Cheap Flights from Key West, FL to Chicago, IL from $220

Return flight: Chicago – Key West
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On Cheapflightsplus.com you will find 2 direct and 41 connecting flights from Key West to Chicago. You can compare airfare deals from 2 airlines and multiple travel sites from $220, 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: $220 (one-way), $377 (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 $220. The fastest direct flight takes 3h 31m and the fastest connecting – 6h 51m.
Price Departure Arrival Flight Duration Airline Flight
from $319
Find flight
15:50
Key West
Key West Int.
 18:21
Chicago
O'Hare International
 3h 31m United Airlines
UA770
from $324
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16:09
Key West
Key West Int.
 18:51
Chicago
O'Hare International
 3h 42m United Airlines
UA1504
from $220
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10:55
Key West
Key West Int.
 18:49
Chicago
O'Hare International
 8h 54m
layover
4h 25m - Miami
 United Airlines
UA3093
UA672
from $244
Find flight
18:00
Key West
Key West Int.
 11:41+1 день
Chicago
O'Hare International
 18h 41m
layover
14h 25m - Tampa
 United Airlines
UA3137
UA408
from $244
Find flight
18:00
Key West
Key West Int.
 13:13+1 день
Chicago
O'Hare International
 20h 13m
layover
15h 56m - Tampa
 United Airlines
UA3137
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
18:00
Key West
Key West Int.
 09:37+1 день
Chicago
O'Hare International
 16h 37m
layover
12h 15m - Tampa
 United Airlines
UA3137
UA2195
from $288
Find flight
19:40
Key West
Key West Int.
 16:38+1 день
Chicago
O'Hare International
 21h 58m
layover
17h 30m - Orlando
 United Airlines
UA3070
UA2061
from $329
Find flight
13:00
Key West
Key West Int.
 18:55
Chicago
O'Hare International
 6h 55m
layover
1h 51m - Washington D.C.
 United Airlines
UA6217
UA1117
from $329
Find flight
16:50
Key West
Key West Int.
 22:45
Chicago
O'Hare International
 6h 55m
layover
1h 0m - Houston
 United Airlines
UA6288
UA321
from $329
Find flight
13:50
Key West
Key West Int.
 20:25
Chicago
O'Hare International
 7h 35m
layover
1h 48m - Newark
 United Airlines
UA1513
UA254
from $329
Find flight
16:50
Key West
Key West Int.
 00:15+1 день
Chicago
O'Hare International
 8h 25m
layover
2h 34m - Houston
 United Airlines
UA6288
UA1858
from $343
Find flight
15:05
Key West
Key West Int.
 21:44
Chicago
O'Hare International
 7h 39m
layover
3h 4m - Orlando
 United Airlines
UA3073
UA2677
from $335
Find flight
14:00
Key West
Key West Int.
 21:43
Chicago
O'Hare International
 8h 43m
layover
1h 10m - Tampa
0h 45m - Newark
 United Airlines
UA3136
UA2045
UA546
from $553
Find flight
15:05
Key West
Key West Int.
 00:15+1 день
Chicago
O'Hare International
 10h 10m
layover
2h 27m - Orlando
0h 50m - Houston
 Gulfstream International Airlines
3M73
UA1692
UA1692
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*Departure and arrival times - local. Prices indicated for one-way flights. Information updated on December 21, 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
16:09 — 18:51
16:09 — 18:51 UA1504 United Airlines
Key West — Chicago
3h 42m
Find flight
from$324
10:55 — 18:49
10:55 — 12:00 UA3093 United Airlines
Key West — Miami
4h 25m stop
16:25 — 18:49 UA672 United Airlines
Miami — Chicago
8h 54m
including layover
Find flight
from$220
10:55 — 10:52
+1 day
10:55 — 12:00 UA3093 United Airlines
Key West — Miami
20h 25m stop
08:25 — 10:52 UA1878 United Airlines
Miami — Chicago
24h 57m
including layover
Find flight
from$220
12:20 — 18:52
12:20 — 15:00 UA326 United Airlines
Key West — Washington D.C.
2h 25m stop
17:25 — 18:52 UA2497 United Airlines
Washington D.C. — Chicago
7h 32m
including layover
Find flight
from$632
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
13:50 — 20:25
13:50 — 16:55 UA1513 United Airlines
Key West — Newark
1h 48m stop
18:43 — 20:25 UA254 United Airlines
Newark — Chicago
7h 35m
including layover
Find flight
from$329
14:00 — 11:41
+1 day
14:00 — 15:15 UA3136 United Airlines
Key West — Tampa
18h 25m stop
09:40 — 11:41 UA408 United Airlines
Tampa — Chicago
22h 41m
including layover
Find flight
from$244
14:00 — 13:13
+1 day
14:00 — 15:15 UA3136 United Airlines
Key West — Tampa
19h 56m stop
11:11 — 13:13 UA1596 United Airlines
Tampa — Chicago
24h 13m
including layover
Find flight
from$244
15:05 — 09:21
+1 day
15:05 — 16:30 UA3073 United Airlines
Key West — Orlando
14h 45m stop
07:30 — 09:33 UA2673 United Airlines
Orlando — Chicago
19h 16m
including layover
Find flight
from$235
15:05 — 13:06
+1 day
15:05 — 16:30 UA3073 United Airlines
Key West — Orlando
18h 30m stop
11:00 — 13:06 UA374 United Airlines
Orlando — Chicago
23h 1m
including layover
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from$235
16:50 — 22:45
16:50 — 19:02 UA6288 United Airlines
Key West — Houston
1h stop
20:02 — 22:45 UA321 United Airlines
Houston — Chicago
6h 55m
including layover
Find flight
from$329
18:00 — 11:41
+1 day
18:00 — 19:15 UA3137 United Airlines
Key West — Tampa
14h 25m stop
09:40 — 11:41 UA408 United Airlines
Tampa — Chicago
18h 41m
including layover
Find flight
from$244
18:00 — 13:13
+1 day
18:00 — 19:15 UA3137 United Airlines
Key West — Tampa
15h 56m stop
11:11 — 13:13 UA1596 United Airlines
Tampa — Chicago
20h 13m
including layover
Find flight
from$244
19:40 — 09:21
+1 day
19:40 — 21:05 UA3070 United Airlines
Key West — Orlando
10h 10m stop
07:30 — 09:33 UA2673 United Airlines
Orlando — Chicago
14h 41m
including layover
Find flight
from$235
19:40 — 13:06
+1 day
19:40 — 21:05 UA3070 United Airlines
Key West — Orlando
13h 55m stop
11:00 — 13:06 UA374 United Airlines
Orlando — Chicago
18h 26m
including layover
Find flight
from$235
*Departure and arrival times - local. Updated on December 21, 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 37m.

  • The fastest flight 3h 31m
  • Average flight time 3h 37m
  • The earliest flight 10:00
  • The latest flight 19:40
  • Distance 1244 ml

The cheapest months to travel to Chicago are january (from 220 $), february (from 220 $), november (from 239 $).

What is the lowest airfare Key West to Chicago?

The cheapest plane ticket found by our users is $220. This airfare is for economy class on one-way UA3093 flight by United Airlines for January 22, 2025 which leaves Key West Int. in Key West at 10:55 am and arrives at Chicago O'Hare International at 18:49.

Economy class
$220
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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 2 regular airlines . Most of the flights on this route are operated by Gulfstream International Airlines - 3 departures per week at the price of from $ 547 . And the most expensive tickets are offered by Gulfstream International Airlines airline - from $ 830.

Direct flights

There are 2 nonstop flights on the route. The fastest direct flight is UA770 by United Airlines takes 3h 31m and the cheapest is UA3093 by United Airlines for $319.

  • UA - United Airlines
    from $319
    Find
See more direct flights

Connecting Flights

There are 41 flights with layovers on the route. The fastest connecting flight is UA3093 by United Airlines takes 6h 51m and the cheapest is UA3093 by United Airlines for $220.

  • 3M - Gulfstream International Airlines
    from $547
    Find
  • UA - United Airlines
    from $220
    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
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  • Key West Int.-EYW
    from $220
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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
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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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Airplanes

There are flights to Chicago from Key West by 2 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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