Cheap flights from Fort Myers to Chicago from $42
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Fort Myers to Chicago departing on 7/9. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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United Airlines flights from Fort Myers to Chicago
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Spirit Airlines flights from Fort Myers to Chicago
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How to get the cheapest flight ticket from Fort Myers to Chicago
Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the cheapest month to fly to Chicago?
The month of January is, on average, the cheapest month to fly to Chicago from Fort Myers, with most prices found around $184. If you’re not able to fly to Chicago in January, then August is your next best option. Flight prices from Fort Myers to Chicago during August average around $199.
What is the cheapest day to depart on your flight to Chicago?
The cheapest day to depart on your flight to Chicago is on a Thursday when prices can be found for as low as $293. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Fort Myers to Chicago for around $410.
What is the cheapest time of day to depart on your flight to Chicago?
Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Fort Myers to Chicago during this time can be as low as $217. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $340.
What is the cheapest Fort Myers SW Florida Intl to Chicago flight route?
Fly from Fort Myers SW Florida Intl to Chicago O'Hare Intl for the best Fort Myers SW Florida Intl - Chicago flight prices
How far in advance should I book a flight to Chicago?
You are more likely to see cheaper flights to Chicago from Fort Myers when booking 16 weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $253 when searching 16 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Fort Myers for as low as $197 on momondo.
What cabin class options are available on Fort Myers SW Florida Intl to Chicago flights?
There are 4 cabin classes available to choose from on Fort Myers SW Florida Intl to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
Can stopping save me money on Fort Myers to Chicago flights?
No. A direct flight is the cheapest option for a flight between Fort Myers to Chicago.
How have Fort Myers to Chicago flight prices changed over time?
As of June 2025, prices for Fort Myers to Chicago flights are approximately 0% more expensive when compared to flights at the same time last year.
What is the cheapest airline that flies from Fort Myers SW Florida Intl to Chicago?
Spirit Airlines, United Airlines, and Southwest are the most popular carriers operating from Fort Myers SW Florida Intl to Chicago
What airlines fly to Chicago?
United Airlines, American Airlines and Spirit Airlines are the top three most popular airlines that fly to Chicago from Fort Myers according to our data. United Airlines is the first choice among our users, with 44% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 7 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.
How many flights depart from Fort Myers to Chicago on average per day?
The number of flights available between Fort Myers and Chicago is 15 per day as of June 2025. The most frequent departure time is 4:00PM, with 57% of daily flights leaving in the afternoon.
How many flights depart from Fort Myers to Chicago on average per week?
As of June 2025, 109 flights take off from Fort Myers and land in Chicago each week. The most common flight departure day for this route is Mon, with 17% of weekly flights taking off on this day.
When to book flights from Fort Myers to Chicago
Cheap Fort Myers to Chicago (RSW to CHI) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Fort Myers to Chicago
How far is Fort Myers SW Florida Intl to Chicago by plane?
Fort Myers SW Florida Intl and Chicago are 1101.2 mi apart from one another. Flights usually cover this in 2h 50m, depending on flying conditions and air traffic around both airports.
When did momondo last update prices for flights from Fort Myers SW Florida Intl Airport to Chicago?
Prices for flights from Fort Myers SW Florida Intl Airport to Chicago refresh daily.
How many operators does momondo search for flights from Fort Myers SW Florida Intl Airport to Chicago?
As of June 2025, there are 6 operators available to choose from for flights from Fort Myers SW Florida Intl Airport to Chicago.
How old do you have to be to fly from Fort Myers SW Florida Intl Airport to Chicago?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Fort Myers SW Florida Intl Airport to Chicago.
What documentation or ID do you need to fly to Chicago?
The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.
What is the most popular plane model from Fort Myers to Chicago?
momondo data reveals that the most frequently booked plane model on the route from Fort Myers to Chicago is Boeing 737-800, representing 27.74% of all bookings. The subsequent popular models are Boeing 737-900 at 12.89%, Boeing 737 MAX 9 at 12.56%, and Airbus A321neo at 12.19%.
What is the most popular airline from Fort Myers to Chicago?
momondo data reveals that the most frequently booked airline on the route from Fort Myers to Chicago is United Airlines, representing 31% of all bookings. The subsequent popular airlines are Spirit Airlines at 31%, American Airlines at 23%, and Southwest at 9%.
Best airlines flying from Fort Myers to Chicago
Compare and see reviews for airlines that fly from Fort Myers to Chicago with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $46 | Free Cancellation | Rating 5.9 3,295 reviews | |||
| PriceFrom $70 | Free Cancellation | Rating 6.3 8,052 reviews | |||
| PriceFrom $159 | Free Cancellation | Rating 7.2 10,000 reviews | |||
| PriceFrom $159 | Free Cancellation | Rating 7.4 8,790 reviews | |||
| PriceFrom $210 | Free Cancellation | Rating 8.0 4,287 reviews | |||
| PriceFrom $216 | Free Cancellation | Rating 8.0 7,950 reviews |
Southwest Flights From Fort Myers to Chicago
Southwest flight deals from Fort Myers to Chicago start from $210 round-trip. Over the 15 Southwest flights for this route in a normal week, average airfare is usually $394 round-trip - but some users have found much cheaper deals with momondo.
United Airlines Flights From Fort Myers to Chicago
United Airlines (7.4/10 from 8,790 reviews) operates around 16 flights from Fort Myers to Chicago in any given week. The average United Airlines airfare for this route is around $335, with deals from around $159 rare but found on momondo. Referenced prices are for round-trip Fort Myers to Chicago flight searches in the last 72 hours.
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Why should I use momondo to find a flight deal from Fort Myers to Chicago?
We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Fort Myers to Chicago for you.
Can I find flights from Fort Myers to Chicago with flexible booking policies on momondo?
Yes. momondo allows you to filter the results for Fort Myers to Chicago flights to just show those with flexible booking policies.
How can momondo help me find flights from Fort Myers to Chicago?
Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Fort Myers.
I’m not ready to book a flight from Fort Myers to Chicago right now. Can momondo alert me if prices change?
Yes momondo offers price alerts on flights to Chicago from Fort Myers. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.