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Did you mean flights from Key West to Chicago?

Flights from Chicago to Key West, United States Last modified: Sep 25, 2016 12:57 AM

TIPSave $414 by flying into Miami instead of Key West from Chicago

Chicago to Key West Last modified: Sep 25, 2016 12:57 AM

We've scanned 23,629,223,180 round trip itineraries and found the cheapest flights from Chicago to Key West. American & United frequently offer the best deals on Chicago to Key West flights, or select your preferred carrier below to see the cheapest days to fly.

American
CHIEYW
Tue 11/29
1 stop
EYWCHI
Tue 12/6
1 stop
$324
Select
United
CHIEYW
Wed 11/16
1 stop
EYWCHI
Sun 11/20
1 stop
$397
Select
United
CHIEYW
Thu 12/1
1 stop
EYWCHI
Sun 12/4
1 stop
$397
Select
United
CHIEYW
Fri 12/9
1 stop
EYWCHI
Tue 12/13
1 stop
$397
Select

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 $353.

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 thinking 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 $0 $521
7-14 days $0 $354
14-21 days $0 $356
21-30 days $0 $356
30-60 days $0 $326
60-90 days $0 $324
90+ days $601 $324

Cheapest Day To Fly from Chicago to Key West

We've examined 23,636,053,052 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 Tuesday. See the chart below to compare prices for other days of the week.

Monday Tuesday Wednesday Thursday Friday Saturday Sunday
$356 $324 $397 $356 $356 $326 $354

Compare Flight Prices from Chicago to Key West 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 Chicago to Key West flights.

Month Origin Destination Carrier Depart Date Return Date Stops Price
September Chicago Key West American 9/27/16 10/6/16 1 $521
October Chicago Key West American 10/29/16 11/5/16 1 $326
November Chicago Key West American 11/29/16 12/6/16 1 $324
December Chicago Key West American 12/10/16 12/15/16 1 $354
January Chicago Key West American 1/31/17 2/7/17 1 $324
February Chicago Key West American 2/1/17 2/7/17 1 $326
March Chicago Key West American 3/7/17 3/14/17 1 $398
April Chicago Key West American 4/10/17 4/13/17 1 $396

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
2 3 4 5 6 7 8
$354
9 10 11 12 13 14 15
$354 $356
16 17 18 19 20 21 22
$356 $545
23 24 25 26 27 28 29
$545 $410
30 31 1 2 3 4 5
$410

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 $360.

The average price for direct flights from Chicago to Key West is not available.

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 not available.

The average price for round trip flights from Chicago to Key West is $360.

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: Miami, FL

Airlines in Chicago flying to Key West Last modified: Sep 25, 2016 12:57 AMNumber of routes searched: 107Number of itineraries searched: 43,006

Wondering which airlines fly out of Chicago to Key West? We've gathered the average price of Chicago airlines with flights to Key West. Different airlines offer different levels of comfort and service, so consider convenience when choosing your airline.

Below is the full flight schedule summary showing which days of the week individual carriers offer flights for the next 30 days.

Chicago to Key West
Airline Connections Mon Tue Wed Thu Fri Sat Sun
American MIA
United FLL
American CLT
United RSW
United TPA
United MCO
American DCA
Delta ATL
United EWR
American CMH
American IND

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 Domestic Flights from Chicago - CHI

FlightsAirlineLowest Price
Flights from Chicago to Miami American, Delta, Frontier, United $107
Flights from Chicago to Orlando American, JetBlue, Delta, Frontier, Spirit, United $107
Flights from Chicago to New York American, Alaska, JetBlue, Delta, Spirit, United $107
Flights from Chicago to Ft Lauderdale American, JetBlue, Delta, Spirit, United $157
Flights from Chicago to Ft Myers American, Delta, Spirit, United $177
Flights from Chicago to Tampa American, Delta, Frontier, Spirit, United $117
Flights from Chicago to Atlanta American, Delta, Spirit, United $87
Flights from Chicago to Las Vegas American, Alaska, Delta, Frontier, Hawaiian, Spirit, United, Virgin America $97
Flights from Chicago to Los Angeles American, Alaska, Delta, Frontier, Spirit, United, Virgin America $117
Flights from Chicago to Dallas - Ft Worth American, Alaska, Delta, Spirit $87
Flights from Chicago to West Palm Beach American, JetBlue, Delta, Frontier, United $77
Flights from Chicago to Houston American, Delta, Spirit, United $76
Flights from Chicago to Washington American, Alaska, JetBlue, Delta, United $87

Cheap International Flights from Chicago - CHI

FlightsAirlineLowest Price
Flights from Chicago to Cancun American, Air Canada, AeroMexico, JetBlue, British Airways, Copa, Delta, Frontier, Spirit, United, WestJet, Volaris $304
Cheap Flights from Chicago to Key West