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 $64 and $159 round-trip. You may be able to fly from Fort Myers to Chicago for 80% less than the average price by searching for these airlines.

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

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 86 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, August is the cheapest month in which you can book a flight from Fort Myers to Chicago (average of $245). Flying from Fort Myers to Chicago 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 day to fly from Fort Myers to Chicago?

Travelers seeking maximum savings on their Fort Myers to Chicago flight should consider departing on Wednesday evenings when fares are most often at their lowest. Monday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Fort Myers to Chicago

The most flights from RSW to CHI are scheduled on a Friday (19 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (9 on average).

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 cheapest flights from Fort Myers to Chicago?

On average you can expect to pay $667 for a flight from Fort Myers to Chicago. The cheapest flight overall is $46 while the most popular route, (Fort Myers SW Florida Intl - Chicago O'Hare Intl) is currently priced at $82.

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 (84%), SWISS (84%) and United Airlines (82%).

What are the most popular airlines that fly from Fort Myers to Chicago?

Before booking your flight from Fort Myers to Chicago check out the most popular airlines for this route: American Airlines, Frontier or Spirit Airlines.

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

Wednesday is generally a great day to depart. Flying on this day could help you save up to 51%.

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

Find a great deal and save up to 125% by booking at least 27 days prior to your desired departure date, rather than waiting until the week of travel. According to our data, there are a number of flights available from Fort Myers to Chicago within the next two weeks, with the cheapest ticket starting at $196.

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

January is one of the best times of the year to fly to Chicago from Fort Myers. Prices for January average $234 per person but you can even find prices for as low as $75. The most expensive prices can be found in the month of October. Opting for a January flight can save you 47% on your journey compared to booking in October

What is the cheapest time of day to fly from RSW to CHI?

It’s typically best to fly out from Fort Myers to Chicago in the evening. Doing so could potentially save you 43% on the flight price compared to flying in the afternoon, which is usually more expensive.

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 13 outbound flights to Chicago per day. 6 airlines have flights to Chicago from Fort Myers SW Florida Intl on a regular basis.

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.

$68+ Flights from Fort Myers to Chicago

Round-trip from	$82 (Cheapflightsfares)
One-way from	$68 (FlightHub)
Popular in	October
Cheapest in	January
Average price	$197

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.

Airline	Cheapest	Average	Flexibility	On-time
Frontier	Cheapest$46	Average$131	FlexibilityNo cancel fee	On-time62%
Spirit Airlines	Cheapest$64	Average$156	FlexibilityNo cancel fee	On-time65%
American Airlines	Cheapest$159	Average$262	FlexibilityNo cancel fee	On-time71%
United Airlines	Cheapest$163	Average$339	FlexibilityNo cancel fee	On-time69%
Southwest	Cheapest$183	Average$386	FlexibilityNo cancel fee	On-time63%
Delta	Cheapest$216	Average$386	FlexibilityNo cancel fee	On-timeN/A

$68+ 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 10/9. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Fort Myers to Chicago with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheapflights Tip: The best prices from Fort Myers SW Florida Intl to Chicago are usually found in January or August, booked 86 days in advance, depart on a Thursday or Friday and return on a Wednesday

Cheap flight deals from Fort Myers to Chicago

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Find flight deals from Fort Myers to Chicago

Cheapest flights from Fort Myers to ChicagoExplore 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 August 16, 2025.

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 August 16, 2025.

Cheapflights Fare Finder

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

The best insider tips for Fort Myers to Chicago flights

Cheapflights partnered with top experts to bring you the best recommendations for your Fort Myers to Chicago trip

Airlines

Spirit Airlines

United Airlines

Airports

RSW

ORD

MDW

Our travel experts

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.

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 August 8, 2025.

What is the cheapest month to book a flight from Fort Myers to Chicago?

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 August 16, 2025.

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 August 10, 2025.

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 August 16, 2025.

Reviews of airlines servicing Chicago

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.

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?

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

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

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

What are the cheapest flights from Fort Myers to Chicago?

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

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

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

What is the cheapest month to book a flight from Fort Myers to Chicago?

Traveling to a place near Chicago?

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.

Top 6 airlines flying from Fort Myers to Chicago

100% Free

Book with Flexibility

Travel Smart

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 August 16, 2025.