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$85+ 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 1/15. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — EYW
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Find cheap flights from O'Hare Intl to Key West with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

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Cheapflights Tip: The best prices from Chicago O'Hare Intl to Key West are usually found in June or July, booked 57 days in advance, depart on a Tuesday or Wednesday and return on a Thursday

Cheap 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 December 18, 2025.

This American Airlines deal was found by Cheapflights users on 12/15. 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 12/316:07 amORD - EYW
1 stop8h 26mAmerican Airlines
Wed 1/77:08 amEYW - ORD
1 stop5h 27mAmerican Airlines
Deal found 12/15$326
This Kiwi.com deal was found by Cheapflights users on 12/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/3112:09 pmORD - EYW
1 stop19h 06mMultiple Airlines
Mon 1/51:10 pmEYW - ORD
1 stop26h 11mMultiple Airlines
Deal found 12/16$328
This Kiwi.com deal was found by Cheapflights users on 12/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/3112:09 pmORD - EYW
1 stop19h 06mMultiple Airlines
Tue 1/612:20 pmEYW - ORD
1 stop23h 54mMultiple Airlines
Deal found 12/16$338
This American Airlines deal was found by Cheapflights users on 12/15. 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 12/238:10 amORD - EYW
Nonstop3h 35mAmerican Airlines
Mon 12/296:26 pmEYW - ORD
Nonstop3h 33mAmerican Airlines
Deal found 12/15$345
This Kiwi.com deal was found by Cheapflights users on 12/17. 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.
Wed 12/311:34 pmORD - EYW
1 stop19h 45mMultiple Airlines
Sun 1/410:37 pmEYW - ORD
2 stops39h 17mMultiple Airlines
Deal found 12/17$350
This United Airlines deal was found by Cheapflights users on 12/15. 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.
Wed 12/247:55 amORD - EYW
Nonstop3h 39mUnited Airlines
Sat 12/274:29 pmEYW - ORD
1 stop8h 45mUnited Airlines
Deal found 12/15$352
This United Airlines deal was found by Cheapflights users on 12/15. 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.
Tue 12/2310:47 amORD - EYW
Nonstop3h 27mUnited Airlines
Mon 12/294:29 pmEYW - ORD
1 stop7h 08mUnited Airlines
Deal found 12/15$355
This American Airlines deal was found by Cheapflights users on 12/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/246:07 amORD - EYW
1 stop8h 26mAmerican Airlines
Wed 12/318:09 pmEYW - ORD
1 stop5h 34mAmerican Airlines
Deal found 12/16$365
This United Airlines deal was found by Cheapflights users on 12/16. 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.
Wed 12/317:55 amORD - EYW
Nonstop3h 39mUnited Airlines
Wed 1/76:05 pmEYW - ORD
1 stop6h 34mUnited Airlines
Deal found 12/16$366
This United Airlines deal was found by Cheapflights users on 12/15. 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.
Wed 12/247:55 amORD - EYW
Nonstop3h 39mUnited Airlines
Sun 12/284:29 pmEYW - ORD
1 stop7h 08mUnited Airlines
Deal found 12/15$371

Find 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 December 18, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$286
(American Airlines)

One-way from

$85
(Priceline)

Popular in

March

Cheapest in

June

Average price

$493

Good round-trip deal

$342 or less

Good one-way deal

$293 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. 12% potential increase in price ($62 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Chicago O'Hare Intl to Key West.
Search Deals
Price to beat on a one-way flight from Chicago O'Hare Intl to Key West.
Search Deals

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 December 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 4/11

11:33 am-7:41 pm

1 stop7h 08m

Key West

Wed 4/15

6:00 pm-11:55 pm

1 stop6h 55m

$294

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Fri 1/2

7:35 am-3:48 pm

1 stop7h 13m

Key West

Thu 1/8

6:05 pm-11:39 pm

1 stop6h 34m

$299

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Sat 1/24

7:10 am-11:26 am

Nonstop3h 16m

Key West

Tue 1/27

2:25 pm-8:13 pm

1 stop6h 48m

$309

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Sat 2/7

7:10 am-11:26 am

Nonstop3h 16m

Key West

Sat 2/14

4:34 pm-12:26 am

1 stop8h 52m

$325

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Fri 4/17

5:45 am-3:50 pm

1 stop9h 05m

Key West

Sun 4/19

4:45 pm-12:30 am

1 stop8h 45m

$339

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Fri 1/16

8:52 am-4:22 pm

1 stop6h 30m

Key West

Fri 1/23

4:15 pm-6:48 pm

Nonstop3h 33m

$353

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Fri 5/29

1:15 pm-7:44 pm

1 stop5h 29m

Key West

Tue 6/2

6:00 pm-11:55 pm

1 stop6h 55m

$378

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Sat 5/16

10:35 am-2:59 pm

Nonstop3h 24m

Key West

Sat 5/23

4:05 pm-6:30 pm

Nonstop3h 25m

$380

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Mon 2/16

10:44 am-3:00 pm

Nonstop3h 16m

Key West

Sat 2/21

3:47 pm-6:26 pm

Nonstop3h 39m

$399

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Sun 1/18

7:58 pm-9:09 am

1 stop12h 11m

$95

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/16

Showing 1-10 of 17 results
1
2

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 December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust 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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago O'Hare Intl Airport-Key West flight deals on Cheapflights vs. eDreams >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 December 12, 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 57 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, January is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Key West (average of $249). Flying from Chicago O'Hare Intl Airport to Key West in October is currently the most expensive (average of $323). 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 December 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 in the afternoon. If you’re flexible enough to do this you can expect to save up to 50% on your trip compared to booking a flight in the evening.

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

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 December 18, 2025.
Read reviews from past customers who have flown Delta, United Airlines, and American Airlines from Chicago O'Hare Intl Airport to Key West. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,005 reviews

Entertainment

7.9

Food

7.3

Boarding

8.1

Comfort

7.9

Crew

8.5

Overall

7.9

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
7.9
Good
8,005 reviews
Delta
7.9
Good
8,005 reviews

Entertainment

7.9

Food

7.3

Boarding

8.1

Comfort

7.9

Crew

8.5

Overall

7.9

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
9,092 reviews
Delta
7.9
Good
8,005 reviews

Entertainment

7.9

Food

7.3

Boarding

8.1

Comfort

7.9

Crew

8.5

Overall

7.9

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
11,055 reviews
Delta
7.9
Good
8,005 reviews

Entertainment

7.9

Food

7.3

Boarding

8.1

Comfort

7.9

Crew

8.5

Overall

7.9

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.
Spirit Airlines
6.3
Okay
8,190 reviews
Delta
7.9
Good
8,005 reviews

Entertainment

7.9

Food

7.3

Boarding

8.1

Comfort

7.9

Crew

8.5

Overall

7.9

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 4 airlines. Key West is conveniently located just 2.6 mi from Key West’s city center.

  • How long is the flight from Chicago O'Hare Intl Airport to Key West?

    Airlines like Delta and United Airlines fly from Chicago O'Hare Intl Airport to Key West in about 7h 08m. The time it takes to get you to your destination can typically vary by up to 05m. The distance from Chicago O'Hare Intl Airport to Key West is about 1253 mi. This flight may include one or multiple stops.

  • 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 $199. Other airlines that can offer you cheap pricing are Delta, from $248, and United Airlines, from $249. These flights start at 54% lower than the current average price 3 months from now.

  • 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 American Airlines (71%), Envoy Air (71%) and United Airlines (66%).

  • 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 $158. While the most popular route (Chicago O'Hare Intl - Key West) can be booked for $169 on average, our data indicates $369 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, January is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Key West (average of $249). Flying from Chicago O'Hare Intl Airport to Key West in October is currently the most expensive (average of $323). 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

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Top 4 airlines flying from O'Hare Intl to Key West

Discover the top 4 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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$199Average$385FlexibilityNo cancel feeOn-time65%
DeltaCheapest$248Average$363FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$249Average$486FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$323Average$459FlexibilityNo cancel feeOn-time71%

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