Allegiant AirDepart10:14
Fri, Nov 13EYW → MDW
3h 50m · 1 stop
$139one way, per person
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- Cheapest fare
- $139
- Cheapest month
- November
- Direct flights
- Not recently
- Quickest trip
- 3h 50m
Allegiant Air · Fri, Nov 13
from $139
Usually 1+ stop
2,000 km
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Cheapest month to fly from Key West to Chicago
Lowest one-way fare per person in each month. Choose a month to see every date.
Cheapest dates in November 2026
The lowest fares we've seen for each day, cheapest first.
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About flights from Key West to Chicago
Key West (EYW) and Chicago (CHI) are about 2,000 km apart. We haven't seen direct fares on this route recently, so expect at least one stop; the quickest journey we've seen takes about 3h 50m. Over the next few months, one-way fares start from $139, and November 2026 is currently the cheapest month to fly.
These prices come from searches travellers made in the last 48 hours, so they move quickly. If you see a good fare, it's worth booking soon. FlightsExp is free to use: you book directly with our travel partner.
Frequently asked questions
How much is a flight from Key West to Chicago?
The cheapest one-way fare we've seen recently is $139 with Allegiant Air, departing Friday, November 13, 2026.
What is the cheapest month to fly from Key West to Chicago?
November 2026 currently has the lowest fares, from $139 one way.
Are there direct flights from Key West to Chicago?
We haven't seen direct fares recently, so most journeys include at least one stop.
How long is the flight from Key West to Chicago?
The quickest journey we've seen takes about 3h 50m. Key West and Chicago are around 2,000 km apart.
Which airlines fly from Key West to Chicago?
Recent fares on this route were with Allegiant Air.
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