HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Illinois

$173+ 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 8/7. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — ORD
Aug 4 — Aug 111
Mon 8/4
Mon 8/11
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

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

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

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 July 30, 2025.

Round-trip from

$269
(Delta)

One-way from

$173
(Mytrip)

Popular in

March

Cheapest in

June

Average price

$358

Good round-trip deal

$415 or less

Good one-way deal

$305 or less
From Key West to Illinois
Search Deals
One-way flight from Key West to Illinois
Search Deals
Highest demand for flights based on searches. 17% potential increase in price ($79 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2025
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

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 July 30, 2025.

This Delta deal was found by Cheapflights users on 7/29. 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.
Wed 9/36:20 pmEYW - ORD
1 stop5h 17mDelta
Mon 9/85:45 amORD - EYW
1 stop6h 20mDelta
Deal found 7/29$269
This Delta deal was found by Cheapflights users on 7/29. 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.
Wed 9/37:00 amEYW - MDW
1 stop7h 36mDelta
Tue 9/96:00 amMDW - EYW
1 stop6h 05mDelta
Deal found 7/29$269
This United Airlines deal was found by Cheapflights users on 7/30. 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 9/53:50 pmEYW - ORD
1 stop8h 35mUnited Airlines
Sun 9/76:00 amORD - EYW
1 stop7h 01mUnited Airlines
Deal found 7/30$299
This Mytrip deal was found by Cheapflights users on 7/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/1410:02 amEYW - ORD
1 stop13h 20mMultiple Airlines
Tue 8/198:12 pmORD - EYW
2 stops16h 11mMultiple Airlines
Deal found 7/29$327
This Delta deal was found by Cheapflights users on 7/28. 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 9/36:20 pmEYW - BMI
1 stop4h 56mDelta
Sat 9/66:00 amBMI - EYW
1 stop6h 05mDelta
Deal found 7/28$348
This American Airlines deal was found by Cheapflights users on 7/30. 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 8/2712:10 pmEYW - ORD
1 stop8h 16mAmerican Airlines
Wed 9/38:20 amORD - EYW
2 stops8h 26mAmerican Airlines
Deal found 7/30$352
This American Airlines deal was found by Cheapflights users on 7/30. 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 10/154:37 pmEYW - PIA
1 stop7h 28mAmerican Airlines
Wed 10/226:01 amPIA - EYW
2 stops10h 15mAmerican Airlines
Deal found 7/30$374
This American Airlines deal was found by Cheapflights users on 7/29. 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.
Wed 9/311:25 amEYW - BMI
2 stops9h 20mAmerican Airlines
Sat 9/67:50 amBMI - EYW
2 stops8h 56mAmerican Airlines
Deal found 7/29$407
This American Airlines deal was found by Cheapflights users on 7/30. 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.
Mon 12/223:10 pmEYW - MLI
1 stop7h 31mAmerican Airlines
Fri 12/2611:18 amMLI - EYW
1 stop5h 17mAmerican Airlines
Deal found 7/30$906

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 July 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

Wed 9/3

6:20 pm-10:37 pm

1 stop5h 17m

Chicago O'Hare Intl

Mon 9/8

5:45 am-1:05 pm

1 stop6h 20m

$269

Key WestChicago

EYW - MDW

EYWMDW

Key West

Wed 9/3

7:00 am-1:36 pm

1 stop7h 36m

Chicago Midway

Wed 9/10

6:00 am-1:05 pm

1 stop6h 05m

$269

Key WestChicago

EYW - ORD

EYWORD

Key West

Fri 9/5

3:50 pm-11:25 pm

1 stop8h 35m

Chicago O'Hare Intl

Sun 9/7

6:00 am-2:01 pm

1 stop7h 01m

$299

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 8/14

10:02 am-10:22 pm

1 stop13h 20m

Chicago O'Hare Intl

Tue 8/19

8:12 pm-1:23 pm

2 stops16h 11m

$327

Key WestBloomington

EYW - BMI

EYWBMI

Key West

Wed 9/3

6:20 pm-10:16 pm

1 stop4h 56m

Bloomington-Normal

Sat 9/6

6:00 am-1:05 pm

1 stop6h 05m

$348

Key WestChicago

EYW - ORD

EYWORD

Key West

Wed 8/27

12:10 pm-7:26 pm

1 stop8h 16m

Chicago O'Hare Intl

Wed 9/3

8:20 am-5:46 pm

2 stops8h 26m

$352

Key WestPeoria

EYW - PIA

EYWPIA

Key West

Wed 10/15

4:37 pm-11:05 pm

1 stop7h 28m

Greater Peoria

Wed 10/22

7:00 am-7:22 pm

2 stops11h 22m

$374

Key WestBloomington

EYW - BMI

EYWBMI

Key West

Wed 9/3

11:25 am-7:45 pm

2 stops9h 20m

Bloomington-Normal

Sat 9/6

7:50 am-5:46 pm

2 stops8h 56m

$407

Key WestMoline

EYW - MLI

EYWMLI

Key West

Mon 12/22

3:10 pm-9:41 pm

1 stop7h 31m

Moline Quad-City

Fri 12/26

11:18 am-5:35 pm

1 stop5h 17m

$906

Key WestBloomington

EYW - BMI

EYWBMI

Key West

Thu 8/7

3:01 pm-7:26 pm

1 stop5h 25m

$173

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

Showing 1-10 of 25 results
1
2
3

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 July 30, 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 July 30, 2025.
Peruse reviews from past customers who have flown with Alaska Airlines, Delta, and United 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.
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Crew

8.5

Food

7.1

Boarding

8.1

Comfort

7.8

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Crew

8.5

Food

7.1

Boarding

8.1

Comfort

7.8

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Delta
8.0
Very good
7,980 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Crew

8.5

Food

7.1

Boarding

8.1

Comfort

7.8

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
United Airlines
7.4
Good
8,896 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Crew

8.5

Food

7.1

Boarding

8.1

Comfort

7.8

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Crew

8.5

Food

7.1

Boarding

8.1

Comfort

7.8

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Allegiant Air
7.2
Good
703 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Crew

8.5

Food

7.1

Boarding

8.1

Comfort

7.8

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.

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 Allegiant Air, with whom users have recently found tickets for as low as $173. 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 - Bloomington-Normal 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: Qatar Airways (77%), American Airlines (67%), Envoy Air( 67%).

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

    The cheapest flight price from Key West to Illinois is $278. On average you can expect to pay $567. The most popular route, (Key West - Chicago O'Hare Intl), can usually be booked for $269.

  • 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Key West to Illinois

See prices for flight routes from nearby airports that may be better suited for you.
Fort Lauderdale to Newark flights
Fort Lauderdale to LaGuardia flights
Miami to Newark flights
Miami to LaGuardia flights
Miami to John F Kennedy Intl flights
Orlando to John F Kennedy Intl flights
Orlando to Newark flights
Fort Lauderdale to John F Kennedy Intl flights
Fort Lauderdale to Las Vegas flights
Orlando to LaGuardia flights
Tampa to John F Kennedy Intl flights
Tampa to Newark flights
Orlando to Seattle flights
West Palm Beach to John F Kennedy Intl flights
Orlando to Las Vegas flights
Tampa to LaGuardia flights
Orlando to Dallas/Fort Worth flights
Tampa to Seattle flights
Fort Lauderdale to Dallas/Fort Worth flights
Tampa to Las Vegas flights
Fort Lauderdale to O'Hare Intl flights
Fort Lauderdale to Los Angeles flights
Fort Lauderdale to Atlanta flights
Miami to O'Hare Intl flights
Miami to Dallas/Fort Worth flights
Tampa to Denver flights
Orlando to O'Hare Intl flights
Orlando to Denver flights
Miami to Los Angeles flights
Fort Lauderdale to Denver flights
Orlando to Los Angeles flights
Tampa to Boston flights
Fort Lauderdale to Boston flights
Miami to Denver flights
West Palm Beach to LaGuardia flights
West Palm Beach to Newark flights
Orlando to Boston flights
Tampa to O'Hare Intl flights
Miami to Atlanta flights
Miami to Las Vegas flights
Tampa to Sky Harbor Intl flights
Jacksonville to Newark flights
Jacksonville to John F Kennedy Intl flights
Fort Lauderdale to Baltimore flights
West Palm Beach to Dallas/Fort Worth flights
Tampa to Dulles Intl flights
Orlando to Islip flights
Miami to Boston flights
Fort Lauderdale to Philadelphia flights
West Palm Beach to Boston flights

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 July 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$224Average$394FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$259Average$377FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.