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$156+ Cheap flights from O'Hare Intl (ORD) to Key West (EYW)

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 7/26. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — EYW
Jun 23 — Jun 301
Mon 6/23
Mon 6/30
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago O'Hare Intl to Key West are usually found in September or October, booked 42 days in advance, depart on a Tuesday or Wednesday and return on a Thursday

Cheap flight deals from O'Hare Intl to Key West

Discover tips and strategies to find the most affordable flight options for your journey from O'Hare Intl (ORD) to Key West (EYW). 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 June 18, 2025.

Round-trip from

$322
(American Airlines)

One-way from

$156
(Mytrip)

Popular in

March

Cheapest in

September

Average price

$460

Good round-trip deal

$413 or less

Good one-way deal

$266 or less
From Chicago O'Hare Intl to Key West
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One-way flight from Chicago O'Hare Intl to Key West
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Highest demand for flights based on searches. 12% potential increase in price ($62 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($9 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 Chicago O'Hare Intl to Key West.
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Price to beat on a one-way flight from Chicago O'Hare Intl to Key West.
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Find flight deals from O'Hare Intl to Key West

Cheapest flights from O'Hare Intl to Key West
Explore the most affordable flight options available from O'Hare Intl to Key West. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 18, 2025.

This American Airlines deal was found by Cheapflights users on 6/18. 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 8/27:05 amORD - EYW
1 stop5h 52mAmerican Airlines
Sat 8/95:01 pmEYW - ORD
1 stop6h 48mAmerican Airlines
Deal found 6/18$322
This Delta deal was found by Cheapflights users on 6/18. 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 8/15:35 amORD - EYW
1 stop6h 33mDelta
Tue 8/1211:52 amEYW - ORD
1 stop5h 36mDelta
Deal found 6/18$324
This Mytrip deal was found by Cheapflights users on 6/16. 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.
Sat 8/165:25 pmORD - EYW
1 stop13h 38mMultiple Airlines
Fri 8/2210:33 amEYW - ORD
3 stops32h 12mMultiple Airlines
Deal found 6/16$326
This United Airlines deal was found by Cheapflights users on 6/16. 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 7/46:00 amORD - EYW
1 stop6h 12mUnited Airlines
Fri 7/112:12 pmEYW - ORD
1 stop8h 24mUnited Airlines
Deal found 6/16$369

Cheapflights Fare Finder

Customize your flight search to find flights from O'Hare Intl to Key West 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 June 18, 2025.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Key West that are best for you.

Fly from

O'Hare Intl

Fly to

Key West

Route

Depart

Return

Price

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Sat 8/2

7:05 am-1:57 pm

1 stop5h 52m

Key West

Sat 8/9

5:01 pm-10:49 pm

1 stop6h 48m

$322

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Fri 8/1

5:35 am-1:08 pm

1 stop6h 33m

Key West

Tue 8/12

11:52 am-4:28 pm

1 stop5h 36m

$324

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Sat 8/16

5:25 pm-8:03 am

1 stop13h 38m

Key West

Fri 8/22

10:33 am-5:45 pm

3 stops32h 12m

$326

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Fri 7/4

6:00 am-1:12 pm

1 stop6h 12m

Key West

Fri 7/11

2:12 pm-9:36 pm

1 stop8h 24m

$369

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Sat 7/26

11:21 am-11:41 am

2 stops23h 20m

$156

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Mon 9/15

9:10 pm-2:00 pm

2 stops15h 50m

$225

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Mon 9/15

5:00 am-6:59 pm

1 stop12h 59m

$268

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Sat 7/26

1:35 pm-7:49 pm

1 stop5h 14m

$269

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/16

The best insider tips for Chicago O'Hare Intl Airport to Key West 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 Chicago O'Hare Intl Airport to Key West trip
Airports
ORD

For a quick departure from ORD, use the 'L' train to avoid Chicago traffic delays.

Read more about ORDby Ramsey Qubein
EYW

At EYW, car rentals are available from major companies; book ahead during busy seasons.

Read more about EYWby Terry Ward
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 O'Hare Intl to Key West

Have a flexible travel schedule? Discover the best time to fly to Key West from O'Hare Intl 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 Chicago O'Hare Intl Airport to Key West

How far ahead should I book a flight from Chicago O'Hare Intl Airport to Key West?

Use this chart to determine the optimal time to book a round-trip flight from O'Hare Intl to Key West. Price data was last updated on June 13, 2025.

The price you pay for your flight from Chicago O'Hare Intl Airport to Key West may vary depending on when you book. For the best chance of a lower fare, look to book 42 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to Key West?

Currently, August is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Key West (average of $328). Flying from Chicago O'Hare Intl Airport to Key West in March is currently the most expensive (average of $493). 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 ORD to EYW?

Find hourly flight availability from O'Hare Intl to Key West. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 18, 2025.

A simple way to save on the total cost of your ticket is to fly from Chicago O'Hare Intl Airport to Key West at noon. If you’re flexible enough to do this you can expect to save up to 40% on your trip compared to booking a flight in the afternoon.

Rainfall in Key West by month

Plan your trip to Key West by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Key West ranges from 1.5 - 6.7 inches per month. September is typically the wettest month, when rainfall can reach 6.7 in. February is typically the driest time to visit Key West when rainfall is around 1.5 in.

Temperature in Key West by month

Plan your trip to Key West by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Key West, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 84.2 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 69.8 F).

Reviews of airlines servicing Key West

Get insights into the airlines that provide service to Key West. 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 Key West. Reviews last updated June 18, 2025.
See what other customers who have flown with Delta, United Airlines and American Airlines from Chicago to Key West have to say. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,964 reviews

Crew

8.5

Entertainment

7.9

Overall

8.0

Boarding

8.2

Comfort

7.9

Food

7.3

Reviews

1 / 20
2.0
Mediocre

Joseph,Aug 2023

MSP - MCO

Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.
Delta
8.0
Very good
7,964 reviews
Delta
8.0
Very good
7,964 reviews

Crew

8.5

Entertainment

7.9

Overall

8.0

Boarding

8.2

Comfort

7.9

Food

7.3

Reviews

1 / 20
2.0
Mediocre

Joseph,Aug 2023

MSP - MCO

Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.
United Airlines
7.4
Good
8,810 reviews
Delta
8.0
Very good
7,964 reviews

Crew

8.5

Entertainment

7.9

Overall

8.0

Boarding

8.2

Comfort

7.9

Food

7.3

Reviews

1 / 20
2.0
Mediocre

Joseph,Aug 2023

MSP - MCO

Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,964 reviews

Crew

8.5

Entertainment

7.9

Overall

8.0

Boarding

8.2

Comfort

7.9

Food

7.3

Reviews

1 / 20
2.0
Mediocre

Joseph,Aug 2023

MSP - MCO

Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.

Related info for your journey

Find useful and relevant information for your journey from O'Hare Intl to Key West. 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 into for flights to Key West from Chicago O'Hare Intl?

    Most people fly into Key West (EYW) if they book a flight to Key West from Chicago O'Hare Intl. On average, Key West has 0 inbound flights from Chicago O'Hare Intl per day from 3 airlines. Key West is conveniently located just 2.6 mi from Key West’s city center.

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

    Cheapflights users have booked flights from Chicago O'Hare Intl Airport to Key West round-trip from $322. Other airlines that can offer you cheap pricing are Delta, from $324, and United Airlines, from $369. These flights start at 26% lower than the current average price 3 months from now.

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

    To fly one-way, consider booking your trip with United Airlines, which is currently one of the cheapest options available, starting at $225. American Airlines flights start at $268 while deals on Delta start at $269 one-way.

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

    The top 3 most reliable airlines when flying from Chicago O'Hare Intl Airport to Key West are United Airlines (90%), Air New Zealand (90%) and American Airlines (61%).

  • What are the cheapest flights from Chicago O'Hare Intl Airport to Key West?

    Looking at all options, your cheapest flight can be booked for $258. While the most popular route (Chicago O'Hare Intl - Key West) can be booked for $255 on average our data indicates $451 when flying from Chicago O'Hare Intl Airport to Key West.

  • Can I find deals for flights from O'Hare Intl to Key West that include hotel bookings?

    Yes. In addition to deals on O'Hare Intl to Key West flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from O'Hare Intl to Key West?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from O'Hare Intl to Key West.

  • Can I find deals for business class flights from O'Hare Intl to Key West?

    Yes. Cheapflights offers flight deals from O'Hare Intl to Key West 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 Chicago O'Hare Intl Airport to Key West?

    Currently, August is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Key West (average of $328). Flying from Chicago O'Hare Intl Airport to Key West in March is currently the most expensive (average of $493). 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.

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Top 3 airlines flying from O'Hare Intl to Key West

Discover the top 3 airlines that operate flights from O'Hare Intl to Key West. 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 June 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$216Average$336FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$265Average$476FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$283Average$441FlexibilityNo cancel feeOn-time71%

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