What are the cheapest airlines flying from Chicago to Key West round-trip?

Our cheapest airline available from Chicago to Key West is American Airlines. Our recent data shows that you can find tickets from as low as $322 on this airline. Additional options worth looking into are Delta and United Airlines, starting at $349 and $365 round-trip. American Airlines is currently priced 25% 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 American Airlines, with whom users have recently found tickets for as low as $162. However, be on the lookout for offers from United Airlines and Delta, as they are both options that can get you from Chicago to Key West for a low price.

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

Travelers seeking maximum savings on their Chicago to Key West flight should consider departing on Wednesday at noon when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

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 $585, our data indicates the cheapest price to be $191. The most popular route (Chicago O'Hare Intl - Key West), is priced around $246.

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 (89%), United Airlines (87%), Air New Zealand( 87%).

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, Delta and United Airlines. Something to consider prior to booking your flight.

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 54%.

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 43 days in advance, which can save you up to 83% on flights from Chicago to Key West compared to booking the week you need them. Waiting 43 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 $419. For sooner than that we have options available in the next 3 days from $439.

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 $434 for the month, but tickets can be as low as $247. Due to multiple factors, prepare for potentially higher prices in March.

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.

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.

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.

$162+ Flights from Chicago to Key West

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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”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

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Cheapflights Tip: The best prices from Chicago to Key West are usually found in August or September, booked 42 days in advance, depart on a Tuesday or Wednesday and return on a Thursday

Cheap flight deals from Chicago to Key West

Most accurate provider	FlightHub 3 stars
Most trusted provider	FlightHub 3 stars
Round-trip from	$322 (American Airlines)
One-way from	$162 (American Airlines)
Popular in	March
Cheapest in	August
Average price	$522
Good round-trip deal	$434 or less
Good one-way deal	$250 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. 8% potential increase in price ($40 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 1% potential price decrease ($9 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in March 2025

Search Deals

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 March 31, 2025.

Wed 7/235:15 amORD - EYW

2 stops6h 40mAmerican Airlines

Sat 7/264:06 pmEYW - ORD

1 stop6h 19mAmerican Airlines

Deal found 3/31

$314

Wed 6/116:30 amORD - EYW

1 stop24h 33mMultiple Airlines

Sun 6/158:53 amEYW - ORD

2 stops33h 02mMultiple Airlines

Deal found 3/30

$337

Wed 5/141:30 pmORD - EYW

1 stop5h 37mDelta

Wed 5/216:25 pmEYW - ORD

1 stop6h 33mDelta

Deal found 3/30

$349

Thu 9/181:05 pmMDW - EYW

1 stop5h 39mDelta

Tue 9/2311:45 amEYW - MDW

1 stop7h 13mDelta

Deal found 3/30

$352

Sat 4/57:10 amORD - EYW

Nonstop3h 05mUnited Airlines

Thu 4/104:04 pmEYW - ORD

Nonstop3h 35mUnited Airlines

Deal found 3/30

$365

Best flights from Chicago to Key West
Discover carefully curated flight deals from Chicago to Key West that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 31, 2025.

Wed 5/1410:00 amORD - EYW

1 stop5h 52mAmerican Airlines

Wed 5/2112:49 pmEYW - ORD

Nonstop3h 39mAmerican Airlines

Deal found 3/30

$322

Wed 6/116:30 amORD - EYW

1 stop24h 33mMultiple Airlines

Sun 6/158:53 amEYW - ORD

2 stops33h 02mMultiple Airlines

Deal found 3/30

$337

Wed 5/141:30 pmORD - EYW

1 stop5h 37mDelta

Wed 5/216:25 pmEYW - ORD

1 stop6h 33mDelta

Deal found 3/30

$349

Sat 4/57:10 amORD - EYW

Nonstop3h 05mUnited Airlines

Thu 4/104:04 pmEYW - ORD

Nonstop3h 35mUnited Airlines

Deal found 3/30

$365

Wed 4/169:52 amMDW - EYW

1 stop6h 25mDelta

Wed 4/236:13 pmEYW - MDW

1 stop5h 09mDelta

Deal found 3/30

$374

Last-minute flights from Chicago to Key West
Discover last-minute flight deals from Chicago to Key West. Data last updated March 31, 2025 and is based on user searches.

Sat 4/51:48 pmORD - EYW

1 stop17h 15mMultiple Airlines

Thu 4/104:24 pmEYW - ORD

3 stops40h 40mMultiple Airlines

Deal found 3/30

$348

Sat 4/57:10 amORD - EYW

Nonstop3h 05mUnited Airlines

Thu 4/104:04 pmEYW - ORD

Nonstop3h 35mUnited Airlines

Deal found 3/30

$365

Mon 4/77:15 amORD - EYW

2 stops12h 11mDelta

Tue 4/87:00 amEYW - ORD

2 stops10h 01mDelta

Deal found 3/30

$1,188

Wed 4/96:55 amORD - EYW

1 stop8h 21mAmerican Airlines

Tue 4/1512:52 pmEYW - ORD

Nonstop3h 37mAmerican Airlines

Deal found 3/30

$330

Thu 4/1012:48 pmMDW - EYW

1 stop6h 38mDelta

Tue 4/156:13 pmEYW - MDW

1 stop5h 09mDelta

Deal found 3/31

$599

Wed 4/169:52 amMDW - EYW

1 stop6h 25mDelta

Wed 4/236:13 pmEYW - MDW

1 stop5h 09mDelta

Deal found 3/30

$374

Sun 4/205:30 amORD - EYW

1 stop7h 35mDelta

Tue 4/291:35 pmEYW - ORD

1 stop7h 41mDelta

Deal found 3/30

$352

One-way flights from Chicago to Key West
Search for one-way flight options from Chicago to Key West. Find affordable one-way fares based on user searches. Data last updated March 31, 2025.

Wed 4/3012:00 pmORD - EYW

1 stop5h 45mAmerican Airlines

Deal found 3/31

$162

Sun 5/410:24 amORD - EYW

2 stops28h 52mMultiple Airlines

Deal found 3/30

$167

Wed 4/3010:59 amORD - EYW

Nonstop3h 05mUnited Airlines

Deal found 3/31

$192

Mon 4/288:45 amORD - EYW

1 stop27h 10mDelta

Deal found 3/31

$217

Sun 4/65:15 amMDW - EYW

1 stop6h 00mMultiple Airlines

Deal found 3/31

$271

Tue 5/136:00 amMDW - EYW

1 stop5h 56mDelta

Deal found 3/29

$299

Sun 4/62:24 pmMDW - EYW

2 stops18h 56mAllegiant Air

Deal found 3/31

$325

Sat 5/317:00 amORD - EYW

3 stops29h 39mAlaska Airlines

Deal found 3/30

$570

Cheapflights Fare Finder

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

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Wed 5/14

10:00 am-4:52 pm

1 stop5h 52m

Key West

Wed 5/21

12:49 pm-3:28 pm

Nonstop3h 39m

$322

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Wed 6/11

6:30 am-8:03 am

1 stop24h 33m

Key West

Sun 6/15

8:53 am-4:55 pm

2 stops33h 02m

$337

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Wed 5/14

1:30 pm-8:07 pm

1 stop5h 37m

Key West

Wed 5/21

6:25 pm-11:58 pm

1 stop6h 33m

$349

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Sat 4/5

7:10 am-11:15 am

Nonstop3h 05m

Key West

Thu 4/10

4:04 pm-6:39 pm

Nonstop3h 35m

$365

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Wed 4/16

9:52 am-5:17 pm

1 stop6h 25m

Key West

Wed 4/23

6:13 pm-10:22 pm

1 stop5h 09m

$374

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Wed 4/30

12:00 pm-6:45 pm

1 stop5h 45m

$162

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Sun 5/4

10:24 am-4:16 pm

2 stops28h 52m

$167

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Wed 4/30

10:59 am-3:04 pm

Nonstop3h 05m

$192

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Mon 4/28

8:45 am-12:55 pm

1 stop27h 10m

$217

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Sun 4/6

5:15 am-12:15 pm

1 stop6h 00m

$271

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/31

Showing 1-10 of 13 results

Compare providers for flights from Chicago to Key West

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 March.

Provider	Price Accuracy	Trust Score*
Expedia	Price Accuracy1 star	Trust Score*3 stars
FlightHub	Price Accuracy3 stars	Trust Score*3 stars
eDreams	Price Accuracy3 stars	Trust Score*3 stars
Priceline	Price Accuracy1 star	Trust 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

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 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 $493). 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?

It’s optimal to fly from Chicago to Key West at noon. By choosing this option you can save up to 59% on the cost of your flight, compared to a flight in the evening.

Weekly flight availability from Chicago to Key West

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

Rainfall in Key West by month

In terms of precipitation, rainfall in Key West ranges from 1.5 - 6.7 inches per month. September is typically the wettest month, when rainfall can reach 6.7 in. February is typically the driest time to visit Key West when rainfall is around 1.5 in.

Temperature in Key West by month

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

To help decide which airline to fly from Chicago to Key West, see what other customers have to say about Alaska Airlines, Delta and United Airlines. 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.

Alaska Airlines

8.0

Very good

9,818 reviews

Reviews

1 / 20

10.0

Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Alaska Airlines

8.0

Very good

9,818 reviews

Alaska Airlines

8.0

Very good

9,818 reviews

Reviews

1 / 20

10.0

Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Delta

8.0

Very good

7,899 reviews

Alaska Airlines

8.0

Very good

9,818 reviews

Reviews

1 / 20

10.0

Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

United Airlines

7.4

Good

8,614 reviews

Alaska Airlines

8.0

Very good

9,818 reviews

Reviews

1 / 20

10.0

Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Allegiant Air

7.3

Good

731 reviews

Alaska Airlines

8.0

Very good

9,818 reviews

Reviews

1 / 20

10.0

Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

American Airlines

7.2

Good

10,000 reviews

Alaska Airlines

8.0

Very good

9,818 reviews

Reviews

1 / 20

10.0

Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Related info for your journey

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.
What are the cheapest airlines flying from Chicago to Key West round-trip?
Our cheapest airline available from Chicago to Key West is American Airlines. Our recent data shows that you can find tickets from as low as $322 on this airline. Additional options worth looking into are Delta and United Airlines, starting at $349 and $365 round-trip. American Airlines is currently priced 25% 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 American Airlines, with whom users have recently found tickets for as low as $162. However, be on the lookout for offers from United Airlines 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: Republic Airways (89%), United Airlines (87%), Air New Zealand( 87%).
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 $585, our data indicates the cheapest price to be $191. The most popular route (Chicago O'Hare Intl - Key West), is priced around $246.
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 $493). 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

Browse thousands of different options on Cheapflights for your next trip

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Other flights to Key West

Top 3 airlines flying from Chicago to Key West

Airline	Cheapest	Average	Flexibility	On-time
Delta	Cheapest$216	Average$365	FlexibilityNo cancel fee	On-timeN/A
American Airlines	Cheapest$256	Average$432	FlexibilityNo cancel fee	On-time71%
United Airlines	Cheapest$261	Average$467	FlexibilityNo cancel fee	On-time69%

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$162+ 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 4/30. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Chicago to Key West with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheapflights Tip: The best prices from Chicago to Key West are usually found in August or September, booked 42 days in advance, depart on a Tuesday or Wednesday and return on a Thursday

Cheap flight deals from Chicago to Key West

Most accurate provider

Most trusted provider

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Good round-trip deal

Good one-way deal

Find flight deals from Chicago to Key West

Cheapest flights from Chicago to Key WestExplore 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 March 31, 2025.

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 March 31, 2025.

Cheapflights Fare Finder

Use the filters below to find and compare flights from Chicago to Key West that are best for you.

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 March.

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.

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 March 28, 2025.

What is the cheapest month to book a flight from Chicago to Key West?

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 March 31, 2025.

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 March 31, 2025.

Rainfall in Key West by month

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

Temperature in Key West by month

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

Reviews of airlines servicing Key West

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?

What are the cheapest airlines flying from Chicago to Key West round-trip?

What are the cheapest airlines to fly from Chicago to Key West one-way?

What are the most reliable airlines from Chicago to Key West?

What are the cheapest flights from Chicago to Key West?

Can I find deals for flights from Chicago to Key West that include hotel bookings?

How can I find direct flights from Chicago to Key West?

Can I find deals for business class flights from Chicago to Key West?

What is the cheapest month to book a flight from Chicago to Key West?

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Chicago to Key West

See prices for flight routes from nearby airports that may be better suited for you.

Top 3 airlines flying from Chicago to Key West

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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 March 31, 2025.