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$109+ 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 11/7. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — EYW
Oct 9 — Oct 161
Thu 10/9
Thu 10/16
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago O'Hare Intl to Key West are usually found in June 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 September 9, 2025.

Round-trip from

$209
(Kiwi.com)

One-way from

$109
(Kiwi.com)

Popular in

March

Cheapest in

June

Average price

$403

Good round-trip deal

$434 or less

Good one-way deal

$272 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 ($64 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 September 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 September 9, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/8. 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.
Tue 9/235:46 pmORD - EYW
1 stop14h 26mMultiple Airlines
Fri 9/269:31 pmEYW - ORD
1 stop13h 46mMultiple Airlines
Deal found 9/8$209
This Kiwi.com deal was found by Cheapflights users on 9/9. 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.
Sun 10/58:49 pmORD - EYW
1 stop10h 26mMultiple Airlines
Thu 10/98:55 amEYW - ORD
1 stop23h 39mMultiple Airlines
Deal found 9/9$212
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 9/245:46 pmORD - EYW
1 stop21h 14mMultiple Airlines
Sat 9/279:52 amEYW - ORD
1 stop25h 26mMultiple Airlines
Deal found 9/9$219
This Kiwi.com deal was found by Cheapflights users on 9/8. 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.
Tue 9/235:46 pmORD - EYW
1 stop14h 26mMultiple Airlines
Wed 10/810:02 amEYW - ORD
1 stop25h 06mMultiple Airlines
Deal found 9/8$221
This Kiwi.com deal was found by Cheapflights users on 9/7. 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.
Fri 10/35:46 pmORD - EYW
1 stop14h 16mMultiple Airlines
Tue 10/711:45 amEYW - ORD
1 stop23h 23mMultiple Airlines
Deal found 9/7$231
This Priceline deal was found by Cheapflights users on 9/8. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/95:05 amORD - EYW
1 stop7h 25mSpirit Airlines
Fri 11/142:25 pmEYW - ORD
1 stop7h 35mSpirit Airlines
Deal found 9/8$235
This Kiwi.com deal was found by Cheapflights users on 9/8. 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.
Thu 10/28:05 amORD - EYW
1 stop22h 17mMultiple Airlines
Mon 10/69:57 amEYW - ORD
1 stop25h 11mMultiple Airlines
Deal found 9/8$236
This Kiwi.com deal was found by Cheapflights users on 9/8. 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.
Tue 11/41:56 pmORD - EYW
1 stop18h 15mMultiple Airlines
Sat 11/89:51 amEYW - ORD
1 stop28h 47mMultiple Airlines
Deal found 9/8$237
This Kiwi.com deal was found by Cheapflights users on 9/8. 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.
Tue 9/235:46 pmORD - EYW
1 stop14h 21mMultiple Airlines
Thu 9/258:55 amEYW - ORD
1 stop8h 17mMultiple Airlines
Deal found 9/8$240
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 10/86:58 pmORD - EYW
1 stop12h 17mMultiple Airlines
Wed 10/1510:47 amEYW - ORD
1 stop24h 21mMultiple Airlines
Deal found 9/9$244

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 September 9, 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

Wed 10/8

6:58 pm-8:15 am

1 stop12h 17m

Key West

Wed 10/15

10:47 am-10:08 am

1 stop24h 21m

$244

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Tue 9/23

11:45 am-9:12 am

2 stops20h 27m

Key West

Fri 9/26

9:31 pm-10:17 am

1 stop13h 46m

$247

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Tue 9/23

11:45 am-9:12 am

2 stops20h 27m

Key West

Wed 10/8

10:02 am-10:08 am

1 stop25h 06m

$258

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Mon 10/27

5:50 pm-11:05 am

2 stops16h 15m

Key West

Fri 10/31

9:45 pm-12:07 pm

1 stop15h 22m

$263

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Tue 12/2

11:15 am-8:03 pm

1 stop7h 48m

Key West

Sat 12/6

6:05 pm-10:44 pm

1 stop5h 39m

$269

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Thu 10/16

6:18 pm-9:17 am

1 stop13h 59m

Key West

Tue 10/21

11:45 am-10:08 am

1 stop23h 23m

$269

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Sat 11/8

10:18 am-8:15 am

1 stop20h 57m

Key West

Wed 11/12

10:47 am-1:59 pm

1 stop28h 12m

$283

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Mon 10/27

11:00 am-3:19 pm

Nonstop3h 19m

Key West

Fri 10/31

2:48 pm-11:34 pm

1 stop9h 46m

$307

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Mon 10/6

6:18 pm-11:05 am

1 stop15h 47m

Key West

Mon 10/13

9:57 am-10:08 am

1 stop25h 11m

$309

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Mon 11/3

11:00 am-3:19 pm

Nonstop3h 19m

Key West

Sat 11/8

4:00 pm-6:46 pm

Nonstop3h 46m

$317

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/9

Showing 1-10 of 23 results
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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 August 29, 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 $491). 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 September 9, 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 morning. If you’re flexible enough to do this you can expect to save up to 17% on your trip compared to booking a flight at noon.

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 September 9, 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
8.0
Very good
7,965 reviews

Boarding

8.2

Overall

8.0

Crew

8.5

Comfort

7.9

Food

7.3

Entertainment

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
8.0
Very good
7,965 reviews
Delta
8.0
Very good
7,965 reviews

Boarding

8.2

Overall

8.0

Crew

8.5

Comfort

7.9

Food

7.3

Entertainment

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
8,943 reviews
Delta
8.0
Very good
7,965 reviews

Boarding

8.2

Overall

8.0

Crew

8.5

Comfort

7.9

Food

7.3

Entertainment

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
10,000 reviews
Delta
8.0
Very good
7,965 reviews

Boarding

8.2

Overall

8.0

Crew

8.5

Comfort

7.9

Food

7.3

Entertainment

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 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.

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

    Airlines like Delta fly from Chicago O'Hare Intl Airport to Key West in about 7h 48m. The time it takes to get you to your destination can typically vary by up to . The distance from Chicago O'Hare Intl Airport to Key West is about 1253 mi.

  • 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 $218. Other airlines that can offer you cheap pricing are United Airlines, from $260, and American Airlines, from $303. These flights start at 50% lower than the current average price 3 months from now.

  • 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 $253. While the most popular route (Chicago O'Hare Intl - Key West) can be booked for $211 on average, our data indicates $386 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 $491). 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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Alternative routes for O'Hare Intl to Key West

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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 September 9, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$218Average$343FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$260Average$479FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$303Average$441FlexibilityNo cancel feeOn-time71%

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