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

United Airlines and American Airlines fly the EYW to ORD nonstop about 8 times a week. United Airlines sets the rhythm here, a few flights a day with a small premium cabin on each, so a date with open space is worth acting on the day you see it. 2LNR tracks confirmed upgrade and award space on American Airlines, on every EYW to ORD 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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8
Nonstop flights a week
1,254 mi
Nonstop distance
Free
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Key West to Chicago flight schedule

Scheduled nonstop departures for EYW to ORD, 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 Key West (EYW) to Chicago (ORD)
Date Flight Airline Departs EYW Arrives ORD Duration Aircraft
UA 3499United Airlines16:0018:553h 55mE7W
UA 3499United Airlines16:0018:553h 55mE7W
UA 3499United Airlines16:0018:553h 55mE7W
UA 3499United Airlines16:0018:553h 55mE7W
UA 3499United Airlines16:0018:553h 55mE7W
UA 3499United Airlines16:0018:553h 55mE7W
UA 3499United Airlines16:0018:553h 55mE7W

Showing all 7 scheduled EYW to ORD 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 EYW to ORD date on the interactive map

Confirmed upgrade & award space on EYW to ORD departures

2LNR tracks confirmed upgrade and award space on American Airlines, segment by segment and date by date. Open the calendar for Key West to Chicago 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 EYW to ORD 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 EYW to ORD on the interactive route map, with schedules, connections, and route statistics.

Airlines flying Key West to Chicago nonstop

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

See EYW to ORD on the interactive map →

Frequently asked questions about EYW to ORD

How far is Chicago from Key West?
EYW to ORD 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 EYW to ORD?
United Airlines and American Airlines fly the route nonstop. 2LNR tracks confirmed upgrade and award space on American Airlines.
How many flights a week are there from EYW to ORD?
About 8 nonstop flights a week run between Key West and Chicago 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 EYW to ORD depart?
In the next 7 days with service, every scheduled EYW to ORD nonstop leaves at 16:00 local time at Key West. The schedule table on this page lists each departure by date.
How do I check upgrade or award availability on EYW to ORD?
Open the EYW to ORD 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 EYW to ORD 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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