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United Flights from Chicago (ORD) to Key West (EYW) from $157

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Amazing United ORD to EYW Flight Deals

The cheapest flights to Key West Intl. found within the past 7 days were round trip and $157 one way. Prices and availability subject to change. Additional terms may apply.

Sun, Apr 11 -
ORD
Chicago
to
EYW
Key West
$157

One way

found 1 day ago

Open ORD to EYW flights search result page
Sun, Apr 11 -
ORD
Chicago
to
EYW
Key West
$166

One way

found 1 day ago

Open ORD to EYW flights search result page
Sun, Apr 18 -
ORD
Chicago
to
EYW
Key West
$171

One way

found 3 days ago

Open ORD to EYW flights search result page
Sun, Mar 7 -
ORD
Chicago
to
EYW
Key West
$182

One way

found 6 days ago

Open ORD to EYW flights search result page
Fri, Apr 2 -
ORD
Chicago
to
EYW
Key West
$183

One way

found 1 day ago

Open ORD to EYW flights search result page
Fri, Apr 2 -
ORD
Chicago
to
EYW
Key West
$192

One way

found 1 day ago

Open ORD to EYW flights search result page
Thu, May 20 -
ORD
Chicago
to
EYW
Key West
$194

One way

found 1 day ago

Open ORD to EYW flights search result page
Sat, May 8 -
ORD
Chicago
to
EYW
Key West
$198

One way

found 2 hours ago

Open ORD to EYW flights search result page
Sat, May 8 -
ORD
Chicago
to
EYW
Key West
$211

One way

found 2 hours ago

Open ORD to EYW flights search result page
Thu, May 13 -
ORD
Chicago
to
EYW
Key West
$214

One way

just found

Open ORD to EYW flights search result page
Fri, Oct 22 -
ORD
Chicago
to
EYW
Key West
$230

One way

just found

Open ORD to EYW flights search result page
Sun, Mar 7 -
ORD
Chicago
to
EYW
Key West
$182

One way

found 6 days ago

Open ORD to EYW flights search result page
Sun, Apr 11 -
ORD
Chicago
to
EYW
Key West
$157

One way

found 1 day ago

Open ORD to EYW flights search result page
Sun, Apr 11 -
ORD
Chicago
to
EYW
Key West
$166

One way

found 1 day ago

Open ORD to EYW flights search result page
Sun, Apr 18 -
ORD
Chicago
to
EYW
Key West
$171

One way

found 3 days ago

Open ORD to EYW flights search result page
Fri, Apr 2 -
ORD
Chicago
to
EYW
Key West
$183

One way

found 1 day ago

Open ORD to EYW flights search result page
Fri, Apr 2 -
ORD
Chicago
to
EYW
Key West
$192

One way

found 1 day ago

Open ORD to EYW flights search result page
Thu, May 20 -
ORD
Chicago
to
EYW
Key West
$194

One way

found 1 day ago

Open ORD to EYW flights search result page
Sat, May 8 -
ORD
Chicago
to
EYW
Key West
$198

One way

found 2 hours ago

Open ORD to EYW flights search result page
Sat, May 8 -
ORD
Chicago
to
EYW
Key West
$211

One way

found 2 hours ago

Open ORD to EYW flights search result page
Thu, May 13 -
ORD
Chicago
to
EYW
Key West
$214

One way

just found

Open ORD to EYW flights search result page
Fri, Oct 22 -
ORD
Chicago
to
EYW
Key West
$230

One way

just found

Open ORD to EYW flights search result page

EYW From ORD Economy Coach Packages on Similar Airlines

Save $241
CHI
CHI-All Airports
to
EYW
Key West Intl.
JetBlue AirwaysEconomy
The Southernmost Inn-Adults Only
2.5 out of 5.0

Fri, Mar 26 - Tue, Mar 30

Old price

$1,518

The price now is $1,277 per person
Flight + Hotel
The Southernmost Inn-Adults Only
Save $353
CHI
CHI-All Airports
to
EYW
Key West Intl.
JetBlue AirwaysEconomy
Oceans Edge Key West Resort, Hotel & Marina
4.0 out of 5.0

Fri, Mar 26 - Tue, Mar 30

Old price

$2,236

The price now is $1,884 per person
Flight + Hotel
Oceans Edge Key West Resort, Hotel & Marina
Save $155
CHI
CHI-All Airports
to
EYW
Key West Intl.
American AirlinesEconomy
Southernmost Beach Resort
4.0 out of 5.0

Thu, May 13 - Mon, May 17

Old price

$1,308

The price now is $1,153 per person
Flight + Hotel
Southernmost Beach Resort

FAQs about United Airlines Flights from ORD to EYW

What terminal is United Airlines at Chicago, IL (ORD-O'Hare Intl.)?

If you're traveling with United Airlines from Chicago, IL (ORD-O'Hare Intl.) to Key West, FL (EYW-Key West Intl.), you might be able to find out the terminal information once you're issued with your ticket. If not, check with your airline.

Are there United Airlines non-stop flights from ORD to EYW?

As you can't go direct from Chicago, IL (ORD-O'Hare Intl.) to Key West, FL (EYW-Key West Intl.) with United Airlines, make the most of your layover. Sit down to a couple of drinks at a welcoming airport bar, or wander about the terminal and enjoy a little retail therapy.

How long is an United Airlines flight from ORD to EYW?

Squeeze in some in-flight shut-eye and arrive at your destination feeling refreshed. You'll have sufficient time to do so when traveling with United Airlines between ORD and EYW, with the flight taking on average 4 hours and 26 minutes.

How many direct and indirect flights does United Airlines fly from ORD to EYW?

You'll have loads of choice if you fly with United Airlines from ORD to EYW. At the moment, it operates no fewer than 2 flights each day.

If I am not able to travel due to COVID-19, can I change my booking to a later date?

For more info about changing your flight to Key West, FL (EYW-Key West Intl.), please visit our Customer Service Portal.

What is the best day to buy a plane ticket?

This just in! Airfares offered on Tuesdays tend to be the cheapest, according to flight demand on Travelocity in 2019. Wednesday and Friday prices are also good, but you may want to prepare your budget if booking on a Monday, as data shows the start of the week is when prices are generally at their highest.

What are the cheapest days to fly?

Frequent travelers may already know this, but earlier in the week can be the cheapest time to fly. In 2019, flights departing on a Tuesday were generally the cheapest of the week, whereas you may pay a premium for weekend flights when demand is usually high. On average, tickets were most expensive for Saturday departures, so if you need to fly out on a weekend, you might look for deals ahead of time.

How far in advance can you book a flight?

Trying to figure out how early you should book your flight? It's possible to start comparing international airfares on Travelocity up to 12 months in advance. However, it does depend on the carrier as not all airlines release their prices that far out. According to our 2019 flight demand trends, last minute planners can still bag a bargain with some of the cheapest fares appearing 1-2 weeks prior to their travel dates.

How can I save money on airline tickets?

We'll let you in on a secret...You can save big on flights if you mix and match your airlines and fare types. In fact, travelers who booked flights on Travelocity in 2019 saved nearly 50% when their return flights consisted of two different airlines or fare types.

*According to flight demand on Travelocity.com from January to December 2019. Savings are subject to change based on departure location, date and destination.

Carrier Flight Depart ORD Arrive EYW Sun
2/28		 Mon
3/1		 Tue
3/2		 Wed
3/3		 Thu
3/4		 Fri
3/5		 Sat
3/6		 Stops
UA 3632 11:15 am 03:29 pm Check fare Check fare Check fare - Check fare Check fare Check fare 0 stop(s)
UA 3577 09:00 am 01:11 pm - - - Check fare Check fare - Check fare 0 stop(s)

Travelers ❤️ these 🏨 after their flight to Key West

Price for 1 night 2 adults*

DoubleTree Resort by Hilton Grand Key - Key West
DoubleTree Resort by Hilton Grand Key - Key West
3.5 out of 5.0 3990 S Roosevelt Blvd, Key West, FL
$349

Per night/room

Mar 1 - Mar 2

4.2/5 (20 reviews)

Very friendly staff and efficient!! I would recommend this property to anyone that wants to stay in Key West without being in the middle of tourism

Reviewed on Jun 30, 2020
This resort features a restaurant, an outdoor pool, and a poolside bar. Traveling on business? Take advantage of the 24-hour business center and free WiFi in ...
Barbary Beach House Key West
Barbary Beach House Key West
4.0 out of 5.0 2001 South Roosevelt Boulevard, Key West, FL
$349

Per night/room

Feb 28 - Mar 1

5.0/5 (4 reviews)

The property was easy to get to, plenty of parking. The staff were all very helpful and accommodating. Especially emjoyed the Trivia night and Sips and Tales night. The sister property is also available to use and we were able to cruise Key Westr in a 57 Chevy, while Amy shared interesting historical ...

Reviewed on Feb 13, 2021
This hotel features a restaurant, an outdoor pool, and a bar/lounge. You'll appreciate the area shuttle, free self parking, and dry cleaning.
Ibis Bay Beach Resort
Ibis Bay Beach Resort
2.5 out of 5.0 3101 N. Roosevelt Blvd, Key West, FL
$314

Per night/room

Mar 3 - Mar 4

4.0/5 (39 reviews)

The property is exactly like the pictures. It is an older hotel, but it is maintained great and was very clean. The shuttle service is great and we used it every day. The staff was friendly. We would stay there again. The breakfast was pretty basic, the same every morning. Coffee was good.

Reviewed on Feb 4, 2021
This Art Deco hotel features a private beach, a marina, and a restaurant. Enjoy a day at the beach kayaking, or relax with sun loungers. Enjoy the outdoor pool ...

Popular United Flight Routes from ORD

Top United Flight Routes from EYW

Top Flights for United originating from ORD

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.