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

United Airlines and American Airlines fly nonstop between Key West (EYW) and Chicago (ORD), roughly 18 times a week. The timetable below shows the nonstop scheduled at 3h 39m to 3h 55m 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 .

See EYW to ORD on the interactive map Get started free
18
Flights a week, 4-week average
3h 39m to 3h 55m
Scheduled flight time
1,254 mi
Nonstop distance
Free
To get started

Key West to Chicago flight schedule

Scheduled nonstop departures for EYW to ORD starting October 23, 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 Key West (EYW) to Chicago (ORD)
Date Flight Airline Departs EYW Arrives ORD Duration Aircraft
UA 3499United Airlines16:0018:553h 55mEmbraer E175
UA 2304United Airlines16:2018:593h 39mBoeing 737-700
UA 3583United Airlines16:0018:503h 50mEmbraer E175
UA 3583United Airlines16:0018:503h 50mEmbraer E175
UA 3583United Airlines16:0018:503h 50mEmbraer E175
UA 3551United Airlines16:1018:593h 49mEmbraer E175
UA 3583United Airlines16:0018:503h 50mEmbraer E175
UA 3551United Airlines16:1018:593h 49mEmbraer E175
UA 3583United Airlines16:0018:503h 50mEmbraer E175
UA 3551United Airlines16:1018:593h 49mEmbraer E175

Showing all 10 scheduled EYW to ORD departures across 7 days with service, starting October 23, 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 EYW to ORD date on the interactive map

Aircraft on the Key West to Chicago nonstop

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

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.

American Airlines award space was open on the one Key West to Chicago 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 EYW to ORD 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 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. Where 2LNR tracks the carrier, its departures show confirmed upgrade or award space by date.

See EYW to ORD on the interactive map →

Frequently asked questions about EYW to ORD

How long is the flight from Key West (EYW) to Chicago (ORD)?
Scheduled flight times from Key West (EYW) to Chicago (ORD) run from 3h 39m to 3h 55m 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 EYW to ORD?
United Airlines and American Airlines fly EYW to ORD nonstop. 2LNR tracks confirmed upgrade and award space on American Airlines.
How many flights a week are there from EYW to ORD?
About 18 nonstop flights a week run between Key West (EYW) and Chicago (ORD) 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?
Scheduled EYW to ORD nonstops in the next 7 days with service leave between 16:00 and 16:20, local time at Key West. The schedule table on this page lists every departure by date, with its arrival time and aircraft.
Which flights operate EYW to ORD nonstop?
In the schedule table on this page, EYW to ORD nonstops fly as UA 2304, UA 3499, UA 3551, and UA 3583 on United Airlines. The table lists each departure by date with its times and aircraft.
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's open by date on this route, the next 14 days free on every product and the full horizon on Pro.

Get started free