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O'Hare Intl

$108+ 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 8/21. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — ORD
Aug 24 — Aug 311
Mon 8/24
Mon 8/31
1 adult, Economy
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Cheap 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 July 25, 2026.

This Kiwi.com deal was found by Cheapflights users on 7/21. 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 9/1110:59 am
EYW
-
ORD
1 stop13h 56m
Multiple Airlines
Mon 9/142:03 pm
ORD
-
EYW
2 stops42h 21m
Multiple Airlines
Deal found 7/21$275
This Kiwi.com deal was found by Cheapflights users on 7/20. 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 9/312:05 pm
EYW
-
ORD
1 stop12h 03m
Multiple Airlines
Sun 9/67:44 pm
ORD
-
EYW
1 stop14h 43m
Multiple Airlines
Deal found 7/20$282
This American Airlines deal was found by Cheapflights users on 7/20. 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 9/34:56 pm
EYW
-
ORD
Nonstop3h 52m
American Airlines
Sun 9/612:08 pm
ORD
-
EYW
Nonstop3h 19m
American Airlines
Deal found 7/20$309
This American Airlines deal was found by Cheapflights users on 7/21. 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 9/3011:30 am
EYW
-
ORD
1 stop7h 37m
American Airlines
Tue 10/69:02 am
ORD
-
EYW
1 stop6h 09m
American Airlines
Deal found 7/21$316
This American Airlines deal was found by Cheapflights users on 7/22. 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 9/121:47 pm
EYW
-
ORD
1 stop6h 51m
American Airlines
Mon 9/146:29 am
ORD
-
EYW
1 stop7h 20m
American Airlines
Deal found 7/22$322
This Kiwi.com deal was found by Cheapflights users on 7/21. 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 9/412:07 pm
EYW
-
ORD
1 stop12h 01m
Multiple Airlines
Mon 9/142:03 pm
ORD
-
EYW
2 stops42h 21m
Multiple Airlines
Deal found 7/21$330

Find 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 July 25, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$275
(Kiwi.com)

One-way from

$108
(Kiwi.com)

Popular in

January

Cheapest in

December

Average price

$329

Good round-trip deal

$446 or less

Good one-way deal

$283 or less
Provider with most accurate pricing for Key West-Chicago O'Hare Intl flight deals.
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Provider most trusted by Cheapflights users for Key West-Chicago O'Hare Intl flights.
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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. 11% potential increase in price ($57 potential increase over avg. RT price).
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Cheapest flight prices on average. 11% potential price decrease ($45 potential savings vs. average RT price).
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Average for round-trip flights in July 2026
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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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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 July 25, 2026.
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

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 9/3

12:05 pm-11:08 pm

1 stop12h 03m

Chicago O'Hare Intl

Sun 9/6

7:44 pm-11:27 am

1 stop14h 43m

$282
Quickest round-trip

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 9/3

4:56 pm-7:48 pm

Nonstop3h 52m

Chicago O'Hare Intl

Sun 9/6

12:08 pm-4:27 pm

Nonstop3h 19m

$309

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 9/3

12:05 pm-11:08 pm

1 stop12h 03m

Chicago O'Hare Intl

Mon 9/7

8:05 am-12:34 pm

2 stops27h 29m

$309

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 9/3

4:56 pm-7:48 pm

Nonstop3h 52m

Chicago O'Hare Intl

Mon 9/7

5:00 am-10:56 am

1 stop4h 56m

$329

Key WestChicago

EYW - ORD

EYWORD

Key West

Fri 9/4

1:50 pm-7:46 pm

1 stop6h 56m

Chicago O'Hare Intl

Mon 9/14

11:50 am-5:55 pm

1 stop5h 05m

$329

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 9/3

11:48 am-6:29 pm

2 stops7h 41m

Chicago O'Hare Intl

Sun 9/6

6:40 am-12:26 pm

1 stop4h 46m

$639
Cheapest one-way
Quickest one-way

Key WestChicago

EYW - ORD

EYWORD

Key West

Tue 12/1

4:05 pm-6:30 pm

Nonstop3h 25m

$279

Key WestChicago

EYW - ORD

EYWORD

Key West

Wed 1/13

12:41 pm-3:30 pm

Nonstop3h 49m

$289

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 1/21

4:05 pm-6:30 pm

Nonstop3h 25m

$289

Key WestChicago

EYW - ORD

EYWORD

Key West

Sat 1/16

6:00 pm-11:50 pm

1 stop6h 50m

$294

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/20

Showing 1-10 of 18 resultsSorted by cheapest first
1
2

Compare providers for flights from Key West to O'Hare Intl

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Key West to O'Hare Intl in July.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Key West-Chicago O'Hare Intl Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Key West-Chicago O'Hare Intl Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Key West-Chicago O'Hare Intl Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Key West-Chicago O'Hare Intl Airport flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Key West-Chicago O'Hare Intl Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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 July 25, 2026.

When flying from Key West to Chicago O'Hare Intl Airport, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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

Airfare is below average for this route at the moment.

Key West to Chicago O'Hare Intl Airport flights typically cost between $341 and $379 in September.
The cheapest round-trip price found within the last 5 days was $275 on Multiple Airlines (Sep 11-Sep 14).

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

AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Key West to Chicago O'Hare Intl Airport trip
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on ORD

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

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

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 July 25, 2026.
Peruse reviews from past customers who have flown with 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.
American Airlines
7.1
Good
11,847 reviews

Boarding

7.5

Overall

7.1

Crew

7.9

Food

6.4

Entertainment

6.8

Comfort

7.2

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

BNA - ORD

My flight was 8 hours delayed, so I missed my connecting flight to Dublin. I understand it’s not the staff’s fault but the lack of sympathy and apology was appalling. I had been sat in the airport since 4am until 3pm and they did not seem understanding. Not good. Need better customer service.
American Airlines
7.1
Good
11,847 reviews
American Airlines
7.1
Good
11,847 reviews

Boarding

7.5

Overall

7.1

Crew

7.9

Food

6.4

Entertainment

6.8

Comfort

7.2

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

BNA - ORD

My flight was 8 hours delayed, so I missed my connecting flight to Dublin. I understand it’s not the staff’s fault but the lack of sympathy and apology was appalling. I had been sat in the airport since 4am until 3pm and they did not seem understanding. Not good. Need better customer service.

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 2 daily outbound flights to Chicago O'Hare Intl from 1 airline.

  • 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 3h 52m. American Airlines provides one of the quickest options available for as low as $309. Airlines will cover a distance of 1253 mi. Generally, flights for this route are nonstop.

  • What is the cheapest airline to fly from Key West to Chicago O'Hare Intl Airport round-trip?

    Currently priced at $329, American Airlines will fly you from Key West to Chicago O'Hare Intl Airport and back. In addition to American Airlines, many other airlines offer competitively priced options for your trip. American Airlines is currently priced 24% 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 Republic Airways (87%), Air New Zealand (82%) or United Airlines (81%) 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 $839 for a flight from Key West to Chicago O'Hare Intl Airport. The cheapest flight overall is $188 while the most popular route, (Key West - Chicago O'Hare Intl) is currently priced at $309.

  • 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.

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
Benton Harbor
Rosemont
Schaumburg
Lake Geneva
Naperville
Oak Brook
Delavan
Oakbrook Terrace
Gurnee
South Holland
Libertyville
Orland Park
Hoffman Estates
Beloit
Downers Grove
Rockford
Racine
Great Lakes
Janesville
Joliet

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Top airline flying from Key West to O'Hare Intl

Discover the top airline 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 July 25, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$329Average$460FlexibilityNo cancel feeOn-time71%

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