Travelers have found it’s best to book a flight 41 days in advance to save up to 31% 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 41 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 $598, or $719 for flights within the next 24 hours.
Our data shows that September tends to be the cheapest month to fly to Key West from Illinois. Users have commonly found prices around $489 for the month, but tickets can be as low as $283. 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 - $288
Route
Depart
Return
Price
Chicago O'Hare IntlKey West
ORD - EYW
ORDEYW
Chicago O'Hare Intl
Sat 11/11
1 stop11h 45m
Key West
Wed 11/15
1 stop6h 51m
Chicago O'Hare IntlKey West
ORD - EYW
ORDEYW
Chicago O'Hare Intl
Fri 1/19
Nonstop3h 13m
Key West
Mon 1/22
Nonstop3h 27m
Chicago O'Hare IntlKey West
ORD - EYW
ORDEYW
Chicago O'Hare Intl
Thu 1/18
1 stop4h 43m
Key West
Mon 1/22
Nonstop3h 27m
Chicago O'Hare IntlKey West
ORD - EYW
ORDEYW
Chicago O'Hare Intl
Wed 2/7
Nonstop3h 13m
Key West
Sat 2/10
1 stop7h 45m
Chicago MidwayKey West
MDW - EYW
MDWEYW
Chicago Midway
Tue 2/13
1 stop4h 52m
Key West
Wed 2/28
1 stop4h 47m
Chicago O'Hare IntlKey West
ORD - EYW
ORDEYW
Chicago O'Hare Intl
Fri 1/5
1 stop4h 30m
Key West
Fri 1/12
1 stop7h 20m
Chicago O'Hare IntlKey West
ORD - EYW
ORDEYW
Chicago O'Hare Intl
Mon 11/6
1 stop14h 05m
Key West
Thu 11/9
1 stop8h 56m
Chicago O'Hare IntlKey West
ORD - EYW
ORDEYW
Chicago O'Hare Intl
Mon 10/16
1 stop14h 05m
Key West
Wed 10/18
1 stop7h 06m
Chicago O'Hare IntlKey West
ORD - EYW
ORDEYW
Chicago O'Hare Intl
Fri 1/5
1 stop7h 14m
Key West
Wed 1/10
Nonstop3h 20m
Entertainment
Overall
Food
Boarding
Comfort
Crew
Reviews
Flight delayed from 7:45 to 1:00 Pm. No effort from delta to reschedule. Left me arriving after my connection departure. I had to rebook. Myself. But no seat assignments. Put me in last seat that doesn’t recline. This was returning from Florida. Going to Florida my flight was cancelled. I had to rebook on another airline that cost me double.
Entertainment
Overall
Food
Boarding
Comfort
Crew
Reviews
Flight delayed from 7:45 to 1:00 Pm. No effort from delta to reschedule. Left me arriving after my connection departure. I had to rebook. Myself. But no seat assignments. Put me in last seat that doesn’t recline. This was returning from Florida. Going to Florida my flight was cancelled. I had to rebook on another airline that cost me double.
Entertainment
Overall
Food
Boarding
Comfort
Crew
Reviews
Flight delayed from 7:45 to 1:00 Pm. No effort from delta to reschedule. Left me arriving after my connection departure. I had to rebook. Myself. But no seat assignments. Put me in last seat that doesn’t recline. This was returning from Florida. Going to Florida my flight was cancelled. I had to rebook on another airline that cost me double.
Entertainment
Overall
Food
Boarding
Comfort
Crew
Reviews
Flight delayed from 7:45 to 1:00 Pm. No effort from delta to reschedule. Left me arriving after my connection departure. I had to rebook. Myself. But no seat assignments. Put me in last seat that doesn’t recline. This was returning from Florida. Going to Florida my flight was cancelled. I had to rebook on another airline that cost me double.
Located just 2.6 mi from the city center, Key West (EYW) is the airport most travelers will use when flying to Key West from Illinois.
Yes, there are multiple flights from Illinois to Key West for under $200. The cheapest flight booked recently is on Multiple Airlines for just $197, but on average you can expect to pay $227.
Cheapflights has at least 20 direct flights from Illinois to Key West under $300. A good price for a nonstop flight from Illinois to Key West is less than $455.
There are currently 20+ open flights from Illinois to Key West within the next 7 days for less than $300.
While some choose either Chicago Midway - Key West or Lambert-St Louis - Key West, Chicago O'Hare Intl - Key West is the most popular route from Illinois to Key West.
American Airlines, Alaska Airlines and Delta are the most popular airlines when flying from Illinois to Key West.
While on average a flight from Illinois to Key West is generally $408, our data shows the cheapest flight currently is $228. When looking at the most popular route, (Chicago O'Hare Intl - Key West), you can expect to pay $227 for that flight.
Great question - ORD to EYW just means Chicago O'Hare Intl Airport to Key West Airport. Now you’ll know what these unique codes when you look for flights! Chicago Midway Airport (MDW), Moline Quad-City Airport (MLI), Greater Peoria Airport (PIA), Bloomington-Normal Airport (BMI), Champaign University-Willard Airport (CMI) are other airports near this flight route and their unique identifiers/IATA codes.