Key West (EYW) to Chicago (ORD) flights
Envoy Air, Republic Airline fly nonstop from Key West International Airport to Chicago O'Hare International Airport, with about 13 flights a week in July 2026. The 1,251-mile flight takes about 3h 42m gate to gate.
- Distance
- 1,251 mi · 2,013 km
- Flight time
- 3h 42m
- Airlines
- 2
- Seats filled
- 79%
Airlines flying EYW to ORD
| Airline | Flights a week | Aircraft | Passengers (12 months) | Flight time |
|---|---|---|---|---|
| Envoy Air | 7 | Embraer E170, Embraer E175 | 22,633 | 3h 40m |
| Republic Airline | 7 | Embraer E175, Embraer E170 | 9,455 | 3h 43m |
| United AirlinesSeasonal or ended | n/a | Boeing 737-700 / MAX 7 | 14,647 | 3h 46m |
Airlines are the operating carrier: regional airlines such as SkyWest or Horizon often fly under a larger airline's brand.
EYW to ORD flight schedule
3 flight numbers flew this route in August 2026, 1 of them almost daily. The first usually leaves at 4:00pm and the last at 4:56pm. Times are local and can change; check with the airline before you book.
| Flight | Departs | Arrives | Days flown in August 2026 | On time (12 months) |
|---|---|---|---|---|
| UA 3499United Airlines · operated by Republic Airline | 4:00pm | 6:55pm | 10 | 84% |
| AA 3996American Airlines · operated by Envoy Air | 4:18pm | 7:06pm | 4 | 67% |
| AA 3954American Airlines · operated by Envoy Air | 4:56pm | 7:48pm | 27 | 74% |
Is EYW to ORD on time?
From September 2025 to August 2026, 69% of 815 flights arrived within 15 minutes of schedule and 1.5% were cancelled. Flights leaving around 1pm were the most punctual (69%), those around 3pm the least (64%). Most delay time was caused by late-arriving aircraft (39%).
| Airline | Flights | On time | Average delay | Cancelled |
|---|---|---|---|---|
| American Airlines | 465 | 68% | 29 min | 1.3% |
| United Airlines | 350 | 70% | 30 min | 1.7% |
Airlines as sold: flights operated by regional partners count under the airline on the ticket. Average delay is across all completed flights, early arrivals counted as zero.
On-time arrivals by departure time
| Scheduled departure | Flights | On time, relative | On time |
|---|---|---|---|
| 7am to 8am | 33 | 84% | |
| 12pm to 1pm | 28 | 89% | |
| 1pm to 2pm | 193 | 69% | |
| 3pm to 4pm | 88 | 64% | |
| 4pm to 5pm | 351 | 67% | |
| 6pm to 7pm | 114 | 65% |
Flights by month
| Month | Flights | Flights, relative | Passengers |
|---|---|---|---|
| August 2025 | 1 | 58 | |
| October 2025 | 5 | 214 | |
| November 2025 | 65 | 3,493 | |
| December 2025 | 88 | 4,858 | |
| January 2026 | 98 | 7,419 | |
| February 2026 | 95 | 6,820 | |
| March 2026 | 106 | 7,555 | |
| April 2026 | 92 | 6,423 | |
| May 2026 | 80 | 4,066 | |
| June 2026 | 55 | 2,907 | |
| July 2026 | 59 | 2,922 |
Related
Source: US Department of Transportation, T-100 Segment data, August 2025 to July 2026.