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Flights from Chicago to Key West – Direct & connecting routes

Non-stop airlines Connecting flights Show map Price search

ORD to EYW flights and routes map ORD to EYW – All flight route options from Chicago O Hare International, Illinois, USA to Key West International, Florida, USA. These routes are operated by 4 airlines. Fly non-stop with United Airlines or American Airlines, or choose from 7 different stopover flights. The shortest flight time is 3 hours and 11 minutes. See the full flight schedule and time table, including departure times, airlines and stopover details to find the best option for you.

From
To
USA ORD Chicago O Hare Chicago, IL, USA
USA EYW Key West , FL, USA
ORD
Chicago O Hare
USAChicago, IL, USA
Key West
USAKey West, FL, USA
EYW
2 direct routes found »
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12 routes with 1 stop found »
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Non-stop route options:

Duration

United Airlines
Non-stop with United Airlines. 1 flight per day.
Begins in 26/10

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3h 11m

Begins in 26/10
United Airlines
Non-stop with United Airlines.
3h 11m
1 flight per day.
Begins in 26/10
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American Airlines
Non-stop with American Airlines. 0-1 flights per day.
Only saturdays

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3h 16m

Only saturdays
American Airlines
Non-stop with American Airlines.
3h 16m
0-1 flights per day.
Only saturdays
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1 stop route options with the same airline:

Duration

Via Atlanta ATL
1 stop with Delta Air Lines. 5 flights per day.

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5h 23m

Via Atlanta ATL
1 stop with Delta Air Lines.
5h 23m
5 flights per day.
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Via Miami MIA
1 stop with American Airlines. 3 flights per day.

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5h 30m

Via Miami MIA
1 stop with American Airlines.
5h 30m
3 flights per day.
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Via Charlotte CLT
1 stop with American Airlines. 4 flights per day.

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5h 52m

Via Charlotte CLT
1 stop with American Airlines.
5h 52m
4 flights per day.
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Via Philadelphia PHL
1 stop with American Airlines. 2 flights per day.

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6h 19m

Via Philadelphia PHL
1 stop with American Airlines.
6h 19m
2 flights per day.
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Via Washington DCA
1 stop with American Airlines. 0-1 flights per day.
Begins in 6/9

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6h 22m

Begins in 6/9
Via Washington DCA
1 stop with American Airlines.
6h 22m
0-1 flights per day.
Begins in 6/9
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1 stop route options with codeshare or different airlines:

Duration

Via Tampa TPA With American Airlines & Silver Airways 0-1 flights per day.
Begins in 2/11

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4h 55m

Begins in 2/11
Via Tampa TPA
4h 55m
With American Airlines & Silver Airways 0-1 flights per day.
Begins in 2/11
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Via Fort Lauderdale FLL With American Airlines & Copa Airlines 0-1 flights per day.
Begins in 2/11
CODESHARE

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5h 20m

Begins in 2/11
Via Fort Lauderdale FLL
5h 20m
With American Airlines & Copa Airlines 0-1 flights per day.
Begins in 2/11
CODESHARE
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Via Charlotte CLT With United Airlines & American Airlines 2 flights per day.

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6h 09m

Via Charlotte CLT
6h 09m
With United Airlines & American Airlines 2 flights per day.
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Via Atlanta ATL With American Airlines & Delta Air Lines 1-2 flights per day.

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6h 39m

Via Atlanta ATL
6h 39m
With American Airlines & Delta Air Lines 1-2 flights per day.
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Via Washington DCA With United Airlines & American Airlines 0-2 flights per day.
Begins in 6/9

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7h 11m

Begins in 6/9
Via Washington DCA
7h 11m
With United Airlines & American Airlines 0-2 flights per day.
Begins in 6/9
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Via Miami MIA With United Airlines & American Airlines 0-1 flights per day.

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7h 12m

Via Miami MIA
7h 12m
With United Airlines & American Airlines 0-1 flights per day.
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Via Philadelphia PHL With American Airlines & Alaska Airlines 2 flights per day.
CODESHARE

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7h 49m

Via Philadelphia PHL
7h 49m
With American Airlines & Alaska Airlines 2 flights per day.
CODESHARE
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Chicago to Key West flights

With over 179 flights every week and 9 different airlines you have a wide range of options. You can fly non-stop to Key West (EYW) from Chicago (ORD) with United Airlines or American Airlines but if a stopover option suits you better you can choose to fly via Tampa, Fort Lauderdale or any other of the 7 alternatives with connectiing airports.

Chicago to Key West with United Airlines

You can fly non-stop every weekday with flights departing at 10:55, 11:00 or 18:00. United Airlines is a Star Alliance member.

Note Non-stop flights with United Airlines will begin in Oct 2025.

With Delta Air Lines

If you fly from Chicago with Delta Air Lines you will do a stopover in Atlanta, ATL before reaching Key West. This flight trip will take 5 hours and 23 minutes and you can fly every weekday with departures between 5:00 am and 1:00 pm. Delta Air Lines is a member of SkyTeam.

Distance & flight times: Chicago O'Hare to Key West International

The shortest flight time between ORD and EYW is 3 hours and 11 minutes.

ViaTotal flight timeLayover timeDistance
Direct3h 11m-1261 miles (2029 km)
TPA Tampa4h 55m1h 0m1261 miles (2029 km)
FLL Fort Lauderdale5h 20m1h 17m1336 miles (2150 km)
MIA Miami5h 30m1h 24m1331 miles (2142 km)
CLT Charlotte5h 52m1h 36m1344 miles (2162 km)
PHL Philadelphia6h 19m42m1810 miles (2912 km)
DCA Washington6h 22m2h 49m1645 miles (2647 km)
ATL Atlanta6h 39m2h 47m1261 miles (2029 km)
The flight times and layover times in the table above are approximate and may vary depending on flight number, aircraft, airline, weather, and time of day.ORD-EYW flight routesChicago to Key West flight routes illustrated on a map.
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Chicago - Key West route map and flight paths
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Show all destinations from ORD Show all destinations from EYW

You can fly non-stop from Chicago (ORD) to Key West (EYW) with United Airlines or American Airlines. The flight takes approximately 3 hours and 11 minutes. If you travel with a connecting flight instead, for example via Tampa, the total flight time will be 4 hours and 55 minutes.

If you're interested in direct flights, United Airlines or American Airlines is available. For flights with stopovers, American Airlines, Silver Airways, Copa Airlines or Delta Air Lines is also an option.

The flight time between Chicago O Hare (ORD) and Key West International (EYW) is approximately 3 hours and 11 minutes. The distance between the two airports is 1344 miles (or 2162 kilometers).

Yes, you can fly non-stop to EYW from ORD with United Airlines or American Airlines.

A codeshare agreement means that cooperating airlines are able to sell seats on each other’s flights. This means that you are able to travel to more destinations than your airline of choice normally offers. Codeshare flights are also beneficial because of the seamless transits you can get with connecting flights from the same airline. The downside of choosing a codeshare flight can be that you in some cases can’t upgrade codeshare flights or use elite benefits.

A connecting or transit flight means that you reach your final destination through two or more flights – in other words a non-direct flight. You will change to a new aircraft after your first flight, this may include moving to another terminal at the airport aswell. The time required to transfer passengers and luggage between flights is called Minimum Connecting Time (MCT) and are always taken into account here on Flightroutes.com.

If you bought your whole flight on a single ticket, the airline will book you on the next available connecting flight.

With connecting flights, checked in luggage is most commonly forwarded to your final destination when buying a single ticket for both flights.

If you miss your connecting flight due to circumstances outside your control such as your first flight being delayed, you should turn to your airline who will provide you with a seat on the next available flight. This is usually done free of charge, and only applies if you purchased your trip as one ticket. If the next connecting flight is the following day, the airline usually provides accommodation and meals.
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