Key West

$92+ Cheap flights from Illinois to Key West (EYW)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 3/25. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — EYW
feb. 25 — mar. 41
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Cheap flight deals from Illinois to Key West

Keep the following information in mind while searching for Illinois to Key West flight deals. Data was last updated febrero 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$219
(American Airlines)

One-way from

$92
(Mytrip)

Popular in

March

Cheapest in

August

Average price

$478

Good round-trip deal

$357 or less

Good one-way deal

$293 or less
Provider with most accurate pricing for Chicago (CHI)-Key West flight deals.
Provider most trusted by Cheapflights users for Chicago (CHI)-Key West flights.
From Illinois to Key West
One-way flight from Illinois to Key West
Highest demand for flights based on searches. 9% potential increase in price ($46 potential increase over avg. RT price).
Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
Average for round-trip flights in February 2025
Price to beat on a round-trip flight from Illinois to Key West.
Price to beat on a one-way flight from Illinois to Key West.

Find flight deals from Illinois to Key West

Cheapest flights from Illinois to Key West
Explore the most affordable flight options available from Illinois to Key West. Find the lowest fares from popular airlines and budget airlines, with prices last updated on febrero 20, 2025.

This American Airlines deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 4/96:21 amPIA - EYW
2 stops11h 34mAmerican Airlines
mié. 4/238:00 amEYW - PIA
2 stops9h 45mAmerican Airlines
Deal found 2/20$219
This American Airlines deal was found by Cheapflights users on 2/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 3/198:49 amSTL - EYW
1 stop6h 55mAmerican Airlines
mié. 3/265:24 pmEYW - STL
1 stop7h 32mAmerican Airlines
Deal found 2/19$269
This Trip.com deal was found by Cheapflights users on 2/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 3/711:00 amSTL - EYW
1 stop22h 10mMultiple Airlines
dom. 3/97:40 pmEYW - STL
1 stop14h 56mMultiple Airlines
Deal found 2/19$287
This Delta deal was found by Cheapflights users on 2/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 3/46:00 amSTL - EYW
1 stop7h 08mDelta
sáb. 3/87:00 amEYW - STL
1 stop5h 46mDelta
Deal found 2/18$289
This Mytrip deal was found by Cheapflights users on 2/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 3/287:10 pmORD - EYW
1 stop18h 15mMultiple Airlines
jue. 4/38:53 amEYW - ORD
2 stops25h 52mMultiple Airlines
Deal found 2/19$306
This American Airlines deal was found by Cheapflights users on 2/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 5/168:10 amORD - EYW
1 stop7h 42mAmerican Airlines
mié. 5/2112:49 pmEYW - ORD
Nonstop3h 39mAmerican Airlines
Deal found 2/19$312
This Delta deal was found by Cheapflights users on 2/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 3/182:55 pmORD - EYW
1 stop4h 35mDelta
mié. 3/267:00 amEYW - ORD
2 stops14h 38mDelta
Deal found 2/19$317
This Delta deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 4/312:48 pmMDW - EYW
1 stop6h 38mDelta
mié. 4/96:10 pmEYW - MDW
1 stop5h 11mDelta
Deal found 2/20$326
This Mytrip deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 9/16:35 pmMDW - EYW
1 stop18h 21mAllegiant Air
dom. 9/77:32 pmEYW - MDW
1 stop17h 28mAllegiant Air
Deal found 2/20$335
This United Airlines deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 4/96:50 amPIA - EYW
1 stop7h 14mUnited Airlines
mié. 4/234:04 pmEYW - PIA
1 stop6h 29mUnited Airlines
Deal found 2/20$335
This United Airlines deal was found by Cheapflights users on 2/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 3/134:42 pmORD - EYW
Nonstop3h 21mUnited Airlines
lun. 3/1710:19 amEYW - ORD
Nonstop3h 50mUnited Airlines
Deal found 2/19$338
This United Airlines deal was found by Cheapflights users on 2/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 3/71:05 pmSTL - EYW
1 stop6h 58mUnited Airlines
lun. 3/104:55 pmEYW - STL
1 stop6h 12mUnited Airlines
Deal found 2/18$374

Find flights from Illinois to Key West within your budget

Customize your flight search to find flights from Illinois to Key West that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated febrero 20, 2025.

Fly from

Illinois

Fly to

Key West

Route

Depart

Return

Price

PeoriaKey West

PIA - EYW

PIAEYW

Greater Peoria

mié. 4/9

6:21 am-6:55 pm

2 stops11h 34m

Key West

mié. 4/23

8:00 am-4:45 pm

2 stops9h 45m

$219

St. LouisKey West

STL - EYW

STLEYW

Lambert-St Louis

mié. 3/19

8:49 am-4:44 pm

1 stop6h 55m

Key West

mié. 3/26

5:24 pm-11:56 pm

1 stop7h 32m

$269

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

vie. 3/28

7:10 pm-2:25 pm

1 stop18h 15m

Key West

jue. 4/3

8:53 am-9:45 am

2 stops25h 52m

$306

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

vie. 5/16

8:10 am-4:52 pm

1 stop7h 42m

Key West

mié. 5/21

12:49 pm-3:28 pm

Nonstop3h 39m

$312

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

mar. 3/18

2:55 pm-8:30 pm

1 stop4h 35m

Key West

mié. 3/26

7:00 am-8:38 pm

2 stops14h 38m

$317

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

jue. 4/3

12:48 pm-8:26 pm

1 stop6h 38m

Key West

mié. 4/9

6:10 pm-10:21 pm

1 stop5h 11m

$326

St. LouisKey West

STL - EYW

STLEYW

Lambert-St Louis

lun. 3/3

5:20 pm-10:10 am

1 stop15h 50m

Key West

lun. 3/10

3:05 pm-11:49 pm

1 stop9h 44m

$331

St. LouisKey West

STL - EYW

STLEYW

Lambert-St Louis

mar. 3/4

10:26 am-5:19 pm

1 stop5h 53m

Key West

sáb. 3/8

7:00 am-11:46 am

1 stop5h 46m

$334

PeoriaKey West

PIA - EYW

PIAEYW

Greater Peoria

mié. 4/9

6:50 am-3:04 pm

1 stop7h 14m

Key West

mié. 4/23

4:04 pm-9:33 pm

1 stop6h 29m

$335

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

jue. 3/13

4:42 pm-9:03 pm

Nonstop3h 21m

Key West

lun. 3/17

10:19 am-1:09 pm

Nonstop3h 50m

$338

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/18

Showing 1-10 of 28 results
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Best time to book a flight from Illinois to Key West

Have a flexible travel schedule? Discover the best time to fly to Key West from Illinois with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Travel insights for flights from Illinois to Key West

Get recent, data-driven insights about flights from Illinois to Key West including ideal travel times, pricing trends, and more.

What is the cheapest month to book a flight from Illinois to Key West?

Currently, August is the cheapest month in which you can book a flight from Illinois to Key West (average of $328). Flying from Illinois to Key West in March is currently the most expensive (average of $510). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from IL to EYW?

Find hourly flight availability from Illinois to Key West. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated febrero 20, 2025.

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.

Weekly flight availability from Illinois to Key West

Explore weekly flight availability from Illinois to Key West. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated febrero 20, 2025.

The most flights from USIL to EYW are scheduled on a Monday (3 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (3 on average).

Rainfall in Key West by month

Plan your trip to Key West by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Key West ranges from 1.5 - 6.7 inches per month. September is typically the wettest month, when rainfall can reach 6.7 in. February is typically the driest time to visit Key West when rainfall is around 1.5 in.

Temperature in Key West by month

Plan your trip to Key West by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Key West, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 84.2 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 69.8 F).

Reviews of airlines servicing Key West

Get insights into the airlines that provide service to Key West. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Key West. Reviews last updated febrero 20, 2025.
Peruse reviews from past customers who have flown with Alaska Airlines, Delta and United Airlines from Illinois to Key West to help guide your decision. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.

Comfort

7.9

Overall

8.0

Crew

8.5

Food

7.1

Boarding

8.2

Entertainment

7.1

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Comfort

7.9

Overall

8.0

Crew

8.5

Food

7.1

Boarding

8.2

Entertainment

7.1

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

8.0
Very good

Comfort

7.9

Overall

8.0

Crew

8.5

Food

7.1

Boarding

8.2

Entertainment

7.1

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Comfort

7.9

Overall

8.0

Crew

8.5

Food

7.1

Boarding

8.2

Entertainment

7.1

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Comfort

7.9

Overall

8.0

Crew

8.5

Food

7.1

Boarding

8.2

Entertainment

7.1

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Comfort

7.9

Overall

8.0

Crew

8.5

Food

7.1

Boarding

8.2

Entertainment

7.1

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Related info for your journey

Find useful and relevant information for your journey from Illinois to Key West. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
  • 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.

  • What are the cheapest airlines to fly from Illinois to Key West one-way?

    The cheapest airline one-way is American Airlines, with whom users have recently found tickets for as low as $100. However, be on the lookout for offers from United Airlines and Delta, as they are both options that can get you from Illinois to Key West for a low price.

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

  • What are the most reliable airlines from Illinois to Key West?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Illinois to Key West on time: Air New Zealand (83%), United Airlines (77%), American Airlines (72%).

  • What are the cheapest flights from Illinois to Key West?

    While on average a flight from Illinois to Key West is generally $431, our data shows the cheapest flight currently is $89. When looking at the most popular route, (Chicago O'Hare Intl - Key West), you can expect to pay $221 for that flight.

  • Can I find deals for flights from Illinois to Key West that include hotel bookings?

    Yes. In addition to deals on Illinois to Key West flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Illinois to Key West?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Illinois to Key West.

  • Can I find deals for business class flights from Illinois to Key West?

    Yes. Cheapflights offers flight deals from Illinois to Key West by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Illinois to Key West?

    Currently, August is the cheapest month in which you can book a flight from Illinois to Key West (average of $328). Flying from Illinois to Key West in March is currently the most expensive (average of $510). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Alternative routes for Illinois to Key West

See prices for flight routes from nearby airports that may be better suited for you.

Top 3 airlines flying from Illinois to Key West

Discover the top 3 airlines that operate flights from Illinois to Key West. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated febrero 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$216Average$483FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$247Average$485FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$254Average$469FlexibilityNo cancel feeOn-time69%
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