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Cheap flights from Chicago (CHI) to Key West (EYW) from $186

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 6/30. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
CHI — EYW
Jun 10 — Jun 171
From?
To?
Mon 6/10
Mon 6/17
1 adult, Economy
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The best prices from Chicago to Key West are usually found in August or September, booked 60 days in advance, depart on a Tuesday or Wednesday and return on a Monday

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 June 5, 2024.

Popular in

March

Cheapest in

August

Round-trip from

$373

One-way from

$215
High demand for flights, 15% potential price rise
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Best time to find cheap flights, 31% potential price drop
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From Chicago (CHI) to Key West
Search Deals
One-way flight from Chicago (CHI) to Key West
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What is the cheapest day to fly round-trip from Chicago to Key West?

Monday is generally a great day to depart. Flying on this day could help you save up to 28%.

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

When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 61 days in advance, which can save you up to 80% on flights from Chicago to Key West compared to booking the week you need them. Waiting 61 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at $355. For sooner than that we have options available in the next 3 days from $408.

What is the cheapest month to fly from Chicago to Key West?

Our data shows that August tends to be the cheapest month to fly to Key West from Chicago. Users have commonly found prices around $452 for the month, but tickets can be as low as $226. Due to multiple factors, prepare for potentially higher prices in March.

What is the cheapest time of day to fly from CHI to EYW?

It’s optimal to fly from Chicago to Key West at noon. By choosing this option you can save up to 37% on the cost of your flight, compared to a flight in the evening.

Cheap Chicago to Key West flights in June & July 2024

Find cheap flight options from Chicago to Key West specifically for the months of June and July 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 3,050,429 searches. Prices were last updated on June 5, 2024.
These are some of the most attractive deals on flights from Chicago to Key West in 2024. Check back soon for alternative fares.
Thu 7/412:00 pmORD - EYW
1 stop6h 38mDelta
Wed 7/102:30 pmEYW - ORD
1 stop7h 37mDelta
Deal found 6/4$248
Sun 6/305:00 amORD - EYW
1 stop7h 01mAmerican Airlines
Thu 7/41:41 pmEYW - ORD
1 stop8h 44mAmerican Airlines
Deal found 6/5$273
Mon 7/16:52 amORD - EYW
1 stop6h 33mAmerican Airlines
Thu 7/41:41 pmEYW - ORD
1 stop8h 44mAmerican Airlines
Deal found 6/5$278
Mon 7/16:52 amORD - EYW
1 stop6h 33mAmerican Airlines
Tue 7/23:10 pmEYW - ORD
2 stops7h 27mAmerican Airlines
Deal found 6/5$283
Thu 7/412:00 pmORD - EYW
1 stop6h 38mDelta
Tue 7/92:30 pmEYW - ORD
1 stop7h 37mDelta
Deal found 6/4$287
Thu 7/412:00 pmORD - EYW
1 stop6h 38mDelta
Thu 7/112:30 pmEYW - ORD
1 stop7h 37mDelta
Deal found 6/4$303
Tue 7/2312:22 pmORD - EYW
1 stop6h 16mDelta
Wed 7/316:03 pmEYW - ORD
1 stop6h 51mDelta
Deal found 6/4$323
Tue 7/26:00 amORD - EYW
2 stops12h 38mDelta
Thu 7/47:23 amEYW - ORD
2 stops13h 02mDelta
Deal found 6/5$325
Thu 7/46:30 pmORD - EYW
2 stops20h 40mMultiple Airlines
Thu 7/112:43 pmEYW - ORD
2 stops19h 31mMultiple Airlines
Deal found 6/4$330

Chicago to Key West 2024 flight deals

Discover exclusive flight deals for travel between Chicago and Key West in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 3,050,429 searches. Data last updated June 5, 2024.
These are some of the most attractive deals on flights from Chicago to Key West in 2024. Check back soon for alternative fares.
Wed 9/412:35 pmMDW - EYW
1 stop6h 03mDelta
Tue 9/107:25 amEYW - MDW
1 stop5h 32mDelta
Deal found 6/4$248
Sat 10/191:16 pmORD - EYW
1 stop5h 17mDelta
Wed 10/237:00 amEYW - ORD
1 stop8h 12mDelta
Deal found 6/5$248
Sun 6/305:00 amORD - EYW
1 stop7h 01mAmerican Airlines
Thu 7/41:41 pmEYW - ORD
1 stop8h 44mAmerican Airlines
Deal found 6/5$273
Mon 7/16:52 amORD - EYW
1 stop6h 33mAmerican Airlines
Thu 7/41:41 pmEYW - ORD
1 stop8h 44mAmerican Airlines
Deal found 6/5$278
Mon 7/16:52 amORD - EYW
1 stop6h 33mAmerican Airlines
Tue 7/23:10 pmEYW - ORD
2 stops7h 27mAmerican Airlines
Deal found 6/5$283
Thu 7/412:00 pmORD - EYW
1 stop6h 38mDelta
Tue 7/92:30 pmEYW - ORD
1 stop7h 37mDelta
Deal found 6/4$287
Wed 8/2110:28 amMDW - EYW
1 stop5h 40mDelta
Thu 8/296:03 pmEYW - MDW
1 stop4h 43mDelta
Deal found 6/4$303
Tue 10/2211:19 amORD - EYW
1 stop7h 14mDelta
Sat 10/267:00 amEYW - ORD
1 stop8h 12mDelta
Deal found 6/5$303
Tue 10/2211:19 amORD - EYW
1 stop7h 14mDelta
Tue 10/297:00 amEYW - ORD
2 stops16h 46mDelta
Deal found 6/5$312

Chicago to Key West flights leaving soon

Find last-minute flight options from Chicago to Key West for spontaneous travel. Discover available flights and compare prices based on user searches. Secure great deals and offers for spontaneous trips with quick booking options. Over the last 7 days, Cheapflights users made 3,050,429 searches. Data last updated June 5, 2024.
Check out these flights departing soon from Chicago to Key West. Users should double check the flight they book to ensure it matches the day, time, and destination they're looking for.
Tue 6/118:34 amORD - EYW
1 stop6h 38mAmerican Airlines
Tue 6/184:59 pmEYW - ORD
1 stop7h 59mAmerican Airlines
Deal found 6/4$368
Tue 6/115:30 amORD - EYW
1 stop5h 36mAmerican Airlines
Tue 6/183:10 pmEYW - ORD
2 stops7h 27mAmerican Airlines
Deal found 6/4$373
Fri 6/146:02 amORD - EYW
1 stop9h 22mAmerican Airlines
Mon 6/1712:05 pmEYW - ORD
1 stop6h 34mAmerican Airlines
Deal found 6/5$388
Fri 6/78:30 amORD - EYW
1 stop6h 59mAmerican Airlines
Fri 6/141:41 pmEYW - ORD
1 stop6h 38mAmerican Airlines
Deal found 6/5$438
Fri 6/75:30 amORD - EYW
2 stops7h 25mAmerican Airlines
Fri 6/145:04 pmEYW - ORD
1 stop6h 30mAmerican Airlines
Deal found 6/5$443
Fri 6/75:30 amORD - EYW
2 stops7h 25mAmerican Airlines
Tue 6/113:10 pmEYW - ORD
2 stops7h 27mAmerican Airlines
Deal found 6/4$448
Tue 6/117:00 amORD - EYW
2 stops10h 59mAmerican Airlines
Tue 6/183:10 pmEYW - ORD
2 stops7h 27mAmerican Airlines
Deal found 6/4$458
Tue 6/189:45 amORD - EYW
1 stop5h 44mAmerican Airlines
Mon 6/2412:05 pmEYW - ORD
1 stop6h 34mAmerican Airlines
Deal found 6/3$467
Wed 6/197:00 amORD - EYW
1 stop8h 24mAmerican Airlines
Sat 6/2212:05 pmEYW - ORD
1 stop6h 34mAmerican Airlines
Deal found 6/4$468

One-way flights to Key West from Chicago

Search for one-way flight options from Chicago to Key West. Find affordable one-way fares based on user searches. Compare prices and availability to plan your one-way journey according to your preferred dates and budget. Over the last 7 days, Cheapflights users made 3,050,429 searches. Data last updated June 5, 2024.
Take a look at some of the best available options we've come across on one-way flights from Chicago to Key West. For those needing a return trip from Chicago, there is a search form available above.
Sun 6/309:24 amORD - EYW
3 stops29h 44mMultiple Airlines
Deal found 6/5$186
Fri 8/96:40 pmORD - EYW
1 stop22h 55mUnited Airlines
Deal found 6/4$207
Wed 8/2812:59 pmORD - EYW
2 stops24h 46mUnited Airlines
Deal found 6/4$212
Sun 6/307:40 pmMDW - EYW
2 stops17h 31mAllegiant Air
Deal found 6/5$215
Sat 8/109:59 amORD - EYW
2 stops29h 19mMultiple Airlines
Deal found 6/4$215
Sat 8/106:20 pmORD - EYW
1 stop21h 00mUnited Airlines
Deal found 6/5$219
Mon 9/27:24 amORD - EYW
1 stop8h 41mUnited Airlines
Deal found 6/4$220
Wed 8/288:50 amORD - EYW
2 stops23h 25mUnited Airlines
Deal found 6/5$224
Fri 8/99:22 amORD - EYW
1 stop6h 46mDelta
Deal found 6/4$254

Find flights from Chicago to Key West within your budget

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 3,050,429 searches. Data last updated June 5, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$248 - $383

Route

Depart

Return

Price

Chicago MidwayKey West

MDW - EYW

MDWEYW

Chicago Midway

Wed 9/4

1 stop6h 03m

Key West

Tue 9/10

1 stop5h 32m

$248

Chicago O'Hare IntlKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Thu 7/4

1 stop6h 38m

Key West

Wed 7/10

1 stop7h 37m

$248

Chicago O'Hare IntlKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Sun 6/30

1 stop7h 01m

Key West

Thu 7/4

1 stop8h 44m

$273

Chicago O'Hare IntlKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Mon 7/1

1 stop6h 33m

Key West

Thu 7/4

1 stop8h 44m

$278

Chicago O'Hare IntlKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Mon 7/1

1 stop6h 33m

Key West

Tue 7/2

2 stops7h 27m

$283

Chicago O'Hare IntlKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Thu 7/4

1 stop6h 38m

Key West

Tue 7/9

1 stop7h 37m

$287

Chicago O'Hare IntlKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Thu 7/4

2 stops20h 40m

Key West

Thu 7/11

2 stops19h 31m

$330

Chicago O'Hare IntlKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Thu 7/4

2 stops20h 40m

Key West

Thu 7/11

3 stops29h 51m

$339

Chicago O'Hare IntlKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Mon 8/19

1 stop7h 09m

Key West

Fri 8/23

2 stops25h 08m

$383

Flights are sorted by cheapest first

Deals found on 6/4

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 May 31, 2024.
The best time to book flights from Chicago to Key West is 60 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.
Search Deals

What is the cheapest day to fly from Chicago to Key West?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Key West. Price data was last updated on June 2, 2024.
Morning
Noon
Afternoon
Evening
All times are departure.
Travelers seeking maximum savings on their Chicago to Key West flight should consider departing on Saturday afternoons when fares are most often at their lowest. Thursday mornings flights should be avoided if possible as fares are typically the most expensive at this time.
Search Deals

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.

Temperature and rainfall in Key West by month

Plan your trip to Key West by taking into account the average temperature and rainfall totals by month.

EYW

Temperature

69.8 - 84.2 °F

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 June 5, 2024.
To help decide which airline to fly from Chicago to Key West, see what other customers have to say about United Airlines, American Airlines and Delta. 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.
Delta
8.0
Very good
10,368 reviews

Boarding

8.2

Comfort

7.9

Overall

8.0

Entertainment

8.0

Crew

8.6

Food

7.4

Reviews

1 / 10

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
10,368 reviews
Delta
8.0
Very good
10,368 reviews

Boarding

8.2

Comfort

7.9

Overall

8.0

Entertainment

8.0

Crew

8.6

Food

7.4

Reviews

1 / 10

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.

Allegiant Air
7.5
Good
994 reviews
Delta
8.0
Very good
10,368 reviews

Boarding

8.2

Comfort

7.9

Overall

8.0

Entertainment

8.0

Crew

8.6

Food

7.4

Reviews

1 / 10

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
10,703 reviews
Delta
8.0
Very good
10,368 reviews

Boarding

8.2

Comfort

7.9

Overall

8.0

Entertainment

8.0

Crew

8.6

Food

7.4

Reviews

1 / 10

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
7.3
Good
14,229 reviews
Delta
8.0
Very good
10,368 reviews

Boarding

8.2

Comfort

7.9

Overall

8.0

Entertainment

8.0

Crew

8.6

Food

7.4

Reviews

1 / 10

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 4 different airlines.

  • Can I find flights from Chicago to Key West for under $300 on Cheapflights?

    Yes, there are multiple flights from Chicago to Key West for under $300. The cheapest flight booked recently is on Delta for just $248, but on average you can expect to pay $315.

  • Are there nonstop flights from Chicago to Key West for under $500 on Cheapflights?

    Cheapflights has at least 11 direct flights from Chicago to Key West under $500. A good price for a nonstop flight from Chicago to Key West is less than $709.

  • Are there last-minute flights available from Chicago to Key West for under $400?

    There are currently 20+ open flights from Chicago to Key West within the next 7 days for less than $400.

  • 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 American Airlines and United Airlines, starting at $273 and $383 round-trip. Delta is currently priced 45% 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 United Airlines, with whom users have recently found tickets for as low as $207. However, be on the lookout for offers from Allegiant Air 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 (90%), American Airlines (67%), Envoy Air( 67%).

  • 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 $437, our data indicates the cheapest price to be $229. The most popular route (Chicago O'Hare Intl - Key West), is priced around $248.

  • What does ORD to EYW mean?

    ORD stands for Chicago O'Hare Intl Airport, while EYW stands for Key West Airport. These codes are often called IATA codes, a set of identifiers established by IATA (International Air Transport Association) that is widely used by airlines and the aviation industry. Ready for more IATA code knowledge? These are related airports for your current travel destination: Chicago Midway Airport (MDW), Chicago Greater Rockford Airport (RFD).

  • Can I find deals for flights from Chicago to Key West that include extra baggage allowance?

    The amount of baggage you can bring on your Chicago to Key West flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Chicago to Key West with specific airlines?

    Yes, Cheapflights allows you to browse and filter Chicago to Key West flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • 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.

  • Can I find deals for flights from Chicago to Key West that allow pets onboard?

    Many airlines flying from Chicago to Key West offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Chicago to Key West?

    Yes, you can often find last-minute deals on Chicago to Key West flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Chicago to Key West flight deals updated?

    The Chicago to Key West flight deals you see on this page were last updated on 6/5.

  • What are the most popular airlines that fly from Chicago to Key West?

    The most popular airlines flying from Chicago to Key West are American Airlines, Alaska Airlines and Delta. Something to consider prior to booking 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 $373). Flying from Chicago to Key West in March is currently the most expensive (average of $503). 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 4 airlines flying from Chicago to Key West

Discover the top 4 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 3,050,429 searches. Data last updated June 5, 2024.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$226Average$461FlexibilityNo cancel feeOn-time71%
DeltaCheapest$226Average$460FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$247Average$469FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$438Average$467FlexibilityNo cancel feeOn-time75%
Dallas to Nashville flights
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San Francisco to Vancouver flights
Houston to Los Angeles flights
Miami to New York flights
Portland to Los Angeles flights
Atlanta to Washington, D.C. flights
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Portland to Las Vegas flights
Chicago to Buenos Aires Ministro Pistarini Airport flights

Search flights from Chicago to Key West by cabin class

Find flights from Chicago to Key West, based on your preferred cabin class, be it economy, premium economy, business, or first class.
First Class
Business Class
Prem Econ Class
Economy Class

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 5, 2024.
Sunday2daily flights
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Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Chicago to Key West?

When you search for this flight from Chicago to Key West, Cheapflights searches on 900+ travel sites to save you time finding great flight deals online. Additionally, we offer filter features so you can choose a preferred cabin class or airline, see different price ranges, and much more so you can book the flight for you.

Why should you use Cheapflights to find cheap flight tickets from Chicago to Key West?

Cheapflights helps you find that perfect flight to Key West from Chicago by searching from hundreds of airlines and agencies you know and love. We are also free to use, in case you were wondering!

Can Cheapflights find flights from Chicago to Key West with no change fees?

Need flexible booking options for your flight to Key West from Chicago? Don’t worry, Cheapflights have you covered. Use our search filter to only show flights with no change fees.

Can Cheapflights notify me if prices for flights from Chicago to Key West become cheaper?

Yes! Start tracking prices for Chicago to Key West flights today and get alerted whenever prices for these flights change. To access this feature, click the bell icon next to the flight deals above, which will prompt you for a valid email address to receive your alerts.

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