Fort Myers to Chicago: what the flight costs
In the last 60 days we checked this route 6 times. The typical return was £446 per person and the lowest £372, taxes and fees included.
| Per person | |
|---|---|
| Lowest seen | £372 |
| Typical (median) | £446 |
| Price checks, 60 days | 6 |
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Trips we picked on this route
Next weekend · from Fort MyersLowest in 30 daysWorth it, if
Chicago
16 – 18 Oct 2026 · 2 nights
- $494 per person, $98 below the typical fare on this route
- Saturday and Sunday forecast: 1% rain chance, highs 52°F and 62°F
- River Hotel in The Loop scores 8.3 from 7,928 reviews
£1,122 for two · 2 nights · flights, hotel, taxes & fees
Flights £745 + hotel £378, taxes in · a checked bag each adds about £181
Frontier · with a stop · 10h 54m
The catch: The Frontier fare has 1 stop and takes 10h 54m, landing at 10:39 PM, while the American nonstop costs $545 per person.
Worth it if a long Friday travel day is fine for $98 per person saved; skip it if Friday evening in the city matters to you.
Every fare we found in the last 30 days
| Checked | Trip dates | Per person | Airline | Stops | Duration | Source |
|---|---|---|---|---|---|---|
| 12 Oct 2026 | 23 – 25 Oct 2026 | £452 | F9 | with a stop | 38h 7m | Kiwi.com |
| 12 Oct 2026 | 23 – 25 Oct 2026 | £372 | Frontier | with a stop | 10h 54m | Google Flights |
| 12 Oct 2026 | 16 – 18 Oct 2026 | £554 | UA | with a stop | 9h 45m | Kiwi.com |
| 12 Oct 2026 | 16 – 18 Oct 2026 | £372 | Frontier | with a stop | 10h 54m | Google Flights |
| 12 Oct 2026 | 23 – 25 Oct 2026 | £534 | UA | with a stop | 8h 55m | Kiwi.com |
| 12 Oct 2026 | 16 – 18 Oct 2026 | £440 | F9 | with a stop | 10h 54m | Kiwi.com |
About Chicago
Chicago offers skyscraper architecture, a lakefront of beaches and parks, blues clubs, deep-dish pizza and museums of world rank.
Chicago from every city: when to go, where to stay, what to do
Questions about Fort Myers to Chicago
What does a return from Fort Myers to Chicago usually cost?
Over the last 60 days the typical price we found was £446 per person, taxes and fees included, across 6 checks; the lowest was £372.
When is the best time to fly from Fort Myers to Chicago?
Chicago is at its best in May, June, July, August, September and October. Avoid December, January, February, March: Bitter cold and wind off the lake
Do I need a passport to fly from Fort Myers to Chicago?
No passport needed for travellers from the United States: a government photo ID is enough for Chicago.
Prices converted from US dollars at the rate of 15 Oct 2026.