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$173+ 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 6/1. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — EYW
May 4 — May 111
Sun 5/4
Sun 5/11
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago O'Hare Intl to Key West are usually found in August or September, booked 69 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 April 29, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$320
(Mytrip)

One-way from

$173
(United Airlines)

Popular in

March

Cheapest in

August

Average price

$468

Good round-trip deal

$411 or less

Good one-way deal

$324 or less
Provider with most accurate pricing for Chicago O'Hare Intl-Key West flight deals.
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Provider most trusted by Cheapflights users for Chicago O'Hare Intl-Key West flights.
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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. 13% potential increase in price ($67 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 29, 2025.

This Trip.com deal was found by Cheapflights users on 4/29. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/299:55 amORD - EYW
1 stop7h 10mMultiple Airlines
Thu 6/58:45 amEYW - ORD
1 stop16h 20mMultiple Airlines
Deal found 4/29$321
This Delta deal was found by Cheapflights users on 4/28. 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.
Sat 6/1411:20 amORD - EYW
1 stop7h 19mDelta
Tue 6/176:29 pmEYW - ORD
1 stop6h 28mDelta
Deal found 4/28$323
This American Airlines deal was found by Cheapflights users on 4/27. 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.
Tue 6/109:22 amORD - EYW
1 stop5h 49mAmerican Airlines
Tue 6/2411:20 amEYW - ORD
2 stops7h 15mAmerican Airlines
Deal found 4/27$328
This United Airlines deal was found by Cheapflights users on 4/27. 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.
Sun 6/16:15 pmORD - EYW
1 stop17h 00mUnited Airlines
Mon 6/26:45 pmEYW - ORD
1 stop15h 39mUnited Airlines
Deal found 4/27$335

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 April 29, 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

Sun 6/1

6:30 am-9:33 am

1 stop26h 03m

Key West

Thu 6/5

8:53 am-11:29 pm

3 stops39h 36m

$320

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Fri 5/30

5:00 am-12:10 pm

1 stop6h 10m

Key West

Wed 6/4

1:39 pm-7:21 pm

1 stop6h 42m

$323

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Tue 5/27

1:30 pm-8:07 pm

1 stop5h 37m

Key West

Tue 6/3

1:51 pm-6:48 pm

1 stop5h 57m

$326

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Sun 6/1

7:36 am-8:00 am

1 stop23h 24m

Key West

Thu 6/5

8:45 am-9:39 am

1 stop25h 54m

$368

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Sun 6/1

7:36 am-12:15 pm

1 stop27h 39m

$173

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Fri 5/16

7:35 pm-4:13 pm

2 stops19h 38m

$179

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Thu 6/26

11:20 am-5:34 pm

1 stop5h 14m

$230

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Wed 7/2

6:16 am-7:02 pm

2 stops11h 46m

$311

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

Compare providers for flights from O'Hare Intl to Key West

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 O'Hare Intl to Key West in April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 stars
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 Chicago O'Hare Intl Airport-Key West flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago O'Hare Intl Airport-Key West flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago O'Hare Intl Airport-Key West flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago O'Hare Intl Airport-Key West 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 Chicago O'Hare Intl Airport-Key West 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 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 April 25, 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 69 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 April 29, 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 April 29, 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
7,936 reviews

Comfort

7.9

Food

7.3

Entertainment

7.9

Crew

8.5

Boarding

8.2

Overall

8.0

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
7,936 reviews
Delta
8.0
Very good
7,936 reviews

Comfort

7.9

Food

7.3

Entertainment

7.9

Crew

8.5

Boarding

8.2

Overall

8.0

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
8,696 reviews
Delta
8.0
Very good
7,936 reviews

Comfort

7.9

Food

7.3

Entertainment

7.9

Crew

8.5

Boarding

8.2

Overall

8.0

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
7,936 reviews

Comfort

7.9

Food

7.3

Entertainment

7.9

Crew

8.5

Boarding

8.2

Overall

8.0

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 1 inbound flight 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 $323. Other airlines that can offer you cheap pricing are American Airlines, from $328, and United Airlines, from $335. These flights start at 24% 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 $173. American Airlines flights start at $198 while deals on Delta start at $230 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 (84%), Republic Airways (79%) and Air New Zealand (76%).

  • 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 $227. While the most popular route (Chicago O'Hare Intl - Key West) can be booked for $245 on average our data indicates $462 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 April 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$216Average$295FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$262Average$471FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$263Average$433FlexibilityNo cancel feeOn-time71%

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