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Key West

$156+ 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 5/16. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — EYW
abr. 22 — abr. 291
mar. 4/22
mar. 4/29
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Key West are usually found in August 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 abril 17, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$323
(Delta)

One-way from

$156
(Mytrip)

Popular in

March

Cheapest in

August

Average price

$456

Good round-trip deal

$412 or less

Good one-way deal

$250 or less
Provider with most accurate pricing for Chicago (CHI)-Key West flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Key West flights.
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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. 10% potential increase in price ($49 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in April 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 abril 17, 2025.

This Delta deal was found by Cheapflights users on 4/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 7/810:35 amMDW - EYW
1 stop5h 40mDelta
mié. 7/96:00 pmEYW - MDW
1 stop4h 47mDelta
Deal found 4/17$323
This American Airlines deal was found by Cheapflights users on 4/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 6/255:00 amORD - EYW
1 stop7h 48mAmerican Airlines
mié. 7/23:02 pmEYW - ORD
1 stop7h 23mAmerican Airlines
Deal found 4/17$323
This Delta deal was found by Cheapflights users on 4/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 6/3011:20 amORD - EYW
1 stop7h 19mDelta
mié. 7/96:00 pmEYW - ORD
1 stop6h 55mDelta
Deal found 4/17$324
This Mytrip deal was found by Cheapflights users on 4/16. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 7/114:38 pmORD - EYW
1 stop21h 30mMultiple Airlines
lun. 7/141:47 pmEYW - ORD
1 stop18h 53mMultiple Airlines
Deal found 4/16$325
This United Airlines deal was found by Cheapflights users on 4/16. 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.
mar. 6/174:20 pmORD - EYW
1 stop24h 45mUnited Airlines
vie. 6/201:00 pmEYW - ORD
1 stop21h 24mUnited Airlines
Deal found 4/16$392

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 abril 17, 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

MDW - EYW

MDWEYW

Chicago Midway

mar. 7/8

10:35 am-5:15 pm

1 stop5h 40m

Key West

mié. 7/9

6:00 pm-9:47 pm

1 stop4h 47m

$323

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

mié. 6/25

5:00 am-1:48 pm

1 stop7h 48m

Key West

mié. 7/2

3:02 pm-9:25 pm

1 stop7h 23m

$323

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

lun. 6/30

11:20 am-7:39 pm

1 stop7h 19m

Key West

mié. 7/9

6:00 pm-11:55 pm

1 stop6h 55m

$324

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

vie. 7/11

4:38 pm-3:08 pm

1 stop21h 30m

Key West

lun. 7/14

1:47 pm-7:40 am

1 stop18h 53m

$325

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

mar. 6/17

4:20 pm-6:05 pm

1 stop24h 45m

Key West

vie. 6/20

1:00 pm-9:24 am

1 stop21h 24m

$392

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

vie. 5/16

7:35 pm-4:13 pm

2 stops19h 38m

$156

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

mié. 4/30

12:07 pm-6:55 pm

1 stop5h 48m

$187

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

dom. 6/1

7:36 am-8:00 am

1 stop23h 24m

$207

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

mié. 5/14

7:10 am-8:07 pm

2 stops11h 57m

$263

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

mié. 5/7

10:25 am-5:30 pm

1 stop6h 05m

$264

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/17

Showing 1-10 of 11 results
1
2

Compare providers for flights from Chicago 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 Chicago to Key West in April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 stars
eDreamsPrice 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-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-Key West flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Key West flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-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-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 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 April 11, 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 abril 17, 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.

Weekly flight availability from Chicago to Key West

Explore weekly flight availability from Chicago to Key West. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated abril 17, 2025.

The most flights from CHI to EYW are scheduled on a Monday (3 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (3 on average).

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 abril 17, 2025.
To help decide which airline to fly from Chicago to Key West, see what other customers have to say about Alaska Airlines, Delta and United Airlines. 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.
Alaska Airlines
8.0
Very good
9,882 reviews

Comfort

7.9

Overall

8.0

Food

7.1

Crew

8.5

Boarding

8.2

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Alaska Airlines
8.0
Very good
9,882 reviews
Alaska Airlines
8.0
Very good
9,882 reviews

Comfort

7.9

Overall

8.0

Food

7.1

Crew

8.5

Boarding

8.2

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Delta
8.0
Very good
7,917 reviews
Alaska Airlines
8.0
Very good
9,882 reviews

Comfort

7.9

Overall

8.0

Food

7.1

Crew

8.5

Boarding

8.2

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
United Airlines
7.4
Good
8,667 reviews
Alaska Airlines
8.0
Very good
9,882 reviews

Comfort

7.9

Overall

8.0

Food

7.1

Crew

8.5

Boarding

8.2

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
9,882 reviews

Comfort

7.9

Overall

8.0

Food

7.1

Crew

8.5

Boarding

8.2

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >

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 3 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 Delta. Our recent data shows that you can find tickets from as low as $323 on this airline. Additional options worth looking into are American Airlines and United Airlines, starting at $323 and $383 round-trip. Delta is currently priced 25% 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 American Airlines, with whom users have recently found tickets for as low as $187. However, be on the lookout for offers from United Airlines and Delta, 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 (84%), Republic Airways (79%), Air New Zealand( 76%).

  • 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 $680, our data indicates the cheapest price to be $206. The most popular route (Chicago O'Hare Intl - Key West), is priced around $255.

  • 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.

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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 abril 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$216Average$383FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$259Average$432FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$262Average$467FlexibilityNo cancel feeOn-time69%

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