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$80+ Cheap flights from Fort Myers (RSW) to Chicago (CHI)

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 12/5. Fares are subject to change and may not be available on all flights or dates of travel.
RSW — CHI
Dec 6 — Dec 131
Sat 12/6
Sat 12/13
1 adult, Economy
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Find cheap flights from Fort Myers to Chicago with Cheapflights

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Cheapflights Tip: The best prices from Fort Myers SW Florida Intl to Chicago are usually found in September or August, booked 31 days in advance, depart on a Friday or Thursday and return on a Wednesday

Find flight deals from Fort Myers to Chicago

Cheapest flights from Fort Myers to Chicago
Explore the most affordable flight options available from Fort Myers to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 6, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/5. 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.
Fri 12/51:15 pmRSW - ORD
Nonstop3h 08mMultiple Airlines
Mon 12/86:11 amORD - RSW
1 stop9h 39mMultiple Airlines
Deal found 11/5$135
This Kiwi.com deal was found by Cheapflights users on 11/4. 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 12/216:15 amRSW - ORD
Nonstop3h 09mSpirit Airlines
Fri 1/24:55 pmORD - RSW
Nonstop3h 05mSpirit Airlines
Deal found 11/4$137
This Kiwi.com deal was found by Cheapflights users on 11/4. 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.
Fri 12/266:15 amRSW - ORD
Nonstop3h 09mSpirit Airlines
Sun 1/44:55 pmORD - RSW
Nonstop3h 05mSpirit Airlines
Deal found 11/4$139
This CheapOair deal was found by Cheapflights users on 11/6. 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.
Sat 11/224:09 pmRSW - ORD
1 stop8h 59mFrontier
Mon 11/245:30 amORD - RSW
1 stop12h 19mFrontier
Deal found 11/6$144
This Priceline deal was found by Cheapflights users on 11/6. 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.
Tue 11/259:28 amRSW - MDW
1 stop10h 36mFrontier
Fri 11/286:05 amMDW - RSW
1 stop7h 52mFrontier
Deal found 11/6$144
This Priceline deal was found by Cheapflights users on 11/6. 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 12/189:55 pmRSW - ORD
Nonstop3h 01mSpirit Airlines
Mon 12/229:19 amORD - RSW
Nonstop3h 10mSpirit Airlines
Deal found 11/6$145
This Kiwi.com deal was found by Cheapflights users on 11/5. 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.
Fri 12/57:14 pmRSW - ORD
1 stop17h 40mMultiple Airlines
Thu 12/118:15 amORD - RSW
Nonstop3h 05mMultiple Airlines
Deal found 11/5$147
This Kiwi.com deal was found by Cheapflights users on 11/5. 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.
Sat 12/612:22 pmRSW - ORD
2 stops21h 20mMultiple Airlines
Sun 12/148:15 amORD - RSW
Nonstop3h 05mMultiple Airlines
Deal found 11/5$148
This Cheapflightsfares deal was found by Cheapflights users on 11/6. 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 12/121:15 pmRSW - ORD
Nonstop3h 08mSpirit Airlines
Mon 12/158:15 amORD - RSW
Nonstop3h 05mSpirit Airlines
Deal found 11/6$149
This Kiwi.com deal was found by Cheapflights users on 11/5. 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.
Fri 12/51:15 pmRSW - ORD
Nonstop3h 08mMultiple Airlines
Sat 12/61:24 pmORD - RSW
2 stops19h 57mMultiple Airlines
Deal found 11/5$150
This Kiwi.com deal was found by Cheapflights users on 11/5. 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.
Fri 12/51:15 pmRSW - ORD
Nonstop3h 08mMultiple Airlines
Tue 12/94:22 pmORD - RSW
2 stops24h 01mMultiple Airlines
Deal found 11/5$152
This Kiwi.com deal was found by Cheapflights users on 11/5. 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.
Thu 12/189:55 pmRSW - ORD
Nonstop3h 01mSpirit Airlines
Sun 12/219:19 amORD - RSW
Nonstop3h 10mSpirit Airlines
Deal found 11/5$154

Cheap flight deals from Fort Myers to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Fort Myers (RSW) to Chicago (CHI). 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 6, 2025.

Most accurate provider

Justfly.com
3 stars

Most trusted provider

Justfly.com
3 stars

Round-trip from

$135
(Kiwi.com)

One-way from

$80
(Southwest)

Popular in

June

Cheapest in

September

Average price

$210
Provider with most accurate pricing for Fort Myers SW Florida Intl-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Fort Myers SW Florida Intl-Chicago (CHI) flights.
Search Deals
From Fort Myers SW Florida Intl to Chicago (CHI)
Search Deals
One-way flight from Fort Myers SW Florida Intl to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($18 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Fort Myers to Chicago 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 November 6, 2025.
Use the filters below to find and compare flights from Fort Myers to Chicago that are best for you.

Fly from

Fort Myers

Fly to

Chicago

Route

Depart

Return

Price

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Thu 12/11

6:30 am-8:25 am

Nonstop2h 55m

Chicago Midway

Sun 12/14

5:35 am-9:20 am

Nonstop2h 45m

$159

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Thu 11/20

11:58 am-7:31 pm

1 stop8h 33m

Chicago Midway

Sun 11/23

8:04 pm-8:33 am

1 stop11h 29m

$166

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Fri 12/5

11:45 am-1:45 pm

Nonstop3h 00m

Chicago Midway

Sun 12/7

7:25 pm-11:10 pm

Nonstop2h 45m

$169

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Fri 12/5

6:25 am-11:08 am

3 stops29h 43m

Chicago O'Hare Intl

Sun 12/7

8:15 am-12:20 pm

Nonstop3h 05m

$182

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Sat 1/10

6:25 am-12:15 pm

1 stop6h 50m

Chicago O'Hare Intl

Sat 1/17

3:45 pm-9:20 pm

1 stop4h 35m

$183

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Fri 11/14

1:39 pm-3:47 pm

Nonstop3h 08m

Chicago O'Hare Intl

Sun 11/16

2:11 pm-6:08 pm

Nonstop2h 57m

$198

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Thu 11/13

10:59 am-1:03 pm

Nonstop3h 04m

Chicago O'Hare Intl

Sun 11/16

2:11 pm-6:08 pm

Nonstop2h 57m

$199

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Fri 11/14

1:39 pm-3:47 pm

Nonstop3h 08m

Chicago O'Hare Intl

Mon 11/17

4:42 pm-8:33 pm

Nonstop2h 51m

$199

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Fri 2/20

6:35 am-8:35 am

Nonstop3h 00m

Chicago Midway

Sun 2/22

7:00 am-11:00 am

Nonstop3h 00m

$203

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Thu 1/15

5:00 am-7:00 am

Nonstop3h 00m

Chicago Midway

Sun 1/18

5:45 pm-9:30 pm

Nonstop2h 45m

$209

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/6

Showing 1-10 of 50 results
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Compare providers for flights from Fort Myers to Chicago

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 Fort Myers to Chicago in November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
CheapflightsfaresPrice Accuracy3 starsTrust Score*2 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
Justfly.comPrice Accuracy3 starsTrust Score*3 stars
JustAirTicketPrice Accuracy-Trust Score*1 star

*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 Fort Myers-Chicago flights, users find the pricing of Justfly.com to be most consistent on Cheapflights vs. Justfly.com Users can find the same prices on Fort Myers-Chicago flight deals on Cheapflights vs. Justfly.com >95% of the time. Price accuracy is based on data collected from Fort Myers-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Fort Myers-Chicago flights, Cheapflights users trust Justfly.com the most. Justfly.com 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 Fort Myers-Chicago 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 Fort Myers to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago 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

How far ahead should I book a flight from Fort Myers to Chicago?

Use this chart to determine the optimal time to book a round-trip flight from Fort Myers to Chicago. Price data was last updated on October 31, 2025.

The price you pay for your flight from Fort Myers to Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 31 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 Fort Myers to Chicago?

Currently, January is the cheapest month in which you can book a flight from Fort Myers to Chicago (average of $31). Flying from Fort Myers to Chicago in June is currently the most expensive (average of $115). 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 CHI?

Find hourly flight availability from Fort Myers to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 6, 2025.

It’s typically best to fly out from Fort Myers to Chicago in the morning. Doing so could potentially save you 26% on the flight price compared to flying at noon, which is usually more expensive.

What is the cheapest day to fly from Fort Myers to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Fort Myers to Chicago. Price data was last updated on November 2, 2025.

Travelers seeking maximum savings on their Fort Myers to Chicago flight should consider departing on Tuesday mornings 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.

Weekly flight availability from Fort Myers to Chicago

Explore weekly flight availability from Fort Myers to Chicago. 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 6, 2025.

The most flights from RSW to CHI are scheduled on a Thursday (24 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (9 on average).

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

The best insider tips for Fort Myers to Chicago 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 trip
Airlines
Spirit Airlines

Spirit's Big Front Seats offer 11 inches more legroom, ideal for a comfortable short flight.


Spirit's self-service bag drop saves time; print your boarding pass to avoid extra fees.

Read more about Spirit Airlinesby Daniel Scheffler
United Airlines

United's Economy Plus offers extra legroom and priority boarding for a more comfortable flight experience.


United's Basic Economy restricts carry-ons; consider upgrading for more baggage flexibility.

Read more about United Airlinesby Harriet Baskas
Southwest

Southwest offers free messaging and in-flight entertainment streamed to your device.


Southwest's open seating policy allows you to choose any available seat upon boarding.

Read more about Southwestby Marisa Garcia
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

Consider taking the “L” train from ORD to the city center to avoid Chicago traffic delays.

Read more about ORDby Ramsey Qubein
MDW

Use the Orange Line train for a quick, 30-minute ride from MDW to Chicago's city center.

Read more about MDWby Ramsey Qubein
Our travel experts
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
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
Marisa Garcia

Marisa Garcia

Expert on Southwest

Marisa Garcia

Marisa Garcia

Marisa knows planes inside and out, spending 16 years working on aircraft in hangars at airports around the world. She is an aviation industry expert, specialized in airline interiors and regulations. Ten years ago, she pivoted to journalism. She shares her insights in leading aviation, travel, and business publications and on her site FlightChic.

Read more
Ramsey Qubein

Ramsey Qubein

Expert on ORD and MDW

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

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated November 6, 2025.
Get a feel of what it's like to fly with Southwest, United Airlines, and American Airlines from Fort Myers to Chicago 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
4,240 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Southwest
8.0
Very good
4,240 reviews
Southwest
8.0
Very good
4,240 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
United Airlines
7.4
Good
9,007 reviews
Southwest
8.0
Very good
4,240 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
American Airlines
7.2
Good
11,040 reviews
Southwest
8.0
Very good
4,240 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Spirit Airlines
6.3
Okay
8,123 reviews
Southwest
8.0
Very good
4,240 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Frontier
5.8
Fair
3,115 reviews
Southwest
8.0
Very good
4,240 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Related info for your journey

Find useful and relevant information for your journey from Fort Myers to Chicago. 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?

    For a flight from Fort Myers to Chicago, you will be flying from SW Florida Intl. Fort Myers SW Florida Intl (RSW) is just 10.0 mi from the center of the city. SW Florida Intl is the only Fort Myers airport and it handles 18 outbound flights to Chicago per day. 6 airlines have flights to Chicago from Fort Myers SW Florida Intl on a regular basis.

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

    Airlines like Frontier, Southwest, and Spirit Airlines fly from Fort Myers to Chicago in about 3h. The time it takes to get you to your destination can typically vary by up to 26h 43m. Airlines will cover a distance of 1106 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    Our cheapest airline available from Fort Myers to Chicago 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 $71 and $158 round-trip. You may be able to fly from Fort Myers to Chicago for 79% less than the average price by searching for these airlines.

  • What are the cheapest airlines to fly from Fort Myers to Chicago one-way?

    To fly one-way, consider booking your trip with United Airlines, which is currently one of the cheapest options available, starting at $84. Southwest flights start at $85 while deals on Frontier start at $103 one-way.

  • What are the most popular routes from Fort Myers to Chicago?

    While some choose either Fort Myers SW Florida Intl - Chicago Midway or Fort Myers SW Florida Intl - Chicago Greater Rockford, Fort Myers SW Florida Intl - Chicago O'Hare Intl is the most popular route from Fort Myers to Chicago.

  • What are the most reliable airlines from Fort Myers to Chicago?

    The top 3 most reliable airlines when flying from Fort Myers to Chicago are Spirit Airlines (97%), United Airlines (90%) and American Airlines (87%).

  • What are the cheapest flights from Fort Myers to Chicago?

    On average you can expect to pay $831 for a flight from Fort Myers to Chicago. The cheapest flight overall is $69 while the most popular route, (Fort Myers SW Florida Intl - Chicago O'Hare Intl) is currently priced at $89.

  • Can I find deals for flights from Fort Myers to Chicago that include hotel bookings?

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

  • How can I find direct flights from Fort Myers to Chicago?

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

  • Can I find deals for business class flights from Fort Myers to Chicago?

    Yes. Cheapflights offers flight deals from Fort Myers to Chicago 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?

    Currently, January is the cheapest month in which you can book a flight from Fort Myers to Chicago (average of $31). Flying from Fort Myers to Chicago in June is currently the most expensive (average of $115). 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?

Book flights to Chicago if you plan to visit one of these locations
Lansing
Hammond
Porter
Benton Harbor
Merrillville

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Top 6 airlines flying from Fort Myers to Chicago

Discover the top 6 airlines that operate flights from Fort Myers to Chicago. 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 November 6, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$46Average$130FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$71Average$155FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$158Average$251FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$159Average$305FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$179Average$377FlexibilityNo cancel feeOn-time63%
DeltaCheapest$216Average$386FlexibilityNo cancel feeOn-timeN/A

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