Cheap Flights from Chicago, IL to Key West, FL from $251
On Cheapflightsplus.com you will find 3 direct and 93 connecting flights from Chicago to Key West. You can compare airfare deals from 1 airlines and multiple travel sites from $251, 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: $251 (one-way), $430 (round-trip).
Direct flights
Check prices for return flight
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 $251. The fastest direct flight takes 3h 6m and the fastest connecting – 5h 50m.
| Price | Departure | Arrival | Flight Duration | Airline | Flight |
|---|---|---|---|---|---|
| from $374 | 10:55 Chicago O'Hare International | 15:01 Key West Key West Int. | 3h 6m | United Airlines | UA325 |
| from $251 | 07:35 Chicago O'Hare International | 17:15 Key West Key West Int. | 8h 40m layover 4h 34m - Tampa | United Airlines | UA2326 UA3137 |
| from $281 | 17:55 Chicago O'Hare International | 10:10+1 день Key West Key West Int. | 15h 15m layover 11h 1m - Orlando | United Airlines | UA2724 UA3075 |
| from $281 | 17:55 Chicago O'Hare International | 14:20+1 день Key West Key West Int. | 19h 25m layover 15h 11m - Orlando | United Airlines | UA2724 UA3071 |
| from $283 | 10:56 Chicago O'Hare International | 10:10+1 день Key West Key West Int. | 22h 14m layover 18h 2m - Orlando | United Airlines | UA2856 UA3075 |
| from $283 | 10:56 Chicago O'Hare International | 14:20+1 день Key West Key West Int. | 26h 24m layover 22h 12m - Orlando | United Airlines | UA2856 UA3071 |
| from $288 | 08:52 Chicago O'Hare International | 18:55 Key West Key West Int. | 9h 3m layover 4h 46m - Miami | United Airlines | UA1932 UA3094 |
| from $288 | 07:10 Chicago O'Hare International | 18:55 Key West Key West Int. | 10h 45m layover 6h 29m - Miami | United Airlines | UA1421 UA3094 |
| from $288 | 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 $288 | 10:55 Chicago O'Hare International | 10:10+1 день Key West Key West Int. | 22h 15m layover 18h 3m - Orlando | United Airlines | UA2100 UA3075 |
| from $288 | 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 $288 | 10:55 Chicago O'Hare International | 14:20+1 день Key West Key West Int. | 26h 25m layover 22h 13m - Orlando | United Airlines | UA2100 UA3071 |
| from $289 | 17:55 Chicago O'Hare International | 10:10+1 день Key West Key West Int. | 15h 15m layover 11h 1m - Orlando | United Airlines | UA2113 UA3075 |
| from $334 | 13:55 Chicago O'Hare International | 10:10+1 день Key West Key West Int. | 19h 15m layover 15h 2m - Orlando | United Airlines | UA2855 UA3075 |
| from $296 | 18:14 Chicago O'Hare International | 10:10+1 день Key West Key West Int. | 14h 56m layover 1h 16m - Washington D.C. 7h 51m - Orlando | United Airlines | UA210 UA689 UA3075 |
| from $375 | 12:53 Chicago O'Hare International | 09:15+1 день Key West Key West Int. | 19h 22m layover 4h 7m - Newark 8h 42m - Tampa | United Airlines | UA2238 UA212 UA3135 |
Show all tickets
*Departure and arrival times - local. Prices indicated for one-way flights. Information updated on May 11, 2025
Flight Schedule Chicago (Illinois) to Key West (Florida)
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$387 |
|
|
10:55 — 15:01
|
10:55 — 15:01
UA325
United Airlines
Chicago — Key West
|
3h 6m |
Find flight
from$374 |
|
|
10:55 — 15:01
|
10:55 — 15:01
UA1385
United Airlines
Chicago — Key West
|
3h 6m |
Find flight
from$418 |
|
|
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$300 |
|
|
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$300 |
|
|
07:30 — 09:15
+1 day
|
07:30 — 11:19
UA2326
United Airlines
Chicago — Tampa
20h 41m stop
08:00 — 09:15
UA3135
United Airlines
Tampa — Key West
|
24h 45m including layover |
Find flight
from$251 |
|
|
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$251 |
|
|
08:52 — 18:55
|
08:52 — 13:04
UA1932
United Airlines
Chicago — Miami
4h 46m stop
17:50 — 18:55
UA3094
United Airlines
Miami — Key West
|
9h 3m including layover |
Find flight
from$288 |
|
|
09:05 — 10:10
+1 day
|
09:02 — 12:53
UA2323
United Airlines
Chicago — Orlando
19h 49m stop
08:45 — 10:10
UA3075
United Airlines
Orlando — Key West
|
24h 5m including layover |
Find flight
from$290 |
|
|
09:05 — 14:20
+1 day
|
09:05 — 12:56
UA2323
United Airlines
Chicago — Orlando
23h 59m stop
12:55 — 14:20
UA3071
United Airlines
Orlando — Key West
|
28h 15m including layover |
Find flight
from$326 |
|
|
10:56 — 10:10
+1 day
|
10:56 — 14:43
UA2856
United Airlines
Chicago — Orlando
18h 2m stop
08:45 — 10:10
UA3075
United Airlines
Orlando — Key West
|
22h 14m including layover |
Find flight
from$283 |
|
|
10:56 — 14:20
+1 day
|
10:56 — 14:43
UA2856
United Airlines
Chicago — Orlando
22h 12m stop
12:55 — 14:20
UA3071
United Airlines
Orlando — Key West
|
26h 24m including layover |
Find flight
from$283 |
|
|
11:14 — 09:15
+1 day
|
11:14 — 15:01
UA540
United Airlines
Chicago — Tampa
16h 59m stop
08:00 — 09:15
UA3135
United Airlines
Tampa — Key West
|
21h 1m including layover |
Find flight
from$293 |
|
|
11:14 — 13:15
+1 day
|
11:14 — 15:01
UA540
United Airlines
Chicago — Tampa
20h 59m stop
12:00 — 13:15
UA3136
United Airlines
Tampa — Key West
|
25h 1m including layover |
Find flight
from$293 |
|
|
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$290 |
|
|
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$290 |
|
|
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$288 |
|
|
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$288 |
|
|
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$353 |
|
|
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$353 |
|
|
17:55 — 10:10
+1 day
|
17:55 — 21:44
UA2724
United Airlines
Chicago — Orlando
11h 1m stop
08:45 — 10:10
UA3075
United Airlines
Orlando — Key West
|
15h 15m including layover |
Find flight
from$281 |
|
|
17:55 — 14:20
+1 day
|
17:55 — 21:44
UA2724
United Airlines
Chicago — Orlando
15h 11m stop
12:55 — 14:20
UA3071
United Airlines
Orlando — Key West
|
19h 25m including layover |
Find flight
from$281 |
|
|
18:05 — 09:15
+1 day
|
18:05 — 21:57
UA2075
United Airlines
Chicago — Tampa
10h 3m stop
08:00 — 09:15
UA3135
United Airlines
Tampa — Key West
|
14h 10m including layover |
Find flight
from$293 |
|
|
18:05 — 13:15
+1 day
|
18:05 — 21:57
UA2075
United Airlines
Chicago — Tampa
14h 3m stop
12:00 — 13:15
UA3136
United Airlines
Tampa — Key West
|
18h 10m including layover |
Find flight
from$293 |
|
|
12:00 — 09:15
+1 day
|
12:00 — 15:15
UA2133
United Airlines
Chicago — Newark
5h stop
20:15 — 23:18
UA212
United Airlines
Newark — Tampa
8h 42m stop
08:00 — 09:15
UA3135
United Airlines
Tampa — Key West
|
20h 15m including layover |
Find flight
from$375 |
|
|
12:53 — 09:15
+1 day
|
12:53 — 16:08
UA2238
United Airlines
Chicago — Newark
4h 7m stop
20:15 — 23:18
UA212
United Airlines
Newark — Tampa
8h 42m stop
08:00 — 09:15
UA3135
United Airlines
Tampa — Key West
|
19h 22m including layover |
Find flight
from$375 |
|
|
15:56 — 14:20
+1 day
|
15:56 — 18:50
UA2430
United Airlines
Chicago — Washington D.C.
3h 35m stop
22:25 — 00:49
UA689
United Airlines
Washington D.C. — Orlando
12h 6m stop
12:55 — 14:20
UA3071
United Airlines
Orlando — Key West
|
21h 24m including layover |
Find flight
from$340 |
|
|
15:56 — 10:10
+1 day
|
15:56 — 18:50
UA1616
United Airlines
Chicago — Washington D.C.
3h 40m stop
22:30 — 00:54
UA689
United Airlines
Washington D.C. — Orlando
7h 51m stop
08:45 — 10:10
UA3075
United Airlines
Orlando — Key West
|
17h 14m including layover |
Find flight
from$376 |
|
*Departure and arrival times - local. Updated on May 11, 2025
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 21:35 from 7 Chicago airports and arrive 05:45 to 21:35 to 2 Key West airports. Average flight time is 3h 6m.
- The fastest flight 3h 6m
- Average flight time 3h 6m
- The earliest flight 05:45
- The latest flight 21:35
- Distance 1244 ml
The cheapest months to travel to Key West are december (from 251 $), november (from 288 $), february (from 300 $).
The most expensive months are january (from 387 $), february (from 300 $), november (from 288 $).
What is the lowest airfare Chicago to Key West?
The cheapest plane ticket found by our users is $251. This airfare is for economy class on one-way UA2326 flight by United Airlines for February 21, 2025 which leaves O'Hare International in Chicago at 07:35 am and arrives at Key West Key West Int. at 17:15.
Economy class
$251
Business class
?
First class
?
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 - 96 departures per week at the price of from $ 251 . And the most expensive tickets are offered by United Airlines airline - from $ 595.
Direct flights
There are 3 nonstop flights on the route. The fastest direct flight is UA325 by United Airlines takes 3h 6m and the cheapest is UA2326 by United Airlines for $374.
- UA - United Airlinesfrom $374Find
See more direct flights
Connecting Flights
There are 93 flights with layovers on the route. The fastest connecting flight is UA1768 by United Airlines takes 5h 50m and the cheapest is UA2326 by United Airlines for $251.
- UA - United Airlinesfrom $251Find
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-ORDfrom $251Find
- Midway-MDWFind
- Dupage County-DPAFind
- Chicago FSS-CHIFind
- Merrill C Meigs (closed)-CGXFind
- Pal-Waukee-PWKFind
- Chicago NAS-NOHFind
Key West airports
- NAS-NQXFind
- Key West Int.-EYWFind
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.
- from $508Find
- from $74Find
- from $76Find
- from $62Find
- from $66Find
- from $70Find
- from $66Find
- from $61Find
- from $65Find
- from $61Find
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.
- from $60Find
- from $72Find
- from $73Find
- from $61Find
- from $79Find
- from $73Find
- from $76Find
- from $60Find
- from $59Find
- from $74Find
How to book a plane 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.