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Key West

$84+ 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 1/27. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — EYW
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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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 October 30, 2025.

This American Airlines deal was found by Cheapflights users on 10/28. 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.
Wed 12/34:36 pmSTL - EYW
1 stop5h 31mAmerican Airlines
Sat 12/64:59 pmEYW - STL
1 stop6h 48mAmerican Airlines
Deal found 10/28$223
This Delta deal was found by Cheapflights users on 10/29. 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.
Sun 12/141:57 pmSTL - EYW
1 stop5h 09mDelta
Sat 12/206:20 pmEYW - STL
1 stop6h 22mDelta
Deal found 10/29$241
This American Airlines deal was found by Cheapflights users on 10/28. 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.
Thu 12/112:09 pmSTL - EYW
1 stop6h 36mAmerican Airlines
Tue 12/167:00 amEYW - STL
2 stops9h 37mAmerican Airlines
Deal found 10/28$246
This American Airlines deal was found by Cheapflights users on 10/28. 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.
Tue 11/116:00 amSTL - EYW
1 stop6h 59mAmerican Airlines
Tue 11/181:23 pmEYW - STL
1 stop6h 02mAmerican Airlines
Deal found 10/28$274
This American Airlines deal was found by Cheapflights users on 10/28. 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.
Tue 11/256:02 amSTL - EYW
1 stop8h 04mAmerican Airlines
Tue 12/22:39 pmEYW - STL
1 stop5h 51mAmerican Airlines
Deal found 10/28$276
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/2710:53 amSTL - EYW
2 stops21h 24mMultiple Airlines
Thu 12/48:55 amEYW - STL
1 stop14h 38mMultiple Airlines
Deal found 10/28$279
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/73:30 pmSTL - EYW
1 stop15h 45mMultiple Airlines
Thu 12/114:34 pmEYW - STL
1 stop17h 25mMultiple Airlines
Deal found 10/28$283
This American Airlines deal was found by Cheapflights users on 10/28. 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.
Tue 12/98:50 amORD - EYW
Nonstop3h 30mAmerican Airlines
Sat 12/137:00 amEYW - ORD
1 stop5h 07mAmerican Airlines
Deal found 10/28$313
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/43:10 pmMDW - EYW
1 stop16h 05mMultiple Airlines
Sun 12/78:55 amEYW - MDW
2 stops14h 17mMultiple Airlines
Deal found 10/29$316
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/31:56 pmORD - EYW
1 stop20h 09mMultiple Airlines
Thu 11/138:55 amEYW - ORD
1 stop15h 11mMultiple Airlines
Deal found 10/29$317
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/62:37 pmORD - EYW
2 stops16h 38mMultiple Airlines
Thu 11/138:55 amEYW - ORD
1 stop15h 11mMultiple Airlines
Deal found 10/29$318
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/242:28 pmORD - EYW
1 stop18h 51mMultiple Airlines
Tue 12/211:45 amEYW - ORD
2 stops22h 32mMultiple Airlines
Deal found 10/28$321

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 October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$218
(Kiwi.com)

One-way from

$84
(Expedia)

Popular in

March

Cheapest in

August

Average price

$451

Good round-trip deal

$390 or less

Good one-way deal

$253 or less
Provider with most accurate pricing for Chicago (CHI)-Key West flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Key West flights.
Search Deals
From Illinois to Key West
Search Deals
One-way flight from Illinois to Key West
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($40 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals
Price to beat on a round-trip flight from Illinois to Key West.
Search Deals
Price to beat on a one-way flight from Illinois to Key West.
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Cheapflights Fare Finder

 
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 October 30, 2025.
Use the filters below to find and compare flights from Illinois to Key West that are best for you.

Fly from

Illinois

Fly to

Key West

Route

Depart

Return

Price

St. LouisKey West

STL - EYW

STLEYW

Lambert-St Louis

Wed 1/28

6:00 am-1:48 pm

1 stop6h 48m

Key West

Tue 2/3

1:28 pm-8:06 pm

1 stop7h 38m

$223

St. LouisKey West

STL - EYW

STLEYW

Lambert-St Louis

Wed 1/28

6:00 am-4:07 pm

1 stop9h 07m

Key West

Tue 2/3

1:33 pm-9:15 pm

2 stops8h 42m

$228

St. LouisKey West

STL - EYW

STLEYW

Lambert-St Louis

Thu 1/8

5:11 pm-12:26 pm

1 stop18h 15m

Key West

Thu 1/15

10:06 am-7:54 am

1 stop22h 48m

$230

St. LouisKey West

STL - EYW

STLEYW

Lambert-St Louis

Tue 12/2

2:05 pm-11:50 pm

2 stops8h 45m

Key West

Sat 12/6

7:00 am-1:18 pm

2 stops7h 18m

$233

St. LouisKey West

STL - EYW

STLEYW

Lambert-St Louis

Wed 1/14

9:33 am-7:10 pm

2 stops8h 37m

Key West

Sat 1/17

6:06 am-3:04 pm

2 stops9h 58m

$233

St. LouisKey West

STL - EYW

STLEYW

Lambert-St Louis

Sun 12/14

1:57 pm-8:06 pm

1 stop5h 09m

Key West

Sat 12/20

6:20 pm-11:42 pm

1 stop6h 22m

$241

St. LouisKey West

STL - EYW

STLEYW

Lambert-St Louis

Tue 1/13

6:52 am-4:49 pm

2 stops8h 57m

Key West

Sun 1/18

6:06 am-2:47 pm

2 stops9h 41m

$251

St. LouisKey West

STL - EYW

STLEYW

Lambert-St Louis

Mon 1/19

9:59 am-5:13 pm

1 stop6h 14m

Key West

Mon 1/26

6:08 pm-11:39 pm

1 stop6h 31m

$259

St. LouisKey West

STL - EYW

STLEYW

Lambert-St Louis

Mon 1/19

9:33 am-7:10 pm

2 stops8h 37m

Key West

Mon 1/26

6:43 pm-11:12 pm

1 stop5h 29m

$264

MolineKey West

MLI - EYW

MLIEYW

Moline Quad-City

Wed 1/7

5:51 am-11:31 am

1 stop4h 40m

Key West

Tue 1/13

6:08 pm-10:32 pm

1 stop5h 24m

$269

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

Showing 1-10 of 60 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.

Cheapflights Insights

Everything you need to know about your flight from Illinois to Key West

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

Currently, November is the cheapest month in which you can book a flight from Illinois to Key West (average of $200). Flying from Illinois to Key West in June is currently the most expensive (average of $308). 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 October 30, 2025.

It’s typically best to fly out from Illinois to Key West in the afternoon. Doing so could potentially save you 31% on the flight price compared to flying in the evening, which is usually more expensive.

How much does it cost to fly round-trip from Illinois to Key West?

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.

  • How long is the flight from Illinois to Key West?

    Delta, American Airlines, and United Airlines can get you from Illinois to Key West in just under 3h 27m. Your travel time can differ by up to 5h 40m. The distance between Illinois and Key West is about 1253 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    The cheapest airline one-way is Allegiant Air, with whom users have recently found tickets for as low as $112. However, be on the lookout for offers from Spirit Airlines and American Airlines, 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?

    While some choose either Lambert-St Louis - Key West or Chicago Midway - Key West, Chicago O'Hare Intl - Key West is the most popular route 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 $763, our data shows the cheapest flight currently is $253. When looking at the most popular route, (Chicago O'Hare Intl - Key West), you can expect to pay $179 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, November is the cheapest month in which you can book a flight from Illinois to Key West (average of $200). Flying from Illinois to Key West in June is currently the most expensive (average of $308). 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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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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$218Average$530FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$254Average$532FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$268Average$471FlexibilityNo cancel feeOn-time71%

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