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Cheap Flights from Chicago to Key West, FL, United States - CHI to EYW

Popular flights from Chicago to Key West

We’ve got the inside scoop on finding the best time to fly for the best price. Not sure when to travel for your next vacation? Find details below on when-to-fly and when-to-buy.

American Airlines
Departure Date Return Date Lowest Price
Jul 19, 2016 Jul 27, 2016 $282
Aug 2, 2016 Aug 6, 2016 $282
Aug 2, 2016 Aug 8, 2016 $282
Aug 7, 2016 Aug 16, 2016 $282
Aug 10, 2016 Aug 15, 2016 $282
United Airlines
Departure Date Return Date Lowest Price
May 25, 2016 Jun 1, 2016 $282
May 29, 2016 Jun 2, 2016 $282
Jun 27, 2016 Jul 7, 2016 $282
Jun 28, 2016 Jul 8, 2016 $282
Jul 3, 2016 Jul 13, 2016 $282

How Much Does it Cost to Fly from Chicago to Key West (CHI to EYW)?

We have collected flight cost data from across the web for travel from Chicago to Key West, and have found the average flight price for this trip to be $282.

When Can I Buy the Cheapest Flight from Chicago to Key West (CHI to EYW)?

Airlines can adjust prices for plane tickets from Chicago to Key West based on the day and time that you decide to book your flight. We have collected data from all airlines, and have discovered that the best days to book flights are Tuesdays, Wednesdays, and Saturdays. Read our article to find more information about the best time to buy airline tickets.

Cheapest Day To Fly from Chicago to Key West

The chart below shows up-to-date information regarding the cheapest days to fly from Chicago to Key West.

Monday Tuesday Wednesday Thursday Friday Saturday Sunday
$282 $282 $282 $282 $282 $282 $282

Lowest Fares Chart By Month from Chicago to Key West

The chart below shows the lowest fare by month when flying from Chicago to Key West.

Month Origin Destination Carrier Depart Date Return Date Stops Price
May Chicago Key West United 5/25/16 6/1/16 1 $282
June Chicago Key West United 6/27/16 7/7/16 1 $282
July Chicago Key West American 7/19/16 7/27/16 1 $282
August Chicago Key West American 8/2/16 8/6/16 1 $282
September Chicago Key West American 9/25/16 9/28/16 1 $280
October Chicago Key West American 10/11/16 10/21/16 1 $282
November Chicago Key West American 11/7/16 11/10/16 1 $280
December Chicago Key West American 12/3/16 12/9/16 1 $282

TIPSave $426 by flying into Ft Lauderdale instead of Key West from Chicago

Round Trip vs One Way Flights from Chicago to Key West (CHI to EYW)

We have found that there is often no price difference between buying a round trip flight versus a one way flight. Increased flexibility is the main benefit when it comes to buying a one way flight from Chicago to Key West. However, booking a round trip flight can be a simpler process. You can compare round trip and one way flights by using our flight comparison.

The average price for one way flights from Chicago to Key West is $194.

The average price for round trip flights from Chicago to Key West is $292.

Chicago to Key West Flight Questions

Below are some common questions that asked about this flight route:

Question: What are the most popular connecting cities when flying from Chicago to Key West?
Answer: Atlanta, GA

Airlines Flying from Chicago to Key West (CHI to EYW)

Below are the different airlines that fly from Chicago to Key West with the average price of their plane tickets. Just remember that different airlines offer different levels of comfort and service, so consider convenience when choosing your airline.

Below is the full flight schedule summary of the next 30 days for flights from Chicago to Key West.

Chicago to Key West
Airline Connections Mon Tue Wed Thu Fri Sat Sun
American MIA X X X X X X X
Delta ATL X X X X X X X
Delta MSP / ATL X X X X X X X

Airports for Your Route

These pages contain information about the major airports in Chicago and Key West, so you can feel comfortable knowing how to get around whether you are about to take off or you just landed.

Cheap Domestic Flights from Chicago - CHI

FlightsAirlineLowest Price
Chicago to Miami American, Alaska, Frontier, United $108
Chicago to Orlando American, JetBlue, Frontier, Spirit, United $132
Chicago to New York American, Alaska, JetBlue, Spirit, United $97
Chicago to Ft Lauderdale American, Alaska, JetBlue, Spirit, United $142
Chicago to Ft Myers American, Spirit, United $157
Chicago to Tampa American, Alaska, Spirit, United $137
Chicago to Atlanta American, Spirit, United $71
Chicago to Las Vegas American, Alaska, Frontier, Spirit, United, Virgin America $85
Chicago to Los Angeles American, Alaska, Frontier, Spirit, United, Virgin America $147
Chicago to Dallas - Ft Worth American, Alaska, Frontier, Spirit, United $85
Chicago to West Palm Beach American, JetBlue, United $249
Chicago to Houston American, Spirit, United $116
Chicago to Washington American, Alaska, Frontier, United $88

Cheap International Flights from Chicago - CHI

FlightsAirlineLowest Price
Chicago to Cancun Silver, Interjet, American, AeroMexico, Alaska, JetBlue, Frontier, Spirit, Sun Country, United, Virgin America, Volaris, Great Lakes $281

Cheap Domestic Flights to Key West - EYW

Cheap Flights from Chicago to Key West, FL, United States, from $282 Round trip from CHI to EYW