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O'Hare Intl

$177+ 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 7/22. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — ORD
Jul 8 — Jul 151
Tue 7/8
Tue 7/15
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 July 3, 2025.

Round-trip from

$324
(Delta)

One-way from

$177
(Mytrip)

Popular in

March

Cheapest in

December

Average price

$428

Good round-trip deal

$1,421 or less

Good one-way deal

$497 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 ($167 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 July 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 July 3, 2025.

This Delta deal was found by Cheapflights users on 7/3. 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.
Fri 9/266:10 pmEYW - ORD
1 stop6h 42mDelta
Sun 9/287:20 amORD - EYW
1 stop4h 42mDelta
Deal found 7/3$324
This American Airlines deal was found by Cheapflights users on 7/3. 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 7/92:44 pmEYW - ORD
1 stop7h 47mAmerican Airlines
Sat 7/128:15 amORD - EYW
Nonstop3h 11mAmerican Airlines
Deal found 7/3$361
This Mytrip deal was found by Cheapflights users on 7/3. 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.
Sun 8/244:36 pmEYW - ORD
2 stops24h 34mMultiple Airlines
Sun 8/315:21 pmORD - EYW
1 stop15h 01mMultiple Airlines
Deal found 7/3$374
This United Airlines deal was found by Cheapflights users on 7/1. 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 8/82:12 pmEYW - ORD
2 stops17h 16mUnited Airlines
Sun 8/109:44 pmORD - EYW
2 stops14h 42mUnited Airlines
Deal found 7/1$518

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 3, 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 9/26

6:10 pm-11:52 pm

1 stop6h 42m

Chicago O'Hare Intl

Sun 9/28

7:20 am-1:02 pm

1 stop4h 42m

$324

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 7/31

4:48 pm-11:57 pm

1 stop8h 09m

Chicago O'Hare Intl

Tue 8/5

5:00 am-12:55 pm

1 stop6h 55m

$364

Key WestChicago

EYW - ORD

EYWORD

Key West

Sun 8/24

4:36 pm-4:10 pm

2 stops24h 34m

Chicago O'Hare Intl

Sun 8/31

5:21 pm-9:22 am

1 stop15h 01m

$374

Key WestChicago

EYW - ORD

EYWORD

Key West

Fri 8/8

2:12 pm-6:28 am

2 stops17h 16m

Chicago O'Hare Intl

Sun 8/10

9:44 pm-1:26 pm

2 stops14h 42m

$518

Key WestChicago

EYW - ORD

EYWORD

Key West

Tue 7/22

10:02 am-7:26 pm

1 stop10h 24m

$177

Key WestChicago

EYW - ORD

EYWORD

Key West

Wed 7/23

6:27 pm-7:49 am

2 stops14h 22m

$259

Key WestChicago

EYW - ORD

EYWORD

Key West

Sat 11/8

4:00 pm-6:46 pm

Nonstop3h 46m

$296

Key WestChicago

EYW - ORD

EYWORD

Key West

Mon 11/10

4:00 pm-11:54 pm

1 stop8h 54m

$305

Key WestChicago

EYW - ORD

EYWORD

Key West

Sat 11/8

11:10 am-1:04 pm

3 stops26h 54m

$678

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/1

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 July 3, 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.

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 3, 2025.
Peruse reviews from past customers who have flown with Alaska Airlines, Delta, and United 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.
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Crew

8.5

Boarding

8.1

Overall

8.0

Entertainment

7.1

Food

7.1

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

Comfort

7.8

Crew

8.5

Boarding

8.1

Overall

8.0

Entertainment

7.1

Food

7.1

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
7,982 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Crew

8.5

Boarding

8.1

Overall

8.0

Entertainment

7.1

Food

7.1

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
8,861 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Crew

8.5

Boarding

8.1

Overall

8.0

Entertainment

7.1

Food

7.1

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

Comfort

7.8

Crew

8.5

Boarding

8.1

Overall

8.0

Entertainment

7.1

Food

7.1

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 $324, 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 $518, respectively. Delta is currently priced 25% 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 ($259), United Airlines ($296), and American Airlines ($305).

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

    Consider Qatar Airways (74%), American Airlines (65%) or Envoy Air (65%) 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 $982 for a flight from Key West to Chicago O'Hare Intl Airport. The cheapest flight overall is $229 while the most popular route, (Key West - Chicago O'Hare Intl) is currently priced at $269.

  • 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?

Book flights to Key West if you plan to visit one of these locations
Schaumburg
Hoffman Estates
Rosemont
Beloit
Skokie
Des Plaines
Arlington Heights
Elgin
Naperville
Orland Park
Elk Grove Village
Racine
Rockford
Tinley Park
Merrillville
Bridgeview
Glenview
Lake Geneva
Joliet
Waukegan

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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 July 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$224Average$394FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$259Average$398FlexibilityNo cancel feeOn-time71%

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