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Key West

$94+ 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 6/1. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — EYW
May 6 — May 131
Tue 5/6
Tue 5/13
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 May 1, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$223
(Delta)

One-way from

$124
(Trip.com)

Popular in

March

Cheapest in

August

Average price

$456

Good round-trip deal

$411 or less

Good one-way deal

$324 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. 9% potential increase in price ($47 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in May 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 May 1, 2025.

This Delta deal was found by Cheapflights users on 4/30. 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 10/11:30 pmSTL - EYW
1 stop5h 14mDelta
Tue 10/72:35 pmEYW - STL
1 stop4h 27mDelta
Deal found 4/30$223
This American Airlines deal was found by Cheapflights users on 4/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/16:00 amSTL - EYW
2 stops7h 40mAmerican Airlines
Tue 10/75:16 pmEYW - STL
1 stop7h 13mAmerican Airlines
Deal found 4/30$228
This American Airlines deal was found by Cheapflights users on 4/29. 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 7/87:00 amMLI - EYW
1 stop8h 18mAmerican Airlines
Tue 7/1511:18 amEYW - MLI
2 stops11h 50mAmerican Airlines
Deal found 4/29$274
This Mytrip deal was found by Cheapflights users on 4/29. 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 6/16:30 amORD - EYW
1 stop26h 03mMultiple Airlines
Thu 6/58:53 amEYW - ORD
3 stops39h 36mMultiple Airlines
Deal found 4/29$320
This Delta deal was found by Cheapflights users on 4/30. 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.
Sat 7/512:44 pmMDW - EYW
1 stop5h 55mDelta
Wed 7/97:00 amEYW - MDW
1 stop5h 53mDelta
Deal found 4/30$323
This Delta deal was found by Cheapflights users on 4/29. 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 6/1411:20 amORD - EYW
1 stop7h 19mDelta
Tue 6/176:29 pmEYW - ORD
1 stop6h 28mDelta
Deal found 4/29$323
This American Airlines deal was found by Cheapflights users on 4/29. 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 11/88:00 amORD - EYW
Nonstop3h 16mAmerican Airlines
Sat 11/151:39 pmEYW - ORD
Nonstop3h 31mAmerican Airlines
Deal found 4/29$327
This Delta deal was found by Cheapflights users on 4/29. 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 5/65:50 amMLI - EYW
1 stop4h 40mDelta
Tue 5/136:25 pmEYW - MLI
1 stop5h 32mDelta
Deal found 4/29$334
This United Airlines deal was found by Cheapflights users on 4/30. 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 6/146:00 amORD - EYW
1 stop25h 00mUnited Airlines
Tue 6/172:12 pmEYW - ORD
1 stop9h 00mUnited Airlines
Deal found 4/30$341
This Mytrip deal was found by Cheapflights users on 4/29. 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 7/3111:37 amMDW - EYW
2 stops27h 59mAllegiant Air
Sun 8/38:54 amEYW - MDW
2 stops30h 02mAllegiant Air
Deal found 4/29$381
This United Airlines deal was found by Cheapflights users on 4/30. 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.
Thu 11/276:45 amMLI - EYW
2 stops24h 15mUnited Airlines
Fri 12/126:45 pmEYW - MLI
2 stops27h 13mUnited Airlines
Deal found 4/30$406
This United Airlines deal was found by Cheapflights users on 4/30. 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.
Mon 6/303:39 pmPIA - EYW
2 stops21h 21mUnited Airlines
Fri 7/41:00 pmEYW - PIA
2 stops28h 43mUnited Airlines
Deal found 4/30$426

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 May 1, 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

Fri 5/30

5:00 am-2:37 pm

2 stops8h 37m

Key West

Tue 6/3

5:24 pm-9:26 pm

1 stop5h 02m

$228

St. LouisKey West

STL - EYW

STLEYW

Lambert-St Louis

Tue 5/20

1:09 pm-8:07 pm

1 stop5h 58m

Key West

Thu 6/5

6:25 pm-11:38 pm

1 stop6h 13m

$259

MolineKey West

MLI - EYW

MLIEYW

Moline Quad-City

Fri 9/5

7:15 am-1:34 pm

1 stop5h 19m

Key West

Mon 9/8

4:01 pm-9:36 pm

2 stops6h 35m

$299

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Sat 7/5

12:44 pm-7:39 pm

1 stop5h 55m

Key West

Wed 7/9

7:00 am-11:53 am

1 stop5h 53m

$323

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Sat 6/14

9:40 am-5:34 pm

1 stop6h 54m

Key West

Tue 6/17

6:29 pm-11:57 pm

1 stop6h 28m

$323

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Sat 5/17

5:05 am-6:05 pm

1 stop12h 00m

Key West

Tue 5/20

8:45 am-11:04 pm

1 stop15h 19m

$326

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Tue 6/10

7:05 am-4:11 pm

1 stop8h 06m

Key West

Tue 6/17

11:20 am-5:35 pm

2 stops7h 15m

$328

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Sat 6/14

6:00 am-8:00 am

1 stop25h 00m

Key West

Tue 6/17

2:12 pm-10:12 pm

1 stop9h 00m

$341

PeoriaKey West

PIA - EYW

PIAEYW

Greater Peoria

Mon 6/30

3:39 pm-2:00 pm

2 stops21h 21m

Key West

Fri 7/4

1:00 pm-4:43 pm

2 stops28h 43m

$426

St. LouisKey West

STL - EYW

STLEYW

Lambert-St Louis

Tue 6/24

8:25 am-8:00 am

2 stops22h 35m

Key West

Mon 6/30

6:45 pm-6:53 pm

2 stops25h 08m

$428

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/1

Showing 1-10 of 23 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 $492). 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 May 1, 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 May 1, 2025.
Peruse reviews from past customers who have flown with Delta, United Airlines and American 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.
Delta
8.0
Very good
7,934 reviews

Boarding

8.2

Food

7.3

Overall

8.0

Comfort

7.9

Entertainment

7.9

Crew

8.5

Reviews

1 / 20
2.0
Mediocre

Mark,Jun 2024

SGF - ATL

One of the worst flights ever. I got to the airport early for my 6:48 pm flight and tried to get on the 4:30 ish flight. The gate agent was one of the worst customer service people in my 20 yrs of flying Delta. Very rude and wouldn’t even talk to me about riding standby. Then flight took off 3 hrs late and when Landed in Atlanta, the gate people wouldn’t even try to get me on the plane. It was still there but door was closed. For all of my almost 2 million miles, the worst experience from Delta. I am highly disappointed as it was not my fault I have to sleep in Atlanta and not Jacksonville Florida
Delta
8.0
Very good
7,934 reviews
Delta
8.0
Very good
7,934 reviews

Boarding

8.2

Food

7.3

Overall

8.0

Comfort

7.9

Entertainment

7.9

Crew

8.5

Reviews

1 / 20
2.0
Mediocre

Mark,Jun 2024

SGF - ATL

One of the worst flights ever. I got to the airport early for my 6:48 pm flight and tried to get on the 4:30 ish flight. The gate agent was one of the worst customer service people in my 20 yrs of flying Delta. Very rude and wouldn’t even talk to me about riding standby. Then flight took off 3 hrs late and when Landed in Atlanta, the gate people wouldn’t even try to get me on the plane. It was still there but door was closed. For all of my almost 2 million miles, the worst experience from Delta. I am highly disappointed as it was not my fault I have to sleep in Atlanta and not Jacksonville Florida
United Airlines
7.4
Good
8,696 reviews
Delta
8.0
Very good
7,934 reviews

Boarding

8.2

Food

7.3

Overall

8.0

Comfort

7.9

Entertainment

7.9

Crew

8.5

Reviews

1 / 20
2.0
Mediocre

Mark,Jun 2024

SGF - ATL

One of the worst flights ever. I got to the airport early for my 6:48 pm flight and tried to get on the 4:30 ish flight. The gate agent was one of the worst customer service people in my 20 yrs of flying Delta. Very rude and wouldn’t even talk to me about riding standby. Then flight took off 3 hrs late and when Landed in Atlanta, the gate people wouldn’t even try to get me on the plane. It was still there but door was closed. For all of my almost 2 million miles, the worst experience from Delta. I am highly disappointed as it was not my fault I have to sleep in Atlanta and not Jacksonville Florida
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,934 reviews

Boarding

8.2

Food

7.3

Overall

8.0

Comfort

7.9

Entertainment

7.9

Crew

8.5

Reviews

1 / 20
2.0
Mediocre

Mark,Jun 2024

SGF - ATL

One of the worst flights ever. I got to the airport early for my 6:48 pm flight and tried to get on the 4:30 ish flight. The gate agent was one of the worst customer service people in my 20 yrs of flying Delta. Very rude and wouldn’t even talk to me about riding standby. Then flight took off 3 hrs late and when Landed in Atlanta, the gate people wouldn’t even try to get me on the plane. It was still there but door was closed. For all of my almost 2 million miles, the worst experience from Delta. I am highly disappointed as it was not my fault I have to sleep in Atlanta and not Jacksonville Florida

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 $173. However, be on the lookout for offers from Delta and American 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: United Airlines (84%), Republic Airways (79%), Air New Zealand (76%).

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

    While on average a flight from Illinois to Key West is generally $462, our data shows the cheapest flight currently is $227. When looking at the most popular route, (Chicago O'Hare Intl - Key West), you can expect to pay $249 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 $492). 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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$216Average$465FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$262Average$503FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$263Average$492FlexibilityNo cancel feeOn-time71%

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