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$117+ 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 4/17. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — ORD
Apr 2 — Apr 91
Wed 4/2
Wed 4/9
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 March 28, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$289
(United Airlines)

One-way from

$117
(Mytrip)

Popular in

July

Cheapest in

August

Average price

$473

Good round-trip deal

$419 or less

Good one-way deal

$338 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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High demand for flights, 6% potential price rise
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Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in March 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 March 28, 2025.

This United Airlines deal was found by Cheapflights users on 3/27. 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 4/114:04 pmEYW - ORD
Nonstop3h 35mUnited Airlines
Tue 4/1510:59 amORD - EYW
Nonstop3h 05mUnited Airlines
Deal found 3/27$289
This American Airlines deal was found by Cheapflights users on 3/26. 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 5/12:17 pmEYW - ORD
1 stop7h 23mAmerican Airlines
Mon 5/58:05 amORD - EYW
Nonstop3h 14mAmerican Airlines
Deal found 3/26$319
This Delta deal was found by Cheapflights users on 3/26. 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 5/13:00 pmEYW - ORD
1 stop6h 50mDelta
Mon 5/57:05 amORD - EYW
1 stop6h 00mDelta
Deal found 3/26$329
This Delta deal was found by Cheapflights users on 3/26. 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 5/17:00 amEYW - MDW
1 stop6h 03mDelta
Mon 5/56:04 amMDW - EYW
1 stop7h 01mDelta
Deal found 3/26$329
This Mytrip deal was found by Cheapflights users on 3/27. 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 3/274:23 pmEYW - ORD
3 stops32h 36mMultiple Airlines
Mon 3/316:45 amORD - EYW
1 stop25h 32mMultiple Airlines
Deal found 3/27$801

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 March 28, 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

Fri 4/11

4:04 pm-6:39 pm

Nonstop3h 35m

Chicago O'Hare Intl

Tue 4/15

10:59 am-3:04 pm

Nonstop3h 05m

$289

Key WestChicago

EYW - ORD

EYWORD

Key West

Fri 5/2

3:06 pm-9:21 pm

1 stop7h 15m

Chicago O'Hare Intl

Mon 5/5

8:05 am-12:19 pm

Nonstop3h 14m

$319

Key WestChicago

EYW - MDW

EYWMDW

Key West

Thu 5/1

7:00 am-12:03 pm

1 stop6h 03m

Chicago Midway

Mon 5/5

6:04 am-2:05 pm

1 stop7h 01m

$329

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 6/19

7:10 am-5:55 pm

2 stops11h 45m

Chicago O'Hare Intl

Sun 6/22

9:00 am-7:40 pm

2 stops9h 40m

$1,333

Key WestChicago

EYW - RFD

EYWRFD

Key West

Thu 4/17

9:03 am-8:08 am

1 stop24h 05m

$117

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 4/17

12:56 pm-3:33 pm

Nonstop3h 37m

$159

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 4/17

9:03 am-6:13 pm

2 stops10h 10m

$161

Key WestChicago

EYW - MDW

EYWMDW

Key West

Thu 4/17

6:13 pm-10:22 pm

1 stop5h 09m

$200

Key WestChicago

EYW - MDW

EYWMDW

Key West

Sun 6/8

8:53 am-2:03 pm

2 stops30h 10m

$205

Key WestChicago

EYW - ORD

EYWORD

Key West

Sat 6/7

6:25 pm-11:17 pm

1 stop5h 52m

$240

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/27

Showing 1-10 of 11 results
1
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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 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 $323). 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 March 28, 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 March 28, 2025.
Delta
8.0
Very good
7,897 reviews

Entertainment

7.9

Overall

8.0

Comfort

8.0

Food

7.3

Boarding

8.2

Crew

8.5

Reviews

1 / 20
2.0
Mediocre

Santiago,Apr 2024

MCO - ATL

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Delta
8.0
Very good
7,897 reviews
Delta
8.0
Very good
7,897 reviews

Entertainment

7.9

Overall

8.0

Comfort

8.0

Food

7.3

Boarding

8.2

Crew

8.5

Reviews

1 / 20
2.0
Mediocre

Santiago,Apr 2024

MCO - ATL

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
United Airlines
7.4
Good
8,603 reviews
Delta
8.0
Very good
7,897 reviews

Entertainment

7.9

Overall

8.0

Comfort

8.0

Food

7.3

Boarding

8.2

Crew

8.5

Reviews

1 / 20
2.0
Mediocre

Santiago,Apr 2024

MCO - ATL

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Allegiant Air
7.3
Good
731 reviews
Delta
8.0
Very good
7,897 reviews

Entertainment

7.9

Overall

8.0

Comfort

8.0

Food

7.3

Boarding

8.2

Crew

8.5

Reviews

1 / 20
2.0
Mediocre

Santiago,Apr 2024

MCO - ATL

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,897 reviews

Entertainment

7.9

Overall

8.0

Comfort

8.0

Food

7.3

Boarding

8.2

Crew

8.5

Reviews

1 / 20
2.0
Mediocre

Santiago,Apr 2024

MCO - ATL

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

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 $117. 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 - Chicago Greater Rockford 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: Republic Airways (89%), Air New Zealand (86%), United Airlines( 84%).

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

    The cheapest flight price from Key West to Illinois is $259. On average you can expect to pay $509. The most popular route, (Key West - Chicago O'Hare Intl), can usually be booked for $289.

  • 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 $323). 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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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 March 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$224Average$379FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$239Average$388FlexibilityNo cancel feeOn-time71%
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