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Cheap Flights from Key West to Chicago, IL, United States - EYW to CHI Last modified: May 29, 2016 1:02 AM

Popular flights from Key West to Chicago Last modified: May 29, 2016 1:02 AM

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
Sep 23, 2016 Sep 25, 2016 $386
JetBlue Airways
Departure Date Return Date Lowest Price
Aug 11, 2016 Aug 15, 2016 $610
United Airlines
Departure Date Return Date Lowest Price
Sep 23, 2016 Sep 25, 2016 $386

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 $477.

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 $233.

The average price for round trip flights from Key West to Chicago is $474.

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) Number of flights searched: 87Last modified: May 29, 2016 1:02 AM

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 / DTW 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 $174
Ft Myers to Chicago American, Spirit, United $177
Miami to Milwaukee American, Alaska, United $294
Ft Lauderdale to Milwaukee American, Alaska, JetBlue, United $297
Miami to Detroit American, United $175
Ft Myers to Milwaukee American, United $345
West Palm Beach to Milwaukee American, United $292
Ft Lauderdale to Detroit American, JetBlue, Spirit, United $80
Ft Lauderdale to Indianapolis American, United $254
Miami to Indianapolis American, United $223
Ft Lauderdale to South Bend American, United $325
Miami to South Bend American, United $455
Ft Myers to Detroit American, Spirit, United $177
Miami to St Louis American, Alaska, United $367
Ft Lauderdale to Grand Rapids American, United $320
Ft Lauderdale to Minneapolis - St Paul American, Alaska, Spirit, United $231
Miami to Washington American, Alaska, United $143
Ft Myers to South Bend American, United $482
Miami to Grand Rapids American, Alaska, United $327
Miami to Minneapolis - St Paul American, Alaska, Frontier, Sun Country, United $291
Miami to Los Angeles American, Alaska, Sun Country, United $214
West Palm Beach to Detroit American, JetBlue, Spirit, United $182
Ft Lauderdale to St Louis American, Alaska, United $361
Miami to Charlotte American, United $367
Ft Lauderdale to Madison American, Alaska, United $389
Miami to Denver American, Alaska, Frontier, United $187
Ft Myers to AtlantaCheck Dates
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 $283
Ft Lauderdale to Toronto Silver, American, Air Canada, Alaska, JetBlue, Spirit, Air Transat, United, Virgin America, Sunwing, WestJet $235
Cheap Flights from Key West to Chicago, IL, United States, from $386 Round trip from EYW to CHI