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

United Airlines and American Airlines fly nonstop between Chicago (ORD) and Key West (EYW), roughly 23 times a week. The timetable below shows the nonstop scheduled at 2h 8m to 3h 31m for the 1,254 miles. 2LNR checks confirmed upgrade and award space on American Airlines flights on this route, so you can see which departures have space before you book.

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

Updated .

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23
Flights a week, 4-week average
2h 8m to 3h 31m
Scheduled flight time
1,254 mi
Nonstop distance
Free
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Chicago to Key West flight schedule

Scheduled nonstop departures for ORD to EYW starting October 22, 2026, last checked against our schedule feed on October 18, 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
UA 752United Airlines11:1014:182h 8mBoeing 737-700
UA 3487United Airlines10:4515:163h 31mEmbraer E175
UA 2070United Airlines10:5515:063h 11mBoeing 737-700
UA 3487United Airlines10:4515:163h 31mEmbraer E175
UA 2070United Airlines10:5515:063h 11mBoeing 737-700
UA 2070United Airlines10:5515:063h 11mBoeing 737-700
UA 3487United Airlines11:0015:293h 29mEmbraer E175
UA 2070United Airlines10:5515:063h 11mBoeing 737-700
UA 3487United Airlines11:0015:293h 29mEmbraer E175
UA 2070United Airlines10:5515:063h 11mBoeing 737-700
UA 3487United Airlines11:0015:293h 29mEmbraer E175
UA 2070United Airlines10:5515:063h 11mBoeing 737-700
UA 3487United Airlines11:0015:293h 29mEmbraer E175

Showing all 13 scheduled ORD to EYW departures across 7 days with service, starting October 22, 2026. 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 hasn't filed that value in the schedule data we hold. Aircraft are the equipment the airline filed, named where the code pins down one type and shown as the family or the bare code where it doesn't. Swaps can happen up to departure.

See every ORD to EYW date on the interactive map

Aircraft on the Chicago to Key West nonstop

United Airlines flies the departures in the schedule table on this page with the Boeing 737-700 and the Embraer E175. Each linked aircraft page shows where that airline schedules it. Airlines can swap aircraft up to departure.

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.

American Airlines award space was open on the one Chicago to Key West departure date from October 19 to November 1 that 2LNR checked in the 7 days to October 19, 2026.

See real availability

Confirmed upgrade or award seats by date on the ORD to EYW departures 2LNR tracks, checked against live inventory so you know what's open before you book.

Set an alert

Premium inventory turns over fast. Watch this route on Pro and 2LNR notifies you when space appears on a date you're 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. Where 2LNR tracks the carrier, its departures show confirmed upgrade or award space by date.

See ORD to EYW on the interactive map →

Frequently asked questions about ORD to EYW

How long is the flight from Chicago (ORD) to Key West (EYW)?
Scheduled flight times from Chicago (ORD) to Key West (EYW) run from 2h 8m to 3h 31m across the departures in the schedule table on this page. The nonstop covers about 1,254 miles, and airlines adjust scheduled times by season, so confirm with the airline before you book.
Which airlines fly nonstop from ORD to EYW?
United Airlines and American Airlines fly ORD to EYW nonstop. 2LNR tracks confirmed upgrade and award space on American Airlines.
How many flights a week are there from ORD to EYW?
About 23 nonstop flights a week run between Chicago (ORD) and Key West (EYW) in the current schedule, operated by United Airlines and American Airlines. Frequency shifts by season, and the schedule table on this page shows what is scheduled next.
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 11:10, local time at Chicago. The schedule table on this page lists every departure by date, with its arrival time and aircraft.
Which flights operate ORD to EYW nonstop?
In the schedule table on this page, ORD to EYW nonstops fly as UA 752, UA 2070, and UA 3487 on United Airlines. The table lists each departure by date with its times 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's open by date on this route, the next 14 days free on every product and the full horizon on Pro.

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