Popular in | March |
---|---|
Cheapest in | August |
Round-trip from | $374 |
One-way from | $108 |
Monday is generally a great day to depart. Flying on this day could help you save up to 33%.
When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 26 days in advance, which can save you up to 75% on flights from Chicago to Key West compared to booking the week you need them. Waiting 26 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at $355. For sooner than that we have options available in the next 3 days from $606.
Our data shows that August tends to be the cheapest month to fly to Key West from Chicago. Users have commonly found prices around $462 for the month, but tickets can be as low as $226. Due to multiple factors, prepare for potentially higher prices in March.
It’s optimal to fly from Chicago to Key West at noon. By choosing this option you can save up to 51% on the cost of your flight, compared to a flight in the evening.
Fly from
Fly to
Budget
$177 - $519
Route
Depart
Return
Price
Chicago O'Hare IntlKey West
ORD - EYW
ORDEYW
Chicago O'Hare Intl
Tue 4/16
Nonstop3h 05m
Key West
Wed 4/24
Nonstop3h 28m
Chicago O'Hare IntlKey West
ORD - EYW
ORDEYW
Chicago O'Hare Intl
Tue 4/23
Nonstop3h 14m
Key West
Wed 4/24
1 stop6h 11m
Chicago O'Hare IntlKey West
ORD - EYW
ORDEYW
Chicago O'Hare Intl
Tue 4/16
1 stop9h 14m
Key West
Wed 4/24
Nonstop3h 28m
Chicago O'Hare IntlKey West
ORD - EYW
ORDEYW
Chicago O'Hare Intl
Tue 4/16
1 stop5h 10m
Key West
Tue 4/23
1 stop7h 01m
Chicago O'Hare IntlKey West
ORD - EYW
ORDEYW
Chicago O'Hare Intl
Tue 4/16
Nonstop3h 14m
Key West
Tue 4/23
1 stop7h 01m
Chicago O'Hare IntlKey West
ORD - EYW
ORDEYW
Chicago O'Hare Intl
Tue 4/23
1 stop7h 15m
Key West
Wed 4/24
1 stop6h 42m
Chicago O'Hare IntlKey West
ORD - EYW
ORDEYW
Chicago O'Hare Intl
Sun 9/1
1 stop6h 39m
Key West
Wed 9/11
1 stop6h 04m
Chicago O'Hare IntlKey West
ORD - EYW
ORDEYW
Chicago O'Hare Intl
Tue 4/30
1 stop8h 25m
Key West
Fri 5/3
1 stop26h 01m
Chicago MidwayKey West
MDW - EYW
MDWEYW
Chicago Midway
Fri 3/22
2 stops35h 20m
Key West
Thu 3/28
1 stop26h 24m
Currently, January is the cheapest month in which you can book a flight from Chicago to Key West (average of $374). Flying from Chicago to Key West in March is currently the most expensive (average of $506). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
January
$374
February
$415
March
$506
April
$503
May
$476
June
$498
July
$478
August
$395
September
$427
October
$475
November
$448
December
$400
EYW Temperature | 69.8 - 84.2 °F |
---|
Crew
Overall
Food
Boarding
Comfort
Entertainment
Reviews
Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.
Crew
Overall
Food
Boarding
Comfort
Entertainment
Reviews
Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.
Crew
Overall
Food
Boarding
Comfort
Entertainment
Reviews
Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.
Crew
Overall
Food
Boarding
Comfort
Entertainment
Reviews
Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.
Crew
Overall
Food
Boarding
Comfort
Entertainment
Reviews
Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.
0%of flight departures | Early morningMidnight to 6 am |
---|---|
100%of flight departures | Morning6 am to noon |
0%of flight departures | AfternoonNoon to 6 pm |
0%of flight departures | Evening6 pm to midnight |
Sunday | 2daily flights |
---|---|
Monday | 2daily flights |
Tuesday | 2daily flights |
Wednesday | 2daily flights |
Thursday | 2daily flights |
Friday | 2daily flights |
Saturday | 2daily flights |
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