Cheap Flights from Key West, FL to Chicago, IL from $154

Return flight: Chicago – Key West
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On Cheapflightsplus.com you will find 3 direct and 85 connecting flights from Key West to Chicago. You can compare airfare deals from 3 airlines and multiple travel sites from $154, book and save on cheap plane tickets and last minute offers. Also check out EYW-CHI flight schedule to find best flight time, convenient departure and arrival airports.

Find One-Way and Round-Trip Key West to Chicago 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: $154 (one-way), $264 (round-trip).
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Best Flights from Key West to Chicago Today

Take a look at the list of non stop flights and flights with layovers from Key West to Chicago with the lowest price of $154. The fastest direct flight takes 3h 21m and the fastest connecting – 5h 58m.
Price Departure Arrival Flight Duration Airline Flight
from $310
Find flight
16:05
Key West
Key West Int.
 18:26
Chicago
O'Hare International
 3h 21m United Airlines
UA2263
from $219
Find flight
10:55
Key West
Key West Int.
 11:46+1 день
Chicago
O'Hare International
 25h 51m
layover
21h 24m - Miami
 United Airlines
UA3093
UA337
from $242
Find flight
14:00
Key West
Key West Int.
 11:41+1 день
Chicago
O'Hare International
 22h 41m
layover
18h 30m - Tampa
 United Airlines
UA3136
UA1291
from $242
Find flight
10:00
Key West
Key West Int.
 11:41+1 день
Chicago
O'Hare International
 26h 41m
layover
22h 30m - Tampa
 United Airlines
UA3135
UA1291
from $243
Find flight
14:00
Key West
Key West Int.
 13:11+1 день
Chicago
O'Hare International
 24h 11m
layover
20h 0m - Tampa
 United Airlines
UA3136
UA1124
from $243
Find flight
14:00
Key West
Key West Int.
 16:32+1 день
Chicago
O'Hare International
 27h 32m
layover
23h 20m - Tampa
 United Airlines
UA3136
UA2147
from $243
Find flight
10:00
Key West
Key West Int.
 13:11+1 день
Chicago
O'Hare International
 28h 11m
layover
24h 0m - Tampa
 United Airlines
UA3135
UA1124
from $244
Find flight
14:00
Key West
Key West Int.
 11:41+1 день
Chicago
O'Hare International
 22h 41m
layover
18h 25m - Tampa
 United Airlines
UA3136
UA408
from $244
Find flight
14:00
Key West
Key West Int.
 13:13+1 день
Chicago
O'Hare International
 24h 13m
layover
19h 56m - Tampa
 United Airlines
UA3136
UA1596
from $244
Find flight
10:00
Key West
Key West Int.
 11:46+1 день
Chicago
O'Hare International
 26h 46m
layover
22h 30m - Tampa
 United Airlines
UA3135
UA408
from $244
Find flight
10:00
Key West
Key West Int.
 13:13+1 день
Chicago
O'Hare International
 28h 13m
layover
23h 56m - Tampa
 United Airlines
UA3135
UA1596
from $246
Find flight
14:00
Key West
Key West Int.
 09:37+1 день
Chicago
O'Hare International
 20h 37m
layover
16h 15m - Tampa
 United Airlines
UA3136
UA2195
from $276
Find flight
19:40
Key West
Key West Int.
 13:03+1 день
Chicago
O'Hare International
 18h 23m
layover
13h 55m - Orlando
 United Airlines
UA3070
UA503
from $320
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15:05
Key West
Key West Int.
 20:03
Chicago
O'Hare International
 5h 58m
layover
1h 30m - Orlando
 United Airlines
UA3073
UA2000
from $154
Find flight
10:53
Key West
Key West Int.
 00:24+1 день
Chicago
O'Hare International
 14h 31m
layover
5h 41m - Tampa
2h 38m - Houston
 Allegiant Air
G43643
NK3127
NK962
from $248
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18:00
Key West
Key West Int.
 14:19+1 день
Chicago
O'Hare International
 21h 19m
layover
13h 45m - Tampa
1h 49m - Washington D.C.
 United Airlines
UA3137
UA2331
UA2331
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*Departure and arrival times - local. Prices indicated for one-way flights. Information updated on November 18, 2024
Full flight schedule will help you in detecting at what time planes fly from Key West to Chicago. 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
15:50 — 18:21
15:50 — 18:21 UA770 United Airlines
Key West — Chicago
3h 31m
Find flight
from$319
16:05 — 18:26
16:05 — 18:26 UA2263 United Airlines
Key West — Chicago
3h 21m
Find flight
from$310
16:09 — 18:51
16:09 — 18:51 UA1504 United Airlines
Key West — Chicago
3h 42m
Find flight
from$324
10:55 — 11:46
+1 day
10:55 — 12:00 UA3093 United Airlines
Key West — Miami
21h 24m stop
09:24 — 11:46 UA337 United Airlines
Miami — Chicago
25h 51m
including layover
Find flight
from$219
12:55 — 20:07
12:55 — 16:02 UA2002 United Airlines
Key West — Newark
2h 23m stop
18:25 — 20:07 UA254 United Airlines
Newark — Chicago
8h 12m
including layover
Find flight
from$320
12:55 — 18:39
12:55 — 16:02 UA2002 United Airlines
Key West — Newark
58m stop
17:15 — 18:54 UA661 United Airlines
Newark — Chicago
6h 44m
including layover
Find flight
from$321
13:00 — 18:55
12:25 — 15:10 UA6217 United Airlines
Key West — Washington D.C.
1h 51m stop
17:36 — 18:55 UA1117 United Airlines
Washington D.C. — Chicago
6h 55m
including layover
Find flight
from$329
13:55 — 21:22
12:55 — 16:02 UA2002 United Airlines
Key West — Newark
2h 41m stop
19:43 — 21:22 UA546 United Airlines
Newark — Chicago
8h 27m
including layover
Find flight
from$320
14:00 — 11:41
+1 day
14:00 — 15:15 UA3136 United Airlines
Key West — Tampa
18h 30m stop
09:45 — 11:41 UA1291 United Airlines
Tampa — Chicago
22h 41m
including layover
Find flight
from$242
14:00 — 13:11
+1 day
14:00 — 15:15 UA3136 United Airlines
Key West — Tampa
20h stop
11:15 — 13:11 UA1124 United Airlines
Tampa — Chicago
24h 11m
including layover
Find flight
from$243
15:05 — 11:33
+1 day
15:05 — 16:30 UA3073 United Airlines
Key West — Orlando
17h stop
09:30 — 11:33 UA2341 United Airlines
Orlando — Chicago
21h 28m
including layover
Find flight
from$233
15:05 — 18:15
+1 day
15:05 — 16:30 UA3073 United Airlines
Key West — Orlando
23h 43m stop
16:15 — 18:17 UA1828 United Airlines
Orlando — Chicago
28h 10m
including layover
Find flight
from$233
18:00 — 11:41
+1 day
18:00 — 19:15 UA3137 United Airlines
Key West — Tampa
14h 30m stop
09:45 — 11:41 UA1291 United Airlines
Tampa — Chicago
18h 41m
including layover
Find flight
from$242
18:00 — 13:11
+1 day
18:00 — 19:15 UA3137 United Airlines
Key West — Tampa
16h stop
11:15 — 13:11 UA1124 United Airlines
Tampa — Chicago
20h 11m
including layover
Find flight
from$243
19:40 — 11:33
+1 day
19:40 — 21:05 UA3070 United Airlines
Key West — Orlando
12h 25m stop
09:30 — 11:33 UA2341 United Airlines
Orlando — Chicago
16h 53m
including layover
Find flight
from$233
19:40 — 18:15
+1 day
19:40 — 21:05 UA3070 United Airlines
Key West — Orlando
19h 8m stop
16:15 — 18:17 UA1828 United Airlines
Orlando — Chicago
23h 35m
including layover
Find flight
from$233
10:53 — 00:24
+1 day
10:53 — 11:54 G43643 Allegiant Air
Key West — Tampa
5h 41m stop
17:35 — 19:09 NK3127 Spirit Airlines
Tampa — Houston
2h 38m stop
21:47 — 00:24 NK962 Spirit Airlines
Houston — Chicago
14h 31m
including layover
Find flight
from$154
*Departure and arrival times - local. Updated on November 18, 2024

Flight Information

Below we will explain in detail what the flights cost on the destination from Key West to Chicago depends on and how to choose the most interesting flight option for you.

Distance between Key West and Chicago is 2001 miles. Time difference between the cities is 1h. Airplanes depart 10:00 to 19:40 from 2 Key West airports and arrive 10:00 to 19:40 to 7 Chicago airports. Average flight time is 3h 31m.

  • The fastest flight 3h 21m
  • Average flight time 3h 31m
  • The earliest flight 10:00
  • The latest flight 19:40
  • Distance 1244 ml

The cheapest months to travel to Chicago are december (from 154 $), january (from 220 $), february (from 220 $).

The most expensive months are november (from 239 $), february (from 220 $), january (from 220 $).

What is the lowest airfare Key West to Chicago?

The cheapest plane ticket found by our users is $154. This airfare is for economy class on one-way G43643 flight by Allegiant Air for December 14, 2024 which leaves Key West Int. in Key West at 10:53 am and arrives at Chicago O'Hare International at 00:24.

Economy class
$154
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Business class
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First class
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Popular Airlines on the Route

The flight Key West — Chicago is served by 3 regular airlines and 1 low-cost airline. Most of the flights on this route are operated by Gulfstream International Airlines - 10 departures per week at the price of from $ 433 . And the most expensive tickets are offered by Gulfstream International Airlines airline - from $ 830.

Direct flights

There are 3 nonstop flights on the route. The fastest direct flight is UA2263 by United Airlines takes 3h 21m and the cheapest is G43643 by Allegiant Air for $310.

  • UA - United Airlines
    from $310
    Find
See more direct flights

Connecting Flights

There are 85 flights with layovers on the route. The fastest connecting flight is UA3073 by United Airlines takes 5h 58m and the cheapest is G43643 by Allegiant Air for $154.

  • 3M - Gulfstream International Airlines
    from $433
    Find
  • UA - United Airlines
    from $219
    Find
  • G4 - Allegiant Air
    from $154
    Find
See more connecting flights

Airports

You can fly from Key West to Chicago from 2 airports (NAS, Key West Int.).

Key West airports

  • NAS-NQX
    Find
  • Key West Int.-EYW
    from $154
    Find

Chicago airports

  • O'Hare International-ORD
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  • Midway-MDW
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  • Dupage County-DPA
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  • Chicago FSS-CHI
    Find
  • Merrill C Meigs (closed)-CGX
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  • Pal-Waukee-PWK
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  • Chicago NAS-NOH
    Find

Airplanes

There are flights to Chicago from Key West by 3 airlines that use 0 aircraft brands. They range from huge modern airplanes to small-sized.

Top Domestic Destinations from Key West

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

Top International Destinations from Key West

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.

    To find a plane ticket, please select dates.

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