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Key West

$153+ Cheap flights from Chicago (CHI) 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 6/21. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — EYW
juin 17 — juin 241
mar. 6/17
mar. 6/24
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Key West are usually found in October or September, booked 42 days in advance, depart on a Tuesday or Wednesday and return on a Thursday

Cheap flight deals from Chicago to Key West

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) 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 juin 12, 2025.

Round-trip from

$323
(American Airlines)

One-way from

$153
(Mytrip)

Popular in

March

Cheapest in

October

Average price

$485

Good round-trip deal

$361 or less

Good one-way deal

$258 or less
From Chicago (CHI) to Key West
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One-way flight from Chicago (CHI) to Key West
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Highest demand for flights based on searches. 7% potential increase in price ($37 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in June 2025
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Price to beat on a round-trip flight from Chicago (CHI) to Key West.
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Price to beat on a one-way flight from Chicago (CHI) to Key West.
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Find flight deals from Chicago to Key West

Cheapest flights from Chicago to Key West
Explore the most affordable flight options available from Chicago to Key West. Find the lowest fares from popular airlines and budget airlines, with prices last updated on juin 12, 2025.

This American Airlines deal was found by Cheapflights users on 6/12. 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.
mar. 7/157:05 amORD - EYW
1 stop6h 04mAmerican Airlines
mar. 7/224:58 pmEYW - ORD
1 stop6h 53mAmerican Airlines
Deal found 6/12$323
This Delta deal was found by Cheapflights users on 6/11. 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.
sam. 7/56:00 amMDW - EYW
1 stop6h 09mDelta
mer. 7/97:00 amEYW - MDW
1 stop5h 58mDelta
Deal found 6/11$324
This Delta deal was found by Cheapflights users on 6/11. 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.
sam. 7/511:20 amORD - EYW
1 stop7h 19mDelta
mer. 7/96:27 pmEYW - ORD
1 stop6h 42mDelta
Deal found 6/11$324
This United Airlines deal was found by Cheapflights users on 6/10. 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.
jeu. 12/1110:55 amORD - EYW
Nonstop3h 11mUnited Airlines
mar. 12/164:05 pmEYW - ORD
Nonstop3h 25mUnited Airlines
Deal found 6/10$329
This Mytrip deal was found by Cheapflights users on 6/12. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 7/3111:11 amORD - EYW
2 stops28h 25mMultiple Airlines
dim. 8/35:35 pmEYW - ORD
2 stops28h 55mMultiple Airlines
Deal found 6/12$331
This Mytrip deal was found by Cheapflights users on 6/12. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dim. 7/2711:37 amMDW - EYW
2 stops27h 59mAllegiant Air
dim. 8/34:20 pmEYW - MDW
1 stop21h 01mAllegiant Air
Deal found 6/12$335

Cheapflights Fare Finder

Customize your flight search to find flights from Chicago 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 juin 12, 2025.
Use the filters below to find and compare flights from Chicago to Key West that are best for you.

Fly from

Chicago

Fly to

Key West

Route

Depart

Return

Price

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

mar. 7/15

7:05 am-2:09 pm

1 stop6h 04m

Key West

mar. 7/22

4:58 pm-10:51 pm

1 stop6h 53m

$323

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

sam. 7/5

6:00 am-1:09 pm

1 stop6h 09m

Key West

mer. 7/9

7:00 am-11:58 am

1 stop5h 58m

$324

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

sam. 7/5

11:20 am-7:39 pm

1 stop7h 19m

Key West

mer. 7/9

6:27 pm-12:09 am

1 stop6h 42m

$324

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

jeu. 7/31

11:11 am-4:36 pm

2 stops28h 25m

Key West

dim. 8/3

5:35 pm-9:30 pm

2 stops28h 55m

$331

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

dim. 7/27

11:37 am-4:36 pm

2 stops27h 59m

Key West

dim. 8/3

4:20 pm-12:21 pm

1 stop21h 01m

$335

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

mar. 7/22

6:00 am-1:12 pm

1 stop6h 12m

Key West

ven. 7/25

2:45 pm-9:34 am

1 stop19h 49m

$341

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

sam. 6/21

7:27 am-8:03 am

1 stop23h 36m

$153

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

ven. 8/1

7:00 am-6:05 pm

1 stop10h 05m

$221

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

sam. 7/26

12:43 pm-7:49 pm

1 stop6h 06m

$264

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

sam. 7/26

11:20 am-7:49 pm

1 stop7h 29m

$264

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

Showing 1-10 of 11 results
1
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The best insider tips for Chicago 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 to Key West trip
Airports
ORD

For a quick departure from ORD, consider taking the 'L' train to avoid Chicago traffic delays.

Read more about ORDby Ramsey Qubein
EYW

After landing at EYW, you can quickly reach most island points within ten minutes by car.

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 Chicago to Key West

Have a flexible travel schedule? Discover the best time to fly to Key West from Chicago 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 to Key West

How far ahead should I book a flight from Chicago to Key West?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Key West. Price data was last updated on June 9, 2025.

The best time to book flights from Chicago to Key West is 42 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

What is the cheapest month to book a flight from Chicago to Key West?

Currently, August is the cheapest month in which you can book a flight from Chicago to Key West (average of $328). Flying from Chicago 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 CHI to EYW?

Find hourly flight availability from Chicago 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 juin 12, 2025.

It’s optimal to fly from Chicago to Key West at noon. By choosing this option you can save up to 59% on the cost of your flight, compared to a flight in the evening.

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 juin 12, 2025.
To help decide which airline to fly from Chicago to Key West, see what other customers have to say about Delta, United Airlines and Allegiant Air. 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
7,950 reviews

Entertainment

7.9

Crew

8.5

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.3

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
7,950 reviews
Delta
8.0
Very good
7,950 reviews

Entertainment

7.9

Crew

8.5

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.3

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
8,790 reviews
Delta
8.0
Very good
7,950 reviews

Entertainment

7.9

Crew

8.5

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.3

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.
Allegiant Air
7.3
Good
725 reviews
Delta
8.0
Very good
7,950 reviews

Entertainment

7.9

Crew

8.5

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.3

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
7,950 reviews

Entertainment

7.9

Crew

8.5

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.3

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 Chicago 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?

    Located just 2.6 mi from the city center, Key West is the airport most travelers will use when flying to Key West from Chicago. Booking flights from Chicago to Key West (EYW) should be relatively easy as there are 0 daily inbound flights from Chicago from 3 different airlines.

  • What are the cheapest airlines flying from Chicago to Key West round-trip?

    Our cheapest airline available from Chicago to Key West is American Airlines. Our recent data shows that you can find tickets from as low as $323 on this airline. Additional options worth looking into are Delta and United Airlines, starting at $324 and $330 round-trip. American Airlines is currently priced 27% below the average price you’ll pay for this route.

  • What are the cheapest airlines to fly from Chicago to Key West one-way?

    The cheapest airline one-way is United Airlines, with whom users have recently found tickets for as low as $174. However, be on the lookout for offers from Delta and American Airlines, as they are both options that can get you from Chicago to Key West for a low price.

  • What are the most reliable airlines from Chicago to Key West?

    Before booking your flight to Key West from Chicago, check out the most reliable airlines to get you to your destination on time: United Airlines (86%), Air New Zealand (86%), American Airlines( 74%).

  • What are the cheapest flights from Chicago to Key West?

    Looking for the cheapest flight from Chicago to Key West? While on average our users pay $434, our data indicates the cheapest price to be $151. The most popular route (Chicago O'Hare Intl - Key West), is priced around $247.

  • Can I find deals for flights from Chicago to Key West that include hotel bookings?

    Yes. In addition to deals on Chicago to Key West flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Key West?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Key West.

  • Can I find deals for business class flights from Chicago to Key West?

    Yes. Cheapflights offers flight deals from Chicago 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 to Key West?

    Currently, August is the cheapest month in which you can book a flight from Chicago to Key West (average of $328). Flying from Chicago 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.

See more FAQs

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Alternative routes for Chicago 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 Chicago to Key West

Discover the top 3 airlines that operate flights from Chicago 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 juin 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$216Average$399FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$263Average$473FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$283Average$443FlexibilityNo cancel feeOn-time71%

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