Your next trip, last seen at €61
Lowest observedWhen to fly
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The lowest fare we observed for each month. Open a month to see its days, then pick your outbound and return. A day with no price is one we will search for you.
- Lowest observed
- €61, departing 21 Jan 2027 (Last checked: 1 Oct 2026)One-way fare · Priced departure days checked in the last 14 days: 87Check live prices for this route
- Airlines seen
- American Airlines, Breeze Airways, Delta Air Lines, Frontier Airlines, Sun Country Airlines, United Airlines
- Reported fastest flight
- 3h 10m
- Non-stop
- Yes
About this route
Explore the fares we observed from Fort Myers to Chicago. Prices move often, so pick your dates to see the latest options.
- Route distance
- 1,774 km
- Reported fastest flight
- 3h 10m
- Airlines seen
- American Airlines, Breeze Airways, Delta Air Lines, Frontier Airlines, Sun Country Airlines, United Airlines
- Alternative airports
- CGX, DPA, MDW, PWK, RFD
Route-level information; individual journeys vary.
Published schedules report non-stop service with American Airlines, Southwest Airlines. Check current timetables.
A clearer picture of your fare
Non-stop airlines seen on this route
| Airline | Non-stop days / priced days | Fastest non-stop |
|---|---|---|
| United Airlines | 46 / 91 | |
| Frontier Airlines | 28 / 91 | |
| American Airlines | 4 / 91 |
Departure days with a non-stop fare checked in the last 14 days. A carrier listed here had a non-stop fare on at least 3 days; schedules may differ.
Airport to city: straight-line distance
- Southwest Florida International Airport (RSW) → Fort Myers, city gazetteer reference point (26.6406, -81.8723): ≈ 17 km.
- Chicago Midway International Airport (MDW) → Chicago, city gazetteer reference point (41.8781, -87.6298): ≈ 14 km.
- Chicago O'Hare International Airport (ORD) → Chicago, city gazetteer reference point (41.8781, -87.6298): ≈ 25 km.
- Chicago Rockford International Airport (RFD) → Chicago, city gazetteer reference point (41.8781, -87.6298): ≈ 126 km.
Approximate distances calculated from coordinates, not road distances or travel times. These airports serve the city; they are not confirmed endpoints of an offer.
Lowest fare by departure month
Cheapest month from Fort Myers to Chicago: November 2026, from €61 (checked 8 Oct 2026).
| Month | Lowest fare | Priced days |
|---|---|---|
| October 2026 | €89 | 20 |
| November 2026 | €61 | 30 |
| December 2026 | €61 | 31 |
| January 2027 | €61 | 6 |
Lowest fare by day of the week
Cheapest day of the week from Fort Myers to Chicago: Monday, from €61 (checked 8 Oct 2026).
| Day | Lowest fare | Priced days |
|---|---|---|
| Monday | €61 | 13 |
| Tuesday | €61 | 13 |
| Wednesday | €91 | 13 |
| Thursday | €61 | 13 |
| Friday | €89 | 13 |
| Saturday | €98 | 11 |
| Sunday | €90 | 11 |
One-way fares checked in the last 14 days. Each figure is the lowest priced departure day we saw, not a guaranteed fare.
Lowest fare by days before departure
Lowest fare from Fort Myers to Chicago by days until departure (31 to 60 days): €61 (checked 8 Oct 2026).
| Days before departure | Lowest fare | Priced days |
|---|---|---|
| 0 to 7 days | €194 | 8 |
| 8 to 30 days | €89 | 23 |
| 31 to 60 days | €61 | 30 |
| 61 days or more | €61 | 26 |
One-way fares checked in the last 14 days. Each figure is the lowest stored fare for that distance to departure, not a price forecast.
Fares for different departure dates, checked now; not a guide to when to book.
Lowest one-way fare we saw per airline
Cheapest airline from Fort Myers to Chicago: Frontier Airlines, from €61 (checked 8 Oct 2026).
| Airline | Lowest fare | Priced days |
|---|---|---|
| Frontier Airlines | €61Nov 23, 2026 | 40 |
| United Airlines | €98Oct 26, 2026 | 53 |
| American Airlines | €138Nov 19, 2026 | 6 |
| Breeze Airways | €142Nov 1, 2026 | 3 |
| Delta Air Lines | €161Mar 17, 2027 | 3 |
One-way fares checked in the last 14 days. An airline listed here had a fare on at least 3 departure days. Each figure is the lowest we saw, not a guaranteed fare. Connecting itineraries are included; the date is the departure day of that fare.
Frequently asked
How much is a flight from Fort Myers to Chicago?
The lowest fare we have observed is €61, found on 1 Oct 2026. Prices move, so read it as a floor rather than a quote.
When is the cheapest month to fly from Fort Myers to Chicago?
Cheapest month from Fort Myers to Chicago: November 2026, from €61 (checked 8 Oct 2026).
Are there direct flights from Fort Myers to Chicago?
Yes. We have seen non-stop flights on this route, flown by American Airlines, Southwest Airlines.
Which airlines fly from Fort Myers to Chicago?
These are the carriers we have seen on the route: American Airlines, Breeze Airways, Delta Air Lines, Frontier Airlines, Sun Country Airlines, United Airlines.
How long does the flight from Fort Myers to Chicago take?
The average journey time across the 90 fares we observed is 5h 45m, including any stops. Individual departures vary; the fastest observed flight is listed in the route facts above.
How many of the observed Fort Myers to Chicago fares were non-stop?
71 of the 91 fares we observed were non-stop; the rest included at least one stop. That describes our observations, not every flight that operates.
Which airlines had non-stop offers on at least 3 departure dates from Fort Myers to Chicago?
For Fort Myers to Chicago, examples of observed one-way non-stop offers checked within the last 14 days: United Airlines (46), Frontier Airlines (28), American Airlines (4). Each number counts distinct departure dates, not weekly flights; check current availability in search.
Which day of the week is cheapest from Fort Myers to Chicago?
Cheapest day of the week from Fort Myers to Chicago: Monday, from €61 (checked 8 Oct 2026).
Which airline has the lowest fare from Fort Myers to Chicago?
Cheapest airline from Fort Myers to Chicago: Frontier Airlines, from €61 (checked 8 Oct 2026).
How observed prices work, what "No data" means and what a fare includes: Read the flight price guide
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Recently observed fares. Prices may change.
Last checked: 8 Oct 2026