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

Popular flights from Key West to Chicago

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
Aug 8, 2016 Aug 12, 2016 $332
JetBlue Airways
Departure Date Return Date Lowest Price
Jun 11, 2016 Jun 13, 2016 $568
United Airlines
Departure Date Return Date Lowest Price
Jun 1, 2016 Jun 8, 2016 $282

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

We have collected flight cost data from across the web for travel from Key West to Chicago, and have found the average flight price for this trip to be $418.

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

Airlines can adjust prices for plane tickets from Key West to Chicago 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.

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

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 Key West to Chicago. 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 Key West to Chicago is $181.

The average price for round trip flights from Key West to Chicago is $520.

Key West to Chicago Flight Questions

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

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

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

Below are the different airlines that fly from Key West to Chicago 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 Key West to Chicago.

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

Airports for Your Route

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

Cheap Domestic Flights to Chicago - CHI

FlightsAirlineLowest Price
West Palm Beach to Chicago American, Spirit, United $241
Ft Myers to Chicago American, Spirit, United $177
Miami to Milwaukee American, United $287
Ft Lauderdale to Milwaukee American, Alaska, United $275
Miami to Detroit American, United $107
Ft Myers to Milwaukee American, United $278
West Palm Beach to Milwaukee American, United $290
Ft Lauderdale to Detroit American, Alaska, JetBlue, Frontier, Spirit, United $80
Ft Lauderdale to Indianapolis American, United $221
Miami to Indianapolis American, United $223
Ft Lauderdale to South Bend United $396
Miami to South Bend American, United $345
Ft Myers to Detroit American, Spirit, United $157
Miami to St Louis American, Alaska, United $344
Ft Lauderdale to Grand Rapids American, United $315
Ft Lauderdale to Minneapolis - St Paul American, Alaska, Spirit, United $215
Miami to Washington American, Alaska, United $105
Ft Myers to South Bend United $445
Miami to Grand Rapids American, United $315
Miami to Minneapolis - St Paul American, Alaska, Sun Country, United $205
Miami to Los Angeles American, Alaska, Sun Country, United $166
West Palm Beach to Detroit American, Spirit, United $183
Ft Lauderdale to St Louis American, Alaska, United $339
Miami to Charlotte American, United $319
Ft Lauderdale to Madison American, Alaska, United $403
Miami to Denver American, Alaska, Frontier, United $127
Ft Myers to Atlanta United $478
Ft Lauderdale to Baltimore American, JetBlue, Spirit, United $80

Cheap International Flights to Chicago - CHI

FlightsAirlineLowest Price
Miami to Toronto Silver, American, Air Canada, Alaska, JetBlue, Frontier, Sun Country, Air Transat, United, Sunwing, WestJet, Great Lakes $258
Ft Lauderdale to Toronto Silver, American, Air Canada, Alaska, JetBlue, Spirit, Air Transat, United, Virgin America, Sunwing, WestJet $207
Cheap Flights from Key West to Chicago, IL, United States, from $282 Round trip from EYW to CHI