Airlines with flights from Key West to Chicago

There are three airlines with scheduled flights between EYW and ORD. Both American Airlines and United operates non-stop flights from Key West International to Chicago O'Hare and the flight time is 3 hours and 48 minutes.

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Direct

$American Airlines from {( $airportFrom->city_name }} to Chicago$

Non-stop

3h 48min

Direct

$United Airlines from {( $airportFrom->city_name }} to Chicago$

Non-stop

3h 25min

Via Miami

4h 50min

Via Atlanta

5h 4min

Via Charlotte

5h 6min

Via Washington

5h 58min

Via Dulles

6h 21min

Via Philadelphia

6h 42min

Via Houston

7h 27min

Schedules

Non-stop with American Airlines

Total flight time: 3 hours and 48 minutes
One World Alliance
Chicago is a American Airlines hub.

10 flights per week
Embraer 170
First class available

EYW

Direct

ORD

Flight

Mon

Jun 15

Tue

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Wed

Jun 17

Thu

Jun 18

Fri

Jun 19

Sat

Jun 20

Sun

Jun 21

AA3996

16:17

16:11

16:17

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The timetable & schedule information was updated at 2026-04-21

Non-stop with United Airlines

Total flight time: 3 hours and 25 minutes
Chicago is a United Airlines hub (Largest hub ).

7 flights per week
Embraer 175 (Enhanced Winglets)
First class available

EYW

Direct

ORD

Flight

Mon

Jun 15

Tue

Jun 16

Wed

Jun 17

Thu

Jun 18

Fri

Jun 19

Sat

Jun 20

Sun

Jun 21

UA3499

15:55

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The timetable & schedule information was updated at 2026-04-21

Via Miami with American Airlines

Total flight time: 4h 50m - 7h 28m.
One World Alliance
Chicago is a American Airlines hub.

107 flights per week
Embraer 170

EYW

Via MIA

ORD

Flight

Mon

Jun 15

Tue

Jun 16

Wed

Jun 17

Thu

Jun 18

Fri

Jun 19

Sat

Jun 20

Sun

Jun 21

AA3515
AA2247