Cheap Flight Tickets from Chicago (ORD) to Key West (EYW), Starting at $208

Good to Know: Cheapest and Fastest ORD - EYW Flights

Useful information for finding best airline tickets from Chicago O'Hare International to Key West International on your next trip.

Cheapest Round Trip Flight

$208

AA American Airlines • 2 stops • 12h 12m

Nov 05 – Nov 10

The cheapest round trip flight from Chicago to Key West (ORD-EYW-ORD) is currently $208

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Cheapest Direct Flight

$244

AA American Airlines • nonstop • 5h 22m

Nov 05

The cheapest nonstop flight from Chicago to Key West (ORD-EYW) is currently $244

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Fastest Flight

5h 22m

The fastest nonstop flight from Chicago to Key West (ORD-EYW) takes 5h 22m

Top Airlines Flying from Chicago to Key West

Delta Airline, DL

Delta Airlines

United Airlines, UA

United Airlines

American Airlines, AA

American Airlines

Latest Flight Deals from Chicago (ORD) to Key West (EYW)

Compare and book low fare round-trip air tickets from Chicago to Key West. Ideal for travelers with confirmed return itineraries.

Nov 05 - Nov 10, Economy
AA
Chicago → Key West
12h 12m
10:55 AM - 7:27 PM • 2 stops
AA
Chicago → Key West
5h 55m
6:35 PM - 9:30 PM • nonstop
$208
American Airlines
Nov 05 - Nov 10, Economy
DL
Chicago → Key West
8h 43m
6:30 AM - 12:53 PM • 1 stop
DL
Chicago → Key West
9h 15m
7:25 AM - 12:20 PM • 1 stop
$322
Delta Airlines
Nov 05 - Nov 10, Economy
F9
Chicago → Key West
33h 33m
1:06 PM - 10:19 AM • 2 stops
MX
Chicago → Key West
50h
1:16 PM - 6:16 PM • 2 stops
$400
Frontier Airlines
Nov 05 - Nov 10, Economy
AA
Chicago → Key West
17h 8m
6:57 AM - 6:25 PM • 1 stop
AA
Chicago → Key West
5h 55m
6:35 PM - 9:30 PM • nonstop
$619
American Airlines
Nov 05 - Nov 10, Economy
DL
Chicago → Key West
40h 53m
3:40 PM - 8:01 PM • 1 stop
DL
Chicago → Key West
16h 56m
7:25 AM - 4:41 PM • 2 stops
$1057
Delta Airlines
Nov 05 - Nov 10, Economy
AA
Chicago → Key West
31h 46m
2:38 PM - 10:44 AM • 1 stop
AA
Chicago → Key West
9h
5:50 PM - 10:30 PM • 1 stop
$1114
American Airlines

Fly from Chicago to Key West with the Best Airfare Deals on FareLeaders

Looking for a cheap last-minute deal or the best round-trip flight from Chicago to Key West? Find the biggest savings on one-way and round-trip tickets right here.

FAQs on Chicago to Key West Flights

What are the airports in Chicago?
MDW,ORD
What’s the most popular airline flying from ORD to EYW?
The most popular airline flying from Chicago to Key West are
Can I fly from ORD to EYW non-stop?
Yes, you can fly ORD to EYW non-stop on
Which airlines fly nonstop between Chicago and Key West?
The non-stop flights between Chicago and Key West are .
What’s the earliest departure time from ORD to EYW Airport?
The earliest flight leaves ORD at 6:30 am and lands in EYW - Key West International
What are the airports in Key West?
EYW
Can I make changes to my Chicago to Key West flight tickets or cancel them on FareLeaders.com?
No. We are an airfare comparison site. All the tickets are booked by the travel agent offering the flight deal and any changes or cancellations to be made are directly done directly by them or the airlines.
Can I cancel my flight tickets from ORD to EYW?
Read the fare rules of the Chicago to Key West air tickets booked. Some airlines allow you to cancel the tickets within a stipulated time period with a cancellation fee.
Which airline alliances offer flights from Chicago and Key West?
operate flights between Chicago and Key West
How long does a flight from Chicago to Key West take?
It takes approximately 3 hour to fly non-stop from ORD to EYW, which is 1251.41 miles by air.
Which airlines provide the cheapest flights from Chicago (ORD) to Key West (EYW) ?
In the past couple of days, the cheapest tickets to EYW from ORD were found on DL : USD 1057
Do I need a passport to fly between ORD and EYW?
No
What’s the latest departure time from ORD to EYW ?
The last flight leaves ORD at 12:1000 pm

Chicago (ORD) to Key West (EYW): Airport Information

Origin Airport Chicago O'Hare International , Chicago, US
Destination Airport Key West International , Key West, US
Distance 1251 miles

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