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Key West

$118+ 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 9/29. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — EYW
Sep 2 — Sep 91
Wed 9/2
Wed 9/9
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago O'Hare Intl to Key West are usually found in May or August, booked 86 days in advance, depart on a Tuesday or Wednesday and return on a Wednesday

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 August 3, 2026.

This Kiwi.com deal was found by Cheapflights users on 8/2. 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 9/57:44 pm
ORD
-
EYW
1 stop14h 41m
Multiple Airlines
Wed 9/910:04 am
EYW
-
ORD
2 stops9h 19m
Multiple Airlines
Deal found 8/2$254
This Kiwi.com deal was found by Cheapflights users on 8/1. 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 8/265:59 pm
ORD
-
EYW
1 stop16h 26m
Multiple Airlines
Wed 9/211:46 am
EYW
-
ORD
2 stops9h 22m
Multiple Airlines
Deal found 8/1$256
This Kiwi.com deal was found by Cheapflights users on 8/1. 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 8/265:59 pm
ORD
-
EYW
1 stop16h 26m
Multiple Airlines
Tue 9/11:14 pm
EYW
-
ORD
2 stops31h 54m
Multiple Airlines
Deal found 8/1$257
This Kiwi.com deal was found by Cheapflights users on 7/30. 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 9/123:50 pm
ORD
-
EYW
1 stop17h 29m
Multiple Airlines
Sat 9/1910:04 am
EYW
-
ORD
2 stops9h 19m
Multiple Airlines
Deal found 7/30$258
This Kiwi.com deal was found by Cheapflights users on 7/31. 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 8/225:59 pm
ORD
-
EYW
1 stop16h 26m
Multiple Airlines
Wed 8/2611:46 am
EYW
-
ORD
2 stops9h 22m
Multiple Airlines
Deal found 7/31$269
This Kiwi.com deal was found by Cheapflights users on 8/1. 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 8/2312:44 am
ORD
-
EYW
2 stops34h 50m
Multiple Airlines
Mon 8/3112:07 pm
EYW
-
ORD
1 stop12h 01m
Multiple Airlines
Deal found 8/1$270
This Kiwi.com deal was found by Cheapflights users on 8/2. 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 9/107:28 pm
ORD
-
EYW
2 stops36h 56m
Multiple Airlines
Thu 9/1710:59 am
EYW
-
ORD
1 stop13h 00m
Multiple Airlines
Deal found 8/2$271
This Kiwi.com deal was found by Cheapflights users on 8/1. 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 9/263:50 pm
ORD
-
EYW
1 stop17h 29m
Multiple Airlines
Wed 9/3010:04 am
EYW
-
ORD
2 stops9h 19m
Multiple Airlines
Deal found 8/1$273
This Kiwi.com deal was found by Cheapflights users on 7/31. 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 10/249:20 am
ORD
-
EYW
2 stops25h 01m
Multiple Airlines
Thu 10/2910:59 am
EYW
-
ORD
1 stop13h 51m
Multiple Airlines
Deal found 7/31$274
This Kiwi.com deal was found by Cheapflights users on 8/1. 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 8/2412:44 am
ORD
-
EYW
2 stops33h 22m
Multiple Airlines
Mon 8/3112:07 pm
EYW
-
ORD
1 stop12h 01m
Multiple Airlines
Deal found 8/1$275
This Kiwi.com deal was found by Cheapflights users on 8/1. 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 11/74:44 pm
ORD
-
EYW
1 stop19h 12m
Multiple Airlines
Wed 11/1110:04 am
EYW
-
ORD
2 stops24h 57m
Multiple Airlines
Deal found 8/1$276

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 August 3, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$254
(Kiwi.com)

One-way from

$118
(Kiwi.com)

Popular in

February

Cheapest in

May

Average price

$370

Good round-trip deal

$349 or less

Good one-way deal

$283 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
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($52 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 2026
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.
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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 August 3, 2026.
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

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Tue 10/20

1:23 pm-8:01 pm

1 stop5h 38m

Key West

Thu 10/29

11:51 am-5:03 pm

1 stop6h 12m

$339

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Sat 8/15

1:50 pm-7:57 pm

1 stop5h 07m

Key West

Sat 8/22

7:40 am-2:48 pm

1 stop8h 08m

$423

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Thu 8/13

11:23 am-7:57 pm

1 stop7h 34m

Key West

Wed 8/19

6:15 pm-11:57 pm

1 stop6h 42m

$448

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Thu 10/22

9:51 am-5:15 pm

1 stop6h 24m

Key West

Mon 10/26

6:10 pm-11:52 pm

1 stop6h 42m

$458

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Tue 9/1

6:40 am-1:00 pm

1 stop5h 20m

Key West

Sat 9/5

1:31 pm-8:30 pm

2 stops7h 59m

$695
Quickest round-trip

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Sat 10/10

6:00 am-1:29 pm

1 stop6h 29m

Key West

Sat 10/17

4:00 pm-5:27 pm

Nonstop2h 27m

$699

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Thu 8/27

8:48 am-7:57 pm

2 stops10h 09m

Key West

Mon 8/31

6:15 pm-11:57 pm

1 stop6h 42m

$723

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Sat 8/22

5:00 am-1:29 pm

1 stop7h 29m

Key West

Wed 8/26

2:15 pm-8:07 pm

1 stop6h 52m

$726

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Fri 10/9

6:30 am-12:53 pm

1 stop5h 23m

Key West

Mon 10/12

7:40 am-2:28 pm

1 stop7h 48m

$775

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Thu 8/20

6:00 am-5:20 pm

2 stops10h 20m

Key West

Sat 8/22

7:40 am-2:48 pm

1 stop8h 08m

$793

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/1

Showing 1-10 of 21 resultsSorted by cheapest first
1
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3

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 August.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice 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 FlightHub the most. FlightHub 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?

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 85 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, May is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Key West (average of $369). Flying from Chicago O'Hare Intl Airport to Key West in February is currently the most expensive (average of $535). 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 August 3, 2026.

When flying from Chicago O'Hare Intl Airport to Key West, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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

Airfare is below average for this route at the moment.

Chicago O'Hare Intl Airport to Key West flights typically cost between $329 and $452 in September.
The cheapest round-trip price found within the last 5 days was $254 on Multiple Airlines (Sep 5-Sep 9).

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
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on ORD

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

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 August 3, 2026.
Read reviews from past customers who have flown Delta,United Airlines, andAmerican 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
7.8
Good
8,483 reviews

Food

7.2

Entertainment

7.8

Boarding

8.1

Crew

8.5

Overall

7.8

Comfort

7.8

Reviews

1 / 20
4.0
Okay

Joel,May 2026

ATL - JAX

The flight was delivered 50 minutes and taxing took what felt like 20 minutes to takeoff.
Delta
7.8
Good
8,483 reviews
Delta
7.8
Good
8,483 reviews

Food

7.2

Entertainment

7.8

Boarding

8.1

Crew

8.5

Overall

7.8

Comfort

7.8

Reviews

1 / 20
4.0
Okay

Joel,May 2026

ATL - JAX

The flight was delivered 50 minutes and taxing took what felt like 20 minutes to takeoff.
United Airlines
7.4
Good
10,058 reviews
Delta
7.8
Good
8,483 reviews

Food

7.2

Entertainment

7.8

Boarding

8.1

Crew

8.5

Overall

7.8

Comfort

7.8

Reviews

1 / 20
4.0
Okay

Joel,May 2026

ATL - JAX

The flight was delivered 50 minutes and taxing took what felt like 20 minutes to takeoff.
American Airlines
7.1
Good
11,842 reviews
Delta
7.8
Good
8,483 reviews

Food

7.2

Entertainment

7.8

Boarding

8.1

Crew

8.5

Overall

7.8

Comfort

7.8

Reviews

1 / 20
4.0
Okay

Joel,May 2026

ATL - JAX

The flight was delivered 50 minutes and taxing took what felt like 20 minutes to takeoff.

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 2 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 5h 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 $206. Other airlines that can offer you cheap pricing are United Airlines, from $249, and American Airlines, from $305. These flights start at 52% 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 United Airlines (84%), Air New Zealand (84%) and Republic Airways (84%).

  • 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 $261. While the most popular route (Chicago O'Hare Intl - Key West) can be booked for $258 on average, our data indicates $407 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, May is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Key West (average of $369). Flying from Chicago O'Hare Intl Airport to Key West in February is currently the most expensive (average of $535). 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

Browse thousands of different options on Cheapflights for your next trip

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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 August 3, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$206Average$418FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$249Average$409FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$305Average$468FlexibilityNo cancel feeOn-time71%

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