$235 Cheap United flights Chicago (ORD) to Key West (EYW)

View $235 flight on Tue, Sep 9, 2025Opens in a new window

$235 Cheap United flights Chicago (ORD) to Key West (EYW)

Prices were available within the past 7 days and start at $235 for one-way flights and $249 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

United
Thu, May 21 - Mon, May 25
ORD
Chicago
EYW
Key West
$249 Roundtrip, just found
$249
Roundtrip
just found
Select United flight, departing Thu, May 21 from Chicago to Key West, returning Mon, May 25, priced at $249 just found
United
Wed, Jan 7 - Mon, Jan 12
ORD
Chicago
EYW
Key West
$259 Roundtrip, just found
$259
Roundtrip
just found
Select United flight, departing Wed, Jan 7 from Chicago to Key West, returning Mon, Jan 12, priced at $259 just found
United
Wed, May 27 - Mon, Jun 1
ORD
Chicago
EYW
Key West
$265 Roundtrip, found 2 days ago
$265
Roundtrip
found 2 days ago
Select United flight, departing Wed, May 27 from Chicago to Key West, returning Mon, Jun 1, priced at $265 found 2 days ago
United
Sun, May 24 - Mon, Jun 1
ORD
Chicago
EYW
Key West
$266 Roundtrip, found 4 days ago
$266
Roundtrip
found 4 days ago
Select United flight, departing Sun, May 24 from Chicago to Key West, returning Mon, Jun 1, priced at $266 found 4 days ago
United
Fri, Jan 9 - Tue, Jan 13
ORD
Chicago
EYW
Key West
$269 Roundtrip, just found
$269
Roundtrip
just found
Select United flight, departing Fri, Jan 9 from Chicago to Key West, returning Tue, Jan 13, priced at $269 just found
United
Wed, Jan 7 - Sun, Jan 11
ORD
Chicago
EYW
Key West
$272 Roundtrip, just found
$272
Roundtrip
just found
Select United flight, departing Wed, Jan 7 from Chicago to Key West, returning Sun, Jan 11, priced at $272 just found
United
Wed, Mar 11 - Sat, Mar 14
ORD
Chicago
EYW
Key West
$273 Roundtrip, found 23 hours ago
$273
Roundtrip
found 23 hours ago
Select United flight, departing Wed, Mar 11 from Chicago to Key West, returning Sat, Mar 14, priced at $273 found 23 hours ago
United
Thu, Jan 8 - Thu, Jan 15
ORD
Chicago
EYW
Key West
$277 Roundtrip, found 5 days ago
$277
Roundtrip
found 5 days ago
Select United flight, departing Thu, Jan 8 from Chicago to Key West, returning Thu, Jan 15, priced at $277 found 5 days ago
United
Fri, Jan 9 - Tue, Jan 13
ORD
Chicago
EYW
Key West
$279 Roundtrip, just found
$279
Roundtrip
just found
Select United flight, departing Fri, Jan 9 from Chicago to Key West, returning Tue, Jan 13, priced at $279 just found
Flights from Chicago (ORD) to Key West (EYW)
Origin airport
O'Hare Intl.
Destination airport
Key West Intl.
Airlines serving
American Airlines, Delta, JetBlue Airways, Spirit Airlines, United
Popular airline
American Airlines
Distance
1254 mi

Frequently asked questions

How much is a United Airlines flight from O'Hare Intl. Airport (ORD) to Key West Intl. Airport (EYW)?
Make use of the "Price (lowest to highest)" filter on Expedia to find cheap United Airlines return flights from $249 from ORD to EYW. Affordable one-way tickets from $235 are also available.**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?
Search for return or one-way flights to Key West in September or August. You could find a cheap fare with United Airlines during these quieter months.
What is the cheapest time to book flights from O'Hare Intl. Airport (ORD) to Key West Intl. Airport (EYW) with United Airlines?
Begin your search one to three months ahead of your departure date to find cheaper fares on United Airlines flights from O'Hare Intl. Airport (ORD) to Key West Intl. Airport (EYW). You can save 25% by booking your domestic flight 34 to 86 days in advance compared to last-minute reservations made 6 to 12 days out. You could also reduce costs by buying your fare on a Sunday, as it's 6% cheaper on average than a Monday, the most expensive day to book.* Time it well, and you can enjoy significant savings on domestic trips.*Ideal booking window recommendation is based on average round-trip ticket prices for January through November for 2024. Best day of the week to book recommendation is based on average round-trip ticket prices for January through October 2024. All data sourced from ARC's global airline sales database.
Does United Airlines fly nonstop from O'Hare Intl. Airport (ORD) to Key West Intl. Airport (EYW)?
Depart on one of United Airlines's 7 weekly direct flights from O'Hare Intl. Airport (ORD) to Key West Intl. Airport (EYW). To view available options, enter your dates, destination and origin and hit search. Then select the "Nonstop" and "Airline" filters.
How long does it take to fly from ORD to EYW with United Airlines?
It takes around 3h 14m to fly nonstop from O'Hare Intl. Airport (ORD) to Key West Intl. Airport (EYW) with United Airlines.
What is the earliest United Airlines flight from ORD to EYW?
The first flight from ORD to EYW with United Airlines departs at 10:35AM UTC-6. You'll land at 2:49PM UTC-5. The final United Airlines flight of the day leaves at 10:36AM UTC-6 and arrives at 2:50PM UTC-5. With 20% fewer cancellations for departures before midday, heading out early is often the wisest option.**Most reliable time of the day recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports does United Airlines fly into in Key West?
Key West Intl. Airport (EYW) is the primary Key West gateway for United Airlines flights from O'Hare Intl. Airport (ORD).
Why fly with United Airlines from ORD to EYW?
A rewarding loyalty program and the ability to collect points through United Mileage Plus are the start of the reasons to travel from ORD to EYW with United Airlines. Plus, when you sign up to our One Key™ program, you can receive OneKeyCash™* on top of any airline loyalty program earnings. It's yours to spend on future bookings.*OneKeyCash™ disclaimer - OneKeyCash™ is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.
What type of plane does United Airlines fly from O'Hare Intl. Airport (ORD) to Key West Intl. Airport (EYW)?
United Airlines typically uses Boeing 737-700 planes for journeys from O'Hare Intl. Airport (ORD) to Key West Intl. Airport (EYW). Keep in mind that aircraft type can change depending on operational demands, so the plane you catch might be different on your travel date.
Can I change or cancel my United Airlines flight from O'Hare Intl. Airport (ORD) to Key West Intl. Airport (EYW)?
Changes are typically free within 24 hours of making your booking, but your airline may add a charge after that. For further details about altering your reservation, go to your "Trips," select your flight and click on "Manage Booking." If you'd like the flexibility to adjust your plans without extra charges, check the "Changes included" or "No cancel fee" filter when organizing your trip.

Explore a world of travel with Expedia

*Available to One Key members.