Find Cheap Flights from Key West to Chicago (EYW - CHI)

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Key West to Chicago Flight Information

Flights Arrive in Chicago
Flights Depart from Key West
Flight Price $280
Distance 1,243 miles
Airlines JetBlue, Delta

FAQs for Booking Key West to Chicago Flights

How long does a flight from Key West to Chicago take?
An average nonstop flight takes 5h 00m, covering a distance of 1243 miles.
How many flights are there between Key West and Chicago?
There are 25 (nonstop) flights between Key West and Chicago per week, averaging 3 per day.
Which airlines provide the cheapest flights from Key West to Chicago?
In the past 3 days, the cheapest round-trip tickets were found on Multiple Airlines ($280), JetBlue ($320) and Delta ($416).
Do I need a passport to fly between Key West and Chicago?
No.
Which airlines fly most frequently between Key West and Chicago?
United Airlines (3 times daily), Air New Zealand (0 times daily) are the most frequent flyers on this route.
What’s the cheapest day of the week to fly Key West to Chicago?
For Key West to Chicago, Friday is the cheapest day to fly on average and Wednesday is the most expensive. Flying from Chicago back to Key West, the best deals are generally found on Saturday, with Monday being the most expensive.

Book cheap flights from Key West to Chicago (round-trip)

Airports
Origin
Key West
$280
only
$280
Destination
Chicago
$280
only
$280
$416
only
$416
Fri, Jan 11
EYW
Key West
ORD
Chicago O'Hare International
8h 38m
Sun, Jan 13
ORD
Chicago O'Hare International
EYW
Key West
6h 45m
Trip: 3 days
Overall 0.0 Poor
Based on 0 reviews
Wed, Dec 26
EYW
Key West
ORD
Chicago O'Hare International
12h 21m
Mon, Jan 7
ORD
Chicago O'Hare International
EYW
Key West
12h 30m
Trip: 13 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 14,881 reviews
Overall
8.2
Boarding
8.3
Comfort
8.3
Crew
8.6
Entertainment
7.9
Food
7.8
JFK
AUS
Excellent 10.0

Pros: We should've missed our flight (NewYork to Austin) because we got stuck in traffic. They pulled the walkway completely away from the plane as we were getting to the gate. The pilot saw us running towards it and waving them down. These amazing/wonderful/fantastic/phenomenal people pulled the walkway back and we made our flight. I will never take another airline EVER again.

FLL
ORH
Good 6.0

Pros: Smooth flight

Cons: Service lousy saw attendants at beginning of flight once then at end to pick up trash

FLL
LAX
Excellent 10.0

Pros: Everything

JFK
FLL
Excellent 10.0

Pros: Videos!

Cons: Video interruptions!

FLL
EWR
Excellent 10.0

Pros: Jet blue us such a pleasure.historic moment in the country and was able to watch. Thank you.

Wed, Jan 9
EYW
Key West
MDW
Chicago Midway
5h 00m
Sun, Jan 13
MDW
Chicago Midway
EYW
Key West
4h 30m
Trip: 5 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 21,832 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.4
CDG
ATL
Excellent 9.0

Pros: I had the chicken beans and rice which was good, the chicken burrito was a little soggy and had to peal it out of the box but taste ok.

Cons: The choice of the movies were either action or kids movies, i would like to see some sports movies, auto race, football or espn. All of the was energetic with great smiles and service except for one that never smiled and lacked enthusiasm. I wondered why she was on the plane.

SYR
ATL
Excellent 10.0

Pros: We got on we took off and arrived as scheduled. Just as it should be.

Cons: N/A

SHV
ATL
Good 7.0

Pros: Basic flight... likedthe tomato juice and snack mix

Cons: Announcements startled me every time due to volume

ATL
MEM
Excellent 10.0

Pros: We got on we took off and arrived on schedule just as it should be.

Cons: N/A

JFK
MSP
Mediocre 2.0

Cons: This was my worst EVER airline experience. It was delayed 27 hours and the snow was not the only problem. When we finally got on board a plane we sat on the runway for over two hours - then they FORGOT to load the luggage!!!

Thu, Mar 7
EYW
Key West
ORD
Chicago O'Hare International
7h 21m
Sun, Mar 10
ORD
Chicago O'Hare International
EYW
Key West
12h 21m
Trip: 4 days
Overall 0.0 Poor
Based on 0 reviews
Wed, Dec 26
EYW
Key West
MDW
Chicago Midway
6h 20m
Mon, Jan 7
MDW
Chicago Midway
EYW
Key West
7h 25m
Trip: 13 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 21,832 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.4
ATL
MLB
Good 6.6

Pros: Got me there Safely

Cons: Couldn’t understand announcements... at all! By flight attendant or pilot

SLC
LGB
Excellent 8.8

Cons: Sat in comfort+, bbut never offered any sort of snack. Not sure why it is considered an upgrade.

CDG
ATL
Excellent 9.0

Pros: I had the chicken beans and rice which was good, the chicken burrito was a little soggy and had to peal it out of the box but taste ok.

Cons: The choice of the movies were either action or kids movies, i would like to see some sports movies, auto race, football or espn. All of the was energetic with great smiles and service except for one that never smiled and lacked enthusiasm. I wondered why she was on the plane.

JFK
SEA
Excellent 8.3

Pros: Good snacks. Nice crew. Nice seats.

Cons: Pay WiFi? JetBlue does it for free..

LGA
ATL
Excellent 10.0

Pros: From the pilot...FAs....gate agents....everyone was very pleasant and professional. Plane was clean as well.

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The fares displayed include all taxes and fees for economy class travel and were found by the provider in the last 72 hours. Seats are limited and may not be available on all flights and days. Fares are subject to change and may not be available on all flights or dates of travel. Some carriers charge additional fees for extra checked bags. Please check the carriers' sites.