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O'Hare Intl

$122+ 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 7/15. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — ORD
juin 17 — juin 241
mar. 6/17
mar. 6/24
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 juin 12, 2025.

Round-trip from

$337
(Mytrip)

One-way from

$122
(Trip.com)

Popular in

March

Cheapest in

December

Average price

$488

Good round-trip deal

$427 or less

Good one-way deal

$293 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. 27% potential increase in price ($166 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 June 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 juin 12, 2025.

This Delta deal was found by Cheapflights users on 6/12. 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.
mer. 10/16:00 pmEYW - ORD
1 stop6h 53mDelta
mer. 10/86:00 amORD - EYW
1 stop6h 08mDelta
Deal found 6/12$289
This American Airlines deal was found by Cheapflights users on 6/12. 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.
mer. 10/17:31 pmEYW - ORD
1 stop5h 17mAmerican Airlines
mer. 10/85:15 amORD - EYW
2 stops6h 45mAmerican Airlines
Deal found 6/12$328
This Mytrip deal was found by Cheapflights users on 6/11. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 7/2910:02 amEYW - ORD
1 stop10h 24mMultiple Airlines
mer. 7/304:36 pmORD - EYW
1 stop23h 09mMultiple Airlines
Deal found 6/11$337
This United Airlines deal was found by Cheapflights users on 6/10. 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.
ven. 8/86:45 pmEYW - ORD
1 stop24h 38mUnited Airlines
dim. 8/1010:45 amORD - EYW
2 stops20h 15mUnited Airlines
Deal found 6/10$378

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 juin 12, 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

mar. 7/29

10:02 am-7:26 pm

1 stop10h 24m

Chicago O'Hare Intl

mer. 7/30

4:36 pm-4:45 pm

1 stop23h 09m

$337

Key WestChicago

EYW - ORD

EYWORD

Key West

ven. 8/8

6:27 pm-12:09 am

1 stop6h 42m

Chicago O'Hare Intl

dim. 8/10

9:50 am-5:32 pm

1 stop6h 42m

$344

Key WestChicago

EYW - ORD

EYWORD

Key West

mer. 7/30

2:31 pm-9:00 pm

1 stop7h 29m

Chicago O'Hare Intl

dim. 8/3

6:00 am-4:12 pm

1 stop9h 12m

$364

Key WestChicago

EYW - ORD

EYWORD

Key West

ven. 8/8

6:45 pm-6:23 pm

1 stop24h 38m

Chicago O'Hare Intl

dim. 8/10

10:45 am-8:00 am

2 stops20h 15m

$378

Key WestChicago

EYW - ORD

EYWORD

Key West

mar. 7/15

6:45 pm-3:42 pm

1 stop21h 57m

$122

Key WestChicago

EYW - ORD

EYWORD

Key West

jeu. 7/17

6:27 pm-12:09 am

1 stop6h 42m

$264

Key WestChicago

EYW - ORD

EYWORD

Key West

lun. 6/30

1:42 pm-7:49 am

2 stops19h 07m

$265

Key WestChicago

EYW - ORD

EYWORD

Key West

dim. 7/20

7:51 pm-7:33 am

2 stops12h 42m

$400

Key WestChicago

EYW - ORD

EYWORD

Key West

sam. 8/9

12:10 pm-12:07 pm

3 stops24h 57m

$728

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

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 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.

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 juin 12, 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 31% on the flight price compared to flying in the morning, which is usually more expensive.

Rainfall in O'Hare Intl by month

Plan your trip to O'Hare Intl by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago O'Hare Intl Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago O'Hare Intl Airport when rainfall is around 1.7 in.

Temperature in O'Hare Intl by month

Plan your trip to O'Hare Intl by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago O'Hare Intl Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 juin 12, 2025.
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Entertainment

7.1

Overall

8.0

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Entertainment

7.1

Overall

8.0

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,950 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Entertainment

7.1

Overall

8.0

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,790 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Entertainment

7.1

Overall

8.0

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Entertainment

7.1

Overall

8.0

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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 $344, Delta will fly you from Key West to Chicago O'Hare Intl Airport and back. In addition to Delta, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from American Airlines and United Airlines - these airlines can fly you to your destination from $364 and $378, respectively. Delta is currently priced 20% 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 Delta ($264), United Airlines ($265), and American Airlines ($400).

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

    Consider United Airlines (69%), Air New Zealand (69%) or American Airlines (59%) 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 $513 for a flight from Key West to Chicago O'Hare Intl Airport. The cheapest flight overall is $141 while the most popular route, (Key West - Chicago O'Hare Intl) is currently priced at $256.

  • 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 Key West?

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Schaumburg
Hoffman Estates
Rosemont
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Orland Park
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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 juin 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$224Average$394FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$289Average$423FlexibilityNo cancel feeOn-time71%

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