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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 $320
Distance 1,244 miles
Airlines Delta

Top Tips for Finding a Cheap Flight

Looking for a cheap flight? 25% of our users found flights on this route for $231 or less.

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 24m, covering a distance of 1244 miles.
How many flights are there between Key West and Chicago?
There are 5 (nonstop) flights between Key West and Chicago per week, averaging 0 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 ($320) and Delta ($406)
Do I need a passport to fly between Key West and Chicago?
No.
Which airlines fly most frequently between Key West and Chicago?
United (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, Thursday is the cheapest day to fly on average and Tuesday 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
$320
only
$320
Destination
Chicago
$320
only
$320
$406
only
$406
Thu, Nov 8
EYW
Key West
ORD
Chicago O'Hare International
15h 50m
Sat, Nov 10
ORD
Chicago O'Hare International
EYW
Key West
14h 16m
Trip: 3 days
Overall 0.0 Poor
Based on 0 reviews
Tue, Oct 23
EYW
Key West
MDW
Chicago Midway
6h 23m
Sun, Oct 28
MDW
Chicago Midway
EYW
Key West
4h 34m
Trip: 6 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 20,314 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
JFK
LAS
Excellent 8.0

The wait

The screen didn’t change in time

LAX
OGG
Okay 4.3

Why use old planes for such a long flight? Toilet overflowed, poor quality tv, and only peanuts?

ATL
LAX
Good 6.3

Seatback tv.

Stewardess berated a man for leaving his backpack on the floor in front of him rather than politely addressing the issue. She told him you know better than that and don’t ever do that again. It was totally uncalled for.

SLC
AMS
Excellent 9.6

You guys did an all around great job and my flight experience was the best I’ve ever had. The quality of the service was exceptional.

SEA
MSP
Okay 4.6

Hostess were professional and warm

Seats was too tight, no leg room and no room for stretching

Tue, Oct 23
EYW
Key West
ORD
Chicago O'Hare International
16h 11m
Sun, Oct 28
ORD
Chicago O'Hare International
EYW
Key West
5h 27m
Trip: 6 days
Overall 0.0 Poor
Based on 0 reviews
Fri, Sep 28
EYW
Key West
ORD
Chicago O'Hare International
17h 36m
Mon, Oct 1
ORD
Chicago O'Hare International
EYW
Key West
17h 18m
Trip: 4 days
Overall 0.0 Poor
Based on 0 reviews
Fri, Sep 28
EYW
Key West
MDW
Chicago Midway
5h 25m
Mon, Oct 1
MDW
Chicago Midway
EYW
Key West
6h 23m
Trip: 4 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 20,314 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
JFK
LAS
Excellent 8.0

The wait

The screen didn’t change in time

SJD
LAX
Excellent 8.3

Crews were nice

DTW
CLT
Excellent 8.0

Didn’t get our beverage and snack till we were almost ready to land at Charlotte

LAX
OGG
Okay 4.3

Why use old planes for such a long flight? Toilet overflowed, poor quality tv, and only peanuts?

AMS
DTW
Excellent 8.0

Didn’t like the fact that online check in didn’t work on the Delta app.di

Tue, Dec 18
EYW
Key West
ORD
Chicago O'Hare International
7h 36m
Sun, Dec 23
ORD
Chicago O'Hare International
EYW
Key West
12h 15m
Trip: 6 days
Overall 0.0 Poor
Based on 0 reviews
Thu, Nov 8
EYW
Key West
MDW
Chicago Midway
6h 05m
Sat, Nov 10
MDW
Chicago Midway
EYW
Key West
9h 06m
Trip: 3 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 20,314 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
SJD
LAX
Excellent 8.3

Crews were nice

AMS
DTW
Excellent 8.0

Didn’t like the fact that online check in didn’t work on the Delta app.di

ATL
LAX
Good 6.3

Seatback tv.

Stewardess berated a man for leaving his backpack on the floor in front of him rather than politely addressing the issue. She told him you know better than that and don’t ever do that again. It was totally uncalled for.

SLC
AMS
Excellent 9.6

You guys did an all around great job and my flight experience was the best I’ve ever had. The quality of the service was exceptional.

SEA
MSP
Okay 4.6

Hostess were professional and warm

Seats was too tight, no leg room and no room for stretching

Sun, Jan 6
EYW
Key West
ORD
Chicago O'Hare International
29h 34m
Fri, Jan 18
ORD
Chicago O'Hare International
EYW
Key West
5h 55m
Trip: 13 days
Overall 0.0 Poor
Based on 0 reviews
Tue, Dec 18
EYW
Key West
MDW
Chicago Midway
5h 24m
Sun, Dec 23
MDW
Chicago Midway
EYW
Key West
9h 27m
Trip: 6 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 20,314 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
DTW
CLT
Excellent 8.0

Didn’t get our beverage and snack till we were almost ready to land at Charlotte

CLT
LGA
Mediocre 3.3

We were deplained twice from two different plains going to LGA. We are now booked on a third plain going to JFK. Hope we can get home. I have a surgical appointment tomorrow.

We bought First Class tickets. But we were downgraded How do you think we should feel ? We have been in Charlotte since 9:30 AM It is now 6:45 PM Should we use the train to go home?

SEA
MSP
Okay 4.6

Hostess were professional and warm

Seats was too tight, no leg room and no room for stretching

MSP
EWR
Okay 4.3

Seats more comfortable, plan wasn’t too full

No charging port for cellphone.

AMS
DTW
Excellent 8.0

Didn’t like the fact that online check in didn’t work on the Delta app.di

*
Prices are per person and are for e–tickets and include all taxes & fees in USD.

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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.

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