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O'Hare Intl

$103+ 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 5/28. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — ORD
may. 23 — may. 301
sáb. 5/23
sáb. 5/30
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 abril 23, 2026.

This Kiwi.com deal was found by Cheapflights users on 4/20. 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.
jue. 5/143:08 pm
EYW
-
ORD
1 stop22h 15m
Multiple Airlines
dom. 5/241:50 pm
ORD
-
EYW
2 stops21h 41m
Multiple Airlines
Deal found 4/20$237
This Kiwi.com deal was found by Cheapflights users on 4/21. 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.
mié. 5/611:46 am
EYW
-
ORD
1 stop22h 41m
Multiple Airlines
dom. 5/108:30 am
ORD
-
EYW
1 stop27h 01m
Multiple Airlines
Deal found 4/21$243
This Kiwi.com deal was found by Cheapflights users on 4/20. 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.
jue. 5/141:57 pm
EYW
-
ORD
1 stop9h 17m
Multiple Airlines
dom. 5/175:30 pm
ORD
-
EYW
1 stop16h 57m
Multiple Airlines
Deal found 4/20$267
This Kiwi.com deal was found by Cheapflights users on 4/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 6/311:46 am
EYW
-
ORD
2 stops9h 05m
Multiple Airlines
sáb. 6/65:11 pm
ORD
-
EYW
1 stop17h 14m
Multiple Airlines
Deal found 4/22$279
This Kiwi.com deal was found by Cheapflights users on 4/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 5/2711:46 am
EYW
-
ORD
2 stops21h 09m
Multiple Airlines
mié. 6/105:25 pm
ORD
-
EYW
1 stop17h 00m
Multiple Airlines
Deal found 4/22$289
This Kiwi.com deal was found by Cheapflights users on 4/23. 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.
vie. 5/81:11 pm
EYW
-
ORD
1 stop24h 12m
Multiple Airlines
mar. 5/121:59 pm
ORD
-
EYW
2 stops20h 07m
Multiple Airlines
Deal found 4/23$290
This United Airlines deal was found by Cheapflights users on 4/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 5/144:05 pm
EYW
-
ORD
Nonstop3h 55m
United Airlines
dom. 5/1710:43 am
ORD
-
EYW
Nonstop3h 24m
United Airlines
Deal found 4/20$309
This American Airlines deal was found by Cheapflights users on 4/20. 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.
mar. 7/77:29 pm
EYW
-
ORD
1 stop5h 30m
American Airlines
mar. 7/2111:22 am
ORD
-
EYW
Nonstop3h 24m
American Airlines
Deal found 4/20$319

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 abril 23, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$237
(Kiwi.com)

One-way from

$103
(Kiwi.com)

Popular in

January

Cheapest in

December

Average price

$499

Good round-trip deal

$479 or less

Good one-way deal

$333 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 ($56 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 11% potential price decrease ($46 potential savings vs. average RT price).
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Average for round-trip flights in April 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 abril 23, 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

mié. 6/3

11:46 am-7:51 pm

2 stops9h 05m

Chicago O'Hare Intl

sáb. 6/6

5:11 pm-11:25 am

1 stop17h 14m

$279

Key WestChicago

EYW - ORD

EYWORD

Key West

jue. 5/14

4:05 pm-7:00 pm

Nonstop3h 55m

Chicago O'Hare Intl

dom. 5/17

10:43 am-3:07 pm

Nonstop3h 24m

$309

Key WestChicago

EYW - ORD

EYWORD

Key West

mié. 5/27

11:46 am-12:23 pm

1 stop25h 37m

Chicago O'Hare Intl

mié. 6/10

5:25 pm-11:25 am

1 stop17h 00m

$309

Key WestChicago

EYW - ORD

EYWORD

Key West

mar. 7/7

1:01 pm-7:54 pm

1 stop7h 53m

Chicago O'Hare Intl

mar. 7/21

11:22 am-3:46 pm

Nonstop3h 24m

$319

Key WestChicago

EYW - ORD

EYWORD

Key West

sáb. 9/5

1:07 pm-10:04 pm

1 stop9h 57m

Chicago O'Hare Intl

mié. 9/9

9:59 am-6:27 pm

2 stops7h 28m

$334

Key WestChicago

EYW - ORD

EYWORD

Key West

vie. 5/29

4:19 pm-7:12 pm

Nonstop3h 53m

Chicago O'Hare Intl

dom. 5/31

7:58 am-4:07 pm

1 stop7h 09m

$346
Quickest round-trip

Key WestChicago

EYW - ORD

EYWORD

Key West

mié. 5/6

1:08 pm-3:55 pm

Nonstop3h 47m

Chicago O'Hare Intl

dom. 5/10

1:50 pm-6:16 pm

Nonstop3h 26m

$369

Key WestChicago

EYW - ORD

EYWORD

Key West

lun. 5/11

1:11 pm-7:51 pm

2 stops31h 40m

Chicago O'Hare Intl

jue. 5/28

5:11 pm-11:27 am

1 stop17h 16m

$371

Key WestChicago

EYW - ORD

EYWORD

Key West

mié. 5/6

4:47 pm-11:15 pm

1 stop7h 28m

Chicago O'Hare Intl

dom. 5/10

10:43 am-3:07 pm

Nonstop3h 24m

$379

Key WestChicago

EYW - ORD

EYWORD

Key West

vie. 5/8

11:48 am-6:35 pm

1 stop7h 47m

Chicago O'Hare Intl

mar. 5/12

6:00 am-1:42 pm

1 stop6h 42m

$389

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/18

Showing 1-10 of 19 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 April.
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 abril 23, 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?

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 abril 23, 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
9,637 reviews

Overall

7.4

Boarding

7.7

Crew

8.1

Comfort

7.3

Entertainment

7.1

Food

6.6

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
9,637 reviews
United Airlines
7.4
Good
9,637 reviews

Overall

7.4

Boarding

7.7

Crew

8.1

Comfort

7.3

Entertainment

7.1

Food

6.6

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
7.1
Good
11,659 reviews
United Airlines
7.4
Good
9,637 reviews

Overall

7.4

Boarding

7.7

Crew

8.1

Comfort

7.3

Entertainment

7.1

Food

6.6

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 4 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 3h 55m. United Airlines provides one of the quickest options available for as low as $309. 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 $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 $344. United Airlines is currently priced 42% below the average price you’ll pay for this route.

  • What are the cheapest airlines to fly from Key West to Chicago O'Hare Intl Airport one-way?

    The cheapest airlines for a one-way flight from Key West to Chicago O'Hare Intl Airport are Spirit Airlines ($90), American Airlines ($178), and United Airlines ($180).

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

    Consider Republic Airways (89%), United Airlines (82%) or Air New Zealand (68%) 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 $441 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 $279.

  • 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
Rosemont
Schaumburg
Naperville
Gurnee
Lake Geneva
Delavan
Hoffman Estates
Downers Grove
Oakbrook Terrace
Benton Harbor
Des Plaines
Oak Brook
South Holland
Libertyville
Elgin
Warrenville
Elk Grove Village
Bridgeview
Great Lakes
Lansing

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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 abril 23, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$249Average$315FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$344Average$561FlexibilityNo cancel feeOn-time71%

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