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Illinois

$85+ 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 1/15. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — ORD
ene. 16 — ene. 231
vie. 1/16
vie. 1/23
1 adult, Economy
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Cheap 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 diciembre 17, 2025.

This American Airlines deal was found by Cheapflights users on 12/15. 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.
lun. 12/291:15 pmEYW - ORD
Nonstop3h 35mAmerican Airlines
lun. 1/128:14 amORD - EYW
Nonstop3h 31mAmerican Airlines
Deal found 12/15$279
This Kiwi.com deal was found by Cheapflights users on 12/15. 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.
mié. 12/1710:47 amEYW - ORD
2 stops29h 15mMultiple Airlines
jue. 1/155:15 amORD - EYW
1 stop5h 41mMultiple Airlines
Deal found 12/15$296
This Delta deal was found by Cheapflights users on 12/15. 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.
lun. 12/291:02 pmEYW - ORD
1 stop6h 57mDelta
lun. 1/125:30 amORD - EYW
1 stop4h 59mDelta
Deal found 12/15$299
This Delta deal was found by Cheapflights users on 12/15. 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.
lun. 12/296:20 pmEYW - MDW
1 stop5h 02mDelta
lun. 1/1211:21 amMDW - EYW
1 stop4h 50mDelta
Deal found 12/15$299
This Kiwi.com deal was found by Cheapflights users on 12/15. 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.
mié. 12/1710:47 amEYW - ORD
2 stops29h 15mMultiple Airlines
jue. 1/2212:44 pmORD - EYW
1 stop22h 42mMultiple Airlines
Deal found 12/15$300
This American Airlines deal was found by Cheapflights users on 12/15. 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.
mié. 12/171:51 pmEYW - ORD
Nonstop3h 43mAmerican Airlines
mar. 4/148:00 amORD - EYW
Nonstop3h 16mAmerican Airlines
Deal found 12/15$315
This Kiwi.com deal was found by Cheapflights users on 12/15. 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.
mié. 12/1710:47 amEYW - ORD
2 stops29h 15mMultiple Airlines
mar. 4/145:38 pmORD - EYW
1 stop16h 39mMultiple Airlines
Deal found 12/15$326
This Delta deal was found by Cheapflights users on 12/15. 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.
mié. 12/1712:38 pmEYW - ORD
1 stop7h 05mDelta
mar. 4/1411:19 amORD - EYW
1 stop4h 53mDelta
Deal found 12/15$335
This Delta deal was found by Cheapflights users on 12/15. 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.
mié. 12/1712:38 pmEYW - MDW
1 stop4h 56mDelta
mar. 4/1410:35 amMDW - EYW
1 stop5h 37mDelta
Deal found 12/15$335
This Kiwi.com deal was found by Cheapflights users on 12/15. 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.
mié. 12/1710:47 amEYW - ORD
2 stops29h 15mMultiple Airlines
mié. 4/17:41 pmORD - EYW
1 stop14h 49mMultiple Airlines
Deal found 12/15$349
This Delta deal was found by Cheapflights users on 12/15. 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.
mié. 12/176:10 pmEYW - MDW
1 stop6h 37mDelta
jue. 1/2210:48 amMDW - EYW
1 stop5h 23mDelta
Deal found 12/15$420
This Delta deal was found by Cheapflights users on 12/15. 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.
mié. 12/177:40 amEYW - MDW
1 stop5h 15mDelta
jue. 1/1511:21 amMDW - EYW
1 stop4h 50mDelta
Deal found 12/15$680

Find 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 diciembre 17, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$249
(American Airlines)

One-way from

$85
(Priceline)

Good round-trip deal

$296 or less

Good one-way deal

$270 or less
Provider with most accurate pricing for Key West-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Key West-Chicago (CHI) flights.
Search Deals
From Key West to Illinois
Search Deals
One-way flight from Key West to Illinois
Search Deals
Price to beat on a round-trip flight from Key West to Illinois.
Search Deals
Price to beat on a one-way flight from Key West to Illinois.
Search Deals

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 diciembre 17, 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. 4/9

6:39 pm-9:20 pm

Nonstop3h 41m

Chicago O'Hare Intl

lun. 4/13

8:00 am-12:16 pm

Nonstop3h 16m

$249

Key WestChicago

EYW - ORD

EYWORD

Key West

mié. 1/21

7:10 am-1:40 pm

1 stop7h 30m

Chicago O'Hare Intl

jue. 1/29

9:55 am-5:11 pm

1 stop6h 16m

$269

Key WestChicago

EYW - MDW

EYWMDW

Key West

mié. 1/21

6:06 pm-10:22 pm

1 stop5h 16m

Chicago Midway

jue. 1/29

10:48 am-5:11 pm

1 stop5h 23m

$269

Key WestChicago

EYW - ORD

EYWORD

Key West

lun. 12/29

12:55 pm-7:22 pm

1 stop7h 27m

Chicago O'Hare Intl

lun. 1/12

10:59 am-3:25 pm

Nonstop3h 26m

$289

Key WestChicago

EYW - ORD

EYWORD

Key West

lun. 12/29

1:02 pm-6:59 pm

1 stop6h 57m

Chicago O'Hare Intl

lun. 1/12

5:30 am-11:29 am

1 stop4h 59m

$299

Key WestChicago

EYW - MDW

EYWMDW

Key West

lun. 12/29

6:20 pm-10:22 pm

1 stop5h 02m

Chicago Midway

lun. 1/12

11:21 am-5:11 pm

1 stop4h 50m

$299

Key WestChicago

EYW - ORD

EYWORD

Key West

mié. 1/21

4:01 pm-6:45 pm

Nonstop3h 44m

Chicago O'Hare Intl

jue. 1/29

10:10 am-6:01 pm

1 stop6h 51m

$307

Key WestChicago

EYW - ORD

EYWORD

Key West

vie. 1/23

4:15 pm-6:48 pm

Nonstop3h 33m

Chicago O'Hare Intl

dom. 1/25

10:50 am-3:17 pm

Nonstop3h 27m

$329

Key WestChicago

EYW - MDW

EYWMDW

Key West

jue. 4/9

6:25 pm-10:29 pm

1 stop5h 04m

Chicago Midway

lun. 4/13

10:35 am-5:12 pm

1 stop5h 37m

$334

Key WestChicago

EYW - MDW

EYWMDW

Key West

jue. 1/1

8:55 am-9:58 pm

1 stop14h 03m

Chicago Midway

lun. 1/5

8:15 am-11:20 am

2 stops26h 05m

$348

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/14

Showing 1-10 of 38 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 diciembre 17, 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 diciembre 17, 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
9,091 reviews

Boarding

7.7

Overall

7.4

Comfort

7.3

Crew

8.1

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
9,091 reviews
United Airlines
7.4
Good
9,091 reviews

Boarding

7.7

Overall

7.4

Comfort

7.3

Crew

8.1

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
11,054 reviews
United Airlines
7.4
Good
9,091 reviews

Boarding

7.7

Overall

7.4

Comfort

7.3

Crew

8.1

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 American Airlines, Delta, and United Airlines fly from Key West to Illinois in about 3h 41m. The time it takes to get you to your destination can typically vary by up to 3h 49m. Key West and Illinois are separated by a distance of 1253 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 United Airlines, with whom users have recently found tickets for as low as $129. However, be on the lookout for offers from American Airlines and Delta, 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 - Moline Quad-City 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: United Airlines (79%), Air New Zealand (79%), Republic Airways( 79%).

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

    The cheapest flight price from Key West to Illinois is $125. On average you can expect to pay $570. The most popular route, (Key West - Chicago O'Hare Intl), can usually be booked for $249.

  • 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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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 diciembre 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$249Average$431FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$289Average$427FlexibilityNo cancel feeOn-time71%

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