HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$58+ 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 4/18. Fares are subject to change and may not be available on all flights or dates of travel.
RSW — CHI
Mar 5 — Mar 121
Thu 3/5
Thu 3/12
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Fort Myers to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.
Cheapflights Tip: The best prices from Fort Myers SW Florida Intl to Chicago are usually found in September or January, booked 59 days in advance, depart on a Friday or Thursday and return on a Tuesday

Cheap 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 February 3, 2026.

This Expedia deal was found by Cheapflights users on 1/31. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/196:00 am
RSW
-
ORD
Nonstop3h 13m
Spirit Airlines
Sat 2/285:22 pm
ORD
-
RSW
Nonstop2h 58m
Spirit Airlines
Deal found 1/31$76
This Cheapflightsfares deal was found by Cheapflights users on 2/3. 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.
Mon 3/97:51 pm
RSW
-
ORD
Nonstop3h 10m
Spirit Airlines
Tue 3/107:20 am
ORD
-
RSW
Nonstop2h 56m
Spirit Airlines
Deal found 2/3$77
This Expedia deal was found by Cheapflights users on 2/3. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/116:00 am
RSW
-
ORD
Nonstop3h 13m
Spirit Airlines
Tue 3/177:36 pm
ORD
-
RSW
Nonstop2h 48m
Spirit Airlines
Deal found 2/3$78
This Cheapflightsfares deal was found by Cheapflights users on 2/3. 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.
Tue 2/107:49 pm
RSW
-
ORD
Nonstop3h 19m
Spirit Airlines
Tue 2/245:22 pm
ORD
-
RSW
Nonstop2h 58m
Spirit Airlines
Deal found 2/3$79
This Frontier deal was found by Cheapflights users on 1/31. 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 2/146:49 pm
RSW
-
ORD
Nonstop3h 32m
Frontier
Sun 2/226:30 am
ORD
-
RSW
Nonstop3h 09m
Frontier
Deal found 1/31$81
This Cheapflightsfares deal was found by Cheapflights users on 2/1. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/196:00 am
RSW
-
ORD
Nonstop3h 13m
Spirit Airlines
Mon 2/235:22 pm
ORD
-
RSW
Nonstop2h 58m
Spirit Airlines
Deal found 2/1$82
This Cheapflightsfares deal was found by Cheapflights users on 2/3. 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.
Wed 3/46:00 am
RSW
-
ORD
Nonstop3h 13m
Spirit Airlines
Sun 3/85:22 pm
ORD
-
RSW
Nonstop2h 58m
Spirit Airlines
Deal found 2/3$83
This Super.com deal was found by Cheapflights users on 2/3. 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 2/126:00 am
RSW
-
ORD
Nonstop3h 13m
Spirit Airlines
Sun 2/155:22 pm
ORD
-
RSW
Nonstop2h 58m
Spirit Airlines
Deal found 2/3$87
This Frontier deal was found by Cheapflights users on 2/3. 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 2/1211:34 am
RSW
-
ORD
Nonstop3h 34m
Frontier
Sat 2/141:37 pm
ORD
-
RSW
Nonstop3h 14m
Frontier
Deal found 2/3$88
This Cheapflightsfares deal was found by Cheapflights users on 2/3. 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 2/126:00 am
RSW
-
ORD
Nonstop3h 13m
Spirit Airlines
Tue 2/175:22 pm
ORD
-
RSW
Nonstop2h 58m
Spirit Airlines
Deal found 2/3$89
This Cheapflightsfares deal was found by Cheapflights users on 2/3. 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.
Sat 2/146:00 am
RSW
-
ORD
Nonstop3h 13m
Spirit Airlines
Wed 2/185:22 pm
ORD
-
RSW
Nonstop2h 58m
Spirit Airlines
Deal found 2/3$90
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/202:41 pm
RSW
-
MDW
1 stop8h 44m
Frontier
Sun 2/229:04 pm
MDW
-
RSW
1 stop13h 57m
Frontier
Deal found 2/2$154

Find 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 February 3, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$76
(Expedia)

One-way from

$58
(Frontier)

Popular in

December

Cheapest in

September

Average price

$211
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. 3% potential increase in price ($8 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
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 February 3, 2026.
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 - ORD

RSWORD

Fort Myers SW Florida Intl

Thu 3/5

12:29 pm-2:55 pm

Nonstop3h 26m

Chicago O'Hare Intl

Sat 3/7

6:10 am-10:10 am

Nonstop3h 00m

$164

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Sat 2/21

6:00 am-8:13 am

Nonstop3h 13m

Chicago O'Hare Intl

Tue 2/24

8:16 pm-12:01 pm

2 stops14h 45m

$175

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Fri 2/27

6:35 am-8:35 am

Nonstop3h 00m

Chicago Midway

Sun 3/1

8:35 pm-12:20 am

Nonstop2h 45m

$199

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Sat 6/13

7:00 am-9:23 am

Nonstop3h 23m

Chicago O'Hare Intl

Sat 6/20

4:20 pm-8:28 pm

Nonstop3h 08m

$211

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Thu 3/5

7:15 am-9:15 am

Nonstop3h 00m

Chicago Midway

Sat 3/7

8:35 pm-12:25 am

Nonstop2h 50m

$211

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Wed 3/4

6:25 pm-10:31 pm

1 stop5h 06m

Chicago Midway

Sun 3/8

6:34 pm-12:01 am

1 stop4h 27m

$217

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Wed 3/4

7:50 am-2:20 pm

1 stop7h 30m

Chicago Midway

Sun 3/8

5:15 am-9:00 am

Nonstop2h 45m

$227

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Sat 2/21

6:20 am-1:30 pm

1 stop8h 10m

Chicago Midway

Sat 2/21

4:05 pm-9:45 pm

1 stop4h 40m

$271

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Tue 6/30

4:38 pm-7:00 pm

Nonstop3h 22m

Chicago O'Hare Intl

Mon 7/6

7:10 am-11:18 am

Nonstop3h 08m

$273

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Sat 6/13

7:00 am-9:23 am

Nonstop3h 23m

Chicago O'Hare Intl

Thu 6/25

4:20 pm-8:28 pm

Nonstop3h 08m

$282

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/1

Showing 1-10 of 49 results
1
2
3
...
5

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 February.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy2 starsTrust Score*2 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
Justfly.comPrice Accuracy3 starsTrust Score*3 stars
JustAirTicketPrice Accuracy-Trust Score*1 star
Super.comPrice Accuracy-Trust 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 Fort Myers-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Fort Myers-Chicago flight deals on Cheapflights vs. FlightHub >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 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 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 January 30, 2026.

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 59 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, March is the cheapest month in which you can book a flight from Fort Myers to Chicago (average of $52). Flying from Fort Myers to Chicago in June is currently the most expensive (average of $116). 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 February 3, 2026.

It’s typically best to fly out from Fort Myers to Chicago in the evening. Doing so could potentially save you 23% on the flight price compared to flying in the afternoon, 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 January 31, 2026.

Travelers seeking maximum savings on their Fort Myers to Chicago 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.

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 February 3, 2026.

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

The best insider tips for Fort Myers to Chicago 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 Fort Myers to Chicago trip
Our travel experts
Daniel Scheffler

Daniel Scheffler

Expert on Spirit Airlines

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 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 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

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 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 February 3, 2026.
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
4,272 reviews

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

Crew

8.6

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
4,272 reviews
Southwest
8.0
Very good
4,272 reviews

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

Crew

8.6

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
9,236 reviews
Southwest
8.0
Very good
4,272 reviews

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

Crew

8.6

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
11,216 reviews
Southwest
8.0
Very good
4,272 reviews

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

Crew

8.6

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
8,405 reviews
Southwest
8.0
Very good
4,272 reviews

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

Crew

8.6

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
5.7
Fair
3,051 reviews
Southwest
8.0
Very good
4,272 reviews

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

Crew

8.6

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 17 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 United Airlines, Southwest, and Delta 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 2h 06m. 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 $37 on this airline. Additional options worth looking into are Spirit Airlines and United Airlines, starting at $58 and $153 round-trip. You may be able to fly from Fort Myers to Chicago for 83% 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 Frontier, which is currently one of the cheapest options available, starting at $31. Spirit Airlines flights start at $42 while deals on Southwest start at $78 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 United Airlines (81%), Alaska Airlines (76%) and Qatar Airways (76%).

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

    On average you can expect to pay $959 for a flight from Fort Myers to Chicago. The cheapest flight overall is $66 while the most popular route, (Fort Myers SW Florida Intl - Chicago O'Hare Intl) is currently priced at $64.

  • 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, March is the cheapest month in which you can book a flight from Fort Myers to Chicago (average of $52). Flying from Fort Myers to Chicago in June is currently the most expensive (average of $116). 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
Merrillville
Hammond
Porter
Benton Harbor

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Fort Myers to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Orlando to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
Miami to O'Hare Intl flights
Tampa to O'Hare Intl flights
Orlando to Midway flights
Tampa to Midway flights
Miami to Midway flights
Fort Lauderdale to Midway flights
West Palm Beach to O'Hare Intl flights
Fort Myers to O'Hare Intl flights
Jacksonville to O'Hare Intl flights
Orlando to St. Louis flights
Sarasota to O'Hare Intl flights
Miami to St. Louis flights
Pensacola to O'Hare Intl flights
Fort Myers to Midway flights
Fort Lauderdale to St. Louis flights
West Palm Beach to Midway flights
Tampa to St. Louis flights
Fort Myers to St. Louis flights
Jacksonville to St. Louis flights
Jacksonville to Midway flights
Sarasota to Midway flights
West Palm Beach to St. Louis flights
Panama City to O'Hare Intl flights
Valparaiso to O'Hare Intl flights
Sarasota to St. Louis flights
Pensacola to St. Louis flights
Tallahassee to O'Hare Intl flights
Pensacola to Midway flights
Orlando to Evansville flights
Orlando to Moline flights
Orlando to Peoria flights
Panama City to Midway flights
Gainesville to O'Hare Intl flights
Orlando Sanford Intl to Rockford flights
Tallahassee to Midway flights
Key West to O'Hare Intl flights
Melbourne to O'Hare Intl flights
Daytona Beach to O'Hare Intl flights
St Petersburg to Rockford flights
Valparaiso to Midway flights
Fort Lauderdale to Moline flights
Valparaiso to St. Louis flights
Panama City to St. Louis flights
Jacksonville to Peoria flights
Melbourne to St. Louis flights
Fort Lauderdale to Rockford flights
Gainesville to Midway flights
Orlando to Bloomington flights

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 February 3, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$37Average$101FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$58Average$151FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$153Average$285FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$157Average$250FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$179Average$367FlexibilityNo cancel feeOn-time63%
DeltaCheapest$216Average$352FlexibilityNo cancel feeOn-timeN/A

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.
Site
©2026 Cheapflights