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$113+ Cheap flights from Key West (EYW) to Illinois

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 1/23. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — ORD
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheap flight deals from Key West to Illinois

Keep the following information in mind while searching for Key West to Illinois flight deals. Data was last updated September 15, 2025.

Round-trip from

$237
(Kiwi.com)

One-way from

$113
(Kiwi.com)

Popular in

March

Cheapest in

June

Average price

$288

Good one-way deal

$304 or less
From Key West to Illinois
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One-way flight from Key West to Illinois
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Highest demand for flights based on searches. 20% potential increase in price ($91 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a one-way flight from Key West to Illinois.
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Find flight deals from Key West to Illinois

Cheapest flights from Key West to Illinois
Explore the most affordable flight options available from Key West to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 15, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/268:47 amEYW - ORD
1 stop14h 11mMultiple Airlines
Tue 9/305:46 pmORD - EYW
1 stop15h 21mMultiple Airlines
Deal found 9/13$237
This Mytrip deal was found by Cheapflights users on 9/13. 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.
Mon 10/272:57 pmEYW - MDW
1 stop5h 37mAllegiant Air
Mon 11/32:45 pmMDW - EYW
1 stop4h 36mAllegiant Air
Deal found 9/13$237
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/138:55 amEYW - ORD
1 stop9h 09mMultiple Airlines
Sat 11/158:00 amORD - EYW
1 stop23h 15mMultiple Airlines
Deal found 9/14$239
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/1310:47 amEYW - ORD
1 stop27h 51mMultiple Airlines
Wed 12/1710:18 amORD - EYW
1 stop20h 57mMultiple Airlines
Deal found 9/13$244
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/78:55 amEYW - MDW
1 stop14h 25mMultiple Airlines
Wed 11/122:06 pmMDW - EYW
2 stops42h 11mMultiple Airlines
Deal found 9/13$250
This Kiwi.com deal was found by Cheapflights users on 9/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/279:52 amEYW - ORD
2 stops25h 39mMultiple Airlines
Tue 9/305:46 pmORD - EYW
1 stop14h 26mMultiple Airlines
Deal found 9/12$251
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1310:59 amEYW - MDW
2 stops10h 32mMultiple Airlines
Sat 11/1511:36 amMDW - EYW
1 stop19h 39mMultiple Airlines
Deal found 9/14$258
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/2912:32 pmEYW - ORD
1 stop22h 46mMultiple Airlines
Fri 10/34:03 pmORD - EYW
2 stops17h 04mMultiple Airlines
Deal found 9/13$261
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/272:57 pmEYW - MDW
1 stop5h 37mMultiple Airlines
Mon 11/36:30 amMDW - EYW
2 stops27h 35mMultiple Airlines
Deal found 9/13$265
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/810:47 amEYW - ORD
1 stop28h 12mMultiple Airlines
Tue 11/1112:37 pmORD - EYW
2 stops20h 30mMultiple Airlines
Deal found 9/14$267
This Delta deal was found by Cheapflights users on 9/14. 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 11/86:17 pmEYW - ORD
1 stop6h 41mDelta
Tue 11/115:32 amORD - EYW
1 stop7h 31mDelta
Deal found 9/14$269
This Delta deal was found by Cheapflights users on 9/13. 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 11/76:17 pmEYW - MDW
1 stop4h 57mDelta
Wed 11/1212:47 pmMDW - EYW
1 stop6h 06mDelta
Deal found 9/13$269

Cheapflights Fare Finder

 
Customize your flight search to find flights from Key West to Illinois 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 September 15, 2025.
Use the filters below to find and compare flights from Key West to Illinois that are best for you.

Fly from

Key West

Fly to

Illinois

Route

Depart

Return

Price

Key WestChicago

EYW - ORD

EYWORD

Key West

Fri 9/26

8:47 am-9:58 pm

1 stop14h 11m

Chicago O'Hare Intl

Tue 9/30

5:46 pm-10:07 am

1 stop15h 21m

$237

Key WestChicago

EYW - MDW

EYWMDW

Key West

Mon 10/27

2:57 pm-7:34 pm

1 stop5h 37m

Chicago Midway

Mon 11/3

2:45 pm-8:21 pm

1 stop4h 36m

$237

Key WestChicago

EYW - ORD

EYWORD

Key West

Sat 12/13

10:47 am-1:38 pm

1 stop27h 51m

Chicago O'Hare Intl

Wed 12/17

10:18 am-8:15 am

1 stop20h 57m

$244

Key WestChicago

EYW - MDW

EYWMDW

Key West

Fri 11/7

8:55 am-10:20 pm

1 stop14h 25m

Chicago Midway

Wed 11/12

2:06 pm-9:17 am

2 stops42h 11m

$250

Key WestChicago

EYW - ORD

EYWORD

Key West

Sat 9/27

9:52 am-10:31 am

2 stops25h 39m

Chicago O'Hare Intl

Tue 9/30

5:46 pm-9:12 am

1 stop14h 26m

$251

Key WestChicago

EYW - ORD

EYWORD

Key West

Mon 9/29

12:32 pm-10:18 am

1 stop22h 46m

Chicago O'Hare Intl

Fri 10/3

4:03 pm-10:07 am

2 stops17h 04m

$261

Key WestChicago

EYW - ORD

EYWORD

Key West

Sat 11/8

10:47 am-1:59 pm

1 stop28h 12m

Chicago O'Hare Intl

Tue 11/11

12:37 pm-10:07 am

2 stops20h 30m

$267

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 11/13

8:55 am-5:04 pm

1 stop9h 09m

Chicago O'Hare Intl

Sat 11/15

5:45 pm-8:15 am

2 stops13h 30m

$268

Key WestChicago

EYW - ORD

EYWORD

Key West

Mon 1/12

1:30 pm-7:25 pm

1 stop6h 55m

Chicago O'Hare Intl

Tue 1/20

11:19 am-7:44 pm

1 stop7h 25m

$269

Key WestChicago

EYW - MDW

EYWMDW

Key West

Thu 2/12

6:00 pm-9:46 pm

1 stop4h 46m

Chicago Midway

Tue 2/17

1:05 pm-7:44 pm

1 stop5h 39m

$269

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/13

Showing 1-10 of 48 results
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Best time to book a flight from Key West to Illinois

Have a flexible travel schedule? Discover the best time to fly to Illinois from Key West 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 Key West to Illinois

What is the cheapest time of day to fly from EYW to IL?

Find hourly flight availability from Key West to Illinois. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 15, 2025.

When flying from Key West to Illinois, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Reviews of airlines servicing Illinois

Get insights into the airlines that provide service to Illinois. 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 Illinois. Reviews last updated September 15, 2025.
Peruse reviews from past customers who have flown with United Airlines and American Airlines from Key West to Illinois to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
8,931 reviews

Overall

7.4

Crew

8.1

Comfort

7.3

Boarding

7.7

Entertainment

7.1

Food

6.6

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
United Airlines
7.4
Good
8,931 reviews
United Airlines
7.4
Good
8,931 reviews

Overall

7.4

Crew

8.1

Comfort

7.3

Boarding

7.7

Entertainment

7.1

Food

6.6

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
American Airlines
7.2
Good
10,000 reviews
United Airlines
7.4
Good
8,931 reviews

Overall

7.4

Crew

8.1

Comfort

7.3

Boarding

7.7

Entertainment

7.1

Food

6.6

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!

Related info for your journey

Find useful and relevant information for your journey from Key West to Illinois. 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 from for flights from Key West to Illinois?

    Key West (EYW) is the airport you will fly out of if you book a flight from Key West to Illinois. It is only a 2.6 mi journey to Key West (EYW) from Key West’s city center.

  • How long is the flight from Key West to Illinois?

    Airlines like Allegiant Air, Delta, and American Airlines fly from Key West to Illinois in about 4h 46m. The time it takes to get you to your destination can typically vary by up to 3h 48m. Key West and Illinois are separated by a distance of 1238 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines to fly from Key West to Illinois one-way?

    The cheapest airline one-way is Spirit Airlines, with whom users have recently found tickets for as low as $123. However, be on the lookout for offers from Delta and American Airlines, as they are both options that can get you from Key West to Illinois for a low price.

  • What are the most popular routes from Key West to Illinois?

    When deciding which route to take from Key West to Illinois consider Key West - Chicago O'Hare Intl, Key West - Chicago Midway or Key West - Greater Peoria as they are the most popular.

  • What are the most reliable airlines from Key West to Illinois?

    Before booking your flight to Illinois from Key West, check out the most reliable airlines to get you to your destination on time: American Airlines (60%), Qatar Airways (60%), Envoy Air( 60%).

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

    The cheapest flight price from Key West to Illinois is $236. On average you can expect to pay $401. The most popular route, (Key West - Chicago O'Hare Intl), can usually be booked for $237.

  • Can I find deals for flights from Key West to Illinois that include hotel bookings?

    Yes. In addition to deals on Key West to Illinois flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Key West to Illinois?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Key West to Illinois.

  • Can I find deals for business class flights from Key West to Illinois?

    Yes. Cheapflights offers flight deals from Key West to Illinois 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 Key West to Illinois?

    Currently, August is the cheapest month in which you can book a flight from Key West to Illinois (average of $245). Flying from Key West to Illinois in March is currently the most expensive (average of $321). 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

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See prices for flight routes from nearby airports that may be better suited for you.
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Top 2 airlines flying from Key West to Illinois

Discover the top 2 airlines that operate flights from Key West to Illinois. 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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$224Average$394FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$259Average$398FlexibilityNo cancel feeOn-time71%

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