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$95+ 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 11/27. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — ORD
nov. 29 — dic. 61
sáb. 11/29
sáb. 12/6
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 octubre 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$193
(Kiwi.com)

One-way from

$95
(Kiwi.com)

Good round-trip deal

$354 or less

Good one-way deal

$288 or less
Provider with most accurate pricing for Key West-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Key West-Chicago (CHI) flights.
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From Key West to Illinois
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One-way flight from Key West to Illinois
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Price to beat on a round-trip flight from Key West to Illinois.
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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 octubre 30, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/139:36 pmEYW - ORD
1 stop26h 30mMultiple Airlines
dom. 11/165:25 amORD - EYW
1 stop14h 21mMultiple Airlines
Deal found 10/28$193
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 11/222:24 pmEYW - ORD
1 stop10h 05mMultiple Airlines
jue. 11/273:37 pmORD - EYW
1 stop16h 40mMultiple Airlines
Deal found 10/29$200
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 11/238:55 amEYW - ORD
1 stop10h 04mMultiple Airlines
jue. 11/273:37 pmORD - EYW
1 stop16h 40mMultiple Airlines
Deal found 10/29$201
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 11/248:55 amEYW - ORD
1 stop9h 20mMultiple Airlines
jue. 11/273:37 pmORD - EYW
1 stop16h 40mMultiple Airlines
Deal found 10/29$204
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 11/218:55 amEYW - ORD
1 stop8h 08mMultiple Airlines
jue. 11/273:37 pmORD - EYW
1 stop16h 40mMultiple Airlines
Deal found 10/29$211
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/2710:59 amEYW - ORD
1 stop12h 37mMultiple Airlines
sáb. 11/296:48 amORD - EYW
1 stop24h 27mMultiple Airlines
Deal found 10/29$213
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 11/248:55 amEYW - MDW
1 stop8h 57mMultiple Airlines
sáb. 11/296:02 pmMDW - EYW
1 stop13h 13mMultiple Airlines
Deal found 10/29$219
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 11/222:24 pmEYW - ORD
1 stop10h 05mSpirit Airlines
mié. 12/33:43 pmORD - EYW
1 stop18h 37mSpirit Airlines
Deal found 10/29$221
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/138:55 amEYW - ORD
1 stop15h 11mMultiple Airlines
lun. 11/171:50 pmORD - EYW
2 stops20h 15mMultiple Airlines
Deal found 10/29$222
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 11/2510:59 amEYW - ORD
1 stop11h 48mMultiple Airlines
jue. 11/273:37 pmORD - EYW
1 stop16h 40mMultiple Airlines
Deal found 10/29$223
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/2710:59 amEYW - ORD
1 stop12h 37mMultiple Airlines
mar. 12/24:22 pmORD - EYW
2 stops16h 45mMultiple Airlines
Deal found 10/29$226
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 11/79:01 amEYW - MDW
1 stop6h 06mMultiple Airlines
sáb. 11/151:37 pmMDW - EYW
2 stops17h 38mMultiple Airlines
Deal found 10/29$229

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 octubre 30, 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

jue. 11/27

10:59 am-10:36 pm

1 stop12h 37m

Chicago O'Hare Intl

mar. 12/2

12:32 pm-10:07 am

1 stop20h 35m

$229

Key WestChicago

EYW - ORD

EYWORD

Key West

sáb. 11/22

2:24 pm-11:29 pm

1 stop10h 05m

Chicago O'Hare Intl

mié. 12/3

8:00 am-8:15 am

2 stops23h 15m

$243

Key WestChicago

EYW - MDW

EYWMDW

Key West

jue. 11/13

8:55 am-6:39 pm

2 stops10h 44m

Chicago Midway

lun. 11/17

6:06 pm-11:05 am

1 stop15h 59m

$254

Key WestChicago

EYW - ORD

EYWORD

Key West

vie. 11/21

8:55 am-4:03 pm

1 stop8h 08m

Chicago O'Hare Intl

mar. 12/2

12:32 pm-10:07 am

1 stop20h 35m

$257

Key WestChicago

EYW - ORD

EYWORD

Key West

mar. 11/25

6:18 pm-12:02 am

1 stop6h 44m

Chicago O'Hare Intl

mar. 12/2

1:20 pm-8:06 pm

1 stop5h 46m

$269

Key WestChicago

EYW - ORD

EYWORD

Key West

vie. 2/13

7:00 am-1:23 pm

1 stop7h 23m

Chicago O'Hare Intl

mar. 2/17

9:30 am-5:13 pm

1 stop6h 43m

$269

Key WestChicago

EYW - ORD

EYWORD

Key West

mar. 2/24

7:00 am-1:23 pm

1 stop7h 23m

Chicago O'Hare Intl

mar. 3/10

11:19 am-5:13 pm

1 stop4h 54m

$269

Key WestChicago

EYW - ORD

EYWORD

Key West

lun. 11/24

6:18 pm-12:02 am

1 stop6h 44m

Chicago O'Hare Intl

sáb. 11/29

5:23 am-11:31 am

1 stop5h 08m

$269

Key WestChicago

EYW - ORD

EYWORD

Key West

lun. 11/24

6:18 pm-12:02 am

1 stop6h 44m

Chicago O'Hare Intl

lun. 12/1

5:23 am-11:31 am

1 stop5h 08m

$269

Key WestChicago

EYW - ORD

EYWORD

Key West

mié. 11/26

6:18 pm-12:02 am

1 stop6h 44m

Chicago O'Hare Intl

lun. 12/1

1:04 pm-7:53 pm

1 stop5h 49m

$269

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

Showing 1-10 of 59 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 octubre 30, 2025.

One of the essential ways to save on airfare from Key West to Illinois is to remain as flexible as possible. Flights that are in the evening tend to be the most expensive. A flight in the afternoon could potentially save you up to 27% on airfare.

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 octubre 30, 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
8,998 reviews

Comfort

7.3

Boarding

7.7

Food

6.6

Overall

7.4

Entertainment

7.1

Crew

8.1

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
8,998 reviews
United Airlines
7.4
Good
8,998 reviews

Comfort

7.3

Boarding

7.7

Food

6.6

Overall

7.4

Entertainment

7.1

Crew

8.1

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
11,035 reviews
United Airlines
7.4
Good
8,998 reviews

Comfort

7.3

Boarding

7.7

Food

6.6

Overall

7.4

Entertainment

7.1

Crew

8.1

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 Delta, American Airlines, and United Airlines fly from Key West to Illinois in about 6h 31m. The time it takes to get you to your destination can typically vary by up to 3h 59m. Key West and Illinois are separated by a distance of 1203 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • 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 - Moline Quad-City as they are the most popular.

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

    The cheapest flight price from Key West to Illinois is $201. On average you can expect to pay $588. The most popular route, (Key West - Chicago O'Hare Intl), can usually be booked for $193.

  • 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.

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 octubre 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$224Average$499FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$289Average$398FlexibilityNo cancel feeOn-time71%

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