Cheap Flights from Chicago, IL to Key West, FL from $101

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On Cheapflightsplus.com you will find 241 connecting flights from Chicago to Key West. You can compare airfare deals from 4 airlines and multiple travel sites from $101, 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: $101 (one-way), $173 (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 $101. Take a look at the list of flights with layovers from Chicago to Key West from $101. There’re no direct flights. The fastest connecting flight – 5h 30m.
Price Departure Arrival Flight Duration Airline Flight
from $101
Find flight
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 $126
Find flight
16:38
Chicago
O'Hare International
 08:03+1 день
Key West
Key West Int.
 14h 25m
layover
10h 33m - Clearwater
 Spirit Airlines
NK529
G4971
from $136
Find flight
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 $144
Find flight
20:36
Chicago
Midway
 15:03+1 день
Key West
Key West Int.
 17h 27m
layover
6h 47m - Fletcher
6h 23m - Clearwater
 Allegiant Air
G4248
G4247
G41071
Show all tickets
*Departure and arrival times - local. Prices indicated for one-way flights. Information updated on September 19, 2025
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
07:27 — 08:03
+1 day
06:30 — 10:08 NK2157 Spirit Airlines
Chicago — Clearwater
19h 49m stop
07:00 — 08:03 G4971 Allegiant Air
Clearwater — Key West
23h 36m
including layover
Find flight
from$144
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$164
07:56 — 09:42
+1 day
07:56 — 11:40 NK2550 Spirit Airlines
Chicago — Sanford
20h 50m stop
08:30 — 09:42 G42861 Allegiant Air
Sanford — Key West
24h 46m
including layover
Find flight
from$165
10:46 — 09:42
+1 day
10:46 — 14:30 NK2189 Spirit Airlines
Chicago — Sanford
18h stop
08:30 — 09:42 G42861 Allegiant Air
Sanford — Key West
21h 56m
including layover
Find flight
from$165
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$133
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$136
16:35 — 09:40
+1 day
16:35 — 20:20 NK2189 Spirit Airlines
Chicago — Sanford
12h 10m stop
08:30 — 09:40 G42859 Allegiant Air
Sanford — Key West
16h 5m
including layover
Find flight
from$179
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$126
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$126
16:38 — 09:12
+1 day
16:38 — 20:27 NK529 Spirit Airlines
Chicago — Clearwater
11h 43m stop
08:10 — 09:12 G4973 Allegiant Air
Clearwater — Key West
15h 34m
including layover
Find flight
from$172
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$101
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$166
19:39 — 13:07
+1 day
19:39 — 23:32 NK507 Spirit Airlines
Chicago — Orlando
12h 20m stop
11:52 — 13:07 MX162 Mexicana
Orlando — Key West
16h 28m
including layover
Find flight
from$168
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$149
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$153
*Departure and arrival times - local. Updated on September 19, 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 22h 27m.

  • The fastest flight 5h 30m
  • Average flight time 22h 27m
  • The earliest flight 05:05
  • The latest flight 21:45
  • Distance 1244 ml

The cheapest months to travel to Key West are august (from 101 $), june (from 136 $), july (from 146 $).

The most expensive months are january (from 388 $), december (from 342 $), november (from 280 $).

What is the lowest airfare Chicago to Key West?

The cheapest plane ticket found by our users is $101. 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
$101
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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 4 regular airlines and 3 low-cost airlines. Most of the flights on this route are operated by Sun Country Airlines - 7 departures per week at the price of from $ 200 . And the most expensive tickets are offered by United Airlines airline - from $ 1212.

Direct flights

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

Connecting Flights

There are 241 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 $101.

  • SY - Sun Country Airlines
    from $200
    Find
  • UA - United Airlines
    from $190
    Find
  • NK - Spirit Airlines
    from $101
    Find
  • G4 - Allegiant Air
    from $144
    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 $101
    Find
  • Midway-MDW
    from $144
    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 4 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.

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