HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Key West

$151+ 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 1/4. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — EYW
Aug 4 — Aug 111
Mon 8/4
Mon 8/11
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Illinois to Key West with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 July 30, 2025.

Round-trip from

$223
(Delta)

One-way from

$151
(Mytrip)

Popular in

March

Cheapest in

November

Average price

$418

Good round-trip deal

$494 or less

Good one-way deal

$293 or less
From Illinois to Key West
Search Deals
One-way flight from Illinois to Key West
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($37 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2025
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

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 July 30, 2025.

This Delta deal was found by Cheapflights users on 7/29. 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 9/1310:15 amSTL - EYW
1 stop6h 00mDelta
Tue 9/166:10 pmEYW - STL
1 stop4h 50mDelta
Deal found 7/29$223
This American Airlines deal was found by Cheapflights users on 7/30. 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 10/228:49 amSTL - EYW
2 stops9h 33mAmerican Airlines
Tue 10/281:38 pmEYW - STL
1 stop8h 48mAmerican Airlines
Deal found 7/30$228
This United Airlines deal was found by Cheapflights users on 7/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/1510:50 amORD - EYW
Nonstop3h 19mUnited Airlines
Sat 12/204:05 pmEYW - ORD
Nonstop3h 25mUnited Airlines
Deal found 7/28$249
This Delta deal was found by Cheapflights users on 7/29. 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.
Wed 12/101:05 pmMDW - EYW
1 stop5h 39mDelta
Wed 12/177:00 amEYW - MDW
1 stop5h 55mDelta
Deal found 7/29$268
This Delta deal was found by Cheapflights users on 7/29. 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 12/1611:19 amORD - EYW
1 stop4h 53mDelta
Sat 12/206:02 pmEYW - ORD
1 stop6h 56mDelta
Deal found 7/29$268
This American Airlines deal was found by Cheapflights users on 7/29. 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 9/238:19 amMLI - EYW
1 stop8h 27mAmerican Airlines
Tue 9/306:17 pmEYW - MLI
1 stop5h 08mAmerican Airlines
Deal found 7/29$269
This Mytrip deal was found by Cheapflights users on 7/29. 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 11/137:00 amORD - EYW
1 stop11h 46mMultiple Airlines
Sun 11/162:25 pmEYW - ORD
1 stop7h 35mMultiple Airlines
Deal found 7/29$287
This FlightHub deal was found by Cheapflights users on 7/30. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/65:05 amORD - EYW
1 stop7h 25mSpirit Airlines
Mon 11/102:25 pmEYW - ORD
1 stop10h 17mSpirit Airlines
Deal found 7/30$303
This Delta deal was found by Cheapflights users on 7/28. 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.
Sat 8/236:00 amMLI - EYW
1 stop6h 05mDelta
Tue 8/266:20 pmEYW - MLI
1 stop5h 28mDelta
Deal found 7/28$309
This American Airlines deal was found by Cheapflights users on 7/28. 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.
Fri 10/316:45 amORD - EYW
1 stop8h 28mAmerican Airlines
Wed 11/51:52 pmEYW - ORD
Nonstop3h 40mAmerican Airlines
Deal found 7/28$313
This American Airlines deal was found by Cheapflights users on 7/30. 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.
Tue 10/286:47 amBMI - EYW
1 stop8h 31mAmerican Airlines
Tue 11/42:39 pmEYW - BMI
1 stop7h 52mAmerican Airlines
Deal found 7/30$317
This Delta deal was found by Cheapflights users on 7/29. 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 11/42:00 pmEVV - EYW
1 stop5h 06mDelta
Sat 11/87:40 amEYW - EVV
1 stop6h 05mDelta
Deal found 7/29$317

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 July 30, 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 9/13

10:15 am-5:15 pm

1 stop6h 00m

Key West

Tue 9/16

6:10 pm-10:00 pm

1 stop4h 50m

$223

St. LouisKey West

STL - EYW

STLEYW

Lambert-St Louis

Wed 10/22

8:49 am-7:22 pm

2 stops9h 33m

Key West

Tue 10/28

1:38 pm-9:26 pm

1 stop8h 48m

$228

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Wed 8/27

1:30 pm-8:12 pm

1 stop5h 42m

Key West

Wed 9/3

6:20 pm-10:37 pm

1 stop5h 17m

$269

MolineKey West

MLI - EYW

MLIEYW

Moline Quad-City

Tue 9/23

8:19 am-5:46 pm

1 stop8h 27m

Key West

Tue 9/30

6:17 pm-10:25 pm

1 stop5h 08m

$269

MolineKey West

MLI - EYW

MLIEYW

Moline Quad-City

Sat 8/23

6:00 am-1:05 pm

1 stop6h 05m

Key West

Tue 8/26

6:20 pm-10:48 pm

1 stop5h 28m

$309

BloomingtonKey West

BMI - EYW

BMIEYW

Bloomington-Normal

Tue 10/28

6:47 am-4:18 pm

1 stop8h 31m

Key West

Tue 11/4

2:39 pm-9:31 pm

1 stop7h 52m

$317

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Wed 8/27

8:12 pm-5:01 pm

2 stops19h 49m

Key West

Thu 9/4

12:29 pm-10:48 pm

2 stops11h 19m

$318

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Sat 8/30

8:20 am-3:19 pm

1 stop5h 59m

Key West

Wed 9/3

12:24 pm-5:23 pm

1 stop5h 59m

$323

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Fri 9/12

10:35 am-5:15 pm

1 stop5h 40m

Key West

Wed 9/17

7:00 am-11:48 am

1 stop5h 48m

$324

BloomingtonKey West

BMI - EYW

BMIEYW

Bloomington-Normal

Sat 8/23

6:05 am-1:05 pm

1 stop6h 00m

Key West

Tue 8/26

6:20 pm-10:16 pm

1 stop4h 56m

$348

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/27

Showing 1-10 of 30 results
1
2
3

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 July 30, 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.

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 July 30, 2025.
Read reviews from past customers who have flown Delta, United Airlines, and American Airlines from Illinois to Key West. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,980 reviews

Entertainment

7.9

Food

7.3

Overall

8.0

Crew

8.5

Boarding

8.2

Comfort

7.9

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
7,980 reviews
Delta
8.0
Very good
7,980 reviews

Entertainment

7.9

Food

7.3

Overall

8.0

Crew

8.5

Boarding

8.2

Comfort

7.9

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
8,896 reviews
Delta
8.0
Very good
7,980 reviews

Entertainment

7.9

Food

7.3

Overall

8.0

Crew

8.5

Boarding

8.2

Comfort

7.9

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
7,980 reviews

Entertainment

7.9

Food

7.3

Overall

8.0

Crew

8.5

Boarding

8.2

Comfort

7.9

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
7.2
Good
703 reviews
Delta
8.0
Very good
7,980 reviews

Entertainment

7.9

Food

7.3

Overall

8.0

Crew

8.5

Boarding

8.2

Comfort

7.9

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!
Spirit Airlines
6.3
Okay
8,048 reviews
Delta
8.0
Very good
7,980 reviews

Entertainment

7.9

Food

7.3

Overall

8.0

Crew

8.5

Boarding

8.2

Comfort

7.9

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 Allegiant Air, with whom users have recently found tickets for as low as $151. 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 Lambert-St Louis - Key West or Chicago Midway - Key West, Chicago O'Hare Intl - Key West is the most popular route from Illinois to Key West.

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

    While on average a flight from Illinois to Key West is generally $474, our data shows the cheapest flight currently is $293. 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.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Illinois to Key West

See prices for flight routes from nearby airports that may be better suited for you.
Newark to Fort Lauderdale flights
Newark to Miami flights
LaGuardia to Fort Lauderdale flights
John F Kennedy Intl to Miami flights
John F Kennedy Intl to Orlando flights
LaGuardia to Miami flights
Newark to Orlando flights
John F Kennedy Intl to Fort Lauderdale flights
LaGuardia to Orlando flights
Dulles Intl to Miami flights
Baltimore to Fort Lauderdale flights
John F Kennedy Intl to West Palm Beach flights
Philadelphia to Orlando flights
Dallas/Fort Worth to Orlando flights
Los Angeles to Miami flights
Boston to Orlando flights
Dallas/Fort Worth to Miami flights
Reagan-National to Miami flights
Atlanta to Miami flights
Baltimore to Miami flights
Atlanta to Fort Lauderdale flights
O'Hare Intl to Orlando flights
Newark to Tampa flights
Dallas/Fort Worth to Fort Lauderdale flights
Dulles Intl to Fort Lauderdale flights
Los Angeles to Orlando flights
Philadelphia to Fort Lauderdale flights
John F Kennedy Intl to Tampa flights
Hartford to Orlando flights
Baltimore to Orlando flights
LaGuardia to Tampa flights
Boston to Fort Lauderdale flights
Cleveland to Orlando flights
Reagan-National to Orlando flights
O'Hare Intl to Fort Lauderdale flights
O'Hare Intl to Miami flights
Los Angeles to Fort Lauderdale flights
Dulles Intl to Orlando flights
LaGuardia to West Palm Beach flights
Denver to Orlando flights
Boston to Miami flights
Philadelphia to Miami flights
Detroit to Orlando flights
Reagan-National to Fort Lauderdale flights
Providence to Orlando flights
Newark to West Palm Beach flights
Dulles Intl to Tampa flights
Hobby to Miami flights
Detroit to Fort Lauderdale flights
White Plains to Orlando flights

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 July 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$216Average$478FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$264Average$528FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$268Average$473FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.