Cheap flights from Fort Myers to Chicago from $79
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 8/19. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
Discover deals from 900+ travel sites with momondo.
Save money when you book flights with momondo
Big names and deals
Big names and deals
Search 100s of travel sites to compare prices.Filter for what you want
Filter for what you want
Free Wi-Fi? Stopover? Instantly customize your results.Trusted and free
Trusted and free
We’re completely free to use - no hidden charges or fees.Price Alerts
Price Alerts
Not ready to book? to track prices.Find the cheapest flights from Fort Myers to Chicago
Cheap round-trip flights
Cheap one-way flights
Cheap last minute flights
Cheap direct flights
Delta flights from Fort Myers to Chicago Midway Airport
Our best Delta deals on Fort Myers to Chicago Midway Airport flight tickets
Frontier flights from Fort Myers to Chicago Midway Airport
Our best Frontier deals on Fort Myers to Chicago Midway Airport flight tickets
See travel insights to Chicago from
How to get the cheapest flight ticket from Fort Myers to Chicago Midway Airport
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 Midway Airport?
The month of February is, on average, the cheapest month to fly to Chicago Midway Airport from Fort Myers, with most prices found around $334. If you are unable to visit Chicago Midway Airport during the month of February, then departing from Fort Myers during the month August is also very affordable. Most momondo users find prices during this month for around $334.
What is the cheapest day to depart on your flight to Chicago Midway Airport?
According to our data, Friday is the cheapest day to fly to Chicago Midway Airport from Fort Myers. The lowest ticket price found for a Friday departure recently was $397. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Sunday is the most expensive day to depart from Fort Myers because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $461.
What is the cheapest time of day to depart on your flight to Chicago Midway Airport?
Flying to Chicago Midway Airport from Fort Myers in the morning is the least expensive time of day to depart. momondo users have found prices as low as $416 when looking at flights departing in the morning. Try not to purchase tickets at noon because they tend to be around $456. Of course, these prices can vary depending on the time of year and what airport you fly to.
What is the cheapest Fort Myers SW Florida Intl to Chicago Midway flight route?
Fly from Fort Myers SW Florida Intl to Chicago Midway for the best Fort Myers SW Florida Intl - Chicago Midway flight prices
What cabin class options are available on Fort Myers SW Florida Intl to Chicago Midway flights?
There are 1 cabin classes available to choose from on Fort Myers SW Florida Intl to Chicago Midway 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 Midway Airport flights?
No. A direct flight is the cheapest option for a flight between Fort Myers to Chicago Midway Airport.
What is the cheapest airline that flies from Fort Myers SW Florida Intl to Chicago Midway?
Southwest, Frontier, and Delta are the most popular carriers operating from Fort Myers SW Florida Intl to Chicago Midway
What airlines fly to Chicago Midway Airport?
Southwest, Delta and Allegiant Air are the top three most popular airlines that fly to Chicago Midway Airport from Fort Myers according to our data. Southwest is the first choice among our users, with 74% of people opting to fly with this airline when traveling to Chicago Midway Airport. Keep in mind that there are 3 different airlines that fly to Chicago Midway Airport on a routine basis, so you have a few additional options to choose from.
How many flights depart from Fort Myers to Chicago Midway Airport on average per day?
As of June 2025, 2 flights take off from Fort Myers and land in Chicago Midway Airport each day. The most common flight departure time for this route is 6:00AM, with 60% of daily flights taking off at noon.
How many flights depart from Fort Myers to Chicago Midway Airport on average per week?
As of June 2025, 15 flights take off from Fort Myers and land in Chicago Midway Airport each week. The most common flight departure day for this route is Mon, with 20% of weekly flights taking off on this day.
When to book flights from Fort Myers to Chicago Midway Airport
Cheap Fort Myers to Chicago Midway Airport (RSW to MDW) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Fort Myers to Chicago Midway Airport
How far is Fort Myers SW Florida Intl to Chicago Midway by plane?
A flight from Fort Myers SW Florida Intl to Chicago Midway will travel around 1097.4 mi. Typically, this will take 2h 50m by plane in normal conditions.
When did momondo last update prices for flights from Fort Myers SW Florida Intl Airport to Chicago Midway Airport?
Prices for flights from Fort Myers SW Florida Intl Airport to Chicago Midway Airport were last updated today.
How many operators does momondo search for flights from Fort Myers SW Florida Intl Airport to Chicago Midway Airport?
There are 2 operators available for flights from Fort Myers SW Florida Intl Airport to Chicago Midway Airport as of June 2025.
How old do you have to be to fly from Fort Myers SW Florida Intl Airport to Chicago Midway Airport?
The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Fort Myers SW Florida Intl Airport to Chicago Midway Airport.
What documentation or ID do you need to fly to Chicago Midway Airport?
The travel and health documents required for your trip to Chicago Midway Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago Midway Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from Fort Myers to Chicago Midway Airport?
momondo data reveals that the most frequently booked plane model on the route from Fort Myers to Chicago Midway Airport is Boeing 737-800, representing 22.18% of all bookings. The subsequent popular models are Boeing 737 MAX 8 at 15.70%, Boeing 737-800 Passenger/BBJ2 (winglets) at 11.09%, and Airbus A320 (sharklets) at 10.92%.
What is the most popular airline from Fort Myers to Chicago Midway Airport?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Fort Myers to Chicago Midway Airport is Southwest (82% of total bookings). The next most popular airline is Delta (18%).
Best airlines flying from Fort Myers to Chicago Midway Airport
Compare and see reviews for airlines that fly from Fort Myers to Chicago Midway Airport with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $210 | Free Cancellation | Rating 8.0 4,279 reviews | |||
| PriceFrom $216 | Free Cancellation | Rating 8.0 7,965 reviews |
Southwest Flights From Fort Myers to Chicago Midway Airport
Southwest flight deals from Fort Myers to Chicago Midway Airport start from $210 round-trip. Over the 15 Southwest flights for this route in a normal week, average airfare is usually $396 round-trip - but some users have found much cheaper deals with momondo.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsWhy use momondo?
Why should I use momondo to find a flight deal from Fort Myers to Chicago?
To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Fort Myers.
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?
momondo provides multiple filters to help you find the best flight to Chicago from Fort Myers. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.
I’m not ready to book a flight from Fort Myers to Chicago right now. Can momondo alert me if prices change?
Of course. momondo tracks the price of Fort Myers to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.