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Key West

$108+ 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 2/10. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — EYW
Oct 18 — Oct 251
Sat 10/18
Sat 10/25
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 18, 2025.

Round-trip from

$215
(Priceline)

One-way from

$108
(Priceline)

Popular in

March

Cheapest in

June

Average price

$404

Good round-trip deal

$411 or less

Good one-way deal

$253 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. 13% potential increase in price ($66 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($10 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 18, 2025.

This Expedia deal was found by Cheapflights users on 9/17. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/125:05 amORD - EYW
1 stop7h 25mSpirit Airlines
Mon 12/152:25 pmEYW - ORD
1 stop10h 17mSpirit Airlines
Deal found 9/17$223
This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
Tue 10/146:18 pmORD - EYW
1 stop13h 54mMultiple Airlines
Tue 10/2811:45 amEYW - ORD
1 stop26h 08mMultiple Airlines
Deal found 9/16$225
This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
Sat 10/116:00 pmORD - EYW
1 stop15h 19mMultiple Airlines
Tue 10/1411:45 amEYW - ORD
1 stop23h 23mMultiple Airlines
Deal found 9/16$229
This Kiwi.com deal was found by Cheapflights users on 9/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/45:17 pmORD - EYW
1 stop13h 58mMultiple Airlines
Wed 10/810:47 amEYW - ORD
1 stop24h 21mMultiple Airlines
Deal found 9/18$238
This Kiwi.com deal was found by Cheapflights users on 9/17. 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.
Fri 10/176:18 pmORD - EYW
1 stop14h 49mMultiple Airlines
Fri 10/248:55 amEYW - ORD
1 stop10h 51mMultiple Airlines
Deal found 9/17$239
This Kiwi.com deal was found by Cheapflights users on 9/17. 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.
Sun 10/266:54 pmORD - EYW
1 stop12h 21mMultiple Airlines
Fri 10/318:55 amEYW - ORD
1 stop10h 51mMultiple Airlines
Deal found 9/17$240
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 10/86:58 pmORD - EYW
1 stop12h 17mMultiple Airlines
Sat 10/1810:47 amEYW - ORD
1 stop5h 58mMultiple Airlines
Deal found 9/17$243
This Kiwi.com deal was found by Cheapflights users on 9/17. 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.
Mon 10/206:18 pmORD - EYW
1 stop15h 47mMultiple Airlines
Tue 10/2811:45 amEYW - ORD
1 stop26h 08mMultiple Airlines
Deal found 9/17$244
This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
Thu 9/254:03 pmORD - EYW
2 stops27h 38mMultiple Airlines
Thu 10/23:30 pmEYW - ORD
1 stop25h 42mMultiple Airlines
Deal found 9/16$246
This Kiwi.com deal was found by Cheapflights users on 9/17. 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.
Thu 11/67:00 amORD - EYW
1 stop25h 17mMultiple Airlines
Mon 11/102:25 pmEYW - ORD
1 stop19h 58mMultiple Airlines
Deal found 9/17$249
This Orbitz deal was found by Cheapflights users on 9/16. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/135:05 amORD - EYW
1 stop7h 25mSpirit Airlines
Sun 11/162:25 pmEYW - ORD
1 stop10h 17mSpirit Airlines
Deal found 9/16$255

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 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 11/15

11:15 am-7:53 pm

1 stop7h 38m

Key West

Wed 11/19

7:40 am-12:04 pm

1 stop5h 24m

$269

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Sat 10/25

1:26 pm-8:06 pm

1 stop5h 40m

Key West

Tue 10/28

6:17 pm-11:58 pm

1 stop6h 41m

$289

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Tue 12/9

9:50 am-5:10 pm

1 stop6h 20m

Key West

Sun 12/14

6:05 pm-12:01 am

1 stop6h 56m

$324

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Mon 12/8

9:50 am-5:10 pm

1 stop6h 20m

Key West

Sat 12/13

1:40 pm-7:25 pm

1 stop6h 45m

$337

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Sat 12/13

5:32 am-2:06 pm

1 stop7h 34m

Key West

Thu 12/18

7:40 am-12:05 pm

1 stop5h 25m

$357

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Fri 12/12

10:50 am-3:09 pm

Nonstop3h 19m

Key West

Tue 12/16

3:02 pm-11:32 pm

1 stop9h 30m

$367

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Sun 12/14

5:32 am-2:06 pm

1 stop7h 34m

Key West

Mon 12/29

11:46 am-9:01 am

2 stops22h 15m

$369

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Mon 12/15

10:50 am-3:09 pm

Nonstop3h 19m

Key West

Thu 12/18

12:22 pm-3:07 pm

Nonstop3h 45m

$377

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Tue 2/17

7:00 am-7:44 pm

2 stops11h 44m

Key West

Thu 2/26

7:00 am-7:25 pm

2 stops13h 25m

$389

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Fri 2/20

7:55 pm-11:03 am

1 stop14h 08m

Key West

Thu 2/26

1:30 pm-7:25 pm

1 stop6h 55m

$394

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

Showing 1-10 of 20 results
1
2

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 September 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 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 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 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.

How much does it cost to fly round-trip from Chicago O'Hare Intl Airport to Key West?

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 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
8.0
Very good
7,961 reviews

Entertainment

7.9

Food

7.3

Overall

8.0

Crew

8.5

Comfort

7.9

Boarding

8.2

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
7,961 reviews
Delta
8.0
Very good
7,961 reviews

Entertainment

7.9

Food

7.3

Overall

8.0

Crew

8.5

Comfort

7.9

Boarding

8.2

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
8,925 reviews
Delta
8.0
Very good
7,961 reviews

Entertainment

7.9

Food

7.3

Overall

8.0

Crew

8.5

Comfort

7.9

Boarding

8.2

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
7,961 reviews

Entertainment

7.9

Food

7.3

Overall

8.0

Crew

8.5

Comfort

7.9

Boarding

8.2

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 38m. 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 $258, 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 $216. While the most popular route (Chicago O'Hare Intl - Key West) can be booked for $215 on average, our data indicates $374 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

See prices for flight routes from nearby airports that may be better suited for you.
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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 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$218Average$345FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$258Average$485FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$303Average$440FlexibilityNo cancel feeOn-time71%

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