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

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Fri 2/23
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Good to Know

Low Season:
September
Best time to beat the crowds
2%
expected price decrease
High Season:
December
Most popular time to fly
8%
expected price increase
Average Price:
$463
(avg. price over the last 2 weeks)
Good Deal:
$396
or less (round trip)

When to Book Flights from Chicago to Key West

Average price per month
Flight prices as travel date approaches
-1 day
-2 days

Top tips for Finding a Cheap Flight

Looking for a cheap flight? 25% of our users found flights on this route for $395 or less.
The cheapest flight from Chicago to Key West was found 89 days before departure, on average.
Book at least 3 weeks before departure in order to get a below-average price.
Morning departure is around 34% more expensive than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

FAQs for Booking Chicago to Key West Flights

How long does a flight from Chicago to Key West take?
An average nonstop flight takes 5h 03m, covering a distance of 1244 miles.
How many flights are there between Chicago and Key West?
There are 16 (nonstop) flights between Chicago and Key West per week, averaging 2 per day.
Which airlines provide the cheapest flights from Chicago to Key West?
In the past 3 days, the cheapest round-trip tickets were found on Multiple Airlines ($255), American Airlines ($364) and Delta ($531).
Do I need a passport to fly between Chicago and Key West?
No.
Which airlines fly most frequently between Chicago and Key West?
United (2 times daily) are the most frequent flyers on this route.
What’s the cheapest day of the week to fly Chicago to Key West?
For Chicago to Key West, Monday is the cheapest day to fly on average and Wednesday is the most expensive. Flying from Key West back to Chicago, the best deals are generally found on Wednesday, with Saturday being the most expensive.

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

Airports
Origin
Chicago
$255
only
$255
$531
only
$531
Destination
Key West
$255
only
$255
Mon, Apr 16
ORD
EYW
8h 18m
Wed, Apr 25
EYW
ORD
10h 20m
Trip: 10 days
Overall 0.0 Poor
Based on 0 reviews
Thu, Aug 23
ORD
EYW
11h 44m
Wed, Aug 29
EYW
ORD
9h 25m
Trip: 7 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 28416 reviews
Overall
7.4
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.7
IND
LAX
Excellent 10.0

The staff

The snack selection and lack of entertainment

LAX
AKL
Okay 4.0

American wins tge coach torture contest!

SYD
LAX
Excellent 9.0

Premium economy is the way to go for a long haul flight. We were comfortable and able to get some sleep.

The crew on the way to Sydney was a little more present. There was always someone milling in the galley between the business class and premium economy cabin. The crew returning came through the cabin often and were attentive if you asked for them but you had to seek them out.

LAX
MIA
Okay 4.0

The low fare was the best part of the flight, but I later found that it came at a cost!!!!

First of all the Crew was rude and their lack of patience was obvious, the flight was delayed and was no fault of any of the passengers yet we were made to feel as if it was our ( passengers) fault. Secondly, the air was turned down, I guess to conserve fuel, and the plane was unbearably hot, And at no time was food offered for purchase or even a beverage service. I have flow AA for 20+ years and this was the FURST flight I have ever experienced. Sadly I believe it will be my last!!!!

LAX
ORD
Good 7.6

I liked having the built in screen on the a321. Americans streaming service has lots to offer but the built in screens have more choices. I get why they want to just offer the streaming but I appreciate all the choices! There was a group number enforcer at the gate to make boarding more organized! She was polite but told the mobs that try to use the premium line to wait their turn.

I asked for upgrades to and from Chicago. I’m a gold member and fly for leisure fairly often. There are so many people looking for an upgrade these days that you’re rarely getting the opportunity

Wed, Apr 11
MDW
EYW
9h 09m
Wed, Apr 18
EYW
MDW
8h 09m
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
BJX
LAX
Excellent 8.0

I liked the check-in kiosk, but only because I had no bags to check. I liked being able to choose my own seat. I liked that the flight was uneventful. I liked the staff at all stages, they were friendly and helpful.

They made me shove my purse into my knapsack to fit within their two bag policy. That's a first for me. My Delta flight did not do that.

PVR
MSP
Good 7.3

They have few movies selection that was good

I like being in a big space faster. And clean good service I

ATL
EWR
Excellent 8.6

No LCD screen for entertainment.

BOS
LGA
Mediocre 2.0

We were in the plane for 3 hours before we could depart. No one offered us a drink or snack.

EWR
DTW
Mediocre 3.3

I've always wanted to go to all five Manhattan boroughs in one day. Thanks to Delta, that happened.

The plane broke down as we were about to take off. Delta rebooked everyone on to new flights because it was pretty obvious that plane was not going to be fixed in time. The crew did their best given the situation. The situation was absolute bs though - we had to take a cab to JFK for our new flight and do the whole security thing again and all that annoying stuff. Thanks for wasting 8 hours of my life, Delta.

Mon, Jun 4
ORD
EYW
7h 17m
Fri, Jun 8
EYW
ORD
6h 22m
Trip: 5 days
Overall 0.0 Poor
Based on 0 reviews
Tue, Mar 6
ORD
EYW
8h 15m
Tue, Mar 13
EYW
ORD
8h 08m
Trip: 7 days
Overall 0.0 Poor
Based on 0 reviews
Wed, Apr 11
ORD
EYW
8h 15m
Wed, Apr 18
EYW
ORD
13h 08m
Trip: 8 days
Overall 0.0 Poor
Based on 0 reviews
Wed, May 9
ORD
EYW
14h 21m
Tue, May 15
EYW
ORD
15h 45m
Trip: 7 days
Overall 0.0 Poor
Based on 0 reviews
Sat, Jul 28
ORD
EYW
6h 50m
Wed, Aug 1
EYW
ORD
7h 51m
Trip: 5 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 28416 reviews
Overall
7.4
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.7
LAX
ORD
Good 7.6

I liked having the built in screen on the a321. Americans streaming service has lots to offer but the built in screens have more choices. I get why they want to just offer the streaming but I appreciate all the choices! There was a group number enforcer at the gate to make boarding more organized! She was polite but told the mobs that try to use the premium line to wait their turn.

I asked for upgrades to and from Chicago. I’m a gold member and fly for leisure fairly often. There are so many people looking for an upgrade these days that you’re rarely getting the opportunity

SYD
LAX
Excellent 9.0

Premium economy is the way to go for a long haul flight. We were comfortable and able to get some sleep.

The crew on the way to Sydney was a little more present. There was always someone milling in the galley between the business class and premium economy cabin. The crew returning came through the cabin often and were attentive if you asked for them but you had to seek them out.

BWI
ORD
Excellent 8.6

Nothing special

BWI check-in crew is not friendly, not related to Japan Airline.

LAX
MEX
Excellent 8.0

American flight attendant service

ORD
LAX
Okay 4.0

Packed like sardines; the seats are getting narrower and the seat pockets are ridiculously small.

Sat, May 12
ORD
EYW
10h 53m
Thu, May 17
EYW
ORD
7h 22m
Trip: 6 days
Overall 0.0 Poor
Based on 0 reviews
Tue, Mar 27
ORD
EYW
5h 03m
Tue, Apr 3
EYW
ORD
4h 58m
Trip: 8 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 28416 reviews
Overall
7.4
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.7
ORD
LAX
Okay 4.0

Packed like sardines; the seats are getting narrower and the seat pockets are ridiculously small.

IND
LAX
Excellent 10.0

The staff

The snack selection and lack of entertainment

BOS
DFW
Excellent 10.0

Everything is excellent!!

BWI
ORD
Excellent 8.6

Nothing special

BWI check-in crew is not friendly, not related to Japan Airline.

DFW
GRR
Excellent 9.0

Everything worked the way it was supposed to. Bag transfer through customs and transfer to domestic was easy.

Snacks and food in general on US operated airlines is generally sad. American Airlines should learn from Qantas about food quality and service.

Sun, Jun 3
ORD
EYW
8h 00m
Fri, Jun 8
EYW
ORD
6h 22m
Trip: 6 days
Overall 0.0 Poor
Based on 0 reviews
Thu, Mar 8
ORD
EYW
7h 05m
Mon, Mar 12
EYW
ORD
5h 39m
Trip: 4 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 28416 reviews
Overall
7.4
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.7
LAX
ORD
Good 7.6

I liked having the built in screen on the a321. Americans streaming service has lots to offer but the built in screens have more choices. I get why they want to just offer the streaming but I appreciate all the choices! There was a group number enforcer at the gate to make boarding more organized! She was polite but told the mobs that try to use the premium line to wait their turn.

I asked for upgrades to and from Chicago. I’m a gold member and fly for leisure fairly often. There are so many people looking for an upgrade these days that you’re rarely getting the opportunity

LAX
MIA
Okay 4.0

The low fare was the best part of the flight, but I later found that it came at a cost!!!!

First of all the Crew was rude and their lack of patience was obvious, the flight was delayed and was no fault of any of the passengers yet we were made to feel as if it was our ( passengers) fault. Secondly, the air was turned down, I guess to conserve fuel, and the plane was unbearably hot, And at no time was food offered for purchase or even a beverage service. I have flow AA for 20+ years and this was the FURST flight I have ever experienced. Sadly I believe it will be my last!!!!

LAX
MEX
Excellent 8.0

American flight attendant service

IND
LAX
Excellent 10.0

The staff

The snack selection and lack of entertainment

ORD
LAX
Okay 4.0

Packed like sardines; the seats are getting narrower and the seat pockets are ridiculously small.

Tue, May 8
MDW
EYW
6h 52m
Tue, May 15
EYW
MDW
8h 08m
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
EWR
DTW
Mediocre 3.3

I've always wanted to go to all five Manhattan boroughs in one day. Thanks to Delta, that happened.

The plane broke down as we were about to take off. Delta rebooked everyone on to new flights because it was pretty obvious that plane was not going to be fixed in time. The crew did their best given the situation. The situation was absolute bs though - we had to take a cab to JFK for our new flight and do the whole security thing again and all that annoying stuff. Thanks for wasting 8 hours of my life, Delta.

PIT
ATL
Excellent 10.0

I have always known of airlines to offer preboarding to those military members in uniform or on official orders. Delta took it one step further and allows prior service members to board also.

ATL
EWR
Excellent 8.6

No LCD screen for entertainment.

BJX
LAX
Excellent 8.0

I liked the check-in kiosk, but only because I had no bags to check. I liked being able to choose my own seat. I liked that the flight was uneventful. I liked the staff at all stages, they were friendly and helpful.

They made me shove my purse into my knapsack to fit within their two bag policy. That's a first for me. My Delta flight did not do that.

GDL
ATL
Excellent 9.6

Expensive food

Tue, May 8
MDW
EYW
6h 52m
Tue, May 15
EYW
MDW
8h 08m
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
ATL
TGU
Mediocre 2.0

The service was horribly they dilate my flight 24 hours and I lose my flight yesterday because from Washington to Atlanta the flight was late and from Atlanta to Tegucigalpa leave early

PVR
MSP
Good 7.3

They have few movies selection that was good

I like being in a big space faster. And clean good service I

SLC
YYZ
Excellent 8.0

was a difficult transition from delta to west jet in Toronto and we almost missed the flight

BOS
LGA
Mediocre 2.0

We were in the plane for 3 hours before we could depart. No one offered us a drink or snack.

FLL
DTW
Excellent 10.0

I like service

Wed, Aug 1
ORD
EYW
14h 21m
Wed, Aug 8
EYW
ORD
13h 31m
Trip: 8 days
Overall 0.0 Poor
Based on 0 reviews
Wed, Jun 13
MDW
EYW
9h 37m
Tue, Jun 19
EYW
MDW
10h 00m
Trip: 7 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
PIT
ATL
Excellent 10.0

I have always known of airlines to offer preboarding to those military members in uniform or on official orders. Delta took it one step further and allows prior service members to board also.

GDL
ATL
Excellent 9.6

Expensive food

FLL
DTW
Excellent 10.0

I like service

EWR
DTW
Mediocre 3.3

I've always wanted to go to all five Manhattan boroughs in one day. Thanks to Delta, that happened.

The plane broke down as we were about to take off. Delta rebooked everyone on to new flights because it was pretty obvious that plane was not going to be fixed in time. The crew did their best given the situation. The situation was absolute bs though - we had to take a cab to JFK for our new flight and do the whole security thing again and all that annoying stuff. Thanks for wasting 8 hours of my life, Delta.

PVR
MSP
Good 7.3

They have few movies selection that was good

I like being in a big space faster. And clean good service I

Sat, Jul 28
ORD
EYW
5h 07m
Sat, Aug 4
EYW
ORD
6h 30m
Trip: 8 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 28416 reviews
Overall
7.4
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.7
LAX
MIA
Okay 4.0

The low fare was the best part of the flight, but I later found that it came at a cost!!!!

First of all the Crew was rude and their lack of patience was obvious, the flight was delayed and was no fault of any of the passengers yet we were made to feel as if it was our ( passengers) fault. Secondly, the air was turned down, I guess to conserve fuel, and the plane was unbearably hot, And at no time was food offered for purchase or even a beverage service. I have flow AA for 20+ years and this was the FURST flight I have ever experienced. Sadly I believe it will be my last!!!!

LAX
MEX
Excellent 8.0

American flight attendant service

BOS
DFW
Excellent 10.0

Everything is excellent!!

LAX
AKL
Okay 4.0

American wins tge coach torture contest!

DFW
GRR
Excellent 9.0

Everything worked the way it was supposed to. Bag transfer through customs and transfer to domestic was easy.

Snacks and food in general on US operated airlines is generally sad. American Airlines should learn from Qantas about food quality and service.

Wed, Aug 1
MDW
EYW
9h 37m
Wed, Aug 8
EYW
MDW
6h 53m
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
PIT
ATL
Excellent 10.0

I have always known of airlines to offer preboarding to those military members in uniform or on official orders. Delta took it one step further and allows prior service members to board also.

SLC
YYZ
Excellent 8.0

was a difficult transition from delta to west jet in Toronto and we almost missed the flight

FLL
DTW
Excellent 10.0

I like service

EWR
DTW
Mediocre 3.3

I've always wanted to go to all five Manhattan boroughs in one day. Thanks to Delta, that happened.

The plane broke down as we were about to take off. Delta rebooked everyone on to new flights because it was pretty obvious that plane was not going to be fixed in time. The crew did their best given the situation. The situation was absolute bs though - we had to take a cab to JFK for our new flight and do the whole security thing again and all that annoying stuff. Thanks for wasting 8 hours of my life, Delta.

BOS
LGA
Mediocre 2.0

We were in the plane for 3 hours before we could depart. No one offered us a drink or snack.

Fri, Aug 10
MDW
EYW
9h 37m
Tue, Aug 14
EYW
MDW
10h 00m
Trip: 5 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
GDL
ATL
Excellent 9.6

Expensive food

DEN
JFK
Good 6.3

Comfortable seats. Good entertainment

Going to Denver was delayed and now return trip delayed We were give 3 separate reasons. Poor communication. Just telling me a flight will be delayed is not communication. Lack of a free snack was disappointing. May have to rethink flying Delta next time.

FLL
DTW
Excellent 10.0

I like service

EWR
DTW
Mediocre 3.3

I've always wanted to go to all five Manhattan boroughs in one day. Thanks to Delta, that happened.

The plane broke down as we were about to take off. Delta rebooked everyone on to new flights because it was pretty obvious that plane was not going to be fixed in time. The crew did their best given the situation. The situation was absolute bs though - we had to take a cab to JFK for our new flight and do the whole security thing again and all that annoying stuff. Thanks for wasting 8 hours of my life, Delta.

SLC
YYZ
Excellent 8.0

was a difficult transition from delta to west jet in Toronto and we almost missed the flight

Mon, Feb 26
ORD
EYW
7h 14m
Fri, Mar 2
EYW
ORD
10h 01m
Trip: 5 days
Overall 0.0 Poor
Based on 0 reviews
Show more results

Chicago to Key West Flight Information

Flights Arrive in Key West
Flights Depart from Chicago
Flight Price $255
Distance 1244 miles
Airlines American Airlines, Delta
*
Prices are per person and are for e–tickets and include all taxes & fees in USD.

We attempt to get accurate prices, however, prices are not guaranteed.

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Why aren’t prices accurate 100% of the time?
Prices on airline seats, hotel rooms and car rentals can change frequently. Several people may also be trying to buy the same travel option simultaneously. As a result, you may find, on occasion, that certain prices are no longer available.

If you have more questions or if you have a bad price to report to us,
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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.