Travelers have found it’s best to book a flight 61 days in advance to save up to 32% 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 $520, or $629 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 $443 for the month, but tickets can be as low as $295. 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.
Chicago O'Hare Intl
Key West
1 stop
12h 09mKey West
Chicago O'Hare Intl
1 stop
12h 43mMultiple Airlines
Chicago O'Hare Intl
Key West
1 stop
5h 52mKey West
Chicago O'Hare Intl
1 stop
5h 20mAmerican Airlines
Chicago O'Hare Intl
Key West
1 stop
6h 02mKey West
Chicago O'Hare Intl
1 stop
5h 55mAmerican Airlines
Chicago O'Hare Intl
Key West
1 stop
12h 09mKey West
Chicago O'Hare Intl
1 stop
12h 43mMultiple Airlines
Chicago O'Hare Intl
Key West
Nonstop
3h 00mKey West
Chicago O'Hare Intl
1 stop
5h 08mAmerican Airlines
Chicago O'Hare Intl
Key West
Nonstop
3h 00mKey West
Chicago O'Hare Intl
1 stop
7h 17mAmerican Airlines
Chicago Midway
Key West
1 stop
6h 08mKey West
Chicago Midway
1 stop
5h 35mDelta
Chicago O'Hare Intl
Key West
1 stop
4h 50mKey West
Chicago O'Hare Intl
1 stop
6h 41mDelta
Chicago Midway
Key West
1 stop
6h 08mKey West
Chicago Midway
1 stop
5h 35mDelta
Chicago O'Hare Intl
Key West
Nonstop
3h 00mKey West
Chicago O'Hare Intl
Nonstop
3h 30mAmerican Airlines
Chicago O'Hare Intl
Key West
Nonstop
3h 00mKey West
Chicago O'Hare Intl
1 stop
5h 08mAmerican Airlines
Chicago O'Hare Intl
Key West
Nonstop
3h 00mKey West
Chicago O'Hare Intl
1 stop
7h 17mAmerican Airlines
Chicago O'Hare Intl
Key West
Nonstop
3h 00mKey West
Chicago O'Hare Intl
Nonstop
3h 30mAmerican Airlines
Chicago O'Hare Intl
Key West
Nonstop
3h 00mKey West
Chicago O'Hare Intl
Nonstop
3h 30mAmerican Airlines
Chicago O'Hare Intl
Key West
Nonstop
3h 10mKey West
Chicago O'Hare Intl
Nonstop
3h 28mUnited Airlines
Chicago O'Hare Intl
Key West
1 stop
5h 37mKey West
Chicago O'Hare Intl
1 stop
7h 15mAmerican Airlines
Chicago O'Hare Intl
Key West
2 stops
8h 04mKey West
Chicago O'Hare Intl
1 stop
7h 15mAmerican Airlines
Chicago O'Hare Intl
Key West
2 stops
10h 00mKey West
Chicago O'Hare Intl
2 stops
11h 13mAmerican Airlines
Chicago O'Hare Intl
Key West
2 stops
20h 28mMultiple Airlines
Chicago O'Hare Intl
Key West
1 stop
21h 15mMultiple Airlines
Chicago O'Hare Intl
Key West
1 stop
11h 21mMultiple Airlines
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.
Some of the carriers operating flights from Illinois to Key West that may be offering flexible cancellation policies are American Airlines, United Airlines, and Delta. Our site will let you filter for all airlines offering greater flexibility due to COVID-19.
Yes, there are multiple flights from Illinois to Key West for under $200. The cheapest flight booked recently is on Multiple Airlines for just $198, but on average you can expect to pay $229.
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 $396.
There are currently 20+ open flights from Illinois to Key West within the next 7 days for less than $400.
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 $769, our data shows the cheapest flight currently is $245. When looking at the most popular route, (Chicago O'Hare Intl - Key West), you can expect to pay $226 for that flight.
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