United Cheap Flights from Chicago to Key West

View €216 flight on Mon, 27 Oct 2025Opens in a new window

  • Plan, book, fly with confidence

  • trending down icon

    Be in the know

    Get alerts if flight prices drop or rise*
  • bex rewards loyalty icon

    Book smarter

    Save up to 15% on select hotels after you book a flight*
  • payments icon

    Earn twice

    Earn your airline miles on top of our rewards
    Sign in

Prices were available within the past 7 days and start at €216 for one-way flights and €281 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

United
Mon, 27 Oct - Wed, 5 Nov
ORD
Chicago
EYW
Key West
€281 Return, found 2 days ago
€281
Return
found 2 days ago
Select United flight, departing Mon, 27 Oct from Chicago to Key West, returning Wed, 5 Nov, priced at €281 found 2 days ago
United
Mon, 27 Oct - Wed, 5 Nov
ORD
Chicago
EYW
Key West
€290 Return, found 2 days ago
€290
Return
found 2 days ago
Select United flight, departing Mon, 27 Oct from Chicago to Key West, returning Wed, 5 Nov, priced at €290 found 2 days ago
United
Mon, 27 Oct - Wed, 5 Nov
ORD
Chicago
EYW
Key West
€344 Return, found 2 days ago
€344
Return
found 2 days ago
Select United flight, departing Mon, 27 Oct from Chicago to Key West, returning Wed, 5 Nov, priced at €344 found 2 days ago
United
Mon, 27 Oct - Wed, 5 Nov
ORD
Chicago
EYW
Key West
€350 Return, found 2 days ago
€350
Return
found 2 days ago
Select United flight, departing Mon, 27 Oct from Chicago to Key West, returning Wed, 5 Nov, priced at €350 found 2 days ago
United
Mon, 27 Oct - Wed, 5 Nov
ORD
Chicago
EYW
Key West
€352 Return, found 2 days ago
€352
Return
found 2 days ago
Select United flight, departing Mon, 27 Oct from Chicago to Key West, returning Wed, 5 Nov, priced at €352 found 2 days ago
United
Mon, 27 Oct - Wed, 5 Nov
ORD
Chicago
EYW
Key West
€358 Return, found 2 days ago
€358
Return
found 2 days ago
Select United flight, departing Mon, 27 Oct from Chicago to Key West, returning Wed, 5 Nov, priced at €358 found 2 days ago
United
Mon, 27 Oct - Wed, 5 Nov
ORD
Chicago
EYW
Key West
€405 Return, found 2 days ago
€405
Return
found 2 days ago
Select United flight, departing Mon, 27 Oct from Chicago to Key West, returning Wed, 5 Nov, priced at €405 found 2 days ago
United
Mon, 27 Oct - Wed, 5 Nov
ORD
Chicago
EYW
Key West
€419 Return, found 2 days ago
€419
Return
found 2 days ago
Select United flight, departing Mon, 27 Oct from Chicago to Key West, returning Wed, 5 Nov, priced at €419 found 2 days ago
United
Mon, 27 Oct - Wed, 5 Nov
ORD
Chicago
EYW
Key West
€440 Return, found 2 days ago
€440
Return
found 2 days ago
Select United flight, departing Mon, 27 Oct from Chicago to Key West, returning Wed, 5 Nov, priced at €440 found 2 days ago
Chicago to Key West route information
Origin airport
O'Hare Intl.
Destination airport
Key West Intl.
Distance
2006 km

Frequently asked questions

How much is a United Airlines flight from O'Hare Intl. Airport (ORD) to Key West Intl. Airport (EYW)?
You'll find affordable round-trip United Airlines flights from €281 from ORD to EYW by organising your results from "Price (lowest to highest)" on Expedia. Or search for bargains from €216 for a one-way trip.**These prices were available on Expedia within the past 7 days, for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
What is the cheapest month to fly from ORD to EYW with United Airlines?
Browse for return or one-way flights to Key West in September or August. You could find lower fares with United Airlines during these quieter months.
Does United Airlines fly nonstop from O'Hare Intl. Airport (ORD) to Key West Intl. Airport (EYW)?
United Airlines has direct flights from O'Hare Intl. Airport (ORD) to Key West Intl. Airport (EYW), with 7 departures each week. Just apply the "Nonstop" and "Airline" filters while searching on Expedia to show all direct United Airlines flights to EYW.
How long does it take to fly from ORD to EYW with United Airlines?
The travel time for a direct United Airlines flight from O'Hare Intl. Airport (ORD) to Key West Intl. Airport (EYW) takes around 3h 14m.
What airports does United Airlines fly into in Key West?
Key West Intl. Airport (EYW) is the main Key West gateway for United Airlines flights from O'Hare Intl. Airport (ORD).
What type of plane does United Airlines fly from O'Hare Intl. Airport (ORD) to Key West Intl. Airport (EYW)?
Catch a United Airlines flight from O'Hare Intl. Airport (ORD) to Key West Intl. Airport (EYW), and you'll probably board a Boeing 737-700. Keep in mind though, that the aircraft type can change due to operational reasons.
Can I change or cancel my United Airlines flight from O'Hare Intl. Airport (ORD) to Key West Intl. Airport (EYW)?
Changes are generally free within 24 hours of booking, but your airline may charge you after that. For further information about altering your flights, check out your "Trips," select your flight and click on "Manage Booking." If you want the flexibility to change your plans without being charged, apply the "No cancel fee" or "Changes included" filter when planning your trip.
*Available to Expedia members.