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O'Hare Intl

$112+ Cheap flights from Key West (EYW) to O'Hare Intl (ORD)

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 1/10. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — ORD
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
1 adult, Economy
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Cheap flight deals from Key West to O'Hare Intl

Discover tips and strategies to find the most affordable flight options for your journey from Key West (EYW) to O'Hare Intl (ORD). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated September 17, 2025.

Round-trip from

$244
(Kiwi.com)

One-way from

$112
(Expedia)

Popular in

March

Cheapest in

December

Average price

$456

Good round-trip deal

$424 or less

Good one-way deal

$304 or less
From Key West to Chicago O'Hare Intl
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One-way flight from Key West to Chicago O'Hare Intl
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Highest demand for flights based on searches. 24% potential increase in price ($147 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($23 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Key West to Chicago O'Hare Intl.
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Price to beat on a one-way flight from Key West to Chicago O'Hare Intl.
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Find flight deals from Key West to O'Hare Intl

Cheapest flights from Key West to O'Hare Intl
Explore the most affordable flight options available from Key West to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 17, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/16. 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 10/238:55 amEYW - ORD
1 stop9h 58mMultiple Airlines
Tue 10/281:56 pmORD - EYW
1 stop19h 11mMultiple Airlines
Deal found 9/16$244
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Fri 9/268:47 amEYW - ORD
1 stop11h 57mMultiple Airlines
Tue 9/305:46 pmORD - EYW
1 stop15h 21mMultiple Airlines
Deal found 9/15$263
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 10/2111:45 amEYW - ORD
2 stops13h 08mMultiple Airlines
Wed 10/295:28 pmORD - EYW
1 stop13h 47mMultiple Airlines
Deal found 9/16$268
This Delta deal was found by Cheapflights users on 9/16. 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 10/227:40 amEYW - ORD
1 stop5h 36mDelta
Mon 10/275:20 amORD - EYW
1 stop5h 07mDelta
Deal found 9/16$269
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 10/238:55 amEYW - ORD
1 stop9h 58mMultiple Airlines
Fri 10/245:50 pmORD - EYW
2 stops15h 17mMultiple Airlines
Deal found 9/16$272
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 10/28:55 amEYW - ORD
1 stop11h 49mMultiple Airlines
Sun 10/58:49 pmORD - EYW
1 stop10h 26mMultiple Airlines
Deal found 9/17$273
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 10/2310:59 amEYW - ORD
2 stops13h 07mMultiple Airlines
Sun 10/266:54 pmORD - EYW
1 stop12h 21mMultiple Airlines
Deal found 9/16$275
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 10/2510:47 amEYW - ORD
1 stop5h 58mMultiple Airlines
Tue 10/281:56 pmORD - EYW
1 stop19h 11mMultiple Airlines
Deal found 9/16$276
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 10/110:47 amEYW - ORD
2 stops24h 44mMultiple Airlines
Sun 10/56:58 pmORD - EYW
1 stop12h 17mMultiple Airlines
Deal found 9/15$284
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 9/258:55 amEYW - ORD
2 stops15h 25mMultiple Airlines
Tue 9/305:46 pmORD - EYW
1 stop15h 21mMultiple Airlines
Deal found 9/15$286
This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
Fri 10/2411:11 amEYW - ORD
2 stops13h 28mMultiple Airlines
Wed 10/295:28 pmORD - EYW
1 stop13h 47mMultiple Airlines
Deal found 9/16$291

Cheapflights Fare Finder

 
Customize your flight search to find flights from Key West to O'Hare Intl 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 September 17, 2025.
Use the filters below to find and compare flights from Key West to Chicago O'Hare Intl Airport that are best for you.

Fly from

Key West

Fly to

O'Hare Intl

Route

Depart

Return

Price

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 10/23

10:59 am-10:08 am

1 stop24h 09m

Chicago O'Hare Intl

Thu 10/30

6:54 pm-8:15 am

1 stop12h 21m

$244

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 10/23

8:55 am-5:53 pm

1 stop9h 58m

Chicago O'Hare Intl

Sun 10/26

6:54 pm-8:15 am

1 stop12h 21m

$244

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 10/23

8:55 am-5:53 pm

1 stop9h 58m

Chicago O'Hare Intl

Tue 10/28

1:56 pm-10:07 am

1 stop19h 11m

$244

Key WestChicago

EYW - ORD

EYWORD

Key West

Tue 10/21

11:45 am-10:08 am

1 stop23h 23m

Chicago O'Hare Intl

Wed 10/29

5:28 pm-8:15 am

1 stop13h 47m

$244

Key WestChicago

EYW - ORD

EYWORD

Key West

Wed 10/22

10:47 am-10:08 am

1 stop24h 21m

Chicago O'Hare Intl

Thu 10/30

6:54 pm-8:15 am

1 stop12h 21m

$244

Key WestChicago

EYW - ORD

EYWORD

Key West

Tue 10/21

11:45 am-10:08 am

1 stop23h 23m

Chicago O'Hare Intl

Sat 10/25

6:58 pm-8:15 am

1 stop12h 17m

$244

Key WestChicago

EYW - ORD

EYWORD

Key West

Fri 10/24

8:55 am-6:46 pm

1 stop10h 51m

Chicago O'Hare Intl

Sun 10/26

6:54 pm-8:15 am

1 stop12h 21m

$244

Key WestChicago

EYW - ORD

EYWORD

Key West

Tue 10/21

7:40 am-12:16 pm

1 stop5h 36m

Chicago O'Hare Intl

Tue 10/28

1:26 pm-8:06 pm

1 stop5h 40m

$269

Key WestChicago

EYW - ORD

EYWORD

Key West

Fri 10/24

6:17 pm-11:58 pm

1 stop6h 41m

Chicago O'Hare Intl

Mon 10/27

6:45 am-1:02 pm

1 stop5h 17m

$269

Key WestChicago

EYW - ORD

EYWORD

Key West

Tue 10/21

7:40 am-12:16 pm

1 stop5h 36m

Chicago O'Hare Intl

Mon 10/27

6:45 am-1:02 pm

1 stop5h 17m

$269

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 20 results
1
2

The best insider tips for Key West to Chicago O'Hare Intl Airport flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
Cheapflights partnered with top experts to bring you the best recommendations for your Key West to Chicago O'Hare Intl Airport trip
Airports
EYW

Security lines at EYW are usually short, rarely exceeding 15-20 minutes. Arrive 1.5 hours early to be safe.

Read more about EYWby Terry Ward
ORD

For quick city access from ORD, take the 'L' train. It's often faster than taxis due to Chicago traffic.

Read more about ORDby Ramsey Qubein
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on ORD

Ramsey Qubein

Ramsey Qubein

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more
Terry Ward

Terry Ward

Expert on EYW

Terry Ward

Terry Ward

Florida-based travel writer and journalist Terry Ward lives in Tampa and has enjoyed watching the city and its hotel offerings grow to match the area's spectacular Gulf of Mexico beaches.

Read more

Best time to book a flight from Key West to O'Hare Intl

Have a flexible travel schedule? Discover the best time to fly to O'Hare Intl 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 Chicago O'Hare Intl Airport

What is the cheapest time of day to fly from EYW to ORD?

Find hourly flight availability from Key West to O'Hare Intl. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 17, 2025.

It’s typically best to fly out from Key West to Chicago O'Hare Intl Airport at noon. Doing so could potentially save you 30% on the flight price compared to flying in the morning, which is usually more expensive.

Reviews of airlines servicing O'Hare Intl

Get insights into the airlines that provide service to O'Hare Intl. 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 O'Hare Intl. Reviews last updated September 17, 2025.
Peruse reviews from past customers who have flown with United Airlines and American Airlines from Key West to Chicago O'Hare Intl Airport to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
8,924 reviews

Entertainment

7.1

Overall

7.4

Food

6.6

Crew

8.1

Comfort

7.3

Boarding

7.7

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
8,924 reviews
United Airlines
7.4
Good
8,924 reviews

Entertainment

7.1

Overall

7.4

Food

6.6

Crew

8.1

Comfort

7.3

Boarding

7.7

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
10,000 reviews
United Airlines
7.4
Good
8,924 reviews

Entertainment

7.1

Overall

7.4

Food

6.6

Crew

8.1

Comfort

7.3

Boarding

7.7

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 O'Hare Intl. 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 Chicago O'Hare Intl?

    Located just 2.6 mi from the city center, Key West is the airport most travelers will use when flying to Chicago O'Hare Intl from Key West. Booking flights from Key West (EYW) to Chicago O'Hare Intl should be relatively easy as there are 0 daily outbound flights to Chicago O'Hare Intl from 2 different airlines.

  • What are the cheapest airlines flying from Key West to Chicago O'Hare Intl Airport round-trip?

    Currently priced at $224, United Airlines will fly you from Key West to Chicago O'Hare Intl Airport and back. In addition to United Airlines, many other airlines offer competitively priced options for your trip. Check Cheapflights for deals on American Airlines for as low as $259. United Airlines is currently priced 50% below the average price you’ll pay for this route.

  • What are the most reliable airlines from Key West to Chicago O'Hare Intl Airport?

    Consider American Airlines (33%), Qatar Airways (33%) or Envoy Air (33%) when booking your flight. These represent the most reliable airlines when flying from Key West to Chicago O'Hare Intl Airport.

  • What are the cheapest flights from Key West to Chicago O'Hare Intl Airport?

    On average you can expect to pay $417 for a flight from Key West to Chicago O'Hare Intl Airport. The cheapest flight overall is $178 while the most popular route, (Key West - Chicago O'Hare Intl) is currently priced at $269.

  • Can I find deals for flights from Key West to O'Hare Intl that include hotel bookings?

    Yes. In addition to deals on Key West to O'Hare Intl flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Key West to O'Hare Intl?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Key West to O'Hare Intl.

  • Can I find deals for business class flights from Key West to O'Hare Intl?

    Yes. Cheapflights offers flight deals from Key West to O'Hare Intl 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 Chicago O'Hare Intl Airport?

    Currently, August is the cheapest month in which you can book a flight from Key West to Chicago O'Hare Intl Airport (average of $245). Flying from Key West to Chicago O'Hare Intl Airport 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

Traveling to a place near Chicago O'Hare Intl Airport?

Book flights to Chicago O'Hare Intl Airport if you plan to visit one of these locations
Schaumburg
Rosemont
Skokie
Gurnee
Hoffman Estates
Des Plaines
Elgin
Arlington Heights
Orland Park
Beloit
Racine
Rockford
Oak Brook
Elk Grove Village
Downers Grove
Naperville
Evanston
Merrillville
Bridgeview
Warrenville

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Key West to O'Hare Intl

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 O'Hare Intl

Discover the top 2 airlines that operate flights from Key West to O'Hare Intl. 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 September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$224Average$394FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$259Average$398FlexibilityNo cancel feeOn-time71%

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