Chicago to Key West (ORD-EYW): nonstop upgrade & award space

United Airlines and American Airlines fly nonstop from Chicago (ORD) to Key West (EYW) just once a week. With so few departures, each one carries the only premium seats on the route that day. 2LNR tracks confirmed upgrade and award space on American Airlines, on every ORD to EYW departure, so you know which flights have space before you book.

Schedule last confirmed . Departure times come from 2LNR's schedule data; confirm with the airline before you book.

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1
Nonstop flights a week
1,254 mi
Nonstop distance
Free
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Chicago to Key West flight schedule

Scheduled nonstop departures for ORD to EYW, last checked against our schedule feed on September 6, 2026. Airlines retime and cancel flights, so confirm with the airline before you book.

Schedule data dated .

Scheduled nonstop departures from Chicago (ORD) to Key West (EYW)
Date Flight Airline Departs ORD Arrives EYW Duration Aircraft
AA 3954American Airlines11:5916:183h 19mE70
UA 752United Airlines11:1014:182h 8m73G
UA 752United Airlines11:1014:182h 8m73G
UA 752United Airlines11:1014:182h 8m73G
UA 752United Airlines11:1014:182h 8m73G
UA 752United Airlines11:1014:182h 8m73G
UA 3487United Airlines10:4515:163h 31mE7W
UA 3597United Airlines10:4515:163h 31mE7W
UA 2070United Airlines10:5515:063h 11m73G

Showing all 9 scheduled ORD to EYW departures across the next 7 days with service. Later dates are on the interactive map.

Departure and arrival times are local at their own airport, so an arrival can fall on a different local date than the departure; the duration column is the true elapsed flying time. A dash means the airline has not filed that value in the schedule data we hold. Aircraft are IATA equipment codes as filed, and can change up to departure.

See every ORD to EYW date on the interactive map

Confirmed upgrade & award space on ORD to EYW departures

2LNR tracks confirmed upgrade and award space on American Airlines, segment by segment and date by date. Open the calendar for Chicago to Key West to see which departures have space, the next 14 days free on every product and the full horizon on Pro.

See real availability

Confirmed upgrade and award seats on each ORD to EYW departure, checked against live inventory so you know what is open before you book.

Set an alert

Premium inventory turns over fast. Watch this route and 2LNR notifies you when space appears on a date you are tracking.

Plan on the map

See ORD to EYW on the interactive route map, with schedules, connections, and route statistics.

Airlines flying Chicago to Key West nonstop

Carriers operating ORD to EYW nonstop in the current schedule. 2LNR tracks confirmed upgrade and award space on each of them.

See ORD to EYW on the interactive map →

Frequently asked questions about ORD to EYW

How far is Key West from Chicago?
ORD to EYW covers about 1,254 miles nonstop. Flight times vary by aircraft and season; the schedule table on this page lists each scheduled departure with its own times.
Which airlines fly nonstop from ORD to EYW?
United Airlines and American Airlines fly the route nonstop. 2LNR tracks confirmed upgrade and award space on American Airlines.
How often does ORD to EYW operate?
The nonstop currently runs once a week. Thin schedules like this change by season, and an alert will catch anything added.
What time do flights from ORD to EYW depart?
Scheduled ORD to EYW nonstops in the next 7 days with service leave between 10:45 and 11:59, local time at Chicago. The schedule table on this page lists every departure by date, with its arrival time and aircraft.
How do I check upgrade or award availability on ORD to EYW?
Open the ORD to EYW route on the interactive map or the matrix to see confirmed upgrade and award space by date on American Airlines, the next 14 days free and the full horizon on Pro. On Pro you can also set an alert on the route and 2LNR notifies you when space opens.

Never miss ORD to EYW upgrade or award space

See what is open by date on this route, the next 14 days free on every product and the full horizon on Pro.

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