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O'Hare Intl

$72+ Cheap flights from Fort Myers (RSW) to O'Hare Intl (ORD)

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 10/24. Fares are subject to change and may not be available on all flights or dates of travel.
RSW — ORD
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
1 adult, Economy
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Cheapflights Tip: The best prices from Fort Myers SW Florida Intl to Chicago O'Hare Intl are usually found in January or August, booked 49 days in advance, depart on a Thursday or Friday and return on a Wednesday

Cheap flight deals from Fort Myers to O'Hare Intl

Discover tips and strategies to find the most affordable flight options for your journey from Fort Myers (RSW) to O'Hare Intl (ORD). 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 September 17, 2025.

Round-trip from

$119
(Cheapflightsfares)

One-way from

$72
(Cheapflightsfares)

Popular in

October

Cheapest in

January

Average price

$238
From Fort Myers SW Florida Intl to Chicago O'Hare Intl
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One-way flight from Fort Myers SW Florida Intl to Chicago O'Hare Intl
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Highest demand for flights based on searches. 11% potential increase in price ($29 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Fort Myers to O'Hare Intl

Cheapest flights from Fort Myers to O'Hare Intl
Explore the most affordable flight options available from Fort Myers to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 17, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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 10/166:40 amRSW - ORD
Nonstop2h 54mSpirit Airlines
Sun 10/194:51 pmORD - RSW
Nonstop2h 50mSpirit Airlines
Deal found 9/15$119
This Priceline deal was found by Cheapflights users on 9/15. 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.
Fri 10/246:40 amRSW - ORD
Nonstop2h 54mSpirit Airlines
Sun 10/265:28 pmORD - RSW
Nonstop2h 49mSpirit Airlines
Deal found 9/15$120
This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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 10/27:00 amRSW - ORD
Nonstop3h 13mSpirit Airlines
Mon 10/66:16 pmORD - RSW
Nonstop2h 53mSpirit Airlines
Deal found 9/15$123
This Priceline deal was found by Cheapflights users on 9/15. 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.
Fri 10/2412:27 pmRSW - ORD
1 stop6h 13mMultiple Airlines
Sun 10/265:28 pmORD - RSW
Nonstop2h 49mMultiple Airlines
Deal found 9/15$132
This Priceline deal was found by Cheapflights users on 9/15. 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.
Thu 9/257:24 pmRSW - ORD
1 stop5h 46mMultiple Airlines
Mon 9/295:23 pmORD - RSW
Nonstop2h 53mMultiple Airlines
Deal found 9/15$136
This Priceline deal was found by Cheapflights users on 9/15. 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.
Fri 10/316:22 amRSW - ORD
Nonstop2h 54mMultiple Airlines
Mon 11/38:26 amORD - RSW
1 stop11h 07mMultiple Airlines
Deal found 9/15$138
This Cheapflightsfares deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/106:40 amRSW - ORD
Nonstop2h 54mSpirit Airlines
Sun 10/124:51 pmORD - RSW
Nonstop2h 50mSpirit Airlines
Deal found 9/15$139
This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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 10/27:00 amRSW - ORD
Nonstop3h 13mSpirit Airlines
Sun 10/54:51 pmORD - RSW
Nonstop2h 50mSpirit Airlines
Deal found 9/15$143
This Frontier deal was found by Cheapflights users on 9/15. 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 11/61:13 pmRSW - ORD
1 stop11h 58mFrontier
Mon 11/108:26 amORD - RSW
1 stop11h 07mFrontier
Deal found 9/15$144
This Trip.com deal was found by Cheapflights users on 9/15. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/306:22 amRSW - ORD
Nonstop2h 54mSpirit Airlines
Sun 11/25:28 pmORD - RSW
Nonstop2h 49mSpirit Airlines
Deal found 9/15$147
This Priceline deal was found by Cheapflights users on 9/17. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/27:24 pmRSW - ORD
1 stop5h 15mMultiple Airlines
Mon 10/66:16 pmORD - RSW
Nonstop2h 53mMultiple Airlines
Deal found 9/17$152

Cheapflights Fare Finder

 
Customize your flight search to find flights from Fort Myers to O'Hare Intl 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 September 17, 2025.
Use the filters below to find and compare flights from Fort Myers to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fort Myers

Fly to

O'Hare Intl

Route

Depart

Return

Price

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Thu 10/16

6:40 am-8:34 am

Nonstop2h 54m

Chicago O'Hare Intl

Mon 10/20

6:16 pm-10:09 pm

Nonstop2h 53m

$119

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Fri 10/10

6:40 am-8:34 am

Nonstop2h 54m

Chicago O'Hare Intl

Mon 10/13

6:16 pm-10:09 pm

Nonstop2h 53m

$119

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Fri 10/31

6:22 am-8:16 am

Nonstop2h 54m

Chicago O'Hare Intl

Mon 11/3

5:28 pm-9:17 pm

Nonstop2h 49m

$119

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Sat 2/28

8:35 pm-10:45 pm

Nonstop3h 10m

Chicago O'Hare Intl

Tue 3/3

7:00 am-10:51 am

Nonstop2h 51m

$130

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Fri 10/3

7:00 am-9:13 am

Nonstop3h 13m

Chicago O'Hare Intl

Sun 10/5

4:51 pm-8:41 pm

Nonstop2h 50m

$143

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Fri 12/12

12:43 pm-2:55 pm

Nonstop3h 12m

Chicago O'Hare Intl

Mon 12/15

7:35 am-3:44 pm

1 stop7h 09m

$198

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Fri 11/14

5:38 pm-12:01 am

1 stop7h 23m

Chicago O'Hare Intl

Sun 11/16

6:03 pm-12:37 am

1 stop5h 34m

$217

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Fri 1/16

4:30 pm-8:38 pm

1 stop5h 08m

Chicago O'Hare Intl

Mon 1/19

7:00 am-1:13 pm

1 stop5h 13m

$217

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Fri 12/12

2:15 pm-6:22 pm

1 stop5h 07m

Chicago O'Hare Intl

Mon 12/15

11:15 am-4:32 pm

1 stop4h 17m

$217

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Thu 10/30

8:00 am-12:40 pm

1 stop5h 40m

Chicago O'Hare Intl

Tue 11/4

5:20 am-11:50 am

1 stop5h 30m

$217

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 22 results
1
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The best insider tips for Fort Myers to Chicago O'Hare Intl Airport flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
Cheapflights partnered with top experts to bring you the best recommendations for your Fort Myers to Chicago O'Hare Intl Airport trip
Airlines
United Airlines

Basic Economy on United prohibits carry-ons, unless you're a MileagePlus member or have a qualifying card.


United Economy Plus offers extra legroom seats towards the front of the economy cabin.

Read more about United Airlinesby Harriet Baskas
Spirit Airlines

Spirit's Big Front Seats offer 11 inches more legroom and larger tray tables.


Spirit's self-service bag drop speeds up airport check-in. Print your boarding pass in advance.

Read more about Spirit Airlinesby Daniel Scheffler
Airports
RSW

During peak tourist seasons, plan an extra 20 minutes at RSW for check-in due to smaller airline ticket counters.

Read more about RSWby Matt Meltzer
ORD

For quick city access from ORD, consider taking the 'L' train from the airport to downtown Chicago.

Read more about ORDby Ramsey Qubein
Our travel experts
Harriet Baskas

Harriet Baskas

Expert on United Airlines

Harriet Baskas

Harriet Baskas

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Read more
Daniel Scheffler

Daniel Scheffler

Expert on Spirit Airlines

Daniel Scheffler

Daniel Scheffler

Daniel Scheffler is a travel writer, podcaster, and producer. Born in Africa, bred in Europe and now living in America he has traveled to 140 countries (and all 50 U.S. states). Plus he has stayed at over 2500 hotels across the globe. His original shows Everywhere and Without Maps (available on Spotify) showcase his beliefs, travel is about humanity and sharing that beauty. And thus it reminds you that you shouldn’t believe everything you think.

Read more
Ramsey Qubein

Ramsey Qubein

Expert on ORD

Ramsey Qubein

Ramsey Qubein

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

Matt Meltzer

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

Best time to book a flight from Fort Myers to O'Hare Intl

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

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

Use this chart to determine the optimal time to book a round-trip flight from Fort Myers to O'Hare Intl. Price data was last updated on September 12, 2025.

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

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

Currently, August is the cheapest month in which you can book a flight from Fort Myers to Chicago O'Hare Intl Airport (average of $245). Flying from Fort Myers to Chicago O'Hare Intl Airport in March is currently the most expensive (average of $321). 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 RSW to ORD?

Find hourly flight availability from Fort Myers to O'Hare Intl. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 17, 2025.

When flying from Fort Myers to Chicago O'Hare Intl Airport, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 53% versus a flight in the afternoon.

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

Use this chart to determine the cheapest time to fly round-trip from Fort Myers to O'Hare Intl. Price data was last updated on September 14, 2025.

Travelers seeking maximum savings on their Fort Myers to Chicago O'Hare Intl Airport flight should consider departing on Thursday evenings when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing O'Hare Intl

Get insights into the airlines that provide service to O'Hare Intl. 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 O'Hare Intl. Reviews last updated September 17, 2025.
Read through reviews of airlines operating flights from Fort Myers to Chicago O'Hare Intl Airport, such as United Airlines, American Airlines, and Spirit Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
8,926 reviews

Entertainment

7.1

Comfort

7.3

Overall

7.4

Crew

8.1

Boarding

7.7

Food

6.6

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
United Airlines
7.4
Good
8,926 reviews
United Airlines
7.4
Good
8,926 reviews

Entertainment

7.1

Comfort

7.3

Overall

7.4

Crew

8.1

Boarding

7.7

Food

6.6

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
American Airlines
7.2
Good
10,000 reviews
United Airlines
7.4
Good
8,926 reviews

Entertainment

7.1

Comfort

7.3

Overall

7.4

Crew

8.1

Boarding

7.7

Food

6.6

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
Spirit Airlines
6.3
Okay
8,023 reviews
United Airlines
7.4
Good
8,926 reviews

Entertainment

7.1

Comfort

7.3

Overall

7.4

Crew

8.1

Boarding

7.7

Food

6.6

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
Frontier
5.8
Fair
3,173 reviews
United Airlines
7.4
Good
8,926 reviews

Entertainment

7.1

Comfort

7.3

Overall

7.4

Crew

8.1

Boarding

7.7

Food

6.6

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!

Related info for your journey

Find useful and relevant information for your journey from Fort Myers to O'Hare Intl. 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 from for flights from Fort Myers to Chicago O'Hare Intl?

    Most people fly from Fort Myers SW Florida Intl (RSW) if they book a flight from Fort Myers to Chicago O'Hare Intl. On average, SW Florida Intl has 14 outbound flights to Chicago O'Hare Intl per day from 4 airlines. Fort Myers SW Florida Intl is conveniently located just 10.0 mi from Fort Myers’s city center.

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

    Departing from Fort Myers to Chicago O'Hare Intl Airport will take you 2h 54m. The distance between Fort Myers and Chicago O'Hare Intl Airport is about 1122 mi. Generally, flights for this route are nonstop.

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

    Our cheapest airline available from Fort Myers to Chicago O'Hare Intl Airport is Frontier. Our recent data shows that you can find tickets from as low as $46 on this airline. Additional options worth looking into are Spirit Airlines and American Airlines, starting at $67 and $158 round-trip. These flights start at 80% lower than the current average price 3 months from now.

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

    The top 3 most reliable airlines when flying from Fort Myers to Chicago O'Hare Intl Airport are Spirit Airlines (91%), SWISS (87%) and United Airlines (87%).

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

    On average you can expect to pay $999 for a flight from Fort Myers to Chicago O'Hare Intl Airport. The cheapest flight overall is $79 while the most popular route, (Fort Myers SW Florida Intl - Chicago O'Hare Intl) is currently priced at $119.

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

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

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

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

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

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

    Currently, August is the cheapest month in which you can book a flight from Fort Myers to Chicago O'Hare Intl Airport (average of $245). Flying from Fort Myers to Chicago O'Hare Intl Airport in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago O'Hare Intl Airport?

Book flights to Chicago O'Hare Intl Airport if you plan to visit one of these locations
Schaumburg
Rosemont
Skokie
Gurnee
Hoffman Estates
Des Plaines
Elgin
Arlington Heights
Orland Park
Beloit
Racine
Rockford
Oak Brook
Elk Grove Village
Downers Grove
Naperville
Evanston
Merrillville
Bridgeview
Warrenville

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Top 4 airlines flying from Fort Myers to O'Hare Intl

Discover the top 4 airlines that operate flights from Fort Myers to O'Hare Intl. 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 September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$46Average$132FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$67Average$156FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$158Average$263FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$166Average$340FlexibilityNo cancel feeOn-time69%

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