Cheap Flights from Chicago, IL to Key West, FL from $80
On Cheapflightsplus.com you will find 136 connecting flights from Chicago to Key West. You can compare airfare deals from 4 airlines and multiple travel sites from $80, 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: $80 (one-way), $137 (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 $80. Take a look at the list of flights with layovers from Chicago to Key West from $80. There’re no direct flights. The fastest connecting flight – 5h 30m.
| Price | Departure | Arrival | Flight Duration | Airline | Flight |
|---|---|---|---|---|---|
| from $80 | 19:39 Chicago O'Hare International | 14:10+1 день Key West Key West Int. | 17h 31m layover 13h 28m - Sanford | Spirit Airlines | NK507 G41340 |
| from $99 | 16:38 Chicago O'Hare International | 14:43+1 день Key West Key West Int. | 21h 5m layover 17h 13m - Clearwater | Spirit Airlines | NK529 G41034 |
| from $105 | 13:03 Chicago O'Hare International | 14:10+1 день Key West Key West Int. | 24h 7m layover 20h 9m - Sanford | Spirit Airlines | NK1108 G41340 |
| from $117 | 20:29 Chicago O'Hare International | 09:33+1 день Key West Key West Int. | 12h 4m layover 8h 11m - Clearwater | Spirit Airlines | NK1763 G4971 |
| from $130 | 07:56 Chicago O'Hare International | 09:43+1 день Key West Key West Int. | 24h 47m layover 20h 52m - Sanford | Spirit Airlines | NK2550 G42877 |
| from $108 | 15:29 Chicago O'Hare International | 14:10+1 день Key West Key West Int. | 21h 41m layover 2h 9m - Miami 14h 0m - Sanford | Spirit Airlines | NK867 NK676 G41340 |
| from $108 | 14:46 Chicago O'Hare International | 14:10+1 день Key West Key West Int. | 22h 24m layover 4h 5m - New Orleans 13h 1m - Sanford | Spirit Airlines | NK1835 NK433 G41340 |
| from $114 | 15:36 Chicago O'Hare International | 14:44+1 день Key West Key West Int. | 22h 8m layover 12h 55m - Nashville 4h 52m - Clearwater | Spirit Airlines | NK1184 G4330 G41048 |
| from $115 | 14:54 Chicago Midway | 15:08+1 день Key West Key West Int. | 23h 14m layover 15h 10m - Knoxville 3h 54m - Clearwater | Allegiant Air | G43025 G43035 G41034 |
| from $122 | 10:31 Chicago Midway | 15:08+1 день Key West Key West Int. | 27h 37m layover 20h 21m - Fletcher 2h 57m - Clearwater | Allegiant Air | G41846 G41846 G41034 |
| from $126 | 08:00 Chicago O'Hare International | 15:26+1 день Key West Key West Int. | 30h 26m layover 9h 3m - Miami 14h 16m - Fletcher | Spirit Airlines | NK1986 G4248 G4975 |
| from $126 | 05:05 Chicago O'Hare International | 15:26+1 день Key West Key West Int. | 33h 21m layover 12h 0m - Miami 14h 16m - Fletcher | Spirit Airlines | NK19 G4248 G4975 |
| from $127 | 05:05 Chicago O'Hare International | 14:43+1 день Key West Key West Int. | 32h 38m layover 5h 55m - Miami 21h 30m - Clearwater | Spirit Airlines | NK19 NK322 G41034 |
| from $128 | 08:00 Chicago O'Hare International | 08:03+1 день Key West Key West Int. | 23h 3m layover 2h 58m - Miami 14h 50m - Clearwater | Spirit Airlines | NK1986 NK322 G4971 |
| from $128 | 05:05 Chicago O'Hare International | 08:03+1 день Key West Key West Int. | 25h 58m layover 5h 55m - Miami 14h 50m - Clearwater | Spirit Airlines | NK19 NK322 G4971 |
| from $132 | 11:37 Chicago Midway | 16:36+1 день Key West Key West Int. | 27h 59m layover 5h 45m - Punta Gorda 14h 18m - Pittsburgh | Allegiant Air | G42467 G42750 G4991 |
Show all tickets
*Departure and arrival times - local. Prices indicated for one-way flights. Information updated on July 03, 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 |
|---|---|---|---|---|
|
06:00 — 14:01
|
06:00 — 09:15
UA1658
United Airlines
Chicago — Newark
1h 15m stop
10:30 — 14:01
UA3687
United Airlines
Newark — Key West
|
7h 1m including layover |
Find flight
from$486 |
|
|
07:30 — 08:00
+1 day
|
07:30 — 11:21
UA1832
United Airlines
Chicago — Tampa
19h 24m stop
06:45 — 08:00
UA3134
United Airlines
Tampa — Key West
|
23h 30m including layover |
Find flight
from$150 |
|
|
07:56 — 09:43
+1 day
|
07:56 — 11:40
NK2550
Spirit Airlines
Chicago — Sanford
20h 52m stop
08:32 — 09:43
G42877
Allegiant Air
Sanford — Key West
|
24h 47m including layover |
Find flight
from$130 |
|
|
13:03 — 14:10
+1 day
|
13:03 — 16:51
NK1108
Spirit Airlines
Chicago — Sanford
20h 9m stop
13:00 — 14:10
G41340
Allegiant Air
Sanford — Key West
|
24h 7m including layover |
Find flight
from$105 |
|
|
13:03 — 13:07
+1 day
|
13:03 — 16:51
NK1108
Spirit Airlines
Chicago — Orlando
19h 1m stop
11:52 — 13:07
MX162
Mexicana
Orlando — Key West
|
23h 4m including layover |
Find flight
from$158 |
|
|
16:38 — 14:43
+1 day
|
16:38 — 20:27
NK529
Spirit Airlines
Chicago — Clearwater
17h 13m stop
13:40 — 14:43
G41034
Allegiant Air
Clearwater — Key West
|
21h 5m including layover |
Find flight
from$99 |
|
|
16:38 — 08:03
+1 day
|
16:38 — 20:27
NK529
Spirit Airlines
Chicago — Clearwater
10h 33m stop
07:00 — 08:03
G4971
Allegiant Air
Clearwater — Key West
|
14h 25m including layover |
Find flight
from$100 |
|
|
19:39 — 14:10
+1 day
|
19:39 — 23:32
NK507
Spirit Airlines
Chicago — Sanford
13h 28m stop
13:00 — 14:10
G41340
Allegiant Air
Sanford — Key West
|
17h 31m including layover |
Find flight
from$80 |
|
|
19:39 — 08:15
+1 day
|
19:39 — 23:32
NK507
Spirit Airlines
Chicago — Orlando
7h 28m stop
07:00 — 08:15
MX159
Mexicana
Orlando — Key West
|
11h 36m including layover |
Find flight
from$131 |
|
|
20:29 — 09:33
+1 day
|
20:29 — 00:19
NK1763
Spirit Airlines
Chicago — Clearwater
8h 11m stop
08:30 — 09:33
G4971
Allegiant Air
Clearwater — Key West
|
12h 4m including layover |
Find flight
from$117 |
|
|
20:29 — 14:44
+1 day
|
20:29 — 00:19
NK1763
Spirit Airlines
Chicago — Clearwater
13h 21m stop
13:40 — 14:44
G41048
Allegiant Air
Clearwater — Key West
|
17h 15m including layover |
Find flight
from$121 |
|
|
21:25 — 12:41
+1 day
|
21:24 — 00:45
UA396
United Airlines
Chicago — Newark
8h 43m stop
09:29 — 12:41
UA1822
United Airlines
Newark — Key West
|
14h 16m including layover |
Find flight
from$278 |
|
|
05:05 — 15:26
+1 day
|
05:05 — 09:10
NK19
Spirit Airlines
Chicago — Miami
12h stop
21:10 — 23:11
G4248
Allegiant Air
Miami — Fletcher
14h 16m stop
13:27 — 15:26
G4975
Allegiant Air
Fletcher — Key West
|
33h 21m including layover |
Find flight
from$126 |
|
|
05:05 — 14:43
+1 day
|
05:05 — 09:10
NK19
Spirit Airlines
Chicago — Miami
5h 55m stop
15:05 — 16:10
NK322
Spirit Airlines
Miami — Clearwater
21h 30m stop
13:40 — 14:43
G41034
Allegiant Air
Clearwater — Key West
|
32h 38m including layover |
Find flight
from$127 |
|
|
08:00 — 15:26
+1 day
|
08:00 — 12:07
NK1986
Spirit Airlines
Chicago — Miami
9h 3m stop
21:10 — 23:11
G4248
Allegiant Air
Miami — Fletcher
14h 16m stop
13:27 — 15:26
G4975
Allegiant Air
Fletcher — Key West
|
30h 26m including layover |
Find flight
from$126 |
|
|
08:00 — 08:03
+1 day
|
08:00 — 12:07
NK1986
Spirit Airlines
Chicago — Miami
2h 58m stop
15:05 — 16:10
NK322
Spirit Airlines
Miami — Clearwater
14h 50m stop
07:00 — 08:03
G4971
Allegiant Air
Clearwater — Key West
|
23h 3m including layover |
Find flight
from$128 |
|
|
10:31 — 15:08
+1 day
|
10:31 — 13:09
G41846
Allegiant Air
Chicago — Fletcher
20h 21m stop
09:30 — 11:08
G41846
Allegiant Air
Fletcher — Clearwater
2h 57m stop
14:05 — 15:08
G41034
Allegiant Air
Clearwater — Key West
|
27h 37m including layover |
Find flight
from$122 |
|
|
10:43 — 09:43
+1 day
|
10:43 — 13:42
NK2708
Spirit Airlines
Chicago — Atlanta
2h 50m stop
16:32 — 18:03
NK2460
Spirit Airlines
Atlanta — Sanford
14h 29m stop
08:32 — 09:43
G42877
Allegiant Air
Sanford — Key West
|
22h including layover |
Find flight
from$158 |
|
|
11:21 — 09:33
+1 day
|
11:21 — 13:51
NK1633
Spirit Airlines
Chicago — Dallas
4h 50m stop
18:41 — 22:14
NK1860
Spirit Airlines
Dallas — Clearwater
10h 16m stop
08:30 — 09:33
G4971
Allegiant Air
Clearwater — Key West
|
21h 12m including layover |
Find flight
from$145 |
|
|
11:37 — 16:36
+1 day
|
11:37 — 15:26
G42467
Allegiant Air
Chicago — Punta Gorda
5h 45m stop
21:11 — 23:36
G42750
Allegiant Air
Punta Gorda — Pittsburgh
14h 18m stop
13:54 — 16:36
G4991
Allegiant Air
Pittsburgh — Key West
|
27h 59m including layover |
Find flight
from$132 |
|
|
14:46 — 14:10
+1 day
|
14:46 — 16:59
NK1835
Spirit Airlines
Chicago — New Orleans
4h 5m stop
21:04 — 23:59
NK433
Spirit Airlines
New Orleans — Sanford
13h 1m stop
13:00 — 14:10
G41340
Allegiant Air
Sanford — Key West
|
22h 24m including layover |
Find flight
from$108 |
|
|
14:54 — 15:08
+1 day
|
14:54 — 17:20
G43025
Allegiant Air
Chicago — Knoxville
15h 10m stop
09:00 — 10:41
G43035
Allegiant Air
Knoxville — Clearwater
3h 54m stop
14:05 — 15:08
G41034
Allegiant Air
Clearwater — Key West
|
23h 14m including layover |
Find flight
from$115 |
|
|
15:29 — 14:10
+1 day
|
15:29 — 19:39
NK867
Spirit Airlines
Chicago — Miami
2h 9m stop
21:48 — 23:00
NK676
Spirit Airlines
Miami — Sanford
14h stop
13:00 — 14:10
G41340
Allegiant Air
Sanford — Key West
|
21h 41m including layover |
Find flight
from$108 |
|
|
15:29 — 14:10
+1 day
|
15:29 — 19:39
NK867
Spirit Airlines
Chicago — Miami
1h 36m stop
21:15 — 22:27
NK196
Spirit Airlines
Miami — Sanford
14h 33m stop
13:00 — 14:10
G41340
Allegiant Air
Sanford — Key West
|
21h 41m including layover |
Find flight
from$108 |
|
*Departure and arrival times - local. Updated on July 3, 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 05:05 to 21:45 from 7 Chicago airports and arrive 05:05 to 21:45 to 2 Key West airports. Average flight time is 23h 4m.
- The fastest flight 5h 30m
- Average flight time 23h 4m
- The earliest flight 05:05
- The latest flight 21:45
- Distance 1244 ml
The cheapest months to travel to Key West are august (from 107 $), july (from 154 $), september (from 175 $).
The most expensive months are january (from 411 $), december (from 362 $), november (from 296 $).
What is the lowest airfare Chicago to Key West?
The cheapest plane ticket found by our users is $80. This airfare is for economy class on one-way NK507 flight by Spirit Airlines for August 16, 2025 which leaves O'Hare International in Chicago at 19:39 am and arrives at Key West Key West Int. at 14:10.
Economy class
$80
Business class
?
First class
?
Popular Airlines on the Route
The flight Chicago — Key West is served by 4 regular airlines and 3 low-cost airlines. Most of the flights on this route are operated by Sun Country Airlines - 2 departures per week at the price of from $ 177 . And the most expensive tickets are offered by United Airlines airline - from $ 486.
Direct flights
There’re no direct flights on this route. Try flights with stops.
Connecting Flights
There are 136 flights with layovers on the route. The fastest connecting flight is UA2326 by United Airlines takes 5h 30m and the cheapest is NK507 by Spirit Airlines for $80.
- SY - Sun Country Airlinesfrom $177Find
- UA - United Airlinesfrom $150Find
- NK - Spirit Airlinesfrom $80Find
- G4 - Allegiant Airfrom $115Find
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 $80Find
- Midway-MDWfrom $115Find
- 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 4 airlines that use 0 aircraft brands. They range from huge modern airplanes to small-sized.
Top Domestic Destinations from Chicago
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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.
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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.