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Fort Myers

$118+ Cheap flights from O'Hare Intl (ORD) 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 8/11. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — RSW
Jun 13 — Jun 201
Sat 6/13
Sat 6/20
1 adult, Economy
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1. Tell us where you want to go

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2. Select your favorite providers

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Cheapflights Tip: The best prices from Chicago O'Hare Intl to Fort Myers SW Florida Intl are usually found in September or August, booked 41 days in advance, depart on a Wednesday or Tuesday and return on a Friday

Cheap flight deals from O'Hare Intl to Fort Myers

Cheapest flights from O'Hare Intl to Fort Myers
Explore the most affordable flight options available from O'Hare Intl to Fort Myers. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 14, 2026.

This United Airlines deal was found by Cheapflights users on 5/13. 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 6/104:26 pm
ORD
-
RSW
Nonstop3h 08m
United Airlines
Tue 6/167:00 am
RSW
-
ORD
Nonstop3h 23m
United Airlines
Deal found 5/13$291
This American Airlines deal was found by Cheapflights users on 5/12. 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.
Wed 7/112:35 pm
ORD
-
RSW
Nonstop2h 54m
American Airlines
Wed 7/85:24 pm
RSW
-
ORD
Nonstop3h 30m
American Airlines
Deal found 5/12$292
This United Airlines deal was found by Cheapflights users on 5/11. 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 7/157:05 am
ORD
-
RSW
Nonstop3h 09m
United Airlines
Sat 7/257:00 am
RSW
-
ORD
Nonstop3h 23m
United Airlines
Deal found 5/11$293
This American Airlines deal was found by Cheapflights users on 5/14. 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 6/137:52 pm
ORD
-
RSW
Nonstop2h 58m
American Airlines
Sat 6/206:15 am
RSW
-
ORD
Nonstop3h 22m
American Airlines
Deal found 5/14$294
This United Airlines deal was found by Cheapflights users on 5/13. 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.
Sat 6/277:05 am
ORD
-
RSW
Nonstop3h 09m
United Airlines
Sat 7/47:00 am
RSW
-
ORD
Nonstop3h 23m
United Airlines
Deal found 5/13$295
This Kiwi.com deal was found by Cheapflights users on 5/13. 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.
Tue 8/111:50 pm
ORD
-
RSW
2 stops19h 23m
Multiple Airlines
Thu 8/2011:43 am
RSW
-
ORD
1 stop25h 40m
Multiple Airlines
Deal found 5/13$300
This American Airlines deal was found by Cheapflights users on 5/13. 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.
Wed 6/108:00 am
ORD
-
RSW
1 stop6h 06m
American Airlines
Wed 7/812:47 pm
RSW
-
ORD
Nonstop3h 18m
American Airlines
Deal found 5/13$301
This United Airlines deal was found by Cheapflights users on 5/14. 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 7/1510:35 am
ORD
-
RSW
Nonstop3h 09m
United Airlines
Mon 7/2012:59 pm
RSW
-
ORD
1 stop6h 45m
United Airlines
Deal found 5/14$303
This United Airlines deal was found by Cheapflights users on 5/10. 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.
Sat 6/277:05 am
ORD
-
RSW
Nonstop3h 09m
United Airlines
Thu 7/212:59 pm
RSW
-
ORD
1 stop6h 45m
United Airlines
Deal found 5/10$305
This Mytrip deal was found by Cheapflights users on 5/9. 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 6/57:07 pm
ORD
-
RSW
1 stop14h 59m
Multiple Airlines
Sun 8/1611:49 am
RSW
-
ORD
1 stop6h 40m
Multiple Airlines
Deal found 5/9$308

Find flight deals from O'Hare Intl to Fort Myers

Discover tips and strategies to find the most affordable flight options for your journey from O'Hare Intl (ORD) 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 14, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$291
(American Airlines)

One-way from

$118
(Kiwi.com)

Popular in

March

Cheapest in

September

Average price

$326
Provider with most accurate pricing for Chicago O'Hare Intl-Fort Myers SW Florida Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago O'Hare Intl-Fort Myers SW Florida Intl flights.
Search Deals
From Chicago O'Hare Intl to Fort Myers SW Florida Intl
Search Deals
One-way flight from Chicago O'Hare Intl to Fort Myers SW Florida Intl
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($24 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from O'Hare Intl 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 14, 2026.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Fort Myers that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Tue 8/11

1:48 pm-9:18 pm

1 stop6h 30m

Fort Myers SW Florida Intl

Tue 8/18

8:04 am-12:36 pm

1 stop5h 32m

$311

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Tue 6/30

6:22 pm-1:02 am

1 stop5h 40m

Fort Myers SW Florida Intl

Thu 7/9

1:16 pm-6:45 pm

1 stop6h 29m

$313

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Fri 6/12

6:22 pm-1:01 am

1 stop5h 39m

Fort Myers SW Florida Intl

Mon 6/15

5:37 am-10:13 am

1 stop5h 36m

$335

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Tue 6/2

4:26 pm-8:34 pm

Nonstop3h 08m

Fort Myers SW Florida Intl

Tue 6/9

12:30 pm-2:55 pm

Nonstop3h 25m

$344
Quickest round-trip

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Fri 7/31

4:26 pm-8:34 pm

Nonstop3h 08m

Fort Myers SW Florida Intl

Sun 8/9

7:00 am-9:23 am

Nonstop3h 23m

$346

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Thu 7/30

8:03 am-4:44 pm

1 stop7h 41m

Fort Myers SW Florida Intl

Sun 8/2

8:03 am-2:27 pm

1 stop7h 24m

$346

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Thu 8/6

3:31 pm-9:18 pm

1 stop4h 47m

Fort Myers SW Florida Intl

Sun 8/9

5:23 am-10:09 am

1 stop5h 46m

$346

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Thu 6/11

10:35 am-2:44 pm

Nonstop3h 09m

Fort Myers SW Florida Intl

Mon 6/15

7:00 am-9:23 am

Nonstop3h 23m

$387

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Wed 6/17

8:08 am-2:45 pm

1 stop5h 37m

Fort Myers SW Florida Intl

Sun 6/21

5:37 am-10:13 am

1 stop5h 36m

$395

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Wed 6/3

2:05 pm-9:59 pm

1 stop6h 54m

Fort Myers SW Florida Intl

Wed 6/10

6:02 am-12:06 pm

1 stop7h 04m

$401

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/11

Showing 1-10 of 23 resultsSorted by cheapest first
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2
3

Compare providers for flights from O'Hare Intl 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 O'Hare Intl to Fort Myers in May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy2 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy2 starsTrust Score*1 star
JustAirTicketPrice Accuracy-Trust Score*1 star
Super.comPrice Accuracy-Trust Score*3 stars
CheapfaremartPrice Accuracy-Trust Score*1 star
CheapOairPrice Accuracy3 starsTrust Score*3 stars
CheapTicketsDealPrice Accuracy1 starTrust Score*3 stars
Trip.comPrice 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 O'Hare Intl Airport-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 O'Hare Intl Airport-Fort Myers flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago O'Hare Intl Airport-Fort Myers flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago O'Hare Intl Airport-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 O'Hare Intl Airport-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 O'Hare Intl to Fort Myers

Have a flexible travel schedule? Discover the best time to fly to Fort Myers from O'Hare Intl 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 O'Hare Intl Airport to Fort Myers

How far ahead should I book a flight from Chicago O'Hare Intl Airport to Fort Myers?

The price you pay for your flight from Chicago O'Hare Intl Airport to Fort Myers may vary depending on when you book. For the best chance of a lower fare, look to book 40 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to Fort Myers?

Currently, September is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Fort Myers (average of $183). Flying from Chicago O'Hare Intl Airport to Fort Myers in March is currently the most expensive (average of $359). 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 ORD to RSW?

Find hourly flight availability from O'Hare Intl 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 14, 2026.

A simple way to save on the total cost of your ticket is to fly from Chicago O'Hare Intl Airport to Fort Myers in the afternoon. If you’re flexible enough to do this you can expect to save up to 10% on your trip compared to booking a flight at noon.

What is the cheapest day to fly from Chicago O'Hare Intl Airport to Fort Myers?

Use this chart to determine the cheapest time to fly round-trip from O'Hare Intl to Fort Myers. Price data was last updated on May 9, 2026.

Travelers seeking maximum savings on their Chicago O'Hare Intl Airport to Fort Myers flight should consider departing on Wednesday 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.

How much does it cost to fly round-trip from Chicago O'Hare Intl Airport to Fort Myers?

The best insider tips for Chicago O'Hare Intl Airport to Fort Myers flights

AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Chicago O'Hare Intl Airport to Fort Myers trip
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on ORD

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more
Matt Meltzer

Matt Meltzer

Expert on RSW

Matt Meltzer has been a travel writer for over a decade, covering U.S. domestic locations and hotels for Thrillist, Fifty Grande, Matador Network, Conde Nast Traveler, and other top publications. He's won multiple travel journalism awards from the Society of American Travel Writers and North American Travel Journalists Association, and currently resides in South Florida.

Read more

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 14, 2026.
Get a feel of what it's like to fly with Southwest,United Airlines, andAmerican Airlines from Chicago O'Hare Intl Airport to Fort Myers by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,299 reviews

Boarding

8.1

Overall

8.0

Comfort

8.0

Entertainment

7.5

Food

7.0

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
4,299 reviews
Southwest
8.0
Very good
4,299 reviews

Boarding

8.1

Overall

8.0

Comfort

8.0

Entertainment

7.5

Food

7.0

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
9,711 reviews
Southwest
8.0
Very good
4,299 reviews

Boarding

8.1

Overall

8.0

Comfort

8.0

Entertainment

7.5

Food

7.0

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
11,664 reviews
Southwest
8.0
Very good
4,299 reviews

Boarding

8.1

Overall

8.0

Comfort

8.0

Entertainment

7.5

Food

7.0

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
8,625 reviews
Southwest
8.0
Very good
4,299 reviews

Boarding

8.1

Overall

8.0

Comfort

8.0

Entertainment

7.5

Food

7.0

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
2,953 reviews
Southwest
8.0
Very good
4,299 reviews

Boarding

8.1

Overall

8.0

Comfort

8.0

Entertainment

7.5

Food

7.0

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 O'Hare Intl 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 O'Hare Intl?

    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 O'Hare Intl. Booking flights from Chicago O'Hare Intl to SW Florida Intl (RSW) should be relatively easy as there are 16 daily inbound flights from Chicago O'Hare Intl from 7 different airlines.

  • How long is the flight from Chicago O'Hare Intl Airport to Fort Myers?

    There are many flights that can get you from Chicago O'Hare Intl Airport to Fort Myers in 3h 08m. Fly via Delta or United Airlines to get the fastest option. Airlines will cover a distance of 1122 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines flying from Chicago O'Hare Intl Airport to Fort Myers round-trip?

    Spirit Airlines, at $66, was found to be the cheapest airline from Chicago O'Hare Intl Airport to Fort Myers.Alternate airlines to your destination round-trip include Frontier and Delta. Spirit Airlines is 75% cheaper than the average price of flights available within the next 90 days to this destination.

  • What are the cheapest airlines to fly from Chicago O'Hare Intl Airport to Fort Myers one-way?

    The cheapest airlines for a one-way flight from Chicago O'Hare Intl Airport to Fort Myers are Frontier ($29), Spirit Airlines ($38), and American Airlines ($78).

  • What are the most reliable airlines from Chicago O'Hare Intl Airport to Fort Myers?

    The top 3 most reliable airlines when flying from Chicago O'Hare Intl Airport to Fort Myers are Southwest (79%), Air New Zealand (78%) and Air Canada (74%).

  • What are the cheapest flights from Chicago O'Hare Intl Airport to Fort Myers?

    On average you can expect to pay $521 for a flight from Chicago O'Hare Intl Airport to Fort Myers. The cheapest flight overall is $94 while the most popular route, (Chicago O'Hare Intl - Fort Myers SW Florida Intl) is currently priced at $291.

  • Can I find deals for flights from O'Hare Intl to Fort Myers that include hotel bookings?

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

  • How can I find direct flights from O'Hare Intl to Fort Myers?

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

  • Can I find deals for business class flights from O'Hare Intl to Fort Myers?

    Yes. Cheapflights offers flight deals from O'Hare Intl 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 O'Hare Intl Airport to Fort Myers?

    Currently, September is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Fort Myers (average of $183). Flying from Chicago O'Hare Intl Airport to Fort Myers in March is currently the most expensive (average of $359). 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
North Fort Myers
Estero
Sanibel

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Top 7 airlines flying from O'Hare Intl to Fort Myers

Discover the top 7 airlines that operate flights from O'Hare Intl 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 14, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$66Average$187FlexibilityNo cancel feeOn-time65%
FrontierCheapest$66Average$181FlexibilityNo cancel feeOn-time62%
DeltaCheapest$130Average$435FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$144Average$230FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$157Average$293FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$160Average$319FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$197Average$363FlexibilityNo cancel feeOn-time63%

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