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Key West

$106+ 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 11/16. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — EYW
Aug 25 — Sep 11
Mon 8/25
Mon 9/1
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Key West are usually found in October or August, 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 August 20, 2025.

Round-trip from

$170
(Kiwi.com)

One-way from

$106
(Kiwi.com)

Popular in

March

Cheapest in

October

Average price

$404

Good round-trip deal

$432 or less

Good one-way deal

$293 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 August 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 August 20, 2025.

This Kiwi.com deal was found by Cheapflights users on 8/18. 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.
Sun 9/216:21 amMDW - EYW
1 stop8h 39mMultiple Airlines
Sat 9/279:52 amEYW - MDW
1 stop27h 52mMultiple Airlines
Deal found 8/18$170
This Kiwi.com deal was found by Cheapflights users on 8/18. 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.
Sun 9/216:21 amMDW - EYW
1 stop8h 39mMultiple Airlines
Thu 10/23:30 pmEYW - MDW
1 stop18h 23mMultiple Airlines
Deal found 8/18$196
This Kiwi.com deal was found by Cheapflights users on 8/18. 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.
Fri 9/266:21 amMDW - EYW
1 stop13h 20mMultiple Airlines
Thu 10/23:30 pmEYW - MDW
1 stop18h 23mMultiple Airlines
Deal found 8/18$197
This Kiwi.com deal was found by Cheapflights users on 8/20. 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 9/135:45 pmORD - EYW
1 stop21h 15mMultiple Airlines
Fri 9/193:26 pmEYW - ORD
1 stop19h 51mMultiple Airlines
Deal found 8/20$212
This Kiwi.com deal was found by Cheapflights users on 8/18. 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 stop20h 23mMultiple Airlines
Fri 10/173:08 pmEYW - ORD
1 stop25h 37mMultiple Airlines
Deal found 8/18$223
This Kiwi.com deal was found by Cheapflights users on 8/18. 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.
Fri 9/266:21 amMDW - EYW
1 stop13h 20mMultiple Airlines
Sat 9/279:52 amEYW - MDW
2 stops14h 25mMultiple Airlines
Deal found 8/18$229
This Kiwi.com deal was found by Cheapflights users on 8/18. 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.
Thu 11/67:00 amORD - EYW
1 stop11h 46mMultiple Airlines
Thu 11/139:36 pmEYW - ORD
1 stop15h 50mMultiple Airlines
Deal found 8/18$231
This Kiwi.com deal was found by Cheapflights users on 8/18. 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.
Fri 9/265:46 pmORD - EYW
1 stop14h 16mMultiple Airlines
Wed 10/110:02 amEYW - ORD
1 stop22h 08mMultiple Airlines
Deal found 8/18$236
This Kiwi.com deal was found by Cheapflights users on 8/18. 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.
Wed 9/245:46 pmORD - EYW
1 stop21h 14mMultiple Airlines
Wed 10/110:02 amEYW - ORD
1 stop22h 08mMultiple Airlines
Deal found 8/18$240
This Kiwi.com deal was found by Cheapflights users on 8/18. 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.
Tue 9/235:46 pmORD - EYW
1 stop14h 26mMultiple Airlines
Wed 10/110:02 amEYW - ORD
1 stop22h 08mMultiple Airlines
Deal found 8/18$243
This Kiwi.com deal was found by Cheapflights users on 8/19. 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 stop20h 23mMultiple Airlines
Sat 10/119:52 amEYW - ORD
1 stop28h 23mMultiple Airlines
Deal found 8/19$246
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 10/156:00 pmORD - EYW
1 stop21h 04mMultiple Airlines
Wed 10/2210:02 amEYW - ORD
1 stop28h 13mMultiple Airlines
Deal found 8/17$249

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 August 20, 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

Sun 9/21

6:21 am-4:00 pm

1 stop8h 39m

Key West

Sat 9/27

9:52 am-12:44 pm

1 stop27h 52m

$170

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Sun 9/21

6:21 am-4:00 pm

1 stop8h 39m

Key West

Thu 10/2

3:30 pm-8:53 am

1 stop18h 23m

$196

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Fri 9/26

6:21 am-8:41 pm

1 stop13h 20m

Key West

Thu 10/2

3:30 pm-8:53 am

1 stop18h 23m

$197

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Sat 9/13

5:45 pm-4:00 pm

1 stop21h 15m

Key West

Fri 9/19

3:26 pm-10:17 am

1 stop19h 51m

$212

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Sat 10/4

5:17 pm-2:40 pm

1 stop20h 23m

Key West

Fri 10/17

3:08 pm-3:45 pm

1 stop25h 37m

$223

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Fri 9/26

6:21 am-8:41 pm

1 stop13h 20m

Key West

Sat 9/27

9:52 am-11:17 pm

2 stops14h 25m

$229

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Fri 9/26

5:46 pm-9:02 am

1 stop14h 16m

Key West

Wed 10/1

10:02 am-7:10 am

1 stop22h 08m

$236

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Sat 9/27

5:45 pm-4:00 pm

1 stop21h 15m

Key West

Wed 10/1

10:02 am-7:10 am

1 stop22h 08m

$236

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Wed 9/24

5:46 pm-4:00 pm

1 stop21h 14m

Key West

Wed 10/1

10:02 am-7:10 am

1 stop22h 08m

$240

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Tue 9/23

5:46 pm-9:12 am

1 stop14h 26m

Key West

Sat 9/27

9:52 am-7:10 am

1 stop22h 18m

$243

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/19

Showing 1-10 of 35 results
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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 August 8, 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 $492). 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 August 20, 2025.

It’s optimal to fly from Chicago to Key West in the morning. By choosing this option you can save up to 44% on the cost of your flight, compared to a flight in the afternoon.

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 20, 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
8.0
Very good
7,982 reviews

Entertainment

7.9

Overall

8.0

Food

7.3

Crew

8.5

Boarding

8.2

Comfort

7.9

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
7,982 reviews
Delta
8.0
Very good
7,982 reviews

Entertainment

7.9

Overall

8.0

Food

7.3

Crew

8.5

Boarding

8.2

Comfort

7.9

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
8,928 reviews
Delta
8.0
Very good
7,982 reviews

Entertainment

7.9

Overall

8.0

Food

7.3

Crew

8.5

Boarding

8.2

Comfort

7.9

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
7,982 reviews

Entertainment

7.9

Overall

8.0

Food

7.3

Crew

8.5

Boarding

8.2

Comfort

7.9

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 Delta. Our recent data shows that you can find tickets from as low as $216 on this airline. Additional options worth looking into are United Airlines and American Airlines, starting at $261 and $295 round-trip. Delta is currently priced 51% below the average price you’ll pay for this route.

  • 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 $414, our data indicates the cheapest price to be $249. The most popular route (Chicago O'Hare Intl - Key West), is priced around $227.

  • 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 $492). 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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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 August 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$216Average$430FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$261Average$479FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$295Average$440FlexibilityNo cancel feeOn-time71%

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