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$69+ 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 12/13. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — RSW
Nov 26 — Dec 31
Tue 11/26
Tue 12/3
1 adult, Economy
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The best prices from Chicago to Fort Myers SW Florida Intl are usually found in August 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

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 November 21, 2024.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Popular in

March

Cheapest in

August

Round-trip from

$132
(Frontier)

One-way from

$69
(FlightHub)
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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High demand for flights, 30% potential price rise
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Best time to find cheap flights, 22% potential price drop
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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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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 November 21, 2024.

This Frontier deal was found by Cheapflights users on 11/20. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/2210:14 pmORD - RSW
1 stop9h 06mFrontier
Thu 12/269:57 amRSW - ORD
Nonstop3h 15mFrontier
Deal found 11/20$132
This FlightHub deal was found by Cheapflights users on 11/21. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/138:20 amORD - RSW
Nonstop3h 03mSpirit Airlines
Mon 12/2310:45 pmRSW - ORD
Nonstop3h 02mSpirit Airlines
Deal found 11/21$133
This Priceline deal was found by Cheapflights users on 11/20. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/1810:22 pmORD - RSW
1 stop8h 58mMultiple Airlines
Sat 12/215:53 pmRSW - ORD
Nonstop3h 07mMultiple Airlines
Deal found 11/20$143
This Delta deal was found by Cheapflights users on 11/20. 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.
Wed 12/115:40 amORD - RSW
1 stop7h 36mDelta
Sat 12/145:42 pmRSW - ORD
1 stop7h 16mDelta
Deal found 11/20$216
This Delta deal was found by Cheapflights users on 11/20. 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.
Sat 12/146:00 amMDW - RSW
1 stop7h 16mDelta
Tue 12/175:25 amRSW - MDW
1 stop5h 25mDelta
Deal found 11/20$216
This JetBlue deal was found by Cheapflights users on 11/21. 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.
Thu 12/128:51 amORD - RSW
1 stop8h 22mJetBlue
Mon 12/166:10 amRSW - ORD
1 stop10h 43mJetBlue
Deal found 11/21$219
This Priceline deal was found by Cheapflights users on 11/20. 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 Priceline 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 11/20$233
This American Airlines deal was found by Cheapflights users on 11/21. 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.
Tue 12/37:00 amORD - RSW
1 stop4h 55mAmerican Airlines
Tue 12/102:20 pmRSW - ORD
Nonstop3h 18mAmerican Airlines
Deal found 11/21$279
This United Airlines deal was found by Cheapflights users on 11/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/64:00 pmORD - RSW
Nonstop3h 00mUnited Airlines
Sun 12/86:05 pmRSW - ORD
1 stop6h 15mUnited Airlines
Deal found 11/20$287
This Southwest deal was found by Cheapflights users on 11/20. 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.
Thu 12/1211:45 amMDW - RSW
Nonstop2h 45mSouthwest
Mon 12/164:40 pmRSW - MDW
1 stop6h 40mSouthwest
Deal found 11/20$287
This Mytrip deal was found by Cheapflights users on 11/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/229:09 pmMDW - RSW
2 stops21h 24mMultiple Airlines
Mon 11/257:41 pmRSW - MDW
1 stop14h 00mMultiple Airlines
Deal found 11/20$446

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 2,629,791 searches. Data last updated November 21, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Sun 12/22

10:14 pm-8:20 am

1 stop9h 06m

Fort Myers SW Florida Intl

Thu 12/26

9:57 am-12:12 pm

Nonstop3h 15m

$132

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Fri 12/13

8:20 am-12:23 pm

Nonstop3h 03m

Fort Myers SW Florida Intl

Mon 12/23

10:45 pm-12:47 am

Nonstop3h 02m

$133

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Thu 1/16

7:35 am-11:36 am

Nonstop3h 01m

Fort Myers SW Florida Intl

Mon 1/20

7:30 am-9:39 am

Nonstop3h 09m

$138

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Sat 2/22

6:40 am-3:46 pm

1 stop8h 06m

Fort Myers SW Florida Intl

Sat 3/1

4:46 pm-12:17 am

1 stop8h 31m

$140

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Sun 1/12

7:00 pm-10:50 pm

Nonstop2h 50m

Fort Myers SW Florida Intl

Sat 1/18

11:15 am-1:20 pm

Nonstop3h 05m

$164

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Tue 2/11

7:15 am-11:21 am

Nonstop3h 06m

Fort Myers SW Florida Intl

Thu 2/27

6:20 pm-11:29 pm

1 stop6h 09m

$187

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Thu 1/23

11:00 am-10:40 pm

1 stop10h 40m

Fort Myers SW Florida Intl

Mon 1/27

6:04 am-3:44 pm

1 stop10h 40m

$190

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Sat 1/11

6:55 am-1:51 pm

1 stop5h 56m

Fort Myers SW Florida Intl

Tue 1/14

3:14 pm-6:49 pm

1 stop4h 35m

$216

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Wed 1/8

2:08 pm-9:18 pm

1 stop6h 10m

Fort Myers SW Florida Intl

Thu 1/23

8:15 am-11:59 am

1 stop4h 44m

$216

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Thu 12/12

12:44 pm-4:36 pm

Nonstop2h 52m

Fort Myers SW Florida Intl

Mon 12/16

1:45 pm-7:28 pm

1 stop6h 43m

$234

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/20

Showing 1-10 of 27 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 November.
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
CheapOairPrice Accuracy2 starsTrust Score*3 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 November 15, 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 $204). Flying from Chicago to Fort Myers in March is currently the most expensive (average of $283). 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 November 21, 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 26% 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 November 18, 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 November 21, 2024.

The most flights from CHI to RSW are scheduled on a Wednesday (20 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (10 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 November 21, 2024.
Get a feel of what it's like to fly with Frontier, Spirit Airlines and Southwest 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
5,015 reviews

Entertainment

7.7

Boarding

8.2

Crew

8.7

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
5,015 reviews
Southwest
8.1
Very good
5,015 reviews

Entertainment

7.7

Boarding

8.2

Crew

8.7

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
8,758 reviews
Southwest
8.1
Very good
5,015 reviews

Entertainment

7.7

Boarding

8.2

Crew

8.7

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.

Porter Airlines
7.8
Good
286 reviews
Southwest
8.1
Very good
5,015 reviews

Entertainment

7.7

Boarding

8.2

Crew

8.7

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
5,015 reviews

Entertainment

7.7

Boarding

8.2

Crew

8.7

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
7.5
Good
3,396 reviews
Southwest
8.1
Very good
5,015 reviews

Entertainment

7.7

Boarding

8.2

Crew

8.7

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 15 daily inbound flights from Chicago from 7 different airlines.

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

    Flying on Frontier is currently your cheapest option to Fort Myers, with prices starting at $132. Additional round-trip tickets that might be worth considering are offered by Spirit Airlines and Southwest, with the lowest prices starting at $134 and $164, respectively. These flights start at 54% 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 ($69), Frontier ($73), and Southwest ($79).

  • 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 (90%), Air Canada (88%) or Spirit Airlines (86%) 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 $696, our data shows the cheapest flight currently is $53. When looking at the most popular route, (Chicago O'Hare Intl - Fort Myers SW Florida Intl), you can expect to pay $98 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 $204). Flying from Chicago to Fort Myers in March is currently the most expensive (average of $283). 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 2,629,791 searches. Data last updated November 21, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$62Average$280FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$63Average$231FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$95Average$364FlexibilityNo cancel feeOn-time69%
Sun Country AirCheapest$120Average$348FlexibilityNo cancel feeOn-time83%
DeltaCheapest$144Average$407FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$159Average$323FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$230Average$468FlexibilityNo cancel feeOn-time63%
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