Cheap Flights from Chicago, IL to Key West, FL from $249

Return flight: Key West – Chicago
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On Cheapflightsplus.com you will find 1 direct and 25 connecting flights from Chicago to Key West. You can compare airfare deals from 1 airlines and multiple travel sites from $249, book and save on cheap plane tickets and last minute offers. Also check out CHI-EYW flight schedule to find best flight time, convenient departure and arrival airports.

Find One-Way and Round-Trip Chicago to Key West Flight Deals

To find the cheapest one way airline ticket select the date with the lowest price on the calendar below and click «Find Flights». To search for round-trip flight deals click on the link «Check prices for return flights» and select the date of the return flight. Cheapest flights in November: $249 (one-way), $427 (round-trip).
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Best Flights from Chicago to Key West Today

Take a look at the list of non stop flights and flights with layovers from Chicago to Key West with the lowest price of $249. The fastest direct flight takes 3h 14m and the fastest connecting – 5h 50m.
Price Departure Arrival Flight Duration Airline Flight
from $322
Find flight
10:35
Chicago
O'Hare International
 14:49
Key West
Key West Int.
 3h 14m United Airlines
UA2070
from $249
Find flight
06:15
Chicago
O'Hare International
 17:15
Key West
Key West Int.
 10h 0m
layover
6h 1m - Tampa
 United Airlines
UA1548
UA3137
from $294
Find flight
17:50
Chicago
O'Hare International
 10:10+1 день
Key West
Key West Int.
 15h 20m
layover
11h 8m - Orlando
 United Airlines
UA2039
UA3075
from $294
Find flight
16:02
Chicago
O'Hare International
 10:10+1 день
Key West
Key West Int.
 17h 8m
layover
12h 56m - Orlando
 United Airlines
UA2413
UA3075
from $294
Find flight
14:33
Chicago
O'Hare International
 10:10+1 день
Key West
Key West Int.
 18h 37m
layover
14h 21m - Orlando
 United Airlines
UA2042
UA3075
from $294
Find flight
13:05
Chicago
O'Hare International
 10:10+1 день
Key West
Key West Int.
 20h 5m
layover
15h 53m - Orlando
 United Airlines
UA455
UA3075
from $294
Find flight
16:02
Chicago
O'Hare International
 14:20+1 день
Key West
Key West Int.
 21h 18m
layover
17h 6m - Orlando
 United Airlines
UA2413
UA3071
from $294
Find flight
10:55
Chicago
O'Hare International
 10:10+1 день
Key West
Key West Int.
 22h 15m
layover
18h 2m - Orlando
 United Airlines
UA1568
UA3075
from $294
Find flight
14:33
Chicago
O'Hare International
 14:20+1 день
Key West
Key West Int.
 22h 47m
layover
18h 31m - Orlando
 United Airlines
UA2042
UA3071
from $294
Find flight
13:05
Chicago
O'Hare International
 14:20+1 день
Key West
Key West Int.
 24h 15m
layover
20h 3m - Orlando
 United Airlines
UA455
UA3071
from $294
Find flight
10:55
Chicago
O'Hare International
 14:20+1 день
Key West
Key West Int.
 26h 25m
layover
22h 12m - Orlando
 United Airlines
UA1568
UA3071
from $298
Find flight
07:35
Chicago
O'Hare International
 17:15
Key West
Key West Int.
 8h 40m
layover
4h 34m - Tampa
 United Airlines
UA2326
UA3137
from $298
Find flight
11:11
Chicago
O'Hare International
 09:15+1 день
Key West
Key West Int.
 21h 4m
layover
16h 58m - Tampa
 United Airlines
UA1834
UA3135
from $332
Find flight
10:50
Chicago
O'Hare International
 18:55
Key West
Key West Int.
 7h 5m
layover
2h 46m - Miami
 United Airlines
UA1775
UA3094
from $332
Find flight
07:35
Chicago
O'Hare International
 16:01
Key West
Key West Int.
 7h 26m
layover
1h 31m - Houston
 United Airlines
UA2482
UA6200
from $368
Find flight
07:30
Chicago
O'Hare International
 14:20
Key West
Key West Int.
 5h 50m
layover
1h 36m - Orlando
 United Airlines
UA1768
UA3071
Show all tickets
*Departure and arrival times - local. Prices indicated for one-way flights. Information updated on December 24, 2024
Full flight schedule will help you in detecting at what time planes fly from Chicago to Key West. You can also specify the concrete flights and airlines on the route and how long the flight actually is. Use the calendar for today, tomorrow or other specific date as some flights are available only on certain days of the week.
Departure Arrival Flight Details Flight Duration Price
10:35 — 14:49
10:35 — 14:49 UA2070 United Airlines
Chicago — Key West
3h 14m
Find flight
from$322
05:45 — 16:01
05:45 — 08:44 UA2622 United Airlines
Chicago — Houston
3h 25m stop
12:09 — 16:01 UA6200 United Airlines
Houston — Key West
9h 16m
including layover
Find flight
from$332
05:45 — 16:03
05:45 — 08:44 UA2606 United Airlines
Chicago — Houston
3h 26m stop
12:10 — 16:03 UA6200 United Airlines
Houston — Key West
9h 18m
including layover
Find flight
from$368
06:15 — 17:15
06:15 — 09:59 UA1548 United Airlines
Chicago — Tampa
6h 1m stop
16:00 — 17:15 UA3137 United Airlines
Tampa — Key West
10h
including layover
Find flight
from$249
06:15 — 09:15
+1 day
06:15 — 09:59 UA1548 United Airlines
Chicago — Tampa
22h 1m stop
08:00 — 09:15 UA3135 United Airlines
Tampa — Key West
26h
including layover
Find flight
from$249
07:35 — 17:15
07:30 — 11:19 UA2326 United Airlines
Chicago — Tampa
4h 34m stop
16:00 — 17:15 UA3137 United Airlines
Tampa — Key West
8h 40m
including layover
Find flight
from$298
07:35 — 16:01
07:35 — 10:38 UA2482 United Airlines
Chicago — Houston
1h 31m stop
12:09 — 16:01 UA6200 United Airlines
Houston — Key West
7h 26m
including layover
Find flight
from$332
08:45 — 18:55
08:45 — 13:00 UA743 United Airlines
Chicago — Miami
4h 50m stop
17:50 — 18:55 UA3094 United Airlines
Miami — Key West
9h 10m
including layover
Find flight
from$333
10:55 — 10:10
+1 day
10:55 — 14:43 UA1568 United Airlines
Chicago — Orlando
18h 2m stop
08:45 — 10:10 UA3075 United Airlines
Orlando — Key West
22h 15m
including layover
Find flight
from$294
10:55 — 14:20
+1 day
10:55 — 14:43 UA1568 United Airlines
Chicago — Orlando
22h 12m stop
12:55 — 14:20 UA3071 United Airlines
Orlando — Key West
26h 25m
including layover
Find flight
from$294
11:11 — 09:15
+1 day
11:11 — 15:02 UA1834 United Airlines
Chicago — Tampa
16h 58m stop
08:00 — 09:15 UA3135 United Airlines
Tampa — Key West
21h 4m
including layover
Find flight
from$298
13:05 — 10:10
+1 day
12:53 — 16:39 UA455 United Airlines
Chicago — Orlando
15h 53m stop
08:45 — 10:10 UA3075 United Airlines
Orlando — Key West
20h 5m
including layover
Find flight
from$294
13:05 — 14:20
+1 day
12:53 — 16:39 UA455 United Airlines
Chicago — Orlando
20h 3m stop
12:55 — 14:20 UA3071 United Airlines
Orlando — Key West
24h 15m
including layover
Find flight
from$294
14:33 — 10:10
+1 day
14:20 — 18:08 UA2042 United Airlines
Chicago — Orlando
14h 21m stop
08:45 — 10:10 UA3075 United Airlines
Orlando — Key West
18h 37m
including layover
Find flight
from$294
14:33 — 14:20
+1 day
14:20 — 18:08 UA2042 United Airlines
Chicago — Orlando
18h 31m stop
12:55 — 14:20 UA3071 United Airlines
Orlando — Key West
22h 47m
including layover
Find flight
from$294
16:02 — 10:10
+1 day
16:02 — 19:49 UA2413 United Airlines
Chicago — Orlando
12h 56m stop
08:45 — 10:10 UA3075 United Airlines
Orlando — Key West
17h 8m
including layover
Find flight
from$294
16:02 — 14:20
+1 day
16:02 — 19:49 UA2413 United Airlines
Chicago — Orlando
17h 6m stop
12:55 — 14:20 UA3071 United Airlines
Orlando — Key West
21h 18m
including layover
Find flight
from$294
17:50 — 10:10
+1 day
17:50 — 21:37 UA2039 United Airlines
Chicago — Orlando
11h 8m stop
08:45 — 10:10 UA3075 United Airlines
Orlando — Key West
15h 20m
including layover
Find flight
from$294
17:50 — 14:20
+1 day
17:50 — 21:37 UA2039 United Airlines
Chicago — Orlando
15h 18m stop
12:55 — 14:20 UA3071 United Airlines
Orlando — Key West
19h 30m
including layover
Find flight
from$294
*Departure and arrival times - local. Updated on December 24, 2024

Flight Information

Below we will explain in detail what the flights cost on the destination from Chicago to Key West depends on and how to choose the most interesting flight option for you.

Distance between Chicago and Key West is 2001 miles. Time difference between the cities is 1h. Airplanes depart 05:45 to 17:50 from 7 Chicago airports and arrive 05:45 to 17:50 to 2 Key West airports. Average flight time is 3h 14m.

  • The fastest flight 3h 14m
  • Average flight time 3h 14m
  • The earliest flight 05:45
  • The latest flight 17:50
  • Distance 1244 ml

The cheapest months to travel to Key West are december (from 209 $), november (from 240 $), february (from 249 $).

The most expensive months are january (from 322 $), february (from 249 $), november (from 240 $).

What is the lowest airfare Chicago to Key West?

The cheapest plane ticket found by our users is $249. This airfare is for economy class on one-way UA1548 flight by United Airlines for February 21, 2025 which leaves O'Hare International in Chicago at 06:15 am and arrives at Key West Key West Int. at 17:15.

Economy class
$249
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Business class
?
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First class
?
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Popular Airlines on the Route

The flight Chicago — Key West is served by 1 regular airline . Most of the flights on this route are operated by United Airlines - 26 departures per week at the price of from $ 249 . And the most expensive tickets are offered by United Airlines airline - from $ 443.

Direct flights

There are 1 nonstop flights on the route. The fastest direct flight is UA2070 by United Airlines takes 3h 14m and the cheapest is UA1548 by United Airlines for $322.

  • UA - United Airlines
    from $322
    Find
See more direct flights

Connecting Flights

There are 25 flights with layovers on the route. The fastest connecting flight is UA1768 by United Airlines takes 5h 50m and the cheapest is UA1548 by United Airlines for $249.

  • UA - United Airlines
    from $249
    Find
See more connecting flights

Airports

You can fly from Chicago to Key West from 7 airports (O'Hare International, Midway, Dupage County, Chicago FSS, Merrill C Meigs (closed), Pal-Waukee, Chicago NAS).

Chicago airports

  • O'Hare International-ORD
    from $249
    Find
  • Midway-MDW
    Find
  • Dupage County-DPA
    Find
  • Chicago FSS-CHI
    Find
  • Merrill C Meigs (closed)-CGX
    Find
  • Pal-Waukee-PWK
    Find
  • Chicago NAS-NOH
    Find

Key West airports

  • NAS-NQX
    Find
  • Key West Int.-EYW
    Find

Airplanes

There are flights to Key West from Chicago by 1 airlines that use 0 aircraft brands. They range from huge modern airplanes to small-sized.

Top Domestic Destinations from Chicago

You may also consider searching for discounted plane tickets to some other popular places from Chicago within United States.

Top International Destinations from Chicago

Our state-of-the art metasearch will definitely provide you with the best airfare on international flights. We’re proud to partner with many reliable travel suppliers located outside the US what gives us an opportunity to offer the most competitive prices on far destinations.

How to book a plane ticket yourself?

How to book an air ticket yourself?
  • Fill in the search parameters — cities of departure and destination, departure and return dates and click «Find flights»
  • Select the best flight that you like. Please, check the airports of departure and arrival. Select the best fare, but pay attention to the following flight details - airports of departure and arrival, flight duration and layovers. Please use filters and sort to find the best flight.
  • Click «Buy» when you are ready — our system will redirect you to the site that sells the selected flight ticket.
  • Fill in all passenger and payment information — passport and contact information, please double check all passengers’ names and make a payment for your itinerary.
  • That's it — you will receive an email with your e-ticket usually within 10 minutes after your flight is confirmed. Please, print the e-ticket and have it with you at the airport. You would need to have only a passport and/or a required form of ID to travel. Please, check your Visa requirements if you travel outside of the United States or Canada.

    To find a plane ticket, please select dates.

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