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Key West

$153+ 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 6/21. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — EYW
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 June 12, 2025.

Round-trip from

$223
(American Airlines)

One-way from

$153
(Mytrip)

Popular in

March

Cheapest in

October

Average price

$485

Good round-trip deal

$361 or less

Good one-way deal

$258 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. 7% potential increase in price ($37 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 12, 2025.

This American Airlines deal was found by Cheapflights users on 6/11. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/237:32 amSTL - EYW
1 stop7h 47mAmerican Airlines
Sat 8/307:40 pmEYW - STL
1 stop5h 19mAmerican Airlines
Deal found 6/11$223
This Mytrip deal was found by Cheapflights users on 6/11. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/152:40 pmPIA - EYW
1 stop23h 25mAllegiant Air
Fri 7/185:26 pmEYW - PIA
1 stop26h 46mAllegiant Air
Deal found 6/11$231
This Delta deal was found by Cheapflights users on 6/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/261:23 pmSTL - EYW
1 stop5h 26mDelta
Wed 7/306:27 pmEYW - STL
1 stop6h 26mDelta
Deal found 6/11$257
This Delta deal was found by Cheapflights users on 6/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/235:55 amMLI - EYW
1 stop6h 13mDelta
Tue 9/306:00 pmEYW - MLI
1 stop5h 30mDelta
Deal found 6/10$283
This American Airlines deal was found by Cheapflights users on 6/11. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/235:30 amMLI - EYW
2 stops11h 16mAmerican Airlines
Tue 9/306:17 pmEYW - MLI
1 stop5h 08mAmerican Airlines
Deal found 6/11$288
This Delta deal was found by Cheapflights users on 6/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/306:05 amBMI - EYW
1 stop6h 04mDelta
Tue 7/16:29 pmEYW - BMI
1 stop5h 17mDelta
Deal found 6/11$309
This American Airlines deal was found by Cheapflights users on 6/12. 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 10/286:00 amBMI - EYW
2 stops9h 53mAmerican Airlines
Tue 11/41:39 pmEYW - BMI
1 stop7h 00mAmerican Airlines
Deal found 6/12$314
This American Airlines deal was found by Cheapflights users on 6/12. 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 7/157:05 amORD - EYW
1 stop6h 04mAmerican Airlines
Tue 7/224:58 pmEYW - ORD
1 stop6h 53mAmerican Airlines
Deal found 6/12$323
This Delta deal was found by Cheapflights users on 6/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/56:00 amMDW - EYW
1 stop6h 09mDelta
Wed 7/97:00 amEYW - MDW
1 stop5h 58mDelta
Deal found 6/11$324
This Delta deal was found by Cheapflights users on 6/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/511:20 amORD - EYW
1 stop7h 19mDelta
Wed 7/96:27 pmEYW - ORD
1 stop6h 42mDelta
Deal found 6/11$324
This United Airlines deal was found by Cheapflights users on 6/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1110:55 amORD - EYW
Nonstop3h 11mUnited Airlines
Tue 12/164:05 pmEYW - ORD
Nonstop3h 25mUnited Airlines
Deal found 6/10$329
This Mytrip deal was found by Cheapflights users on 6/12. 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.
Thu 7/3111:11 amORD - EYW
2 stops28h 25mMultiple Airlines
Sun 8/35:35 pmEYW - ORD
2 stops28h 55mMultiple Airlines
Deal found 6/12$331

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 June 12, 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

Sat 8/23

7:32 am-4:19 pm

1 stop7h 47m

Key West

Sat 8/30

7:40 pm-11:59 pm

1 stop5h 19m

$223

PeoriaKey West

PIA - EYW

PIAEYW

Greater Peoria

Tue 7/15

2:40 pm-3:05 pm

1 stop23h 25m

Key West

Fri 7/18

5:26 pm-7:12 pm

1 stop26h 46m

$231

St. LouisKey West

STL - EYW

STLEYW

Lambert-St Louis

Sat 7/26

1:23 pm-7:49 pm

1 stop5h 26m

Key West

Wed 7/30

6:27 pm-11:53 pm

1 stop6h 26m

$257

MolineKey West

MLI - EYW

MLIEYW

Moline Quad-City

Tue 9/23

5:55 am-1:08 pm

1 stop6h 13m

Key West

Tue 9/30

6:00 pm-10:30 pm

1 stop5h 30m

$283

MolineKey West

MLI - EYW

MLIEYW

Moline Quad-City

Tue 9/23

5:30 am-5:46 pm

2 stops11h 16m

Key West

Tue 9/30

6:17 pm-10:25 pm

1 stop5h 08m

$288

BloomingtonKey West

BMI - EYW

BMIEYW

Bloomington-Normal

Mon 6/30

6:05 am-1:09 pm

1 stop6h 04m

Key West

Wed 7/2

6:29 pm-10:46 pm

1 stop5h 17m

$309

BloomingtonKey West

BMI - EYW

BMIEYW

Bloomington-Normal

Tue 10/28

6:00 am-4:53 pm

2 stops9h 53m

Key West

Tue 11/4

1:39 pm-7:39 pm

1 stop7h 00m

$314

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Tue 7/15

7:05 am-2:09 pm

1 stop6h 04m

Key West

Tue 7/22

4:58 pm-10:51 pm

1 stop6h 53m

$323

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Sat 7/5

6:00 am-1:09 pm

1 stop6h 09m

Key West

Wed 7/9

7:00 am-11:58 am

1 stop5h 58m

$324

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Sat 7/5

11:20 am-7:39 pm

1 stop7h 19m

Key West

Wed 7/9

6:27 pm-12:09 am

1 stop6h 42m

$324

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

Showing 1-10 of 30 results
1
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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 $493). 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 June 12, 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.

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 June 12, 2025.
Peruse reviews from past customers who have flown with Delta, United Airlines and Allegiant Air 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.
Delta
8.0
Very good
7,950 reviews

Food

7.3

Boarding

8.2

Comfort

7.9

Overall

8.0

Entertainment

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,950 reviews
Delta
8.0
Very good
7,950 reviews

Food

7.3

Boarding

8.2

Comfort

7.9

Overall

8.0

Entertainment

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,790 reviews
Delta
8.0
Very good
7,950 reviews

Food

7.3

Boarding

8.2

Comfort

7.9

Overall

8.0

Entertainment

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Allegiant Air
7.3
Good
725 reviews
Delta
8.0
Very good
7,950 reviews

Food

7.3

Boarding

8.2

Comfort

7.9

Overall

8.0

Entertainment

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,950 reviews

Food

7.3

Boarding

8.2

Comfort

7.9

Overall

8.0

Entertainment

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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 United Airlines, with whom users have recently found tickets for as low as $174. 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 (86%), Air New Zealand (86%), American Airlines (74%).

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

    While on average a flight from Illinois to Key West is generally $434, our data shows the cheapest flight currently is $151. When looking at the most popular route, (Chicago O'Hare Intl - Key West), you can expect to pay $247 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 $493). 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 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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$216Average$472FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$263Average$524FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$268Average$493FlexibilityNo cancel feeOn-time71%

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