Flight attendant stepped in and addressed my elderly fathers shivering by turning up the heat in our area. He also found a blanket for him quickly. We had accidentally packed his coat in the checked bag.
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Fares from $135 One Way, $293 Round Trip from Key West to Chicago
Prices starting at $293 for return flights and $135 for one-way flights to Chicago were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
Mon, Aug 24 -
EYW
Key Westto
ORD
Chicago$135
Sat, Sep 12 -
EYW
Key Westto
ORD
Chicago$140
Fri, Aug 28 -
EYW
Key Westto
ORD
Chicago$144
Mon, Aug 24 -
EYW
Key Westto
ORD
Chicago$146
Thu, Dec 3 -
EYW
Key Westto
ORD
Chicago$147
Mon, Aug 3 - Fri, Aug 7
EYW
Key Westto
ORD
Chicago$293
Thu, Aug 6 - Mon, Aug 10
EYW
Key Westto
ORD
Chicago$300
Thu, Aug 6 - Mon, Aug 10
EYW
Key Westto
ORD
Chicago$303
Thu, Aug 6 - Mon, Aug 10
EYW
Key Westto
ORD
Chicago$305
Thu, Aug 6 - Mon, Aug 10
EYW
Key Westto
ORD
Chicago$305
Mon, Aug 24 -
EYW
Key Westto
ORD
Chicago$135
Fri, Aug 28 -
EYW
Key Westto
ORD
Chicago$144
Mon, Aug 24 -
EYW
Key Westto
ORD
Chicago$146
Mon, Aug 3 - Fri, Aug 7
EYW
Key Westto
ORD
Chicago$293
Thu, Aug 6 - Mon, Aug 10
EYW
Key Westto
ORD
Chicago$300
Thu, Aug 6 - Mon, Aug 10
EYW
Key Westto
ORD
Chicago$303
Thu, Aug 6 - Mon, Aug 10
EYW
Key Westto
ORD
Chicago$305
Thu, Aug 6 - Mon, Aug 10
EYW
Key Westto
ORD
Chicago$305
Sat, Sep 12 -
EYW
Key Westto
ORD
Chicago$140
Thu, Dec 3 -
EYW
Key Westto
ORD
Chicago$147
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Flights from Key West to Chicago - Frequently Asked Questions
Are there non-stop flights from Key West to Chicago?
There sure are, which is great news if you're not a fan of stopovers. United Airlines and American Airlines operate direct flights from Key West, FL (EYW-Key West Intl.) to Chicago, IL (ORD-O'Hare Intl.).
What is the shortest flight from Key West to Chicago?
From Key West, the thrilling sights and sounds of Chicago are at least 3 hours and 15 minutes away. Book your favorite seat, or perhaps even one with a bit more legroom, and fly to your destination in comfort.
What airlines have the most flights from Key West to Chicago?
United Airlines (UA) offers 37 flights every month between Key West, FL (EYW-Key West Intl.) to Chicago, IL (ORD-O'Hare Intl.). Your next exciting adventure is only a few clicks away. Alternatively, secure your favorite seat with American Airlines (AA). You'll have 22 monthly flights between Key West and Chicago to choose from with this airline.
Route Information for Flights from Key West to Chicago
| Origin Airport IATA Code | EYW |
|---|---|
| Destination Airport IATA Code | CHI |
| Distance | 1254 mi |
| Direct Flight Airlines | American Airlines, United Airlines |
| Earliest Flight Arrival | 8:57PM UTC |
| Latest Flight Arrival | 7:54PM UTC |
Flights Review
Airports near Key West
Airports near Chicago
Key West to Chicago
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^Savings based on all package bookings with Flight + Hotel made on Orbitz.com from January 1, 2019 to December 31, 2019 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.
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