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Key West

$93+ 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 3/4. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — EYW
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
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 January 29, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
Sat 2/75:42 pm
STL
-
EYW
1 stop14h 24m
Multiple Airlines
Thu 2/129:46 am
EYW
-
STL
1 stop15h 13m
Multiple Airlines
Deal found 1/28$199
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 2/223:49 pm
STL
-
EYW
1 stop19h 37m
Multiple Airlines
Thu 3/59:46 am
EYW
-
STL
1 stop22h 16m
Multiple Airlines
Deal found 1/28$219
This American Airlines deal was found by Cheapflights users on 1/27. 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 3/1811:22 am
STL
-
EYW
1 stop6h 50m
American Airlines
Wed 3/257:42 pm
EYW
-
STL
1 stop5h 16m
American Airlines
Deal found 1/27$223
This American Airlines deal was found by Cheapflights users on 1/27. 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 4/156:00 am
STL
-
EYW
2 stops9h 30m
American Airlines
Wed 4/222:01 pm
EYW
-
STL
1 stop6h 29m
American Airlines
Deal found 1/27$228
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 2/153:49 pm
STL
-
EYW
1 stop19h 37m
Multiple Airlines
Thu 2/1911:01 am
EYW
-
STL
2 stops20h 50m
Multiple Airlines
Deal found 1/28$241
This American Airlines deal was found by Cheapflights users on 1/28. 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.
Mon 5/116:27 am
STL
-
EYW
1 stop6h 22m
American Airlines
Tue 5/196:45 am
EYW
-
STL
1 stop4h 31m
American Airlines
Deal found 1/28$251
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 2/283:49 pm
STL
-
EYW
1 stop16h 17m
Multiple Airlines
Wed 3/412:40 pm
EYW
-
STL
2 stops46h 09m
Multiple Airlines
Deal found 1/27$258
This United Airlines deal was found by Cheapflights users on 1/27. 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.
Sat 4/116:00 am
STL
-
EYW
1 stop8h 57m
United Airlines
Wed 4/153:47 pm
EYW
-
STL
1 stop7h 10m
United Airlines
Deal found 1/27$259
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 4/118:36 am
STL
-
EYW
1 stop23h 30m
Multiple Airlines
Wed 4/1511:51 am
EYW
-
STL
2 stops23h 39m
Multiple Airlines
Deal found 1/27$260
This Delta deal was found by Cheapflights users on 1/26. 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.
Wed 3/411:55 am
STL
-
EYW
1 stop6h 47m
Delta
Tue 3/106:25 pm
EYW
-
STL
1 stop6h 33m
Delta
Deal found 1/26$266
This American Airlines deal was found by Cheapflights users on 1/28. 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 4/156:00 am
MLI
-
EYW
2 stops9h 30m
American Airlines
Wed 4/226:45 pm
EYW
-
MLI
1 stop6h 01m
American Airlines
Deal found 1/28$288
This Delta deal was found by Cheapflights users on 1/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/2412:45 pm
MDW
-
EYW
1 stop5h 57m
Delta
Thu 3/55:56 pm
EYW
-
MDW
1 stop5h 35m
Delta
Deal found 1/28$289

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 January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$219
(Kiwi.com)

One-way from

$93
(Kiwi.com)

Popular in

March

Cheapest in

January

Average price

$391

Good round-trip deal

$329 or less

Good one-way deal

$258 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 ($42 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
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.
Search Deals

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 January 29, 2026.
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

Sat 2/7

5:42 pm-9:06 am

1 stop14h 24m

Key West

Thu 2/12

9:46 am-11:59 pm

1 stop15h 13m

$199

St. LouisKey West

STL - EYW

STLEYW

Lambert-St Louis

Sat 4/18

11:43 am-7:40 pm

1 stop6h 57m

Key West

Wed 4/22

6:19 pm-11:34 pm

1 stop6h 15m

$223

St. LouisKey West

STL - EYW

STLEYW

Lambert-St Louis

Sat 4/11

6:00 am-3:57 pm

1 stop8h 57m

Key West

Wed 4/15

3:47 pm-9:57 pm

1 stop7h 10m

$259

St. LouisKey West

STL - EYW

STLEYW

Lambert-St Louis

Wed 3/4

11:55 am-7:42 pm

1 stop6h 47m

Key West

Tue 3/10

6:25 pm-11:58 pm

1 stop6h 33m

$266

St. LouisKey West

STL - EYW

STLEYW

Lambert-St Louis

Wed 3/4

3:49 pm-9:06 am

1 stop16h 17m

Key West

Tue 3/10

1:01 pm-9:49 am

2 stops21h 48m

$273

St. LouisKey West

STL - EYW

STLEYW

Lambert-St Louis

Tue 2/17

6:00 am-2:40 pm

2 stops7h 40m

Key West

Tue 2/24

6:54 pm-11:48 pm

1 stop5h 54m

$284

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Sat 2/14

5:45 pm-10:09 pm

Nonstop3h 24m

Key West

Thu 2/19

6:35 pm-11:43 pm

1 stop6h 08m

$289

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Wed 2/25

10:49 am-5:01 pm

1 stop5h 12m

Key West

Wed 3/4

5:56 pm-10:31 pm

1 stop5h 35m

$289

St. LouisKey West

STL - EYW

STLEYW

Lambert-St Louis

Sat 4/18

12:11 pm-10:36 pm

2 stops9h 25m

Key West

Tue 4/21

3:58 pm-10:24 pm

1 stop7h 26m

$291

St. LouisKey West

STL - EYW

STLEYW

Lambert-St Louis

Wed 3/4

3:49 pm-9:06 am

1 stop16h 17m

Key West

Mon 3/9

1:06 pm-11:19 pm

1 stop11h 13m

$300

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

Showing 1-10 of 49 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 January 29, 2026.

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 January 29, 2026.

The most flights from USIL to EYW are scheduled on a Monday (4 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (2 on average).

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, United Airlines, and American Airlines can get you from Illinois to Key West in just under 6h 57m. Your travel time can differ by up to 3h 57m. 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 United Airlines, with whom users have recently found tickets for as low as $158. However, be on the lookout for offers from American 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: United Airlines (83%), Air New Zealand (79%), Republic Airways (75%).

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

    While on average a flight from Illinois to Key West is generally $448, 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 $131 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.

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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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$145Average$385FlexibilityNo cancel feeOn-time65%
DeltaCheapest$248Average$498FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$249Average$515FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$268Average$449FlexibilityNo cancel feeOn-time71%

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