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O'Hare Intl

$90+ 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 2/5. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — ORD
Feb 7 — Feb 141
Sat 2/7
Sat 2/14
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 January 8, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$174
(Kiwi.com)

One-way from

$90
(Kiwi.com)

Popular in

March

Cheapest in

December

Average price

$289

Good round-trip deal

$413 or less

Good one-way deal

$352 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. 20% potential increase in price ($104 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($27 potential savings vs. average RT price).
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Average for round-trip flights in January 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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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 January 8, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/6. 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 1/293:46 pmEYW - ORD
1 stop19h 49mMultiple Airlines
Wed 2/412:44 pmORD - EYW
1 stop19h 22mMultiple Airlines
Deal found 1/6$174
This Super.com deal was found by Cheapflights users on 1/6. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/302:25 pmEYW - ORD
1 stop6h 13mSpirit Airlines
Sun 2/15:15 amORD - EYW
1 stop5h 41mSpirit Airlines
Deal found 1/6$188
This Kiwi.com deal was found by Cheapflights users on 1/6. 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 1/301:06 pmEYW - ORD
1 stop28h 34mMultiple Airlines
Sun 2/14:43 pmORD - EYW
1 stop15h 26mMultiple Airlines
Deal found 1/6$190
This Kiwi.com deal was found by Cheapflights users on 1/6. 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 2/53:46 pmEYW - ORD
1 stop19h 49mMultiple Airlines
Mon 2/95:15 amORD - EYW
1 stop7h 15mMultiple Airlines
Deal found 1/6$194
This Kiwi.com deal was found by Cheapflights users on 1/7. 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 2/53:46 pmEYW - ORD
1 stop19h 49mMultiple Airlines
Sun 2/85:15 amORD - EYW
1 stop5h 41mMultiple Airlines
Deal found 1/7$199
This Kiwi.com deal was found by Cheapflights users on 1/7. 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 2/53:46 pmEYW - ORD
1 stop19h 49mMultiple Airlines
Sat 2/75:32 pmORD - EYW
2 stops14h 34mMultiple Airlines
Deal found 1/7$206
This Kiwi.com deal was found by Cheapflights users on 1/7. 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 2/410:49 amEYW - ORD
1 stop7h 09mMultiple Airlines
Sat 2/75:32 pmORD - EYW
1 stop17h 24mMultiple Airlines
Deal found 1/7$214
This Kiwi.com deal was found by Cheapflights users on 1/7. 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 2/410:49 amEYW - ORD
1 stop7h 09mMultiple Airlines
Sun 2/88:43 pmORD - EYW
1 stop15h 47mMultiple Airlines
Deal found 1/7$220
This Kiwi.com deal was found by Cheapflights users on 1/7. 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 1/2210:06 amEYW - ORD
1 stop8h 46mMultiple Airlines
Mon 1/268:43 pmORD - EYW
2 stops36h 26mMultiple Airlines
Deal found 1/7$222
This Kiwi.com deal was found by Cheapflights users on 1/7. 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 1/231:06 pmEYW - ORD
1 stop7h 35mMultiple Airlines
Tue 1/2710:07 amORD - EYW
1 stop23h 02mMultiple Airlines
Deal found 1/7$237

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 January 8, 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

Key West

Fly to

O'Hare Intl

Route

Depart

Return

Price

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 1/29

3:46 pm-10:35 am

1 stop19h 49m

Chicago O'Hare Intl

Wed 2/4

12:44 pm-9:06 am

1 stop19h 22m

$174

Key WestChicago

EYW - ORD

EYWORD

Key West

Fri 1/30

2:25 pm-7:38 pm

1 stop6h 13m

Chicago O'Hare Intl

Sun 2/1

5:15 am-11:56 am

1 stop5h 41m

$188

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 2/5

12:51 pm-7:38 pm

1 stop7h 47m

Chicago O'Hare Intl

Sun 2/8

5:15 am-11:56 am

1 stop5h 41m

$188

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 2/5

3:46 pm-10:35 am

1 stop19h 49m

Chicago O'Hare Intl

Mon 2/9

5:15 am-1:30 pm

1 stop7h 15m

$194

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 2/5

3:46 pm-10:35 am

1 stop19h 49m

Chicago O'Hare Intl

Sun 2/8

5:15 am-11:56 am

1 stop5h 41m

$199

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 2/5

3:46 pm-10:35 am

1 stop19h 49m

Chicago O'Hare Intl

Sat 2/7

5:32 pm-9:06 am

2 stops14h 34m

$206

Key WestChicago

EYW - ORD

EYWORD

Key West

Wed 2/4

10:49 am-4:58 pm

1 stop7h 09m

Chicago O'Hare Intl

Sun 2/8

8:43 pm-1:30 pm

1 stop15h 47m

$220

Key WestChicago

EYW - ORD

EYWORD

Key West

Wed 2/4

10:49 am-4:58 pm

1 stop7h 09m

Chicago O'Hare Intl

Sat 2/7

5:32 pm-9:06 am

2 stops14h 34m

$226

Key WestChicago

EYW - ORD

EYWORD

Key West

Fri 1/30

1:06 pm-4:40 pm

1 stop28h 34m

Chicago O'Hare Intl

Sun 2/1

8:43 pm-12:26 pm

2 stops14h 43m

$232

Key WestChicago

EYW - ORD

EYWORD

Key West

Fri 1/23

1:06 pm-7:41 pm

1 stop7h 35m

Chicago O'Hare Intl

Tue 1/27

2:53 pm-10:09 am

2 stops18h 16m

$246

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/7

Showing 1-10 of 21 results
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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 January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice 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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Key West-Chicago O'Hare Intl Airport flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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 January 8, 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.

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
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

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 January 8, 2026.
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
9,139 reviews

Comfort

7.3

Entertainment

7.1

Food

6.6

Boarding

7.7

Crew

8.1

Overall

7.4

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
United Airlines
7.4
Good
9,139 reviews
United Airlines
7.4
Good
9,139 reviews

Comfort

7.3

Entertainment

7.1

Food

6.6

Boarding

7.7

Crew

8.1

Overall

7.4

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
American Airlines
7.2
Good
11,095 reviews
United Airlines
7.4
Good
9,139 reviews

Comfort

7.3

Entertainment

7.1

Food

6.6

Boarding

7.7

Crew

8.1

Overall

7.4

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.

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 5 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 6h 13m. Spirit Airlines provides one of the quickest options available for as low as $188. Airlines will cover a distance of 1253 mi.

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

    Currently priced at $249, 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 $289. United Airlines is currently priced 40% 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 (83%), United Airlines (80%) or Air New Zealand (77%) 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 $590 for a flight from Key West to Chicago O'Hare Intl Airport. The cheapest flight overall is $221 while the most popular route, (Key West - Chicago O'Hare Intl) is currently priced at $188.

  • 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
Schaumburg
Rosemont
Gurnee
Elgin
Naperville
Hoffman Estates
Beloit
Delavan
Oak Brook
Downers Grove
Des Plaines
Elk Grove Village
Skokie
Lake Geneva
Bridgeview
Kenosha
Warrenville
Waukegan
Aurora
Evanston

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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 January 8, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$249Average$431FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$289Average$427FlexibilityNo cancel feeOn-time71%

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