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O'Hare Intl

$113+ 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 10/8. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — ORD
Aug 24 — Aug 311
Sun 8/24
Sun 8/31
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 August 19, 2025.

Round-trip from

$289
(United Airlines)

One-way from

$113
(Kiwi.com)

Popular in

March

Cheapest in

December

Average price

$358

Good round-trip deal

$199 or less

Good one-way deal

$373 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. 25% potential increase in price ($155 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($24 potential savings vs. average RT price).
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Average for round-trip flights in August 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 August 19, 2025.

This United Airlines deal was found by Cheapflights users on 8/18. 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 stop7h 06mUnited Airlines
Tue 9/96:00 amORD - EYW
1 stop7h 01mUnited Airlines
Deal found 8/18$289
This Delta deal was found by Cheapflights users on 8/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/166:10 pmEYW - ORD
1 stop5h 04mDelta
Tue 9/239:50 amORD - EYW
1 stop6h 25mDelta
Deal found 8/17$320
This American Airlines deal was found by Cheapflights users on 8/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/163:45 pmEYW - ORD
1 stop8h 27mAmerican Airlines
Tue 9/239:51 amORD - EYW
2 stops8h 08mAmerican Airlines
Deal found 8/17$328
This American Airlines deal was found by Cheapflights users on 8/18. 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.
Sat 11/158:00 amEYW - ORD
1 stop7h 14mAmerican Airlines
Sun 11/168:30 amORD - EYW
Nonstop3h 21mAmerican Airlines
Deal found 8/18$354
This American Airlines deal was found by Cheapflights users on 8/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2312:10 pmEYW - ORD
1 stop8h 16mAmerican Airlines
Sat 8/308:35 amORD - EYW
2 stops9h 32mAmerican Airlines
Deal found 8/17$415
This American Airlines deal was found by Cheapflights users on 8/18. 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.
Fri 9/51:59 pmEYW - ORD
1 stop5h 14mAmerican Airlines
Tue 9/99:51 amORD - EYW
2 stops8h 08mAmerican Airlines
Deal found 8/18$419
This Delta deal was found by Cheapflights users on 8/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/232:00 pmEYW - ORD
1 stop6h 09mDelta
Sat 8/301:30 pmORD - EYW
1 stop5h 42mDelta
Deal found 8/17$435
This American Airlines deal was found by Cheapflights users on 8/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/295:02 pmEYW - ORD
1 stop6h 47mAmerican Airlines
Mon 9/15:20 amORD - EYW
1 stop5h 26mAmerican Airlines
Deal found 8/17$457

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 August 19, 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

Fri 9/5

3:50 pm-9:56 pm

1 stop7h 06m

Chicago O'Hare Intl

Tue 9/9

6:00 am-2:01 pm

1 stop7h 01m

$289

Key WestChicago

EYW - ORD

EYWORD

Key West

Tue 9/16

6:10 pm-10:14 pm

1 stop5h 04m

Chicago O'Hare Intl

Tue 9/23

9:50 am-5:15 pm

1 stop6h 25m

$320

Key WestChicago

EYW - ORD

EYWORD

Key West

Tue 9/16

3:45 pm-11:12 pm

1 stop8h 27m

Chicago O'Hare Intl

Tue 9/23

9:51 am-6:59 pm

2 stops8h 08m

$328

Key WestChicago

EYW - ORD

EYWORD

Key West

Sat 11/15

8:00 am-2:14 pm

1 stop7h 14m

Chicago O'Hare Intl

Sun 11/16

8:30 am-12:51 pm

Nonstop3h 21m

$354

Key WestChicago

EYW - ORD

EYWORD

Key West

Fri 9/5

1:59 pm-6:13 pm

1 stop5h 14m

Chicago O'Hare Intl

Tue 9/9

9:51 am-6:59 pm

2 stops8h 08m

$419

Key WestChicago

EYW - ORD

EYWORD

Key West

Fri 8/29

5:02 pm-10:49 pm

1 stop6h 47m

Chicago O'Hare Intl

Mon 9/1

5:20 am-11:46 am

1 stop5h 26m

$457

Key WestChicago

EYW - ORD

EYWORD

Key West

Fri 8/29

12:50 pm-7:09 pm

1 stop7h 19m

Chicago O'Hare Intl

Sun 8/31

7:00 am-12:58 pm

1 stop4h 58m

$457

Key WestChicago

EYW - ORD

EYWORD

Key West

Mon 11/24

12:00 pm-6:05 pm

1 stop7h 05m

Chicago O'Hare Intl

Sat 11/29

8:30 am-12:51 pm

Nonstop3h 21m

$461

Key WestChicago

EYW - ORD

EYWORD

Key West

Wed 10/8

10:02 am-12:45 pm

1 stop27h 43m

$113

Key WestChicago

EYW - ORD

EYWORD

Key West

Tue 2/10

2:25 pm-11:42 pm

1 stop10h 17m

$135

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/17

Showing 1-10 of 16 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 August 19, 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.

How much does it cost to fly round-trip from Key West to Chicago O'Hare Intl Airport?

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 August 19, 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
8,922 reviews

Entertainment

7.1

Crew

8.1

Food

6.6

Boarding

7.7

Comfort

7.3

Overall

7.4

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
8,922 reviews
United Airlines
7.4
Good
8,922 reviews

Entertainment

7.1

Crew

8.1

Food

6.6

Boarding

7.7

Comfort

7.3

Overall

7.4

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
8,922 reviews

Entertainment

7.1

Crew

8.1

Food

6.6

Boarding

7.7

Comfort

7.3

Overall

7.4

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.

  • How long is the flight from Key West to Chicago O'Hare Intl Airport?

    A quick flight from Key West to Chicago O'Hare Intl Airport can take about 5h 04m. United Airlines provides one of the quickest options available for as low as $320. Airlines will cover a distance of 1253 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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 49% 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 (57%), Qatar Airways (57%) or Envoy Air (57%) 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 $416 for a flight from Key West to Chicago O'Hare Intl Airport. The cheapest flight overall is $199 while the most popular route, (Key West - Chicago O'Hare Intl) is currently priced at $289.

  • 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
Beloit
Hoffman Estates
Skokie
Des Plaines
Elgin
Gurnee
Arlington Heights
Racine
Rockford
Great Lakes
Orland Park
Merrillville
Naperville
Waukegan
Elk Grove Village
Downers Grove
Tinley Park
Evanston

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Alternative routes for Key West to O'Hare Intl

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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 August 19, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$224Average$394FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$259Average$398FlexibilityNo cancel feeOn-time71%

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