Flights from Chicago to Key West, United States

Did you mean flights from Key West to Chicago?

Chicago to Key West Last modified: Jan 22, 2024 9:21 -05:00

We've scanned 115,678,683 round trip itineraries and found the cheapest flights to Key West. Major Airlines & United frequently offer the best deals to Key West flights, or select your preferred carrier below to see the cheapest days to fly.

Major Airlines
CHIEYW
Tue 2/27
1 stop
EYWCHI
Tue 3/5
1 stop
$248
United
CHIEYW
Mon 3/4
nonstop
EYWCHI
Tue 3/12
nonstop
$309
American
CHIEYW
Mon 2/12
nonstop
EYWCHI
Fri 2/16
nonstop
$557
Multiple Airlines
CHIEYW
Mon 2/5
1 stop
EYWCHI
Mon 2/12
1 stop
$683

How Much is a Flight from Chicago to Key West?

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 $263.

Where To Buy Cheap Flights from Chicago to Key West?

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 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 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 Chicago to Key West?

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

Non Stop versus Connecting
Advanced PurchaseNon StopConnecting
< 7 days $479 $418
7-14 days $420 $288
14-21 days $329 $248
21-30 days $309 $248
30-60 days $355 $248
60-90 days $355 $248
90+ days $309 $248

Cheapest Day To Fly from Chicago to Key West

We've examined 231,357,366 itinerary searches that we've seen for departures in the next 90 days and found that the cheapest day to fly from Chicago to Key West is Sunday. See the chart below to compare prices for other days of the week.

Monday Tuesday Wednesday Thursday Friday Saturday Sunday
$248$248$318$268$248 $248

Cheap Last Minute Flights from Chicago to Key West

Looking for cheap last minute flights or a weekend getaway? We've got you covered with weekend flight deals from Chicago to Key West. 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
$509
14 15 16 17 18 19 20
$509 $288
21 22 23 24 25 26 27
$288 $248
28 29 30 31 1 2 3
$248 $318
4 5 6 7 8 9 10
$318 $268
11 12 13 14 15 16 17
$268

Connecting Flights vs Direct Flights from Chicago to Key West

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 Chicago to Key West is $336.

The average price for direct flights from Chicago to Key West is $479.

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

Weekly Direct Flights from Chicago to Key West - By Carrier
CarrierMonTueWedThuFriSatSunEarliest FlightLatest Flight
American 1 1 1 1 1 1 1 03:20 03:20
United 2 2 2 2 2 2 2 03:00 06:25

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

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 $248.

The average price for round trip flights from Chicago to Key West is $336.

Chicago to Key West Flight Questions

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

Question: How long is the flight from Chicago to Key West?
Answer: The average Chicago to Key West flight time is 3 hours and 8 minutes.
Question: How far is Key West from Chicago?
Answer: The distance from Chicago to Key West is 1,253 miles (2,016 kilometers).
Question: How common are direct flights from Chicago to Key West?
Answer: There are 21 direct flights from Chicago to Key West.
Question: What are the most popular Chicago airlines for direct flights from Chicago to Key West?
Answer: United Airlines provides 66% of the non-stop flights between Chicago and Key West.

Chicago to Key West Airports

These are the major commercial airports we're currently monitoring in Chicago and Key West. 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 Flights from Chicago to Key West