn-time69%
Sun Country AirCheapest$120Average$348FlexibilityNo cancel feeOn-time83%
DeltaCheapest$144Average$407FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$158Average$324FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$235Average$445FlexibilityNo cancel feeOn-time63%
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