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Key West

$129+ 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 10/17. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — EYW
Aug 21 — Aug 281
Fri 8/21
Fri 8/28
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

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

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Cheapflights Tip: The best prices from Chicago to Key West are usually found in June or July, booked 70 days in advance, depart on a Tuesday or Wednesday and return on a Wednesday

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 July 22, 2026.

This Kiwi.com deal was found by Cheapflights users on 7/17. 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.
Thu 10/298:00 am
ORD
-
EYW
1 stop27h 19m
Multiple Airlines
Fri 11/612:59 pm
EYW
-
ORD
2 stops31h 45m
Multiple Airlines
Deal found 7/17$246
This Kiwi.com deal was found by Cheapflights users on 7/17. 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.
Sat 10/314:44 pm
ORD
-
EYW
1 stop19h 54m
Multiple Airlines
Fri 11/612:59 pm
EYW
-
ORD
2 stops31h 45m
Multiple Airlines
Deal found 7/17$256
This Kiwi.com deal was found by Cheapflights users on 7/17. 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.
Thu 10/298:00 am
ORD
-
EYW
1 stop27h 19m
Multiple Airlines
Wed 11/410:04 am
EYW
-
ORD
2 stops10h 40m
Multiple Airlines
Deal found 7/17$262
This Kiwi.com deal was found by Cheapflights users on 7/17. 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.
Sat 10/314:44 pm
ORD
-
EYW
1 stop19h 54m
Multiple Airlines
Wed 11/412:54 pm
EYW
-
ORD
1 stop27h 32m
Multiple Airlines
Deal found 7/17$266
This Kiwi.com deal was found by Cheapflights users on 7/18. 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 8/132:49 pm
MDW
-
EYW
1 stop17h 52m
Multiple Airlines
Thu 8/2011:04 am
EYW
-
MDW
2 stops12h 43m
Multiple Airlines
Deal found 7/18$272
This Kiwi.com deal was found by Cheapflights users on 7/17. 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.
Fri 10/308:00 am
ORD
-
EYW
1 stop24h 24m
Multiple Airlines
Fri 11/612:59 pm
EYW
-
ORD
2 stops31h 45m
Multiple Airlines
Deal found 7/17$272
This Kiwi.com deal was found by Cheapflights users on 7/17. 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.
Thu 10/292:03 pm
ORD
-
EYW
2 stops21h 16m
Multiple Airlines
Sun 11/18:36 pm
EYW
-
ORD
1 stop12h 45m
Multiple Airlines
Deal found 7/17$282
This Kiwi.com deal was found by Cheapflights users on 7/17. 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.
Thu 8/135:13 pm
ORD
-
EYW
1 stop17h 14m
Multiple Airlines
Thu 8/2012:05 pm
EYW
-
ORD
1 stop12h 03m
Multiple Airlines
Deal found 7/17$289
This Kiwi.com deal was found by Cheapflights users on 7/19. 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 8/295:59 pm
ORD
-
EYW
1 stop16h 36m
Multiple Airlines
Wed 9/211:46 am
EYW
-
ORD
2 stops26h 04m
Multiple Airlines
Deal found 7/19$290
This Kiwi.com deal was found by Cheapflights users on 7/21. 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 8/208:05 am
ORD
-
EYW
2 stops10h 08m
Multiple Airlines
Thu 8/2712:05 pm
EYW
-
ORD
1 stop12h 03m
Multiple Airlines
Deal found 7/21$291
This Delta deal was found by Cheapflights users on 7/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/186:05 am
MDW
-
EYW
1 stop5h 55m
Delta
Tue 8/256:15 pm
EYW
-
MDW
1 stop5h 21m
Delta
Deal found 7/19$316
This Kiwi.com deal was found by Cheapflights users on 7/20. 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.
Sun 8/162:49 pm
MDW
-
EYW
1 stop17h 52m
Multiple Airlines
Fri 8/2112:07 pm
EYW
-
MDW
2 stops11h 40m
Multiple Airlines
Deal found 7/20$318

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 July 22, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$246
(Kiwi.com)

One-way from

$129
(Kiwi.com)

Popular in

November

Cheapest in

June

Average price

$377

Good round-trip deal

$382 or less

Good one-way deal

$278 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. 3% potential increase in price ($16 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 July 2026
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 July 22, 2026.
Use the filters below to find and compare flights from Chicago to Key West that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Wed 9/23

1:00 pm-8:00 pm

1 stop6h 00m

Key West

Sat 9/26

6:19 pm-10:44 pm

1 stop5h 25m

$316

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Sat 9/19

11:35 am-8:00 pm

1 stop7h 25m

Key West

Sat 10/3

6:19 pm-10:44 pm

1 stop5h 25m

$316

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Sat 10/31

1:26 pm-7:51 pm

1 stop5h 25m

Key West

Thu 11/5

6:11 pm-11:51 pm

1 stop6h 40m

$329

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Fri 10/30

1:26 pm-7:51 pm

1 stop5h 25m

Key West

Thu 11/5

11:43 am-6:59 pm

1 stop8h 16m

$329

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Tue 10/27

10:34 am-5:16 pm

1 stop5h 42m

Key West

Sun 11/1

6:11 pm-11:51 pm

1 stop6h 40m

$354

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Thu 10/29

1:26 pm-7:51 pm

1 stop5h 25m

Key West

Sat 10/31

7:40 am-2:29 pm

1 stop7h 49m

$384

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Sun 10/18

1:00 pm-7:51 pm

1 stop5h 51m

Key West

Sat 10/24

6:11 pm-10:25 pm

1 stop5h 14m

$394
Quickest round-trip

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Tue 10/6

6:00 am-1:29 pm

1 stop6h 29m

Key West

Sat 10/10

4:00 pm-5:27 pm

Nonstop2h 27m

$403

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Fri 8/14

12:46 pm-7:57 pm

1 stop6h 11m

Key West

Mon 8/17

6:15 pm-10:36 pm

1 stop5h 21m

$404

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Tue 9/22

1:00 pm-8:00 pm

1 stop6h 00m

Key West

Mon 9/28

6:19 pm-10:44 pm

1 stop5h 25m

$417

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/20

Showing 1-10 of 42 resultsSorted by cheapest first
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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 July.
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-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 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-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

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 $380). Flying from Chicago to Key West in March is currently the most expensive (average of $531). 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 July 22, 2026.

When flying from Chicago 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.

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 July 22, 2026.

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

How much does it cost to fly round-trip from Chicago to Key West?

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

The best time to book flights from Chicago to Key West is 85 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.

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
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 July 22, 2026.
Peruse reviews from past customers who have flown with Delta,United Airlines, andAmerican 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
7.8
Good
8,476 reviews

Entertainment

7.8

Comfort

7.8

Food

7.2

Crew

8.5

Boarding

8.1

Overall

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
8,476 reviews
Delta
7.8
Good
8,476 reviews

Entertainment

7.8

Comfort

7.8

Food

7.2

Crew

8.5

Boarding

8.1

Overall

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
10,020 reviews
Delta
7.8
Good
8,476 reviews

Entertainment

7.8

Comfort

7.8

Food

7.2

Crew

8.5

Boarding

8.1

Overall

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
11,834 reviews
Delta
7.8
Good
8,476 reviews

Entertainment

7.8

Comfort

7.8

Food

7.2

Crew

8.5

Boarding

8.1

Overall

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 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 American Airlines and Delta fly from Chicago to Key West in about 3h 19m. The time it takes to get you to your destination can typically vary by up to 2h 41m. Chicago and Key West are separated by a distance of 1253 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 $206 on this airline. Additional options worth looking into are United Airlines and American Airlines, starting at $249 and $308 round-trip. Delta is currently priced 52% 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: Republic Airways (96%), United Airlines (94%), American Airlines( 90%).

  • 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 $383, our data indicates the cheapest price to be $261. The most popular route (Chicago O'Hare Intl - Key West), is priced around $296.

  • 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 $380). Flying from Chicago to Key West in March is currently the most expensive (average of $531). 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 July 22, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$206Average$441FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$249Average$412FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$308Average$477FlexibilityNo cancel feeOn-time71%

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