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Key West

$116+ 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 8/29. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — EYW
Jul 8 — Jul 151
Wed 7/8
Wed 7/15
1 adult, Economy
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Find cheap flights from Chicago to Key West with Cheapflights

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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 July or January, booked 33 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 June 8, 2026.

This American Airlines deal was found by Cheapflights users on 6/4. 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.
Thu 8/1311:59 am
ORD
-
EYW
Nonstop3h 19m
American Airlines
Mon 8/178:09 pm
EYW
-
ORD
1 stop5h 26m
American Airlines
Deal found 6/4$319
This Kiwi.com deal was found by Cheapflights users on 6/6. 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 8/275:30 pm
ORD
-
EYW
1 stop16h 57m
Multiple Airlines
Mon 8/3112:07 pm
EYW
-
ORD
1 stop12h 07m
Multiple Airlines
Deal found 6/6$322
This Kiwi.com deal was found by Cheapflights users on 6/4. 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 7/221:50 pm
ORD
-
EYW
2 stops44h 17m
Multiple Airlines
Fri 7/3112:07 pm
EYW
-
ORD
1 stop12h 03m
Multiple Airlines
Deal found 6/4$323
This Kiwi.com deal was found by Cheapflights users on 6/7. 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 7/122:48 pm
MDW
-
EYW
1 stop17h 53m
Multiple Airlines
Thu 7/1612:05 pm
EYW
-
MDW
2 stops10h 58m
Multiple Airlines
Deal found 6/7$327
This Kiwi.com deal was found by Cheapflights users on 6/7. 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 8/275:30 pm
ORD
-
EYW
1 stop16h 57m
Multiple Airlines
Thu 9/312:05 pm
EYW
-
ORD
1 stop12h 09m
Multiple Airlines
Deal found 6/7$327
This American Airlines deal was found by Cheapflights users on 6/5. 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 7/205:07 am
ORD
-
EYW
1 stop6h 07m
American Airlines
Mon 7/277:33 pm
EYW
-
ORD
1 stop5h 28m
American Airlines
Deal found 6/5$328
This Delta deal was found by Cheapflights users on 6/4. 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.
Wed 7/2911:05 am
MDW
-
EYW
1 stop7h 46m
Delta
Wed 8/56:15 pm
EYW
-
MDW
1 stop5h 21m
Delta
Deal found 6/4$329
This American Airlines deal was found by Cheapflights users on 6/8. 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.
Thu 8/1311:59 am
ORD
-
EYW
Nonstop3h 19m
American Airlines
Tue 8/181:50 pm
EYW
-
ORD
1 stop6h 56m
American Airlines
Deal found 6/8$329
This Kiwi.com deal was found by Cheapflights users on 6/8. 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 9/124:49 pm
ORD
-
EYW
1 stop16h 30m
Multiple Airlines
Fri 9/2512:59 pm
EYW
-
ORD
2 stops31h 45m
Multiple Airlines
Deal found 6/8$334
This Kiwi.com deal was found by Cheapflights users on 6/6. 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 9/124:49 pm
ORD
-
EYW
1 stop16h 30m
Multiple Airlines
Wed 9/1610:04 am
EYW
-
ORD
2 stops30h 22m
Multiple Airlines
Deal found 6/6$337
This Delta deal was found by Cheapflights users on 6/8. 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.
Thu 8/1312:46 pm
MDW
-
EYW
1 stop6h 11m
Delta
Tue 8/186:15 pm
EYW
-
MDW
1 stop5h 21m
Delta
Deal found 6/8$339
This Delta deal was found by Cheapflights users on 6/7. 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.
Thu 8/131:50 pm
ORD
-
EYW
1 stop5h 07m
Delta
Mon 8/177:40 am
EYW
-
ORD
1 stop7h 29m
Delta
Deal found 6/7$339

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 June 8, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$319
(American Airlines)

One-way from

$116
(Kiwi.com)

Popular in

March

Cheapest in

July

Average price

$435

Good round-trip deal

$349 or less

Good one-way deal

$188 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. 10% potential increase in price ($49 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 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 June 8, 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

Tue 8/18

6:05 am-1:00 pm

1 stop5h 55m

Key West

Tue 8/25

6:15 pm-10:36 pm

1 stop5h 21m

$329

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Fri 8/7

1:50 pm-7:54 pm

1 stop5h 04m

Key West

Tue 8/11

1:57 pm-6:49 pm

1 stop5h 52m

$329

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Wed 8/19

6:05 am-1:00 pm

1 stop5h 55m

Key West

Wed 8/26

6:15 pm-10:36 pm

1 stop5h 21m

$339

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Thu 8/13

12:46 pm-7:54 pm

1 stop6h 08m

Key West

Tue 8/18

6:15 pm-10:36 pm

1 stop5h 21m

$339

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Fri 8/14

12:46 pm-7:57 pm

1 stop6h 11m

Key West

Tue 8/18

6:15 pm-10:36 pm

1 stop5h 21m

$339

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Wed 7/29

12:41 pm-7:51 pm

1 stop6h 10m

Key West

Wed 8/5

11:48 am-4:15 pm

1 stop5h 27m

$339

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Fri 7/17

10:55 am-3:19 pm

Nonstop3h 24m

Key West

Mon 7/20

2:26 pm-10:06 pm

1 stop8h 40m

$376

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Sun 9/6

10:56 am-5:20 pm

1 stop5h 24m

Key West

Sat 9/12

6:00 pm-9:46 pm

1 stop4h 46m

$384
Quickest round-trip

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Fri 7/31

10:55 am-3:19 pm

Nonstop3h 24m

Key West

Tue 8/4

4:00 pm-6:55 pm

Nonstop3h 55m

$410

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Sun 8/16

6:05 am-1:00 pm

1 stop5h 55m

Key West

Sun 8/23

6:15 pm-10:36 pm

1 stop5h 21m

$449

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/5

Showing 1-10 of 41 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 June.
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, February is the cheapest month in which you can book a flight from Chicago to Key West (average of $104). Flying from Chicago to Key West in June is currently the most expensive (average of $249). 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 June 8, 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 June 8, 2026.

The most flights from CHI to EYW are scheduled on a Monday (3 on average). You will have fewer flight options on Tuesday, 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 14 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 June 8, 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
7.9
Good
8,394 reviews

Boarding

8.1

Comfort

7.8

Food

7.2

Overall

7.9

Entertainment

7.8

Crew

8.5

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
7.9
Good
8,394 reviews
Delta
7.9
Good
8,394 reviews

Boarding

8.1

Comfort

7.8

Food

7.2

Overall

7.9

Entertainment

7.8

Crew

8.5

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
9,796 reviews
Delta
7.9
Good
8,394 reviews

Boarding

8.1

Comfort

7.8

Food

7.2

Overall

7.9

Entertainment

7.8

Crew

8.5

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
11,640 reviews
Delta
7.9
Good
8,394 reviews

Boarding

8.1

Comfort

7.8

Food

7.2

Overall

7.9

Entertainment

7.8

Crew

8.5

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 Delta and United Airlines fly from Chicago to Key West in about 3h 24m. The time it takes to get you to your destination can typically vary by up to 2h 31m. 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 (97%), Air New Zealand (91%), United Airlines( 89%).

  • 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 $360, our data indicates the cheapest price to be $188. The most popular route (Chicago O'Hare Intl - Key West), is priced around $269.

  • 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, February is the cheapest month in which you can book a flight from Chicago to Key West (average of $104). Flying from Chicago to Key West in June is currently the most expensive (average of $249). 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 June 8, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$206Average$443FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$249Average$414FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$308Average$481FlexibilityNo cancel feeOn-time71%

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