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Key West to Chicago Flight Information

Below are some common questions asked about this flight route:

When can I book the cheapest flight from Key West to Chicago?

Airlines adjust prices for plane tickets based on the day and time that you book your flight. After analyzing data from all airlines, we have discovered that the best days to book flights from Key West to Chicago are Tuesdays, Wednesdays, and Saturdays.

What are the airlines flying from Key West to Chicago?

Airlines flying from Key West to Chicago include American Airlines,United Airlines.

What is the most popular airline for non-stop flights from Key West to Chicago?

provides 1000 of the non-stop flights between Key West and Chicago.

How many airports are there in Chicago?

Average duration of direct flights: 3h29m
Airports at destination:
Flight route:
Price starting from:

Key West to Chicago Flight Schedule

Flight info.
Departure
Arrival
RouteWeekly Schedule

08:45

EYW

11:15

ORD

Key West to ChicagoSMT-TFSSearch

09:30

EYW

12:00

ORD

Key West to ChicagoSMTWTFSSearch

12:20

EYW

14:53

ORD

Key West to ChicagoSMTWTFSSearch

12:25

EYW

14:55

ORD

Key West to ChicagoSMTW-FSSearch

12:30

EYW

14:55

ORD

Key West to ChicagoSMTWTFSSearch

13:00

EYW

15:15

ORD

Key West to Chicago-------Search

13:15

EYW

15:38

ORD

Key West to Chicago-----F-Search

13:24

EYW

15:55

ORD

Key West to Chicago-----F-Search

13:28

EYW

16:00

ORD

Key West to ChicagoSMTWTFSSearch

16:11

EYW

18:44

ORD

Key West to ChicagoSM-WTFSSearch

16:15

EYW

18:48

ORD

Key West to Chicago----TF-Search

16:18

EYW

18:46

ORD

Key West to Chicago--T----Search

16:20

EYW

18:50

ORD

Key West to ChicagoSMTWTFSSearch
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Roundtrip vs One-Way Flights from Key West to Chicago

There is usually no major price difference between buying a roundtrip flight versus a one-way flight. Increased flexibility is the main benefit when it comes to buying a one-way flight from Key West to Chicago. However, booking a roundtrip flight is a simpler process. You can compare roundtrip and one-way flights by using our flight comparison tool.

Travel from Key West to Chicago

Chicago attracts thousands of visitors every year for both business and pleasure. Planning a trip from Key West to Chicago is easy when you use Trip.com to help you make travel arrangements. With Trip.com, you can search for available flights and hotel rooms, and then make your booking quickly and easily online.

A Trip to Remember

Make your journey from Key West to Chicago a trip to remember when you use Trip.com to review city attractions before you arrive. With a preview of what's available at your destination, you can make any necessary reservations in advance for the best travel experience possible.