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$122+ 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 7/15. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — ORD
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 June 12, 2025.

Round-trip from

$337
(Mytrip)

One-way from

$122
(Trip.com)

Popular in

March

Cheapest in

June

Average price

$268

Good round-trip deal

$427 or less

Good one-way deal

$293 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. 17% potential increase in price ($78 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in June 2025
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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 June 12, 2025.

This Delta deal was found by Cheapflights users on 6/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/16:00 pmEYW - ORD
1 stop6h 53mDelta
Wed 10/86:00 amORD - EYW
1 stop6h 08mDelta
Deal found 6/12$289
This American Airlines deal was found by Cheapflights users on 6/12. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/17:31 pmEYW - ORD
1 stop5h 17mAmerican Airlines
Wed 10/85:15 amORD - EYW
2 stops6h 45mAmerican Airlines
Deal found 6/12$328
This Mytrip deal was found by Cheapflights users on 6/11. 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.
Tue 7/2910:02 amEYW - ORD
1 stop10h 24mMultiple Airlines
Wed 7/304:36 pmORD - EYW
1 stop23h 09mMultiple Airlines
Deal found 6/11$337
This United Airlines deal was found by Cheapflights users on 6/10. 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.
Fri 8/86:45 pmEYW - ORD
1 stop24h 38mUnited Airlines
Sun 8/1010:45 amORD - EYW
2 stops20h 15mUnited Airlines
Deal found 6/10$378
This Mytrip deal was found by Cheapflights users on 6/12. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/810:02 amEYW - PIA
3 stops34h 47mMultiple Airlines
Sat 7/198:02 pmPIA - EYW
1 stop11h 02mMultiple Airlines
Deal found 6/12$441
This Delta deal was found by Cheapflights users on 6/11. 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 7/97:00 amEYW - MDW
1 stop5h 58mDelta
Mon 7/1412:43 pmMDW - EYW
1 stop6h 06mDelta
Deal found 6/11$484
This American Airlines deal was found by Cheapflights users on 6/12. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/81:25 pmEYW - BMI
2 stops11h 22mAmerican Airlines
Sat 7/197:00 amBMI - EYW
1 stop7h 26mAmerican Airlines
Deal found 6/12$502
This American Airlines deal was found by Cheapflights users on 6/12. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/84:48 pmEYW - PIA
1 stop8h 24mAmerican Airlines
Sat 7/196:00 amPIA - EYW
2 stops8h 26mAmerican Airlines
Deal found 6/12$512
This United Airlines deal was found by Cheapflights users on 6/12. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/82:12 pmEYW - PIA
3 stops21h 07mUnited Airlines
Sat 7/193:39 pmPIA - EYW
2 stops21h 21mUnited Airlines
Deal found 6/12$560
This Delta deal was found by Cheapflights users on 6/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/811:48 amEYW - BMI
1 stop4h 42mDelta
Sat 7/196:00 amBMI - EYW
1 stop6h 08mDelta
Deal found 6/12$793

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 June 12, 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

Tue 7/29

10:02 am-7:26 pm

1 stop10h 24m

Chicago O'Hare Intl

Wed 7/30

4:36 pm-4:45 pm

1 stop23h 09m

$337

Key WestChicago

EYW - ORD

EYWORD

Key West

Fri 8/8

6:27 pm-12:09 am

1 stop6h 42m

Chicago O'Hare Intl

Sun 8/10

9:50 am-5:32 pm

1 stop6h 42m

$344

Key WestChicago

EYW - ORD

EYWORD

Key West

Wed 7/30

2:31 pm-9:00 pm

1 stop7h 29m

Chicago O'Hare Intl

Sun 8/3

6:00 am-4:12 pm

1 stop9h 12m

$364

Key WestChicago

EYW - ORD

EYWORD

Key West

Fri 8/8

6:45 pm-6:23 pm

1 stop24h 38m

Chicago O'Hare Intl

Sun 8/10

10:45 am-8:00 am

2 stops20h 15m

$378

Key WestPeoria

EYW - PIA

EYWPIA

Key West

Tue 7/8

10:02 am-7:49 pm

3 stops34h 47m

Greater Peoria

Sat 7/19

8:02 pm-8:04 am

1 stop11h 02m

$441

Key WestChicago

EYW - MDW

EYWMDW

Key West

Wed 7/9

7:00 am-11:58 am

1 stop5h 58m

Chicago Midway

Mon 7/14

12:43 pm-7:49 pm

1 stop6h 06m

$484

Key WestBloomington

EYW - BMI

EYWBMI

Key West

Tue 7/8

1:25 pm-11:47 pm

2 stops11h 22m

Bloomington-Normal

Sat 7/19

7:00 am-3:26 pm

1 stop7h 26m

$502

Key WestPeoria

EYW - PIA

EYWPIA

Key West

Tue 7/8

4:48 pm-12:12 am

1 stop8h 24m

Greater Peoria

Sat 7/19

6:00 am-3:26 pm

2 stops8h 26m

$512

Key WestPeoria

EYW - PIA

EYWPIA

Key West

Tue 7/8

2:12 pm-10:19 am

3 stops21h 07m

Greater Peoria

Sat 7/19

3:39 pm-2:00 pm

2 stops21h 21m

$560

Key WestBloomington

EYW - BMI

EYWBMI

Key West

Tue 7/8

11:48 am-3:30 pm

1 stop4h 42m

Bloomington-Normal

Sat 7/19

6:00 am-1:08 pm

1 stop6h 08m

$793

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

Showing 1-10 of 16 results
1
2

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 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.

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 June 12, 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.

Rainfall in Illinois by month

Plan your trip to Illinois by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Illinois ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Illinois when rainfall is around 1.7 in.

Temperature in Illinois by month

Plan your trip to Illinois by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Illinois, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 June 12, 2025.
Get a feel of what it's like to fly with Alaska Airlines, Delta and United Airlines from Key West to Illinois by reading reviews from past customers. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Entertainment

7.1

Overall

8.0

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Entertainment

7.1

Overall

8.0

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,950 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Entertainment

7.1

Overall

8.0

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,790 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Entertainment

7.1

Overall

8.0

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Entertainment

7.1

Overall

8.0

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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.

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

    The cheapest airline one-way is Delta, with whom users have recently found tickets for as low as $264. However, be on the lookout for offers from United Airlines 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 - 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 (69%), Air New Zealand (69%), American Airlines( 59%).

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

    The cheapest flight price from Key West to Illinois is $141. On average you can expect to pay $513. The most popular route, (Key West - Chicago O'Hare Intl), can usually be booked for $256.

  • 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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Alternative routes for Key West to Illinois

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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$224Average$394FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$289Average$423FlexibilityNo cancel feeOn-time71%

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