HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Illinois

$50+ 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 3/5. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — ORD
Mar 3 — Mar 101
Tue 3/3
Tue 3/10
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

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 February 1, 2026.

This Expedia deal was found by Cheapflights users on 2/1. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/52:25 pm
EYW
-
ORD
1 stop5h 46m
Spirit Airlines
Sun 3/85:15 am
ORD
-
EYW
1 stop7h 15m
Spirit Airlines
Deal found 2/1$145
This Kiwi.com deal was found by Cheapflights users on 2/1. 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.
Thu 3/59:46 am
EYW
-
ORD
1 stop24h 20m
Multiple Airlines
Sun 3/88:16 pm
ORD
-
EYW
2 stops15h 10m
Multiple Airlines
Deal found 2/1$225
This Kiwi.com deal was found by Cheapflights users on 1/31. 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.
Sat 2/710:49 am
EYW
-
ORD
1 stop7h 09m
Multiple Airlines
Sat 2/144:42 pm
ORD
-
EYW
2 stops15h 24m
Multiple Airlines
Deal found 1/31$241
This American Airlines deal was found by Cheapflights users on 1/30. 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.
Thu 4/96:45 pm
EYW
-
ORD
Nonstop3h 52m
American Airlines
Mon 4/131:51 pm
ORD
-
EYW
Nonstop3h 24m
American Airlines
Deal found 1/30$249
This Kiwi.com deal was found by Cheapflights users on 1/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/2211:51 am
EYW
-
ORD
2 stops26h 09m
Multiple Airlines
Sun 4/268:24 pm
ORD
-
EYW
1 stop11h 45m
Multiple Airlines
Deal found 1/30$254
This United Airlines deal was found by Cheapflights users on 1/31. 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.
Thu 2/266:35 pm
EYW
-
ORD
1 stop6h 08m
United Airlines
Mon 3/210:44 am
ORD
-
EYW
Nonstop3h 16m
United Airlines
Deal found 1/31$259
This Kiwi.com deal was found by Cheapflights users on 1/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/3112:25 pm
EYW
-
ORD
1 stop8h 26m
Multiple Airlines
Mon 4/67:20 am
ORD
-
EYW
1 stop27h 10m
Multiple Airlines
Deal found 1/30$277
This American Airlines deal was found by Cheapflights users on 1/30. 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.
Tue 3/316:49 pm
EYW
-
ORD
Nonstop3h 47m
American Airlines
Mon 4/68:20 am
ORD
-
EYW
Nonstop3h 34m
American Airlines
Deal found 1/30$286
This Delta deal was found by Cheapflights users on 1/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/145:56 pm
EYW
-
MDW
1 stop5h 35m
Delta
Wed 2/1812:45 pm
MDW
-
EYW
1 stop5h 57m
Delta
Deal found 1/30$364
This United Airlines deal was found by Cheapflights users on 1/31. 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 10/272:30 pm
EYW
-
PIA
2 stops10h 44m
United Airlines
Sat 10/315:20 pm
PIA
-
EYW
1 stop21h 46m
United Airlines
Deal found 1/31$453
This Delta deal was found by Cheapflights users on 1/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/247:10 am
EYW
-
MDW
1 stop5h 49m
Delta
Tue 3/312:45 pm
MDW
-
EYW
1 stop5h 57m
Delta
Deal found 1/30$454
This Delta deal was found by Cheapflights users on 1/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/97:30 am
EYW
-
MDW
1 stop5h 32m
Delta
Mon 4/1310:43 am
MDW
-
EYW
1 stop5h 40m
Delta
Deal found 1/30$484

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 February 1, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$249
(American Airlines)

One-way from

$88
(Kiwi.com)

Good round-trip deal

$403 or less

Good one-way deal

$304 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 February 1, 2026.
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

Thu 3/5

2:25 pm-7:11 pm

1 stop5h 46m

Chicago O'Hare Intl

Sun 3/8

5:15 am-1:30 pm

1 stop7h 15m

$145

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 3/5

6:53 pm-9:40 pm

Nonstop3h 47m

Chicago O'Hare Intl

Sun 3/8

1:53 pm-6:19 pm

Nonstop3h 26m

$249

Key WestChicago

EYW - ORD

EYWORD

Key West

Wed 4/22

6:45 pm-9:37 pm

Nonstop3h 52m

Chicago O'Hare Intl

Sun 4/26

8:10 am-12:37 pm

Nonstop3h 27m

$249

Key WestChicago

EYW - ORD

EYWORD

Key West

Tue 2/24

6:54 pm-9:40 pm

Nonstop3h 46m

Chicago O'Hare Intl

Tue 3/3

1:59 pm-6:24 pm

Nonstop3h 25m

$249

Key WestChicago

EYW - ORD

EYWORD

Key West

Wed 4/22

11:51 am-1:00 pm

2 stops26h 09m

Chicago O'Hare Intl

Sun 4/26

8:24 pm-9:09 am

1 stop11h 45m

$254

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 2/26

6:35 pm-11:43 pm

1 stop6h 08m

Chicago O'Hare Intl

Mon 3/2

10:44 am-3:00 pm

Nonstop3h 16m

$259

Key WestChicago

EYW - MDW

EYWMDW

Key West

Tue 2/24

7:10 am-11:59 am

1 stop5h 49m

Chicago Midway

Tue 3/3

12:45 pm-7:42 pm

1 stop5h 57m

$454

Key WestChicago

EYW - MDW

EYWMDW

Key West

Thu 4/9

7:30 am-12:02 pm

1 stop5h 32m

Chicago Midway

Mon 4/13

10:43 am-5:23 pm

1 stop5h 40m

$484

Key WestMoline

EYW - MLI

EYWMLI

Key West

Sat 2/14

4:34 pm-11:43 am

2 stops20h 09m

Moline Quad-City

Wed 2/18

3:52 pm-10:09 pm

1 stop5h 17m

$498

Key WestChicago

EYW - MDW

EYWMDW

Key West

Tue 3/31

7:30 am-12:02 pm

1 stop5h 32m

Chicago Midway

Mon 4/6

12:47 pm-7:41 pm

1 stop5h 54m

$529

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/1

Showing 1-10 of 40 results
1
2
3
4

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 February 1, 2026.

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.

Weekly flight availability from Key West to Illinois

Explore weekly flight availability from Key West to Illinois. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated February 1, 2026.

The most flights from EYW to USIL are scheduled on a Saturday (7 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (3 on average).

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 February 1, 2026.
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
9,222 reviews

Overall

7.4

Crew

8.1

Comfort

7.3

Food

6.6

Boarding

7.7

Entertainment

7.1

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
9,222 reviews
United Airlines
7.4
Good
9,222 reviews

Overall

7.4

Crew

8.1

Comfort

7.3

Food

6.6

Boarding

7.7

Entertainment

7.1

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
11,211 reviews
United Airlines
7.4
Good
9,222 reviews

Overall

7.4

Crew

8.1

Comfort

7.3

Food

6.6

Boarding

7.7

Entertainment

7.1

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, United Airlines, and Delta fly from Key West to Illinois in about 3h 49m. The time it takes to get you to your destination can typically vary by up to 2h 19m. 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 (85%), Republic Airways (84%), Air New Zealand( 80%).

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

    The cheapest flight price from Key West to Illinois is $248. On average you can expect to pay $675. 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

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 John F Kennedy Intl flights
Miami to John F Kennedy Intl flights
Orlando to John F Kennedy Intl flights
Miami to LaGuardia flights
Fort Lauderdale to Newark flights
Fort Lauderdale to LaGuardia flights
Miami to Newark flights
Orlando to Las Vegas flights
Orlando to LaGuardia flights
Fort Lauderdale to Las Vegas flights
Orlando to Newark flights
Orlando to Dulles Intl flights
Tampa to John F Kennedy Intl flights
West Palm Beach to Newark flights
Orlando to Seattle flights
Miami to Denver flights
Tampa to LaGuardia flights
Orlando to Los Angeles flights
Orlando to Denver flights
Tampa to Newark flights
Tampa to Las Vegas flights
Tampa to Denver flights
West Palm Beach to John F Kennedy Intl flights
Tampa to Seattle flights
Tampa to Atlanta flights
Miami to Las Vegas flights
Orlando to Reagan-National flights
Miami to Los Angeles flights
Orlando to Baltimore flights
Tampa to Boston flights
Fort Lauderdale to Atlanta flights
Fort Lauderdale to Denver flights
Orlando to O'Hare Intl flights
Fort Lauderdale to Detroit flights
Miami to Atlanta flights
West Palm Beach to LaGuardia flights
Orlando to Dallas/Fort Worth flights
Orlando to Sky Harbor Intl flights
Orlando to New Orleans flights
Jacksonville to John F Kennedy Intl flights
Miami to Dallas/Fort Worth flights
Fort Lauderdale to Los Angeles flights
West Palm Beach to Atlanta flights
Tampa to Hobby flights
Tampa to Los Angeles flights
Fort Lauderdale to Dallas/Fort Worth flights
Tampa to Sky Harbor Intl flights
Orlando to Boston flights
Fort Lauderdale to Baltimore flights
Orlando to San Francisco 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 February 1, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$249Average$364FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$309Average$457FlexibilityNo 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.