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Key West

$109+ 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 11/7. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — EYW
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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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 September 11, 2025.

Round-trip from

$190
(Kiwi.com)

One-way from

$109
(Kiwi.com)

Popular in

March

Cheapest in

October

Average price

$407

Good round-trip deal

$434 or less

Good one-way deal

$272 or less
From Illinois to Key West
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One-way flight from Illinois to Key West
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Highest demand for flights based on searches. 8% potential increase in price ($39 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Illinois to Key West.
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Price to beat on a one-way flight from Illinois to Key West.
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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 September 11, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/10. 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 10/58:05 amORD - EYW
1 stop23h 55mMultiple Airlines
Sat 10/119:52 amEYW - ORD
1 stop28h 23mMultiple Airlines
Deal found 9/10$190
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 10/58:05 amORD - EYW
1 stop23h 55mMultiple Airlines
Fri 10/103:08 pmEYW - ORD
1 stop25h 37mMultiple Airlines
Deal found 9/10$193
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 10/58:05 amORD - EYW
1 stop23h 55mMultiple Airlines
Thu 10/93:30 pmEYW - ORD
1 stop17h 04mMultiple Airlines
Deal found 9/10$202
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 10/76:18 pmORD - EYW
1 stop13h 54mMultiple Airlines
Sat 10/119:52 amEYW - ORD
1 stop28h 23mMultiple Airlines
Deal found 9/10$203
This Kiwi.com deal was found by Cheapflights users on 9/10. 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.
Sat 10/45:17 pmORD - EYW
1 stop20h 23mMultiple Airlines
Thu 10/93:30 pmEYW - ORD
1 stop17h 04mMultiple Airlines
Deal found 9/10$204
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 10/76:18 pmORD - EYW
1 stop13h 54mMultiple Airlines
Thu 10/93:30 pmEYW - ORD
1 stop17h 04mMultiple Airlines
Deal found 9/10$208
This Kiwi.com deal was found by Cheapflights users on 9/11. 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 11/27:05 amORD - EYW
1 stop11h 38mMultiple Airlines
Wed 11/510:01 amEYW - ORD
1 stop28h 58mMultiple Airlines
Deal found 9/11$210
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 10/58:05 amORD - EYW
1 stop23h 55mMultiple Airlines
Wed 10/810:02 amEYW - ORD
1 stop25h 06mMultiple Airlines
Deal found 9/10$215
This Kiwi.com deal was found by Cheapflights users on 9/11. 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.
Sat 10/116:58 pmORD - EYW
1 stop18h 42mMultiple Airlines
Tue 10/1411:45 amEYW - ORD
1 stop23h 23mMultiple Airlines
Deal found 9/11$217
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 9/245:46 pmORD - EYW
1 stop21h 14mMultiple Airlines
Sat 9/279:52 amEYW - ORD
1 stop25h 26mMultiple Airlines
Deal found 9/9$219
This Kiwi.com deal was found by Cheapflights users on 9/8. 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 9/235:46 pmORD - EYW
1 stop14h 26mMultiple Airlines
Wed 10/810:02 amEYW - ORD
1 stop25h 06mMultiple Airlines
Deal found 9/8$221
This American Airlines deal was found by Cheapflights users on 9/10. 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 10/226:00 amSTL - EYW
1 stop6h 52mAmerican Airlines
Tue 10/285:47 pmEYW - STL
1 stop7h 09mAmerican Airlines
Deal found 9/10$223

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 September 11, 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 10/22

6:00 am-1:52 pm

1 stop6h 52m

Key West

Tue 10/28

5:47 pm-11:56 pm

1 stop7h 09m

$223

St. LouisKey West

STL - EYW

STLEYW

Lambert-St Louis

Wed 11/12

1:55 pm-7:53 pm

1 stop4h 58m

Key West

Wed 11/19

6:18 pm-9:58 pm

1 stop4h 40m

$223

St. LouisKey West

STL - EYW

STLEYW

Lambert-St Louis

Tue 11/4

6:00 am-3:28 pm

1 stop8h 28m

Key West

Sat 11/8

12:46 pm-9:00 pm

1 stop9h 14m

$223

St. LouisKey West

STL - EYW

STLEYW

Lambert-St Louis

Wed 12/3

10:13 am-5:52 pm

1 stop6h 39m

Key West

Sat 12/6

4:59 pm-10:47 pm

1 stop6h 48m

$223

St. LouisKey West

STL - EYW

STLEYW

Lambert-St Louis

Wed 11/12

9:38 am-7:23 pm

2 stops8h 45m

Key West

Wed 11/19

2:39 pm-7:30 pm

1 stop5h 51m

$228

St. LouisKey West

STL - EYW

STLEYW

Lambert-St Louis

Fri 11/28

8:00 am-3:19 pm

1 stop6h 19m

Key West

Wed 12/3

3:53 pm-9:40 pm

1 stop6h 47m

$241

St. LouisKey West

STL - EYW

STLEYW

Lambert-St Louis

Tue 10/14

9:10 am-5:21 pm

1 stop7h 11m

Key West

Thu 10/30

1:57 pm-6:02 pm

1 stop5h 05m

$241

St. LouisKey West

STL - EYW

STLEYW

Lambert-St Louis

Tue 10/7

6:00 am-12:58 pm

1 stop5h 58m

Key West

Tue 10/14

7:52 pm-11:56 pm

1 stop5h 04m

$241

St. LouisKey West

STL - EYW

STLEYW

Lambert-St Louis

Fri 11/14

10:15 am-5:51 pm

1 stop6h 36m

Key West

Tue 11/18

4:10 pm-10:27 pm

1 stop7h 17m

$241

EvansvilleKey West

EVV - EYW

EVVEYW

Evansville Dress Regional

Fri 11/21

3:02 pm-4:38 pm

1 stop24h 36m

Key West

Wed 11/26

3:55 pm-7:42 pm

1 stop4h 47m

$253

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/9

Showing 1-10 of 55 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, 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 $491). 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 September 11, 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.

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 Allegiant Air can get you from Illinois to Key West in just under 4h 58m. Your travel time can differ by up to 19h 38m. 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 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 cheapest flights from Illinois to Key West?

    While on average a flight from Illinois to Key West is generally $386, 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 $193 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 $491). 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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$218Average$497FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$260Average$527FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$268Average$465FlexibilityNo cancel feeOn-time71%

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