Route
Chicago to Key West: what the flight costs
In the last 60 days we checked this route 1 times. The typical round trip was $319 per person and the lowest $319, taxes and fees included.
| Per person | |
|---|---|
| Lowest seen | $319 |
| Typical (median) | $319 |
| Price checks, 60 days | 1 |
Every fare we found in the last 30 days
| Checked | Trip dates | Per person | Airline | Stops | Duration | Source |
|---|---|---|---|---|---|---|
| Oct 12, 2026 | Nov 7–10, 2026 | $319 | F9 + MX | with a stop | 13h 44m | Kiwi.com |
About Key West
Key West is the end of the road, a small island of pastel conch houses, sunset celebrations and reef snorkelling at the tip of the Florida Keys.
Key West from every city: when to go, where to stay, what to do
Questions about Chicago to Key West
What does a round trip from Chicago to Key West usually cost?
Over the last 60 days the typical price we found was $319 per person, taxes and fees included, across 1 checks; the lowest was $319.
When is the best time to fly from Chicago to Key West?
Key West is at its best in January, February, March, April, May, November and December. Avoid August, September, October: Peak hurricane season; many visitors wait until November
Do I need a passport to fly from Chicago to Key West?
No, a government photo ID is enough for US citizens.