$144+ 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 6/19. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — ORD
May 6 — May 131
1 adult, Economy
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Find cheap flights from Key West to Illinois 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
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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 Key West to Illinois
Keep the following information in mind while searching for Key West to Illinois flight deals. Data was last updated May 1, 2025.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | eDreams 3 stars |
Round-trip from | $251 (Mytrip) |
One-way from | $144 (Trip.com) |
Popular in | March |
Cheapest in | June |
Average price | $406 |
Good round-trip deal | $403 or less |
Good one-way deal | $269 or less |
Find flight deals from Key West to Illinois
Cheapest flights from Key West to IllinoisExplore 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 May 1, 2025.
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 May 1, 2025.
This Mytrip deal was found by Cheapflights users on 4/28. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/155:35 pmEYW - RFD
1 stop24h 16mAllegiant Air
Wed 5/218:33 amRFD - EYW
1 stop6h 23mAllegiant Air
Deal found 4/28![Allegiant Air logo]()
$251
This American Airlines deal was found by Cheapflights users on 4/28. 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.
Tue 7/84:48 pmEYW - PIA
1 stop8h 24mAmerican Airlines
Sun 8/35:00 amPIA - EYW
1 stop8h 14mAmerican Airlines
Deal found 4/28![American Airlines logo]()
$269
This American Airlines deal was found by Cheapflights users on 4/28. 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.
Tue 7/84:48 pmEYW - MLI
1 stop6h 20mAmerican Airlines
Sun 8/35:00 amMLI - EYW
1 stop6h 00mAmerican Airlines
Deal found 4/28![American Airlines logo]()
$269
This Delta deal was found by Cheapflights users on 4/28. 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.
Wed 7/96:27 pmEYW - MLI
1 stop5h 19mDelta
Sun 8/35:55 amMLI - EYW
1 stop6h 13mDelta
Deal found 4/28![Delta logo]()
$294
This Mytrip deal was found by Cheapflights users on 4/28. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/158:53 amEYW - ORD
2 stops32h 32mMultiple Airlines
Wed 5/216:30 amORD - EYW
1 stop8h 26mMultiple Airlines
Deal found 4/28![Multiple Airlines logo]()
$312
This Delta deal was found by Cheapflights users on 4/29. 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.
Mon 6/26:25 pmEYW - ORD
1 stop6h 33mDelta
Tue 6/1711:20 amORD - EYW
1 stop7h 19mDelta
Deal found 4/29![Delta logo]()
$314
This Delta deal was found by Cheapflights users on 4/28. 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.
Thu 5/151:51 pmEYW - MDW
1 stop4h 52mDelta
Wed 5/2112:48 pmMDW - EYW
1 stop6h 19mDelta
Deal found 4/28![Delta logo]()
$349
This American Airlines deal was found by Cheapflights users on 4/28. 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.
Tue 7/84:48 pmEYW - BMI
2 stops8h 04mAmerican Airlines
Sun 8/36:01 amBMI - EYW
2 stops9h 08mAmerican Airlines
Deal found 4/28![American Airlines logo]()
$354
This American Airlines deal was found by Cheapflights users on 4/29. 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.
Thu 5/2912:49 pmEYW - ORD
Nonstop3h 39mAmerican Airlines
Thu 6/55:00 amORD - EYW
1 stop7h 48mAmerican Airlines
Deal found 4/29![American Airlines logo]()
$375
This United Airlines deal was found by Cheapflights users on 4/28. 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 6/26:45 pmEYW - ORD
1 stop26h 22mUnited Airlines
Tue 6/171:04 pmORD - EYW
2 stops28h 01mUnited Airlines
Deal found 4/28![United Airlines logo]()
$400
This United Airlines deal was found by Cheapflights users on 4/28. 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.
Tue 7/86:45 pmEYW - PIA
2 stops22h 58mUnited Airlines
Sun 8/33:39 pmPIA - EYW
2 stops21h 21mUnited Airlines
Deal found 4/28![United Airlines logo]()
$481
This Delta deal was found by Cheapflights users on 4/28. 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.
Tue 7/86:27 pmEYW - BMI
1 stop4h 59mDelta
Sun 8/36:00 amBMI - EYW
1 stop6h 08mDelta
Deal found 4/28![Delta logo]()
$488
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 May 1, 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 - RFD
EYWRFD
Key West
Thu 5/15
5:35 pm-4:51 pm
1 stop24h 16m
Chicago Greater Rockford
Wed 5/21
8:33 am-3:56 pm
1 stop6h 23m
$251
Key WestPeoria
EYW - PIA
EYWPIA
Key West
Tue 7/8
4:48 pm-12:12 am
1 stop8h 24m
Greater Peoria
Sun 8/3
5:00 am-2:14 pm
1 stop8h 14m
$269
Key WestMoline
EYW - MLI
EYWMLI
Key West
Tue 7/8
4:48 pm-10:08 pm
1 stop6h 20m
Moline Quad-City
Sun 8/3
5:00 am-12:00 pm
1 stop6h 00m
$269
Key WestMoline
EYW - MLI
EYWMLI
Key West
Wed 7/9
6:27 pm-10:46 pm
1 stop5h 19m
Moline Quad-City
Sun 8/3
5:55 am-1:08 pm
1 stop6h 13m
$294
Key WestChicago
EYW - ORD
EYWORD
Key West
Thu 5/15
8:53 am-4:25 pm
2 stops32h 32m
Chicago O'Hare Intl
Wed 5/21
6:30 am-3:56 pm
1 stop8h 26m
$312
Key WestChicago
EYW - ORD
EYWORD
Key West
Mon 6/2
6:25 pm-11:58 pm
1 stop6h 33m
Chicago O'Hare Intl
Tue 6/17
11:20 am-7:39 pm
1 stop7h 19m
$314
Key WestChicago
EYW - MDW
EYWMDW
Key West
Thu 5/15
1:51 pm-5:43 pm
1 stop4h 52m
Chicago Midway
Wed 5/21
12:48 pm-8:07 pm
1 stop6h 19m
$349
Key WestBloomington
EYW - BMI
EYWBMI
Key West
Tue 7/8
4:48 pm-11:52 pm
2 stops8h 04m
Bloomington-Normal
Sun 8/3
6:01 am-4:09 pm
2 stops9h 08m
$354
Key WestChicago
EYW - ORD
EYWORD
Key West
Thu 5/29
12:49 pm-3:28 pm
Nonstop3h 39m
Chicago O'Hare Intl
Thu 6/5
5:00 am-1:48 pm
1 stop7h 48m
$375
Key WestChicago
EYW - ORD
EYWORD
Key West
Mon 6/2
6:45 pm-8:07 pm
1 stop26h 22m
Chicago O'Hare Intl
Tue 6/17
1:04 pm-6:05 pm
2 stops28h 01m
$400
Showing 1-10 of 27 results
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 May 1, 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 May 1, 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.
Comfort
7.9
Boarding
8.2
Entertainment
7.1
Overall
8.0
Crew
8.5
Food
7.1
Reviews
1 / 20
10.0
ExcellentJames,Apr 2025
LAX - SFO
Comfort
7.9
Boarding
8.2
Entertainment
7.1
Overall
8.0
Crew
8.5
Food
7.1
Reviews
1 / 20
10.0
ExcellentJames,Apr 2025
LAX - SFO
Comfort
7.9
Boarding
8.2
Entertainment
7.1
Overall
8.0
Crew
8.5
Food
7.1
Reviews
1 / 20
10.0
ExcellentJames,Apr 2025
LAX - SFO
Comfort
7.9
Boarding
8.2
Entertainment
7.1
Overall
8.0
Crew
8.5
Food
7.1
Reviews
1 / 20
10.0
ExcellentJames,Apr 2025
LAX - SFO
Comfort
7.9
Boarding
8.2
Entertainment
7.1
Overall
8.0
Crew
8.5
Food
7.1
Reviews
1 / 20
10.0
ExcellentJames,Apr 2025
LAX - SFO
Comfort
7.9
Boarding
8.2
Entertainment
7.1
Overall
8.0
Crew
8.5
Food
7.1
Reviews
1 / 20
10.0
ExcellentJames,Apr 2025
LAX - SFO
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.
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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.
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 May 1, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$224 | Average$394 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$259 | Average$388 | FlexibilityNo cancel fee | On-time71% |