Cheap flights from Illinois to Key West (EYW)

ORD — EYW
Aug 16 — Aug 231

How far in advance should I book a flight from Illinois to Key West?

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.

What is the cheapest month to fly from Illinois to Key West?

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.

When is the cheapest time to fly from Illinois to Key West (IL - EYW)?

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.

Cheap flights from Illinois to Key West in August, September 2022

The best prices found for Illinois to EYW flights for August, September
Aug 26 - Aug 29
ORD

Chicago O'Hare Intl

EYW

Key West

1 stop

12h 09m
EYW

Key West

ORD

Chicago O'Hare Intl

1 stop

12h 43m
$198

Multiple Airlines

Pick Dates

Deal found 8/9/22

Sep 10 - Sep 17
ORD

Chicago O'Hare Intl

EYW

Key West

1 stop

5h 52m
EYW

Key West

ORD

Chicago O'Hare Intl

1 stop

5h 20m
$223

American Airlines

Pick Dates

Deal found 8/11/22

Sep 17 - Sep 20
ORD

Chicago O'Hare Intl

EYW

Key West

1 stop

6h 02m
EYW

Key West

ORD

Chicago O'Hare Intl

1 stop

5h 55m
$224

American Airlines

Pick Dates

Deal found 8/11/22

Illinois to Key West 2022 flight deals

Cheap flights to Key West from Illinois found for this year
Aug 26 - Aug 29
ORD

Chicago O'Hare Intl

EYW

Key West

1 stop

12h 09m
EYW

Key West

ORD

Chicago O'Hare Intl

1 stop

12h 43m
$198

Multiple Airlines

Pick Dates

Deal found 8/9/22

Dec 12 - Dec 20
ORD

Chicago O'Hare Intl

EYW

Key West

Nonstop

3h 00m
EYW

Key West

ORD

Chicago O'Hare Intl

1 stop

5h 08m
$215

American Airlines

Pick Dates

Deal found 8/10/22

Dec 5 - Dec 10
ORD

Chicago O'Hare Intl

EYW

Key West

Nonstop

3h 00m
EYW

Key West

ORD

Chicago O'Hare Intl

1 stop

7h 17m
$217

American Airlines

Pick Dates

Deal found 8/10/22

Cheap Delta flights from Illinois to Key West

Sep 17 - Sep 20
MDW

Chicago Midway

EYW

Key West

1 stop

6h 08m
EYW

Key West

MDW

Chicago Midway

1 stop

5h 35m
$226

Delta

Pick Dates

Deal found 8/11/22

Oct 18 - Oct 25
ORD

Chicago O'Hare Intl

EYW

Key West

1 stop

4h 50m
EYW

Key West

ORD

Chicago O'Hare Intl

1 stop

6h 41m
$263

Delta

Pick Dates

Deal found 8/9/22

Sep 17 - Sep 24
MDW

Chicago Midway

EYW

Key West

1 stop

6h 08m
EYW

Key West

MDW

Chicago Midway

1 stop

5h 35m
$266

Delta

Pick Dates

Deal found 8/9/22

Cheap American Airlines flights from Illinois to Key West

Jan 10 - Jan 14
ORD

Chicago O'Hare Intl

EYW

Key West

Nonstop

3h 00m
EYW

Key West

ORD

Chicago O'Hare Intl

Nonstop

3h 30m
$208

American Airlines

Pick Dates

Deal found 8/10/22

Dec 12 - Dec 20
ORD

Chicago O'Hare Intl

EYW

Key West

Nonstop

3h 00m
EYW

Key West

ORD

Chicago O'Hare Intl

1 stop

5h 08m
$215

American Airlines

Pick Dates

Deal found 8/10/22

Dec 5 - Dec 10
ORD

Chicago O'Hare Intl

EYW

Key West

Nonstop

3h 00m
EYW

Key West

ORD

Chicago O'Hare Intl

1 stop

7h 17m
$217

American Airlines

Pick Dates

Deal found 8/10/22

Non-stop flights to Key West from Illinois

Save time with Illinois to Key West direct flight deals
Jan 10 - Jan 14
ORD

Chicago O'Hare Intl

EYW

Key West

Nonstop

3h 00m
EYW

Key West

ORD

Chicago O'Hare Intl

Nonstop

3h 30m
$208

American Airlines

Pick Dates

Deal found 8/10/22

Jan 21 - Jan 28
ORD

Chicago O'Hare Intl

EYW

Key West

Nonstop

3h 00m
EYW

Key West

ORD

Chicago O'Hare Intl

Nonstop

3h 30m
$273

American Airlines

Pick Dates

Deal found 8/11/22

Jan 19 - Jan 25
ORD

Chicago O'Hare Intl

EYW

Key West

Nonstop

3h 10m
EYW

Key West

ORD

Chicago O'Hare Intl

Nonstop

3h 28m
$309

United Airlines

Pick Dates

Deal found 8/9/22

Last minute flights from Illinois to Key West

Late deals on return flights to Key West from Illinois, departing today and this week
Aug 17 - Aug 22
ORD

Chicago O'Hare Intl

EYW

Key West

1 stop

5h 37m
EYW

Key West

ORD

Chicago O'Hare Intl

1 stop

7h 15m
$353

American Airlines

Pick Dates

Deal found 8/10/22

Aug 17 - Aug 22
ORD

Chicago O'Hare Intl

EYW

Key West

2 stops

8h 04m
EYW

Key West

ORD

Chicago O'Hare Intl

1 stop

7h 15m
$357

American Airlines

Pick Dates

Deal found 8/10/22

Aug 20 - Aug 22
ORD

Chicago O'Hare Intl

EYW

Key West

2 stops

10h 00m
EYW

Key West

ORD

Chicago O'Hare Intl

2 stops

11h 13m
$362

American Airlines

Pick Dates

Deal found 8/10/22

One-way flights to Key West from Illinois

The cheapest one-way flights from Illinois to Key West
Aug 30
ORD

Chicago O'Hare Intl

EYW

Key West

2 stops

20h 28m
$90

Multiple Airlines

Pick Dates

Deal found 8/10/22

Aug 30
ORD

Chicago O'Hare Intl

EYW

Key West

1 stop

21h 15m
$100

Multiple Airlines

Pick Dates

Deal found 8/10/22

Oct 28
ORD

Chicago O'Hare Intl

EYW

Key West

1 stop

11h 21m
$124

Multiple Airlines

Pick Dates

Deal found 8/9/22

Related info for your journey

Useful info, stats and facts about Illinois to Key West flights.

What airport do you fly into for flights to Key West from Illinois?

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.

Which airlines flying from Illinois to Key West have flexible cancellations due to COVID-19?

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.

Can I find flights from Illinois to Key West for under $200 on Cheapflights?

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.

Are there nonstop flights from Illinois to Key West for under $300 on Cheapflights?

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.

Are there last-minute flights available from Illinois to Key West for under $400?

There are currently 20+ open flights from Illinois to Key West within the next 7 days for less than $400.

What are the most popular routes from Illinois to Key West?

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.

What are the most popular airlines that fly from Illinois to Key West?

American Airlines, Alaska Airlines and Delta are the most popular airlines when flying from Illinois to Key West.

What are the cheapest flights 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.

Departure points for flights from Illinois to Key West

Select to see more specific information for flights to Key West from all departure points in Illinois

Top 4 airlines flying from Illinois to Key West

The chart below displays the airlines Cheapflights users traveling from Illinois to Key West choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
AirlineCheapestAverageFlexibilityOn-timeCOVID-19 safety
Juneyao AirlinesCheapest$10Average$22FlexibilityNo cancel feeOn-time66%COVID-19 safety
Search Juneyao Airlines flights
DeltaCheapest$168Average$477FlexibilityNo cancel feeOn-timeN/ACOVID-19 safety
Search Delta flights
United AirlinesCheapest$220Average$513FlexibilityNo cancel feeOn-time69%COVID-19 safety
Search United Airlines flights
American AirlinesCheapest$236Average$454FlexibilityNo cancel feeOn-time71%COVID-19 safety
Search American Airlines flights

Hourly flight availability from Illinois to Key West

See what time of day planes typically take off from Illinois to Key West
0%of flight departuresEarly morningMidnight to 6 am
100%of flight departuresMorning6 am to noon
0%of flight departuresAfternoonNoon to 6 pm
0%of flight departuresEvening6 pm to midnight
Midnight
6 AM
Noon
6 PM