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Key West

$85+ 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 1/15. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — EYW
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheap 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 December 18, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/17. 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.
Tue 12/232:36 pmMLI - EYW
1 stop15h 31mMultiple Airlines
Mon 12/2910:01 pmEYW - MLI
1 stop16h 45mMultiple Airlines
Deal found 12/17$300
This United Airlines deal was found by Cheapflights users on 12/17. 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.
Wed 12/248:05 amSTL - EYW
1 stop6h 07mUnited Airlines
Thu 12/2512:22 pmEYW - STL
1 stop6h 32mUnited Airlines
Deal found 12/17$303
This United Airlines deal was found by Cheapflights users on 12/17. 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.
Wed 12/248:05 amSTL - EYW
1 stop6h 07mUnited Airlines
Sun 12/284:29 pmEYW - STL
1 stop6h 26mUnited Airlines
Deal found 12/17$311
This Kiwi.com deal was found by Cheapflights users on 12/17. 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 12/2110:14 amMLI - EYW
1 stop25h 16mMultiple Airlines
Mon 12/2910:01 pmEYW - MLI
1 stop16h 45mMultiple Airlines
Deal found 12/17$317
This American Airlines deal was found by Cheapflights users on 12/15. 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 12/316:07 amORD - EYW
1 stop8h 26mAmerican Airlines
Wed 1/77:08 amEYW - ORD
1 stop5h 27mAmerican Airlines
Deal found 12/15$326
This Kiwi.com deal was found by Cheapflights users on 12/16. 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.
Wed 12/3112:09 pmORD - EYW
1 stop19h 06mMultiple Airlines
Mon 1/51:10 pmEYW - ORD
1 stop26h 11mMultiple Airlines
Deal found 12/16$328
This American Airlines deal was found by Cheapflights users on 12/16. 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 12/305:00 amSTL - EYW
1 stop6h 08mAmerican Airlines
Thu 1/18:00 amEYW - STL
1 stop6h 14mAmerican Airlines
Deal found 12/16$329
This Kiwi.com deal was found by Cheapflights users on 12/16. 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.
Wed 12/3112:09 pmORD - EYW
1 stop19h 06mMultiple Airlines
Tue 1/612:20 pmEYW - ORD
1 stop23h 54mMultiple Airlines
Deal found 12/16$338
This United Airlines deal was found by Cheapflights users on 12/17. 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.
Wed 12/246:30 amSTL - EYW
1 stop7h 42mUnited Airlines
Fri 12/261:25 pmEYW - STL
2 stops11h 18mUnited Airlines
Deal found 12/17$342
This American Airlines deal was found by Cheapflights users on 12/15. 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 12/238:10 amORD - EYW
Nonstop3h 35mAmerican Airlines
Mon 12/296:26 pmEYW - ORD
Nonstop3h 33mAmerican Airlines
Deal found 12/15$345
This Kiwi.com deal was found by Cheapflights users on 12/17. 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.
Wed 12/311:34 pmORD - EYW
1 stop19h 45mMultiple Airlines
Sun 1/410:37 pmEYW - ORD
2 stops39h 17mMultiple Airlines
Deal found 12/17$350
This United Airlines deal was found by Cheapflights users on 12/15. 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.
Wed 12/247:55 amORD - EYW
Nonstop3h 39mUnited Airlines
Sat 12/274:29 pmEYW - ORD
1 stop8h 45mUnited Airlines
Deal found 12/15$352

Find 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 December 18, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$185
(Kiwi.com)

One-way from

$85
(Priceline)

Popular in

June

Cheapest in

January

Average price

$444

Good round-trip deal

$342 or less

Good one-way deal

$293 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. 1% potential increase in price ($8 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 December 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 December 18, 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

8:22 pm-11:56 am

2 stops14h 34m

Key West

Thu 2/5

9:46 am-10:23 am

1 stop25h 37m

$208

St. LouisKey West

STL - EYW

STLEYW

Lambert-St Louis

Tue 2/10

3:54 pm-9:47 pm

1 stop4h 53m

Key West

Wed 2/25

11:47 am-5:27 pm

1 stop6h 40m

$223

St. LouisKey West

STL - EYW

STLEYW

Lambert-St Louis

Tue 2/10

1:00 pm-7:40 pm

1 stop5h 40m

Key West

Wed 2/25

6:07 pm-11:36 pm

1 stop6h 29m

$223

St. LouisKey West

STL - EYW

STLEYW

Lambert-St Louis

Wed 3/18

1:36 pm-11:56 pm

2 stops9h 20m

Key West

Wed 3/25

6:45 am-10:32 am

1 stop4h 47m

$228

St. LouisKey West

STL - EYW

STLEYW

Lambert-St Louis

Wed 1/28

9:33 am-7:10 pm

2 stops8h 37m

Key West

Sat 1/31

6:06 am-3:04 pm

2 stops9h 58m

$233

St. LouisKey West

STL - EYW

STLEYW

Lambert-St Louis

Thu 2/26

11:19 am-7:20 pm

1 stop7h 01m

Key West

Tue 3/3

4:02 pm-10:05 pm

1 stop7h 03m

$251

St. LouisKey West

STL - EYW

STLEYW

Lambert-St Louis

Wed 1/7

12:00 pm-7:40 pm

1 stop6h 40m

Key West

Fri 1/30

1:28 pm-8:06 pm

1 stop7h 38m

$279

St. LouisKey West

STL - EYW

STLEYW

Lambert-St Louis

Fri 1/9

12:00 pm-5:11 pm

1 stop4h 11m

Key West

Tue 1/13

6:06 pm-11:39 pm

1 stop6h 33m

$279

St. LouisKey West

STL - EYW

STLEYW

Lambert-St Louis

Fri 1/9

1:35 pm-11:56 pm

2 stops9h 21m

Key West

Tue 1/13

11:18 am-5:23 pm

1 stop7h 05m

$284

MolineKey West

MLI - EYW

MLIEYW

Moline Quad-City

Wed 1/21

11:28 am-9:47 pm

2 stops9h 19m

Key West

Thu 2/5

2:43 pm-9:58 pm

1 stop8h 15m

$291

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/16

Showing 1-10 of 57 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 $300). 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 December 18, 2025.

It’s typically best to fly out from Illinois to Key West in the afternoon. Doing so could potentially save you 32% on the flight price compared to flying in the evening, which is usually more expensive.

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?

    American Airlines, Delta, and Spirit Airlines can get you from Illinois to Key West in just under 4h 53m. Your travel time can differ by up to 19h 53m. The distance between Illinois and Key West is about 1102 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 American Airlines, with whom users have recently found tickets for as low as $176. 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?

    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 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: American Airlines (71%), Envoy Air (71%), United Airlines (66%).

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

    While on average a flight from Illinois to Key West is generally $369, our data shows the cheapest flight currently is $158. When looking at the most popular route, (Chicago O'Hare Intl - Key West), you can expect to pay $169 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 $300). 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 4 airlines flying from Illinois to Key West

Discover the top 4 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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$199Average$385FlexibilityNo cancel feeOn-time65%
DeltaCheapest$248Average$486FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$249Average$562FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$268Average$453FlexibilityNo cancel feeOn-time71%

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