Cheap Flights from Chicago, IL to Key West, FL from $93

Return flight: Key West – Chicago

On Cheapflightsplus.com you will find 184 connecting flights from Chicago to Key West. You can compare airfare deals from 6 airlines and multiple travel sites from $93, 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: $93 (one-way), $159 (round-trip).
Direct flights
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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
05:00 — 11:23
05:00 — 08:59 AA1163 American Airlines
Chicago — Miami
1h 30m stop
10:29 — 11:23 AA4558 American Airlines
Miami — Key West
5h 23m
including layover
Find flight
from$144
05:36 — 11:19
05:36 — 09:40 AA1411 American Airlines
Chicago — Miami
45m stop
10:25 — 11:19 AA4558 American Airlines
Miami — Key West
4h 43m
including layover
Find flight
from$146
06:00 — 20:56
06:00 — 09:58 AA1438 American Airlines
Chicago — Miami
10h 2m stop
20:00 — 20:56 AA4694 American Airlines
Miami — Key West
13h 56m
including layover
Find flight
from$149
07:00 — 13:08
07:00 — 11:12 AA2507 American Airlines
Chicago — Miami
59m stop
12:11 — 13:08 AA4396 American Airlines
Miami — Key West
5h 8m
including layover
Find flight
from$145
07:19 — 13:58
07:19 — 10:18 AA2052 American Airlines
Chicago — Charlotte
1h 25m stop
11:43 — 13:58 AA4648 American Airlines
Charlotte — Key West
5h 39m
including layover
Find flight
from$145
09:50 — 10:30
+1 day
09:50 — 13:32 AA2921 American Airlines
Chicago — Tampa
19h 43m stop
09:15 — 10:30 3M134 Gulfstream International Airlines
Tampa — Key West
23h 40m
including layover
Find flight
from$115
09:50 — 11:15
+1 day
09:50 — 13:32 AA2921 American Airlines
Chicago — Tampa
20h 28m stop
10:00 — 11:15 3M135 Gulfstream International Airlines
Tampa — Key West
24h 25m
including layover
Find flight
from$115
10:15 — 12:15
+1 day
10:15 — 14:05 AA2398 American Airlines
Chicago — Orlando
20h 50m stop
10:55 — 12:15 3M75 Gulfstream International Airlines
Orlando — Key West
25h
including layover
Find flight
from$115
10:55 — 14:50
+1 day
10:55 — 15:18 UA722 United Airlines
Chicago — Miami
22h 27m stop
13:45 — 14:50 3M93 Gulfstream International Airlines
Miami — Key West
26h 55m
including layover
Find flight
from$117
11:15 — 12:15
+1 day
11:15 — 14:55 UA754 United Airlines
Chicago — Orlando
20h stop
10:55 — 12:15 3M75 Gulfstream International Airlines
Orlando — Key West
24h
including layover
Find flight
from$169
12:11 — 19:30
12:11 — 16:27 AA335 American Airlines
Chicago — Miami
2h 10m stop
18:37 — 19:30 AA4481 American Airlines
Miami — Key West
6h 19m
including layover
Find flight
from$146
14:24 — 14:50
+1 day
14:24 — 18:45 UA490 United Airlines
Chicago — Miami
19h stop
13:45 — 14:50 3M93 Gulfstream International Airlines
Miami — Key West
23h 26m
including layover
Find flight
from$110
14:24 — 17:40
+1 day
14:24 — 18:45 UA490 United Airlines
Chicago — Miami
21h 45m stop
16:30 — 17:40 3M94 Gulfstream International Airlines
Miami — Key West
26h 16m
including layover
Find flight
from$117
15:11 — 11:15
+1 day
15:11 — 18:53 NK729 Spirit Airlines
Chicago — Tampa
15h 7m stop
10:00 — 11:15 3M135 Gulfstream International Airlines
Tampa — Key West
19h 4m
including layover
Find flight
from$93
17:00 — 14:50
+1 day
17:00 — 21:10 NK425 Spirit Airlines
Chicago — Miami
16h 35m stop
13:45 — 14:50 3M93 Gulfstream International Airlines
Miami — Key West
20h 50m
including layover
Find flight
from$106
18:15 — 12:15
+1 day
18:15 — 22:07 NK929 Spirit Airlines
Chicago — Orlando
12h 48m stop
10:55 — 12:15 3M75 Gulfstream International Airlines
Orlando — Key West
17h
including layover
Find flight
from$93
18:28 — 11:40
+1 day
18:28 — 22:41 NK425 Spirit Airlines
Chicago — Miami
11h 54m stop
10:35 — 11:40 UA3093 United Airlines
Miami — Key West
16h 12m
including layover
Find flight
from$93
19:55 — 14:50
+1 day
19:55 — 23:50 WN1430 Southwest Airlines
Chicago — Miami
13h 55m stop
13:45 — 14:50 3M93 Gulfstream International Airlines
Miami — Key West
17h 55m
including layover
Find flight
from$133
06:40 — 12:15
+1 day
06:40 — 09:30 WN950 Southwest Airlines
Chicago — Philadelphia
5h 59m stop
15:29 — 18:08 F91167 Frontier Airlines
Philadelphia — Orlando
16h 47m stop
10:55 — 12:15 3M75 Gulfstream International Airlines
Orlando — Key West
28h 35m
including layover
Find flight
from$131
08:30 — 20:56
08:30 — 11:39 AA1211 American Airlines
Chicago — Newark
3h 21m stop
15:00 — 18:11 AA1060 American Airlines
Newark — Miami
1h 49m stop
20:00 — 20:56 AA4694 American Airlines
Miami — Key West
11h 26m
including layover
Find flight
from$197
08:30 — 20:56
08:30 — 11:39 AA367 American Airlines
Chicago — New York
3h 50m stop
15:29 — 18:50 AA1626 American Airlines
New York — Miami
1h 10m stop
20:00 — 20:56 AA4694 American Airlines
Miami — Key West
11h 26m
including layover
Find flight
from$197
11:15 — 20:56
11:15 — 14:14 AA2588 American Airlines
Chicago — Philadelphia
1h 31m stop
15:45 — 18:56 AA2571 American Airlines
Philadelphia — Miami
1h 4m stop
20:00 — 20:56 AA4694 American Airlines
Miami — Key West
8h 41m
including layover
Find flight
from$160
12:04 — 20:56
12:04 — 15:04 AA2372 American Airlines
Chicago — Charlotte
1h 26m stop
16:30 — 18:43 AA156 American Airlines
Charlotte — Miami
1h 17m stop
20:00 — 20:56 AA4694 American Airlines
Miami — Key West
7h 52m
including layover
Find flight
from$158
13:50 — 10:30
+1 day
13:50 — 16:00 WN1164 Southwest Airlines
Chicago — Cleveland
2h 30m stop
18:30 — 20:56 NK177 Spirit Airlines
Cleveland — Tampa
12h 19m stop
09:15 — 10:30 3M134 Gulfstream International Airlines
Tampa — Key West
19h 40m
including layover
Find flight
from$190
13:50 — 11:15
+1 day
13:50 — 16:00 WN1164 Southwest Airlines
Chicago — Cleveland
2h 30m stop
18:30 — 20:56 NK177 Spirit Airlines
Cleveland — Tampa
13h 4m stop
10:00 — 11:15 3M135 Gulfstream International Airlines
Tampa — Key West
20h 25m
including layover
Find flight
from$190
15:16 — 11:15
+1 day
15:16 — 18:29 AA1464 American Airlines
Chicago — Philadelphia
2h 1m stop
20:30 — 23:08 AA2556 American Airlines
Philadelphia — Tampa
10h 52m stop
10:00 — 11:15 3M135 Gulfstream International Airlines
Tampa — Key West
18h 59m
including layover
Find flight
from$148
16:41 — 11:15
+1 day
16:41 — 19:51 AA2853 American Airlines
Chicago — Philadelphia
39m stop
20:30 — 23:08 AA2556 American Airlines
Philadelphia — Tampa
10h 52m stop
10:00 — 11:15 3M135 Gulfstream International Airlines
Tampa — Key West
17h 34m
including layover
Find flight
from$155
20:04 — 14:50
+1 day
20:04 — 22:30 NK903 Spirit Airlines
Chicago — Dallas
7h 5m stop
05:35 — 09:29 NK1972 Spirit Airlines
Dallas — Miami
4h 16m stop
13:45 — 14:50 3M93 Gulfstream International Airlines
Miami — Key West
17h 46m
including layover
Find flight
from$113
20:37 — 14:50
+1 day
20:37 — 23:40 NK635 Spirit Airlines
Chicago — Atlanta
6h 35m stop
06:15 — 08:10 NK1877 Spirit Airlines
Atlanta — Miami
5h 35m stop
13:45 — 14:50 3M93 Gulfstream International Airlines
Miami — Key West
17h 13m
including layover
Find flight
from$117
22:10 — 11:19
+1 day
22:10 — 00:27 AA3155 American Airlines
Chicago — Detroit
6h 13m stop
06:40 — 09:43 AA1020 American Airlines
Detroit — Miami
42m stop
10:25 — 11:19 AA4558 American Airlines
Miami — Key West
12h 9m
including layover
Find flight
from$177
*Departure and arrival times - local. Updated on May 28, 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 05:00 to 22:10 from 7 Chicago airports and arrive 05:00 to 22:10 to 2 Key West airports. Average flight time is 15h 24m.

  • The fastest flight 4h 43m
  • Average flight time 15h 24m
  • The earliest flight 05:00
  • The latest flight 22:10
  • Distance 1244 ml

What is the lowest airfare Chicago to Key West?

The cheapest plane ticket found by our users is $93. This airfare is for economy class on one-way NK425 flight by Spirit Airlines for August 11, 2020 which leaves O'Hare International in Chicago at 18:28 am and arrives at Key West Key West Int. at 11:40.

Economy class
$93
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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 6 regular airlines and 3 low-cost airlines. Most of the flights on this route are operated by American Airlines - 78 departures per week at the price of from $ 115 . And the most expensive tickets are offered by Southwest Airlines airline - from $ 602.

Direct flights

There’re no direct flights on this route. Try flights with stops.

Connecting Flights

There are 184 flights with layovers on the route. The fastest connecting flight is AA1411 by American Airlines takes 4h 43m and the cheapest is NK425 by Spirit Airlines for $93.

  • AA - American Airlines
    from $115
    Find
  • F9 - Frontier Airlines
    from $141
    Find
  • WN - Southwest Airlines
    from $131
    Find
  • DL - Delta Air Lines Inc.
    from $242
    Find
  • UA - United Airlines
    from $110
    Find
  • NK - Spirit Airlines
    from $93
    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 $93
    Find
  • Midway-MDW
    from $131
    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

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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