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Key West

$100+ 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 8/16. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — EYW
Apr 5 — Apr 121
Sat 4/5
Sat 4/12
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 March 31, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$199
(American Airlines)

One-way from

$100
(American Airlines)

Popular in

March

Cheapest in

August

Average price

$522

Good round-trip deal

$387 or less

Good one-way deal

$250 or less
Provider with most accurate pricing for Chicago (CHI)-Key West flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Key West flights.
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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 ($40 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in March 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 March 31, 2025.

This American Airlines deal was found by Cheapflights users on 3/31. 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 4/191:48 pmSTL - EYW
1 stop5h 23mAmerican Airlines
Wed 4/232:38 pmEYW - STL
1 stop5h 51mAmerican Airlines
Deal found 3/31$199
This Delta deal was found by Cheapflights users on 3/31. 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 9/3011:51 amSTL - EYW
1 stop6h 53mDelta
Tue 10/72:35 pmEYW - STL
1 stop4h 27mDelta
Deal found 3/31$217
This Mytrip deal was found by Cheapflights users on 3/30. 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.
Sun 4/138:17 pmPIA - EYW
1 stop11h 48mAllegiant Air
Thu 4/179:03 amEYW - PIA
1 stop11h 29mAllegiant Air
Deal found 3/30$259
This Delta deal was found by Cheapflights users on 3/30. 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 5/276:00 amMLI - EYW
1 stop5h 56mDelta
Tue 6/36:25 pmEYW - MLI
1 stop5h 32mDelta
Deal found 3/30$268
This American Airlines deal was found by Cheapflights users on 3/31. 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.
Sun 5/255:00 amMLI - EYW
1 stop6h 10mAmerican Airlines
Tue 6/35:24 pmEYW - MLI
1 stop5h 50mAmerican Airlines
Deal found 3/31$289
This American Airlines deal was found by Cheapflights users on 3/31. 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 7/235:15 amORD - EYW
2 stops6h 40mAmerican Airlines
Sat 7/264:06 pmEYW - ORD
1 stop6h 19mAmerican Airlines
Deal found 3/31$314
This Mytrip deal was found by Cheapflights users on 3/30. 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.
Sun 4/136:07 pmPIA - EYW
2 stops21h 13mMultiple Airlines
Thu 4/179:03 amEYW - PIA
1 stop11h 29mMultiple Airlines
Deal found 3/30$325
This Mytrip deal was found by Cheapflights users on 3/30. 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.
Wed 6/116:30 amORD - EYW
1 stop24h 33mMultiple Airlines
Sun 6/158:53 amEYW - ORD
2 stops33h 02mMultiple Airlines
Deal found 3/30$337
This Delta deal was found by Cheapflights users on 3/30. 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 5/141:30 pmORD - EYW
1 stop5h 37mDelta
Wed 5/216:25 pmEYW - ORD
1 stop6h 33mDelta
Deal found 3/30$349
This Delta deal was found by Cheapflights users on 3/30. 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.
Thu 9/181:05 pmMDW - EYW
1 stop5h 39mDelta
Tue 9/2311:45 amEYW - MDW
1 stop7h 13mDelta
Deal found 3/30$352
This United Airlines deal was found by Cheapflights users on 3/30. 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 4/57:10 amORD - EYW
Nonstop3h 05mUnited Airlines
Thu 4/104:04 pmEYW - ORD
Nonstop3h 35mUnited Airlines
Deal found 3/30$365
This Delta deal was found by Cheapflights users on 3/31. 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 8/271:30 pmEVV - EYW
1 stop5h 16mDelta
Sun 8/316:00 pmEYW - EVV
1 stop5h 05mDelta
Deal found 3/31$377

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 March 31, 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 4/19

1:48 pm-8:11 pm

1 stop5h 23m

Key West

Wed 4/23

2:38 pm-7:29 pm

1 stop5h 51m

$199

PeoriaKey West

PIA - EYW

PIAEYW

Greater Peoria

Sun 4/13

8:17 pm-9:05 am

1 stop11h 48m

Key West

Thu 4/17

9:03 am-7:32 pm

1 stop11h 29m

$259

MolineKey West

MLI - EYW

MLIEYW

Moline Quad-City

Tue 5/27

6:00 am-12:56 pm

1 stop5h 56m

Key West

Tue 6/3

6:25 pm-10:57 pm

1 stop5h 32m

$268

MolineKey West

MLI - EYW

MLIEYW

Moline Quad-City

Sun 5/25

5:00 am-12:10 pm

1 stop6h 10m

Key West

Tue 6/3

5:24 pm-10:14 pm

1 stop5h 50m

$289

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Wed 5/14

10:00 am-4:52 pm

1 stop5h 52m

Key West

Wed 5/21

12:49 pm-3:28 pm

Nonstop3h 39m

$322

PeoriaKey West

PIA - EYW

PIAEYW

Greater Peoria

Sun 4/13

6:07 pm-4:20 pm

2 stops21h 13m

Key West

Thu 4/17

9:03 am-7:32 pm

1 stop11h 29m

$325

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Wed 6/11

6:30 am-8:03 am

1 stop24h 33m

Key West

Sun 6/15

8:53 am-4:55 pm

2 stops33h 02m

$337

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Wed 5/14

1:30 pm-8:07 pm

1 stop5h 37m

Key West

Wed 5/21

6:25 pm-11:58 pm

1 stop6h 33m

$349

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Sat 4/5

7:10 am-11:15 am

Nonstop3h 05m

Key West

Thu 4/10

4:04 pm-6:39 pm

Nonstop3h 35m

$365

St. LouisKey West

STL - EYW

STLEYW

Lambert-St Louis

Sat 6/7

12:59 pm-8:07 pm

1 stop6h 08m

Key West

Tue 6/10

6:29 pm-11:42 pm

1 stop6h 13m

$369

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/31

Showing 1-10 of 29 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 $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 March 31, 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.

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 March 31, 2025.

The most flights from USIL to EYW are scheduled on a Monday (3 on average). You will have fewer flight options on Friday, which is when the least amount of flights are scheduled (2 on average).

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 March 31, 2025.
Peruse reviews from past customers who have flown with Alaska Airlines, Delta and United Airlines 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.
Alaska Airlines
8.0
Very good
9,818 reviews

Boarding

8.2

Crew

8.5

Comfort

7.9

Food

7.1

Entertainment

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Alaska Airlines
8.0
Very good
9,818 reviews
Alaska Airlines
8.0
Very good
9,818 reviews

Boarding

8.2

Crew

8.5

Comfort

7.9

Food

7.1

Entertainment

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Delta
8.0
Very good
7,899 reviews
Alaska Airlines
8.0
Very good
9,818 reviews

Boarding

8.2

Crew

8.5

Comfort

7.9

Food

7.1

Entertainment

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
United Airlines
7.4
Good
8,614 reviews
Alaska Airlines
8.0
Very good
9,818 reviews

Boarding

8.2

Crew

8.5

Comfort

7.9

Food

7.1

Entertainment

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Allegiant Air
7.3
Good
731 reviews
Alaska Airlines
8.0
Very good
9,818 reviews

Boarding

8.2

Crew

8.5

Comfort

7.9

Food

7.1

Entertainment

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
9,818 reviews

Boarding

8.2

Crew

8.5

Comfort

7.9

Food

7.1

Entertainment

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

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 American Airlines, with whom users have recently found tickets for as low as $100. However, be on the lookout for offers from Delta and United 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 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: Republic Airways (89%), United Airlines (87%), Air New Zealand (87%).

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

    While on average a flight from Illinois to Key West is generally $585, our data shows the cheapest flight currently is $191. When looking at the most popular route, (Chicago O'Hare Intl - Key West), you can expect to pay $246 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 March 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$216Average$464FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$252Average$489FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$261Average$488FlexibilityNo cancel feeOn-time69%
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