Popular in | March |
---|---|
Cheapest in | August |
Round-trip from | $373 |
One-way from | $215 |
Monday is generally a great day to depart. Flying on this day could help you save up to 28%.
When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 61 days in advance, which can save you up to 80% on flights from Chicago to Key West compared to booking the week you need them. Waiting 61 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 $408.
Our data shows that August tends to be the cheapest month to fly to Key West from Chicago. Users have commonly found prices around $452 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 37% on the cost of your flight, compared to a flight in the evening.
Fly from
Fly to
Budget
$232 - $352
Route
Depart
Return
Price
Chicago MidwayKey West
MDW - EYW
MDWEYW
Chicago Midway
Wed 9/4
1 stop6h 03m
Key West
Tue 9/10
1 stop5h 32m
Chicago O'Hare IntlKey West
ORD - EYW
ORDEYW
Chicago O'Hare Intl
Wed 9/4
1 stop4h 47m
Key West
Tue 9/10
1 stop6h 09m
Chicago O'Hare IntlKey West
ORD - EYW
ORDEYW
Chicago O'Hare Intl
Mon 9/9
1 stop6h 46m
Key West
Sat 9/14
1 stop6h 09m
Chicago O'Hare IntlKey West
ORD - EYW
ORDEYW
Chicago O'Hare Intl
Wed 8/28
1 stop6h 42m
Key West
Sun 9/1
1 stop5h 58m
Chicago O'Hare IntlKey West
ORD - EYW
ORDEYW
Chicago O'Hare Intl
Wed 8/28
2 stops7h 53m
Key West
Sun 9/1
1 stop5h 58m
Chicago O'Hare IntlKey West
ORD - EYW
ORDEYW
Chicago O'Hare Intl
Mon 7/1
1 stop6h 33m
Key West
Tue 7/2
2 stops7h 27m
Chicago O'Hare IntlKey West
ORD - EYW
ORDEYW
Chicago O'Hare Intl
Fri 11/8
1 stop5h 20m
Key West
Fri 11/15
Nonstop3h 29m
Chicago O'Hare IntlKey West
ORD - EYW
ORDEYW
Chicago O'Hare Intl
Mon 11/18
Nonstop3h 10m
Key West
Tue 11/26
Nonstop3h 24m
Chicago O'Hare IntlKey West
ORD - EYW
ORDEYW
Chicago O'Hare Intl
Sat 6/29
2 stops20h 34m
Key West
Thu 7/4
2 stops20h 18m
EYW Temperature | 69.8 - 84.2 °F |
---|
If weather is an important factor for your trip to Key West, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 84.2 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 69.8 F).
Food
Entertainment
Comfort
Boarding
Crew
Overall
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.
Food
Entertainment
Comfort
Boarding
Crew
Overall
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.
Food
Entertainment
Comfort
Boarding
Crew
Overall
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.
Food
Entertainment
Comfort
Boarding
Crew
Overall
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.
Food
Entertainment
Comfort
Boarding
Crew
Overall
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.
Airline | Cheapest | Average | Flexibility | On-time |
---|---|---|---|---|
American Airlines | Cheapest$226 | Average$461 | FlexibilityNo cancel fee | On-time71% |
Delta | Cheapest$226 | Average$460 | FlexibilityNo cancel fee | On-timeN/A |
United Airlines | Cheapest$247 | Average$469 | FlexibilityNo cancel fee | On-time69% |
Alaska Airlines | Cheapest$438 | Average$467 | FlexibilityNo cancel fee | On-time75% |
Sunday | 2daily flights |
---|---|
Monday | 2daily flights |
Tuesday | 2daily flights |
Wednesday | 2daily flights |
Thursday | 2daily flights |
Friday | 2daily flights |
Saturday | 2daily flights |