Flights from Key West to Chicago, United States

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Did you mean flights from Chicago to Key West?

Key West to Chicago Last modified: Oct 12, 2021 6:16 -04:00

We've scanned 25,942 round trip itineraries and found the cheapest flights to Chicago. United frequently offer the best deals to Chicago flights, or select your preferred carrier below to see the cheapest days to fly.

United
EYWCHI
Thu 12/30
2 stops
CHIEYW
Mon 1/3
2 stops
$395

How Much is a Flight from Key West to Chicago?

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 $320.

Where To Buy Cheap Flights from Key West to Chicago?

The best way to find a great deal on airfare is to search multiple sites. When you run a search on FareCompare, we search multiple sites and fare sources all at once so you don't have to - which is why we think FareCompare is the best place to find cheap tickets. Airlines can adjust prices for 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 found that Tuesdays, Wednesdays, and Saturdays are often the best days to book flights. If you'd like to learn more, read our article about the best time to buy airline tickets.

How far in advance should I book tickets from Key West to Chicago?

The chart below shows up-to-date information regarding how far in advance to book your flight from Key West to Chicago.

Non Stop versus Connecting
Advanced PurchaseNon StopConnecting
< 7 days $315 $323
7-14 days $526 $323
14-21 days $315 $318
21-30 days $315 $301
30-60 days $186 $454
60-90 days $557 $395
90+ days $315 $323

Cheapest Day To Fly from Key West to Chicago

We've examined 3,945,672 itinerary searches that we've seen for departures in the next 90 days and found that the cheapest day to fly from Key West to Chicago is Sunday. See the chart below to compare prices for other days of the week.

Monday Tuesday Wednesday Thursday Friday Saturday Sunday
$357$316$315$384$301$315$248

Compare Flight Prices from Key West to Chicago by Month

Low priced flights are most commonly available by purchasing between one and three months in advance. International or holiday flights may need to be purchased even further in advance. The chart below shows the cheapest flight prices by month for Key West to Chicago flights.

Month Origin Destination Carrier Depart Date Return Date Stops Price
March Key West Chicago American 3/23/21 3/30/21 0 $315
April Key West Chicago JetBlue 4/16/21 4/25/21 1 $301
December Key West Chicago United 12/30/21 1/3/22 2 $395
June Key West Chicago American 6/15/21 6/22/21 0 $316
July Key West Chicago American 7/7/21 7/12/21 0 $315
August Key West Chicago American 8/17/21 8/24/21 1 $302
September Key West Chicago American 9/9/21 9/12/21 0 $295
October Key West Chicago American 10/2/21 10/6/21 2 $282

Cheap Last Minute Flights from Key West to Chicago

Looking for cheap last minute flights or a weekend getaway? We've got you covered with weekend flight deals from Key West to Chicago. The chart below shows the best last minute deals and cheap flights this weekend we could find.

Next 30 Days

SunMonTueWedThuFriSat
7 8 9 10 11 12 13
$296
14 15 16 17 18 19 20
$296
21 22 23 24 25 26 27
$416
28 29 30 31 1 2 3
$416 $264
4 5 6 7 8 9 10
$264 $261
11 12 13 14 15 16 17
$261 $257
18 19 20 21 22 23 24
$257

Connecting Flights vs Direct Flights from Key West to Chicago

Flights between some cities may be significantly cheaper if you choose a multi-stop airline ticket. Although these connecting flights sacrifice some convenience, on average, travelers save 20%-60% when they choose to fly multi-stop versus a direct flight.

The average price for connecting flights from Key West to Chicago is $395.

The average price for direct flights from Key West to Chicago is $557.

The chart below shows up to date information regarding non-stop flights from Key West to Chicago.

Weekly Direct Flights from Key West to Chicago - By Carrier
CarrierMonTueWedThuFriSatSunEarliest FlightLatest Flight
American 1 1 1 1 1 1 1 08:00 08:00
United 2 2 2 2 2 2 2 07:25 11:18

One Way Flights vs Round Trip Flights from Key West to Chicago

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 $96.

The average price for round trip flights from Key West to Chicago is $395.

Key West to Chicago Flight Questions

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

Question: How long is the flight from Key West to Chicago?
Answer: The average Key West to Chicago flight time is 3 hours and 23 minutes.
Question: How far is Chicago from Key West?
Answer: The distance from Key West to Chicago is 1,253 miles (2,016 kilometers).
Question: How common are direct flights from Key West to Chicago?
Answer: There are 21 direct flights from Key West to Chicago.
Question: What are the most popular Key West airlines for direct flights from Key West to Chicago?
Answer: United Airlines provides 66% of the non-stop flights between Key West and Chicago.

Key West to Chicago Airports

These are the major commercial airports we're currently monitoring in Key West and Chicago. If your route includes a city with multiple airports, you may be able to find substantial savings by choosing an alternate airport.

Farecompare Research Tools

FareCompare's Flight Schedule Search Tool helps you find information about airline schedule filings, including flight numbers, depart times, and travel distance.

Cheap International Flights to Chicago - CHI Last modified: Oct 18, 2021 10:01 -04:00

Cheap Flights from Key West to Chicago