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Key West

$82+ 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 2/25. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — EYW
Jan 2 — Jan 91
Fri 1/2
Fri 1/9
1 adult, Economy
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Find cheap flights from Chicago to Key West with Cheapflights

1. Tell us where you want to go

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Cheapflights Tip: The best prices from Chicago to Key West are usually found in July or August, booked 77 days in advance, depart on a Tuesday or Wednesday and return on a Thursday

Cheap 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 December 3, 2025.

This American Airlines deal was found by Cheapflights users on 12/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/318:10 amORD - EYW
Nonstop3h 35mAmerican Airlines
Wed 1/712:00 pmEYW - ORD
1 stop5h 20mAmerican Airlines
Deal found 12/1$286
This Kiwi.com deal was found by Cheapflights users on 12/2. 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 12/113:10 pmMDW - EYW
1 stop16h 05mMultiple Airlines
Mon 12/158:55 amEYW - MDW
2 stops24h 51mMultiple Airlines
Deal found 12/2$289
This American Airlines deal was found by Cheapflights users on 12/2. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/224:05 pmORD - EYW
1 stop5h 39mAmerican Airlines
Mon 12/291:15 pmEYW - ORD
Nonstop3h 35mAmerican Airlines
Deal found 12/2$289
This Kiwi.com deal was found by Cheapflights users on 12/1. 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.
Fri 12/121:34 pmORD - EYW
1 stop26h 22mMultiple Airlines
Tue 12/1611:45 amEYW - ORD
1 stop25h 54mMultiple Airlines
Deal found 12/1$291
This Kiwi.com deal was found by Cheapflights users on 12/1. 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.
Fri 12/1912:39 pmORD - EYW
2 stops17h 28mMultiple Airlines
Tue 12/2312:20 pmEYW - ORD
1 stop13h 10mMultiple Airlines
Deal found 12/1$292
This Mytrip deal was found by Cheapflights users on 11/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/75:00 amORD - EYW
1 stop5h 20mSpirit Airlines
Thu 12/1112:20 pmEYW - ORD
3 stops27h 01mSpirit Airlines
Deal found 11/30$294
This Kiwi.com deal was found by Cheapflights users on 12/1. 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.
Tue 12/94:22 pmORD - EYW
2 stops16h 45mMultiple Airlines
Sun 12/1412:20 pmEYW - ORD
1 stop23h 48mMultiple Airlines
Deal found 12/1$295
This Mytrip deal was found by Cheapflights users on 12/1. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/225:00 amORD - EYW
1 stop7h 30mSpirit Airlines
Mon 12/292:30 pmEYW - ORD
2 stops19h 01mSpirit Airlines
Deal found 12/1$297
This Kiwi.com deal was found by Cheapflights users on 12/2. 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.
Wed 12/246:05 amORD - EYW
2 stops25h 10mMultiple Airlines
Sat 12/272:30 pmEYW - ORD
1 stop11h 00mMultiple Airlines
Deal found 12/2$298
This Kiwi.com deal was found by Cheapflights users on 12/1. 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 12/103:26 pmORD - EYW
1 stop18h 54mMultiple Airlines
Tue 12/1611:45 amEYW - ORD
1 stop25h 54mMultiple Airlines
Deal found 12/1$300
This Kiwi.com deal was found by Cheapflights users on 12/1. 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.
Thu 12/1111:44 amORD - EYW
2 stops19h 31mMultiple Airlines
Wed 12/174:31 pmEYW - ORD
1 stop21h 08mMultiple Airlines
Deal found 12/1$304
This Kiwi.com deal was found by Cheapflights users on 12/1. 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.
Fri 12/1912:39 pmORD - EYW
2 stops17h 28mMultiple Airlines
Sun 12/218:55 amEYW - ORD
1 stop11h 26mMultiple Airlines
Deal found 12/1$305

Find 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 December 3, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$286
(American Airlines)

One-way from

$82
(Mytrip)

Popular in

March

Cheapest in

July

Average price

$436

Good round-trip deal

$381 or less

Good one-way deal

$293 or less
Provider with most accurate pricing for Chicago (CHI)-Key West flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Key West flights.
Search Deals
From Chicago (CHI) to Key West
Search Deals
One-way flight from Chicago (CHI) to Key West
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($33 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to Key West.
Search Deals
Price to beat on a one-way flight from Chicago (CHI) to Key West.
Search Deals

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 December 3, 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

Tue 2/10

12:48 pm-7:40 pm

1 stop5h 52m

Key West

Tue 2/17

6:07 pm-10:44 pm

1 stop5h 37m

$289

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Tue 2/10

12:48 pm-7:40 pm

1 stop5h 52m

Key West

Thu 2/19

6:07 pm-6:37 pm

2 stops25h 30m

$292

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Fri 1/23

10:48 am-5:11 pm

1 stop5h 23m

Key West

Mon 1/26

6:06 pm-10:22 pm

1 stop5h 16m

$294

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Thu 1/22

10:48 am-5:11 pm

1 stop5h 23m

Key West

Mon 1/26

6:06 pm-10:22 pm

1 stop5h 16m

$319

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Fri 1/23

5:30 am-11:25 am

1 stop4h 55m

Key West

Mon 1/26

6:06 pm-11:56 pm

1 stop6h 50m

$319

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Wed 2/11

12:48 pm-7:40 pm

1 stop5h 52m

Key West

Thu 2/19

6:07 pm-10:42 pm

1 stop5h 35m

$324

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Wed 2/11

12:48 pm-7:40 pm

1 stop5h 52m

Key West

Wed 2/18

6:07 pm-10:42 pm

1 stop5h 35m

$324

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Wed 2/11

12:48 pm-7:40 pm

1 stop5h 52m

Key West

Tue 2/17

6:07 pm-10:44 pm

1 stop5h 37m

$324

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Wed 2/11

12:48 pm-7:40 pm

1 stop5h 52m

Key West

Fri 2/20

6:07 pm-10:42 pm

1 stop5h 35m

$324

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Fri 2/6

12:48 pm-7:40 pm

1 stop5h 52m

Key West

Mon 2/9

6:06 pm-10:22 pm

1 stop5h 16m

$334

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/2

Showing 1-10 of 41 results
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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 December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago-Key West flight deals on Cheapflights vs. eDreams >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 November 28, 2025.

The best time to book flights from Chicago to Key West is 77 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, November is the cheapest month in which you can book a flight from Chicago to Key West (average of $211). Flying from Chicago to Key West in August is currently the most expensive (average of $336). 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 December 3, 2025.

It’s optimal to fly from Chicago to Key West in the afternoon. By choosing this option you can save up to 50% 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 December 3, 2025.

The most flights from CHI to EYW are scheduled on a Tuesday (3 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (2 on average).

The best insider tips for Chicago 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 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

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 December 3, 2025.
Peruse reviews from past customers who have flown with Delta, United Airlines, and American Airlines from Chicago to Key West to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,011 reviews

Crew

8.5

Comfort

7.9

Entertainment

7.9

Overall

7.9

Food

7.3

Boarding

8.1

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
7.9
Good
8,011 reviews
Delta
7.9
Good
8,011 reviews

Crew

8.5

Comfort

7.9

Entertainment

7.9

Overall

7.9

Food

7.3

Boarding

8.1

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
9,063 reviews
Delta
7.9
Good
8,011 reviews

Crew

8.5

Comfort

7.9

Entertainment

7.9

Overall

7.9

Food

7.3

Boarding

8.1

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
11,045 reviews
Delta
7.9
Good
8,011 reviews

Crew

8.5

Comfort

7.9

Entertainment

7.9

Overall

7.9

Food

7.3

Boarding

8.1

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 2 daily inbound flights from Chicago from 3 different airlines.

  • How long is the flight from Chicago to Key West?

    Airlines like Delta and United Airlines fly from Chicago to Key West in about 5h 52m. The time it takes to get you to your destination can typically vary by up to 38m. Chicago and Key West are separated by a distance of 1238 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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 $248 on this airline. Additional options worth looking into are United Airlines and American Airlines, starting at $250 and $322 round-trip. Delta is currently priced 44% below the average price you’ll pay for this route.

  • 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: American Airlines (75%), Envoy Air (75%), United Airlines( 68%).

  • 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 $377, our data indicates the cheapest price to be $141. The most popular route (Chicago O'Hare Intl - Key West), is priced around $184.

  • 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, November is the cheapest month in which you can book a flight from Chicago to Key West (average of $211). Flying from Chicago to Key West in August is currently the most expensive (average of $336). 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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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 December 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$248Average$396FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$251Average$488FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$320Average$456FlexibilityNo cancel feeOn-time71%

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