Travelers have found it’s best to book a flight 26 days in advance to save up to 75% 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 26 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 $606 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 $462 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
$216 - $445
Route
Depart
Return
Price
Chicago O'Hare IntlKey West
ORD - EYW
ORDEYW
Chicago O'Hare Intl
mar. 7/9
1 stop4h 44m
Key West
mié. 7/17
1 stop7h 57m
Chicago MidwayKey West
MDW - EYW
MDWEYW
Chicago Midway
vie. 5/31
1 stop5h 58m
Key West
mar. 6/4
1 stop4h 51m
Chicago O'Hare IntlKey West
ORD - EYW
ORDEYW
Chicago O'Hare Intl
vie. 5/31
1 stop6h 11m
Key West
jue. 6/6
1 stop6h 44m
Chicago O'Hare IntlKey West
ORD - EYW
ORDEYW
Chicago O'Hare Intl
vie. 7/5
1 stop6h 07m
Key West
mar. 7/16
1 stop5h 57m
Chicago O'Hare IntlKey West
ORD - EYW
ORDEYW
Chicago O'Hare Intl
sáb. 6/1
1 stop7h 55m
Key West
mié. 6/5
1 stop7h 00m
Chicago O'Hare IntlKey West
ORD - EYW
ORDEYW
Chicago O'Hare Intl
sáb. 7/6
1 stop6h 04m
Key West
mar. 7/16
1 stop5h 57m
Chicago MidwayKey West
MDW - EYW
MDWEYW
Chicago Midway
mar. 5/28
1 stop6h 00m
Key West
mar. 6/4
1 stop4h 51m
Chicago O'Hare IntlKey West
ORD - EYW
ORDEYW
Chicago O'Hare Intl
mié. 8/14
1 stop7h 09m
Key West
dom. 8/18
1 stop23h 06m
Chicago MidwayKey West
MDW - EYW
MDWEYW
Chicago Midway
lun. 7/8
1 stop6h 57m
Key West
dom. 7/14
1 stop19h 43m
No data available for this route at this time. Please check back soon.
Crew
Overall
Entertainment
Comfort
Food
Boarding
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
Entertainment
Comfort
Food
Boarding
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
Entertainment
Comfort
Food
Boarding
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
Entertainment
Comfort
Food
Boarding
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 |
Cheapflights goes through 900+ travel sites to look for the best flight deals for flights from Illinois to Key West. Too many options? Cheapflights also provides filters for things like airlines, price ranges, and number of stops to help you make a decision easily.
Cheapflights helps you find that perfect flight to Key West from Illinois by searching from hundreds of airlines and agencies you know and love. We are also free to use, in case you were wondering!
Users can book flights with no change fees policies with our dedicated filters. Book flights from Illinois to Key West flexibly with Cheapflights today.
Not ready to book yet? You can track prices for flights from Illinois to Key West on Cheapflights with our Price Alert feature and get notified when better prices are available.