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Cheap flights from Chicago (CHI) to Fort Myers (RSW) - Compare and Save

CHI — RSW
May 2 — May 91
Sat 5/2
Sat 5/9
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Fort Myers SW Florida Intl are usually found in August or September, booked 87 days in advance, depart on a Wednesday or Tuesday and return on a Friday

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 April 2, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$126
(Kiwi.com)

One-way from

$53
(Super.com)

Popular in

December

Cheapest in

August

Average price

$273
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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Highest demand for flights based on searches. 19% potential increase in price ($67 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in April 2026
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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 April 2, 2026.

This Kiwi.com deal was found by Cheapflights users on 4/1. 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.
Sun 4/197:00 am
ORD
-
RSW
Nonstop3h 21m
Multiple Airlines
Fri 4/2411:12 am
RSW
-
ORD
Nonstop3h 02m
Multiple Airlines
Deal found 4/1$126
This Super.com deal was found by Cheapflights users on 3/30. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/188:35 am
ORD
-
RSW
Nonstop3h 21m
Frontier
Thu 4/2312:17 pm
RSW
-
ORD
Nonstop3h 30m
Frontier
Deal found 3/30$127
This Kiwi.com deal was found by Cheapflights users on 3/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/197:00 am
ORD
-
RSW
Nonstop3h 21m
Frontier
Sun 4/2610:32 am
RSW
-
ORD
Nonstop3h 30m
Frontier
Deal found 3/29$128
This Kiwi.com deal was found by Cheapflights users on 3/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/136:50 am
ORD
-
RSW
Nonstop2h 47m
Multiple Airlines
Thu 4/1612:17 pm
RSW
-
ORD
Nonstop3h 30m
Multiple Airlines
Deal found 3/30$132
This Kiwi.com deal was found by Cheapflights users on 3/28. 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.
Mon 4/137:42 pm
ORD
-
RSW
Nonstop2h 48m
Multiple Airlines
Thu 4/1612:17 pm
RSW
-
ORD
Nonstop3h 30m
Multiple Airlines
Deal found 3/28$135
This Super.com deal was found by Cheapflights users on 3/28. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/167:00 am
ORD
-
RSW
Nonstop3h 21m
Frontier
Thu 4/2312:17 pm
RSW
-
ORD
Nonstop3h 30m
Frontier
Deal found 3/28$136
This Frontier deal was found by Cheapflights users on 3/29. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/167:00 am
ORD
-
RSW
Nonstop3h 21m
Frontier
Thu 4/2312:17 pm
RSW
-
ORD
Nonstop3h 30m
Frontier
Deal found 3/29$137
This Frontier deal was found by Cheapflights users on 3/29. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/188:35 am
ORD
-
RSW
Nonstop3h 21m
Frontier
Sun 4/2610:32 am
RSW
-
ORD
Nonstop3h 30m
Frontier
Deal found 3/29$138
This Frontier deal was found by Cheapflights users on 4/2. 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.
Thu 4/167:00 am
ORD
-
RSW
Nonstop3h 21m
Frontier
Thu 4/2312:17 pm
RSW
-
ORD
Nonstop3h 30m
Frontier
Deal found 4/2$139
This CheapOair deal was found by Cheapflights users on 3/30. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/136:50 am
ORD
-
RSW
Nonstop2h 47m
Multiple Airlines
Thu 4/1612:17 pm
RSW
-
ORD
Nonstop3h 30m
Multiple Airlines
Deal found 3/30$140
This Kiwi.com deal was found by Cheapflights users on 3/28. 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.
Mon 4/136:50 am
ORD
-
RSW
Nonstop2h 47m
Multiple Airlines
Sat 4/181:51 pm
RSW
-
ORD
Nonstop3h 30m
Multiple Airlines
Deal found 3/28$142
This Frontier deal was found by Cheapflights users on 3/30. 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 4/135:15 am
ORD
-
RSW
1 stop11h 35m
Frontier
Thu 4/1612:17 pm
RSW
-
ORD
Nonstop3h 30m
Frontier
Deal found 3/30$144

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 April 2, 2026.
Use the filters below to find and compare flights from Chicago to Fort Myers that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Sat 5/2

3:40 pm-7:25 pm

Nonstop2h 45m

Fort Myers SW Florida Intl

Mon 5/4

9:30 am-2:55 pm

1 stop6h 25m

$247

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Fri 5/1

10:30 am-2:25 pm

Nonstop2h 55m

Fort Myers SW Florida Intl

Mon 5/11

3:15 pm-5:30 pm

Nonstop3h 15m

$257

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Sat 5/16

6:23 am-12:21 pm

1 stop4h 58m

Fort Myers SW Florida Intl

Thu 5/21

12:40 pm-6:33 pm

1 stop6h 53m

$276

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Mon 5/4

10:30 am-2:25 pm

Nonstop2h 55m

Fort Myers SW Florida Intl

Sat 5/9

10:00 am-12:10 pm

Nonstop3h 10m

$295
Quickest round-trip

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Thu 7/9

6:55 pm-10:40 pm

Nonstop2h 45m

Fort Myers SW Florida Intl

Mon 7/13

11:40 am-1:30 pm

Nonstop2h 50m

$295

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Tue 5/5

2:10 pm-10:41 pm

1 stop7h 31m

Fort Myers SW Florida Intl

Wed 5/13

2:30 pm-4:53 pm

Nonstop3h 23m

$297

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Thu 4/23

5:15 am-1:54 pm

1 stop7h 39m

Fort Myers SW Florida Intl

Tue 4/28

5:30 am-10:09 am

1 stop5h 39m

$297

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Tue 4/28

6:00 am-1:54 pm

1 stop6h 54m

Fort Myers SW Florida Intl

Tue 5/5

8:00 am-12:43 pm

1 stop5h 43m

$297

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Sat 4/18

3:40 pm-7:25 pm

Nonstop2h 45m

Fort Myers SW Florida Intl

Sat 4/25

6:25 am-12:15 pm

2 stops6h 50m

$302

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Tue 5/5

7:50 am-3:40 pm

2 stops6h 50m

Fort Myers SW Florida Intl

Wed 5/13

7:00 am-8:55 am

Nonstop2h 55m

$306

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/28

Showing 1-10 of 48 resultsSorted by cheapest first
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5

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 April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy2 starsTrust Score*2 stars
JustAirTicketPrice Accuracy-Trust Score*1 star
Kiwi.comPrice Accuracy3 starsTrust Score*3 stars
CheapOairPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
Super.comPrice Accuracy-Trust Score*3 stars
CheapTicketsDealPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust 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.

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 March 13, 2026.

The best time to book flights from Chicago to Fort Myers is 87 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, March is the cheapest month in which you can book a flight from Chicago to Fort Myers (average of $37). Flying from Chicago to Fort Myers in November is currently the most expensive (average of $133). 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 April 2, 2026.

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 7% on your trip compared to booking a flight in the morning.

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 28, 2026.

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 April 2, 2026.

The most flights from CHI to RSW are scheduled on a Wednesday (34 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (15 on average).

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

How often are flights from Chicago to Fort Myers delayed?

About 18% of weekly flights between Chicago and Fort Myers have experienced delays in the past year, with the average delay time being 148 minutes.

What is the most punctual flight time for Chicago to Fort Myers flights?

Historically, flights departing at night are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Tuesday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on Chicago to Fort Myers flights?

Over the last year, United Airlines have had the lowest number of delays on this route, with just 13% of flights being delayed.

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 April 2, 2026.
Read reviews from past customers who have flown Southwest,United Airlines, andAmerican Airlines from Chicago to Fort Myers. 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.
Southwest
8.0
Very good
4,337 reviews

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
6.0
Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.
Southwest
8.0
Very good
4,337 reviews
Southwest
8.0
Very good
4,337 reviews

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
6.0
Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.
United Airlines
7.4
Good
9,533 reviews
Southwest
8.0
Very good
4,337 reviews

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
6.0
Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.
American Airlines
7.1
Good
11,549 reviews
Southwest
8.0
Very good
4,337 reviews

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
6.0
Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.
Spirit Airlines
6.3
Okay
8,576 reviews
Southwest
8.0
Very good
4,337 reviews

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
6.0
Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.
Frontier
5.7
Fair
3,004 reviews
Southwest
8.0
Very good
4,337 reviews

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
6.0
Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.

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 23 daily inbound flights from Chicago from 7 different airlines.

  • How long is the flight from Chicago to Fort Myers?

    Airlines like Southwest, Delta, and United Airlines fly from Chicago to Fort Myers in about 2h 45m. The time it takes to get you to your destination can typically vary by up to 4h 46m. The distance between Chicago and Fort Myers is about 1106 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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 $58. Additional round-trip tickets that might be worth considering are offered by Spirit Airlines and Delta, with the lowest prices starting at $66 and $130, respectively. These flights start at 78% 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 ($30), Spirit Airlines ($38), and American Airlines ($78).

  • 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 (83%), United Airlines (82%) or Air Canada (79%) 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 $478, our data shows the cheapest flight currently is $52. When looking at the most popular route, (Chicago O'Hare Intl - Fort Myers SW Florida Intl), you can expect to pay $96 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, March is the cheapest month in which you can book a flight from Chicago to Fort Myers (average of $37). Flying from Chicago to Fort Myers in November is currently the most expensive (average of $133). 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 Fort Myers?

Book flights to Fort Myers 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 April 2, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$58Average$174FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$66Average$182FlexibilityNo cancel feeOn-time65%
DeltaCheapest$130Average$357FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$143Average$230FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$158Average$278FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$159Average$312FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$171Average$351FlexibilityNo cancel feeOn-time63%

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