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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 4/15. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — EYW
Jan 26 — Feb 21
Sun 1/26
Sun 2/2
1 adult, Economy
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Cheap flight deals from Illinois to Key West

Discover tips and strategies to find the most affordable flight options for your journey from Illinois (USIL) to Key West (EYW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 21, 2025.

Round-trip from

$269
(American Airlines)

One-way from

$100
(American Airlines)

Good round-trip deal

$400 or less

Good one-way deal

$313 or less
From Illinois to Key West
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One-way flight from Illinois to Key West
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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 January 21, 2025.

This Delta deal was found by Cheapflights users on 1/20. 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 7/11:30 pmSTL - EYW
1 stop5h 16mDelta
Thu 7/107:00 amEYW - STL
1 stop6h 24mDelta
Deal found 1/20$259
This American Airlines deal was found by Cheapflights users on 1/20. 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 2/1811:55 amSTL - EYW
1 stop5h 51mAmerican Airlines
Tue 2/254:59 pmEYW - STL
1 stop7h 57mAmerican Airlines
Deal found 1/20$269
This American Airlines deal was found by Cheapflights users on 1/20. 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 2/248:06 amORD - EYW
Nonstop3h 22mAmerican Airlines
Wed 3/57:29 pmEYW - ORD
1 stop5h 41mAmerican Airlines
Deal found 1/20$279
This United Airlines deal was found by Cheapflights users on 1/21. 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.
Fri 3/710:51 amORD - EYW
Nonstop3h 12mUnited Airlines
Tue 3/113:59 pmEYW - ORD
Nonstop3h 41mUnited Airlines
Deal found 1/21$284
This Mytrip deal was found by Cheapflights users on 1/20. 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.
Sat 3/15:45 pmORD - EYW
1 stop14h 40mMultiple Airlines
Wed 3/53:06 pmEYW - ORD
2 stops11h 12mMultiple Airlines
Deal found 1/20$286
This Delta deal was found by Cheapflights users on 1/20. 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 3/312:44 pmMDW - EYW
1 stop6h 27mDelta
Wed 3/127:00 amEYW - MDW
1 stop6h 06mDelta
Deal found 1/20$289
This Delta deal was found by Cheapflights users on 1/20. 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.
Fri 10/106:00 amORD - EYW
1 stop6h 09mDelta
Wed 10/157:00 amEYW - ORD
1 stop6h 09mDelta
Deal found 1/20$289
This American Airlines deal was found by Cheapflights users on 1/20. 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 2/45:00 amMLI - EYW
1 stop6h 17mAmerican Airlines
Sat 2/82:44 pmEYW - MLI
1 stop7h 45mAmerican Airlines
Deal found 1/20$294
This Trip.com deal was found by Cheapflights users on 1/20. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/55:05 pmSTL - EYW
1 stop20h 15mMultiple Airlines
Fri 2/73:05 pmEYW - STL
1 stop9h 26mMultiple Airlines
Deal found 1/20$321
This Delta deal was found by Cheapflights users on 1/21. 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.
Fri 9/55:55 amMLI - EYW
1 stop6h 14mDelta
Mon 9/86:00 pmEYW - MLI
1 stop5h 29mDelta
Deal found 1/21$349
This American Airlines deal was found by Cheapflights users on 1/20. 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 4/225:00 amPIA - EYW
1 stop6h 06mAmerican Airlines
Thu 4/245:20 pmEYW - PIA
1 stop7h 37mAmerican Airlines
Deal found 1/20$354
This Delta deal was found by Cheapflights users on 1/21. 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 9/16:01 amBMI - EYW
1 stop6h 08mDelta
Tue 9/306:00 pmEYW - BMI
1 stop5h 23mDelta
Deal found 1/21$379

Find flights from Illinois to Key West within your budget

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 21, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

St. LouisKey West

STL - EYW

STLEYW

Lambert-St Louis

Tue 7/1

1:30 pm-7:46 pm

1 stop5h 16m

Key West

Thu 7/10

7:00 am-12:24 pm

1 stop6h 24m

$259

St. LouisKey West

STL - EYW

STLEYW

Lambert-St Louis

Tue 2/18

11:55 am-6:46 pm

1 stop5h 51m

Key West

Tue 2/25

4:59 pm-11:56 pm

1 stop7h 57m

$269

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Mon 2/24

8:06 am-12:28 pm

Nonstop3h 22m

Key West

Wed 3/5

7:29 pm-12:10 am

1 stop5h 41m

$279

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Fri 3/7

10:51 am-3:03 pm

Nonstop3h 12m

Key West

Tue 3/11

3:59 pm-6:40 pm

Nonstop3h 41m

$284

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Sat 3/1

5:45 pm-9:25 am

1 stop14h 40m

Key West

Wed 3/5

3:06 pm-1:18 am

2 stops11h 12m

$286

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Mon 2/24

6:59 pm-2:08 pm

2 stops18h 09m

Key West

Wed 3/5

6:14 pm-10:20 pm

1 stop5h 06m

$288

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Tue 2/25

6:00 am-8:11 pm

2 stops13h 11m

Key West

Wed 2/26

6:14 pm-11:49 pm

1 stop6h 35m

$290

MolineKey West

MLI - EYW

MLIEYW

Moline Quad-City

Tue 2/4

5:00 am-12:17 pm

1 stop6h 17m

Key West

Sat 2/8

2:44 pm-9:29 pm

1 stop7h 45m

$294

St. LouisKey West

STL - EYW

STLEYW

Lambert-St Louis

Wed 2/5

5:05 pm-2:20 pm

1 stop20h 15m

Key West

Fri 2/7

3:05 pm-11:31 pm

1 stop9h 26m

$321

PeoriaKey West

PIA - EYW

PIAEYW

Greater Peoria

Tue 4/22

5:00 am-12:06 pm

1 stop6h 06m

Key West

Thu 4/24

5:20 pm-11:57 pm

1 stop7h 37m

$354

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/20

Showing 1-10 of 32 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.

Travel insights for flights from Illinois to Key West

Get recent, data-driven insights about flights from Illinois to Key West including ideal travel times, pricing trends, and more.

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 $531). 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 21, 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 January 21, 2025.

The most flights from USIL to EYW are scheduled on a Monday (3 on average). You will have fewer flight options on Tuesday, 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 January 21, 2025.
Peruse reviews from past customers who have flown with American Airlines, United Airlines and Delta 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
9,706 reviews

Comfort

7.9

Food

7.1

Boarding

8.2

Overall

8.0

Entertainment

7.1

Crew

8.5

Reviews

1 / 10

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
9,706 reviews
Alaska Airlines
8.0
Very good
9,706 reviews

Comfort

7.9

Food

7.1

Boarding

8.2

Overall

8.0

Entertainment

7.1

Crew

8.5

Reviews

1 / 10

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
8,521 reviews
Alaska Airlines
8.0
Very good
9,706 reviews

Comfort

7.9

Food

7.1

Boarding

8.2

Overall

8.0

Entertainment

7.1

Crew

8.5

Reviews

1 / 10

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
8,984 reviews
Alaska Airlines
8.0
Very good
9,706 reviews

Comfort

7.9

Food

7.1

Boarding

8.2

Overall

8.0

Entertainment

7.1

Crew

8.5

Reviews

1 / 10

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
7.4
Good
801 reviews
Alaska Airlines
8.0
Very good
9,706 reviews

Comfort

7.9

Food

7.1

Boarding

8.2

Overall

8.0

Entertainment

7.1

Crew

8.5

Reviews

1 / 10

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
9,706 reviews

Comfort

7.9

Food

7.1

Boarding

8.2

Overall

8.0

Entertainment

7.1

Crew

8.5

Reviews

1 / 10

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 (100%), American Airlines (89%), Air New Zealand (83%).

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

    While on average a flight from Illinois to Key West is generally $638, our data shows the cheapest flight currently is $274. When looking at the most popular route, (Chicago O'Hare Intl - Key West), you can expect to pay $214 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 $531). 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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Alternative routes for Illinois to Key West

See prices for flight routes from nearby airports that may be better suited for you.
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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 January 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$216Average$487FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$247Average$485FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$259Average$484FlexibilityNo cancel feeOn-time69%
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