Travelers have found it’s best to book a flight 61 days in advance to save up to 80% compared to booking the same week of travel. As your travel date approaches, the cost of this flight route may potentially increase. While opting to book 61 days out may not be an option for all, there are still additional ways to secure a deal in the near future. You might find a flight from Illinois to Key West 1-2 weeks in advance for as low as $355, or $408 for flights within the next 24 hours.
Our data shows that August tends to be the cheapest month to fly to Key West from Illinois. Users have commonly found prices around $454 for the month, but tickets can be as low as $226. Due to multiple factors, prepare for potentially higher prices in March.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Illinois to Key West as you normally would.
Fly from
Fly to
Budget
$197 - $259
Route
Depart
Return
Price
Chicago O'Hare IntlKey West
ORD - EYW
ORDEYW
Chicago O'Hare Intl
Sun 9/1
1 stop5h 26m
Key West
Thu 9/5
1 stop7h 44m
Lambert-St LouisKey West
STL - EYW
STLEYW
Lambert-St Louis
Sat 8/3
1 stop6h 51m
Key West
Tue 8/6
1 stop4h 54m
Chicago O'Hare IntlKey West
ORD - EYW
ORDEYW
Chicago O'Hare Intl
Sun 9/1
2 stops7h 39m
Key West
Thu 9/5
1 stop7h 44m
Lambert-St LouisKey West
STL - EYW
STLEYW
Lambert-St Louis
Thu 8/22
1 stop5h 34m
Key West
Tue 8/27
1 stop4h 54m
Chicago O'Hare IntlKey West
ORD - EYW
ORDEYW
Chicago O'Hare Intl
Sun 11/17
Nonstop3h 10m
Key West
Sat 11/23
Nonstop3h 24m
Chicago MidwayKey West
MDW - EYW
MDWEYW
Chicago Midway
Wed 9/4
1 stop4h 47m
Key West
Tue 9/10
1 stop6h 28m
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 04m
Chicago O'Hare IntlKey West
ORD - EYW
ORDEYW
Chicago O'Hare Intl
Wed 7/31
1 stop13h 55m
Key West
Wed 8/7
2 stops17h 17m
Chicago O'Hare IntlKey West
ORD - EYW
ORDEYW
Chicago O'Hare Intl
Wed 7/31
1 stop13h 55m
Key West
Wed 8/7
2 stops17h 17m
No data available for this route at this time. Please check back soon.
Boarding
Comfort
Food
Crew
Entertainment
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.
Boarding
Comfort
Food
Crew
Entertainment
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.
Boarding
Comfort
Food
Crew
Entertainment
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.
Boarding
Comfort
Food
Crew
Entertainment
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.
Boarding
Comfort
Food
Crew
Entertainment
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.
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