Cheap Flights from Chicago, IL to Key West, FL from $97

One way Round trip

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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 $97, 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: $97 (one-way), $166 (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 $97. Take a look at the list of flights with layovers from Chicago to Key West from $97. There’re no direct flights. The fastest connecting flight – 4h 43m.

Price	Departure	Arrival	Flight Duration	Airline	Flight
from $97 Find flight	15:11 Chicago O'Hare International	11:15+1 день Key West Key West Int.	19h 4m layover 15h 7m - Tampa	Spirit Airlines	NK729 3M135
from $151 Find flight	05:00 Chicago O'Hare International	11:23 Key West Key West Int.	5h 23m layover 1h 30m - Miami	American Airlines	AA1163 AA4558
from $151 Find flight	14:00 Chicago O'Hare International	20:56 Key West Key West Int.	5h 56m layover 1h 43m - Miami	American Airlines	AA791 AA4694
from $152 Find flight	07:00 Chicago O'Hare International	13:08 Key West Key West Int.	5h 8m layover 0h 59m - Miami	American Airlines	AA2507 AA4396
from $152 Find flight	07:19 Chicago O'Hare International	13:58 Key West Key West Int.	5h 39m layover 1h 25m - Charlotte	American Airlines	AA2052 AA4648
from $153 Find flight	05:36 Chicago O'Hare International	11:19 Key West Key West Int.	4h 43m layover 0h 45m - Miami	American Airlines	AA1411 AA4558
from $153 Find flight	12:11 Chicago O'Hare International	19:30 Key West Key West Int.	6h 19m layover 2h 10m - Miami	American Airlines	AA335 AA4481
from $153 Find flight	14:15 Chicago O'Hare International	21:37 Key West Key West Int.	6h 22m layover 2h 4m - Miami	American Airlines	AA1308 AA4694
from $161 Find flight	06:30 Chicago O'Hare International	12:52 Key West Key West Int.	5h 22m layover 1h 26m - Miami	American Airlines	AA2498 AA4396
from $161 Find flight	05:36 Chicago O'Hare International	12:52 Key West Key West Int.	6h 16m layover 2h 20m - Miami	American Airlines	AA1411 AA4396
from $165 Find flight	09:10 Chicago O'Hare International	16:40 Key West Key West Int.	6h 30m layover 2h 22m - Orlando	United Airlines	UA730 3M70
from $159 Find flight	10:40 Chicago O'Hare International	18:28 Key West Key West Int.	6h 48m layover 0h 50m - Charlotte 0h 55m - Miami	American Airlines	AA1668 AA1698 AA4481
from $164 Find flight	07:00 Chicago O'Hare International	16:40 Key West Key West Int.	8h 40m layover 1h 0m - Washington D.C. 2h 15m - Orlando	United Airlines	UA2198 UA402 3M70

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*Departure and arrival times - local. Prices indicated for one-way flights. Information updated on July 27, 2024

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	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$151
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$153
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$156
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$152
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$152
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$121
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$121
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$121
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$123
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$177
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$153
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$115
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$123
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$97
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$112
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$97
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$97
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$139
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$137
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$206
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$206
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$167
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$166
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$199
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$199
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$155
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$163
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$119
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$123
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$186

Departure	Arrival	Flight Details	Flight Time	Price
		stop stop	including layover	Find flight from$

*Departure and arrival times - local. Updated on July 27, 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 $97. 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

$97

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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 $ 121 . And the most expensive tickets are offered by Southwest Airlines airline - from $ 631.

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 $97.

AA - American Airlines

from $121

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F9 - Frontier Airlines

from $148

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WN - Southwest Airlines

from $137

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DL - Delta Air Lines Inc.

from $254

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UA - United Airlines

from $115

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NK - Spirit Airlines

from $97

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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 $97
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Midway-MDW

from $137
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Dupage County-DPA

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Chicago FSS-CHI

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Merrill C Meigs (closed)-CGX

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Pal-Waukee-PWK

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Chicago NAS-NOH

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Key West airports

NAS-NQX

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Key West Int.-EYW

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Airplanes

There are flights to Key West from Chicago by 6 airlines that use 10 aircraft brands. They range from huge modern airplanes to small-sized.

Airbus A321

from $151

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Airbus A321-100/200

from $152

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Boeing 737-800

from $153

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Airbus A319

from $164

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Boeing 757-300

from $165

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Boeing 737-900

from $169

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Bombardier CRJ 700

from $186

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Airbus A320-100/200

from $324

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Embraer 170

from $327

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Bombardier CRJ 900

from $332

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Top Domestic Destinations from Chicago

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

Chicago — Las Vegas

from $508

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Chicago — Tampa

from $63

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Chicago — Los Angeles

from $181

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Chicago — Orlando

from $62

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Chicago — New York

from $74

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Chicago — Dallas

from $70

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Chicago — San Antonio

from $59

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Chicago — Atlanta

from $76

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Chicago — Miami

from $66

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Chicago — Denver

from $61

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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.

Chicago — London

from $60

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Chicago — Manchester

from $58

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Chicago — Zurich

from $61

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Chicago — Cancun

from $72

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Chicago — Dublin

from $59

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Chicago — Madrid

from $72

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Chicago — Rome

from $79

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Chicago — Paris

from $61

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Chicago — Tel Aviv

from $628

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Chicago — Mumbai

from $74

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All flights from Chicago | All flights to Key West

How to book a plane ticket yourself?

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