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 $323 on this airline. Additional options worth looking into are American Airlines and United Airlines, starting at $328 and $335 round-trip. Delta 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 United Airlines, with whom users have recently found tickets for as low as $173. However, be on the lookout for offers from American 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 $462, our data indicates the cheapest price to be $227. The most popular route (Chicago O'Hare Intl - Key West), is priced around $245.

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 (84%), Republic Airways (79%), Air New Zealand( 76%).

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 95% 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 $416. For sooner than that we have options available in the next 3 days from $488.

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 $435 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 eDreams the most. eDreams 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 is 1 daily inbound flight 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.

$173+ Flights from Chicago to Key West - Compare & Save Big

Home Search by date Vacation packages Hotels Flight deals Car rental Travel tips & news

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.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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	eDreams 3 stars
Round-trip from	$320 (Mytrip)
One-way from	$173 (United Airlines)
Popular in	March
Cheapest in	August
Average price	$456
Good round-trip deal	$411 or less
Good one-way deal	$324 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. 9% potential increase in price ($47 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 April 2025

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

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 April 29, 2025.

Thu 5/299:55 amORD - EYW

1 stop7h 10mMultiple Airlines

Thu 6/58:45 amEYW - ORD

1 stop16h 20mMultiple Airlines

Deal found 4/29

$321

Sat 6/1411:20 amORD - EYW

1 stop7h 19mDelta

Tue 6/176:29 pmEYW - ORD

1 stop6h 28mDelta

Deal found 4/28

$323

Fri 8/156:00 amMDW - EYW

1 stop6h 09mDelta

Tue 8/196:00 pmEYW - MDW

1 stop4h 47mDelta

Deal found 4/28

$326

Tue 6/109:22 amORD - EYW

1 stop5h 49mAmerican Airlines

Tue 6/2411:20 amEYW - ORD

2 stops7h 15mAmerican Airlines

Deal found 4/27

$328

Sun 6/16:15 pmORD - EYW

1 stop17h 00mUnited Airlines

Mon 6/26:45 pmEYW - ORD

1 stop15h 39mUnited Airlines

Deal found 4/27

$335

Thu 7/3111:37 amMDW - EYW

2 stops27h 59mAllegiant Air

Sun 8/38:54 amEYW - MDW

2 stops30h 02mAllegiant Air

Deal found 4/29

$381

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 April 29, 2025.

Sun 6/16:30 amORD - EYW

1 stop26h 03mMultiple Airlines

Thu 6/58:53 amEYW - ORD

3 stops39h 36mMultiple Airlines

Deal found 4/29

$320

Sat 6/1411:20 amORD - EYW

1 stop7h 19mDelta

Tue 6/176:29 pmEYW - ORD

1 stop6h 28mDelta

Deal found 4/29

$323

Tue 6/109:22 amORD - EYW

1 stop5h 49mAmerican Airlines

Tue 6/2411:20 amEYW - ORD

2 stops7h 15mAmerican Airlines

Deal found 4/27

$328

Sun 6/16:15 pmORD - EYW

1 stop17h 00mUnited Airlines

Mon 6/26:45 pmEYW - ORD

1 stop15h 39mUnited Airlines

Deal found 4/27

$335

Sun 7/2011:37 amMDW - EYW

2 stops27h 59mAllegiant Air

Sun 7/278:54 amEYW - MDW

2 stops25h 47mAllegiant Air

Deal found 4/28

$425

Tue 5/2012:48 pmMDW - EYW

1 stop6h 19mDelta

Wed 5/287:00 amEYW - MDW

1 stop5h 53mDelta

Deal found 4/27

$326

Thu 6/122:44 pmMDW - EYW

2 stops22h 16mMultiple Airlines

Thu 6/192:45 pmEYW - MDW

2 stops21h 55mMultiple Airlines

Deal found 4/28

$422

Last-minute flights from Chicago to Key West
Discover last-minute flight deals from Chicago to Key West. Data last updated April 29, 2025 and is based on user searches.

Mon 5/510:47 amORD - EYW

1 stop6h 18mUnited Airlines

Mon 5/126:45 pmEYW - ORD

2 stops21h 10mUnited Airlines

Deal found 4/28

$562

Tue 5/68:05 amORD - EYW

Nonstop3h 14mAmerican Airlines

Tue 5/1311:28 amEYW - ORD

1 stop5h 37mAmerican Airlines

Deal found 4/27

$361

Tue 5/61:15 pmORD - EYW

1 stop6h 15mDelta

Tue 5/136:25 pmEYW - ORD

1 stop6h 33mDelta

Deal found 4/27

$370

Tue 5/66:04 amMDW - EYW

1 stop7h 01mDelta

Tue 5/137:00 amEYW - MDW

1 stop5h 53mDelta

Deal found 4/29

$409

Tue 5/209:39 amORD - EYW

1 stop6h 51mDelta

Wed 5/286:25 pmEYW - ORD

1 stop6h 33mDelta

Deal found 4/27

$326

Tue 5/2012:48 pmMDW - EYW

1 stop6h 19mDelta

Sat 5/247:30 amEYW - MDW

1 stop5h 23mDelta

Deal found 4/29

$348

Thu 5/299:55 amORD - EYW

1 stop7h 10mMultiple Airlines

Thu 6/58:45 amEYW - ORD

1 stop16h 20mMultiple Airlines

Deal found 4/29

$321

Thu 5/2911:44 amORD - EYW

1 stop6h 05mAmerican Airlines

Tue 6/35:30 pmEYW - ORD

1 stop6h 18mAmerican Airlines

Deal found 4/28

$323

Sat 5/316:15 pmORD - EYW

1 stop17h 00mUnited Airlines

Fri 6/66:45 pmEYW - ORD

1 stop15h 39mUnited Airlines

Deal found 4/27

$353

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 April 29, 2025.

Sun 6/17:36 amORD - EYW

1 stop27h 39mUnited Airlines

Deal found 4/29

$173

Fri 5/167:35 pmORD - EYW

2 stops19h 38mMultiple Airlines

Deal found 4/29

$179

Thu 8/285:20 amORD - EYW

1 stop5h 39mAmerican Airlines

Deal found 4/28

$198

Thu 6/2611:20 amORD - EYW

1 stop5h 14mDelta

Deal found 4/29

$230

Tue 5/2010:25 amMDW - EYW

1 stop6h 05mDelta

Deal found 4/28

$314

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

Sun 6/1

6:30 am-9:33 am

1 stop26h 03m

Key West

Thu 6/5

8:53 am-11:29 pm

3 stops39h 36m

$320

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Fri 5/30

5:00 am-12:10 pm

1 stop6h 10m

Key West

Wed 6/4

1:39 pm-7:21 pm

1 stop6h 42m

$323

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Tue 5/27

1:30 pm-8:07 pm

1 stop5h 37m

Key West

Tue 6/3

1:51 pm-6:48 pm

1 stop5h 57m

$326

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Tue 5/20

12:48 pm-8:07 pm

1 stop6h 19m

Key West

Sat 5/24

7:30 am-11:53 am

1 stop5h 23m

$348

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Sun 6/1

7:36 am-8:00 am

1 stop23h 24m

Key West

Thu 6/5

8:45 am-9:39 am

1 stop25h 54m

$368

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Sun 6/1

7:36 am-12:15 pm

1 stop27h 39m

$173

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Fri 5/16

7:35 pm-4:13 pm

2 stops19h 38m

$179

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Thu 6/26

12:44 pm-7:39 pm

1 stop5h 55m

$230

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Thu 6/26

11:20 am-5:34 pm

1 stop5h 14m

$230

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Wed 7/2

6:16 am-7:02 pm

2 stops11h 46m

$311

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

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 April.

Provider	Price Accuracy	Trust Score*
Expedia	Price Accuracy1 star	Trust Score*3 stars
FlightHub	Price Accuracy3 stars	Trust Score*2 stars
eDreams	Price Accuracy3 stars	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 eDreams the most. eDreams 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.

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 Delta, United Airlines and Allegiant Air. 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

7,929 reviews

Reviews

1 / 20

2.0

Mediocre

Joseph,Aug 2023

MSP - MCO

Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.

Delta

8.0

Very good

7,929 reviews

Delta

8.0

Very good

7,929 reviews

Reviews

1 / 20

2.0

Mediocre

Joseph,Aug 2023

MSP - MCO

United Airlines

7.4

Good

8,696 reviews

Delta

8.0

Very good

7,929 reviews

Reviews

1 / 20

2.0

Mediocre

Joseph,Aug 2023

MSP - MCO

Allegiant Air

7.3

Good

734 reviews

Delta

8.0

Very good

7,929 reviews

Reviews

1 / 20

2.0

Mediocre

Joseph,Aug 2023

MSP - MCO

American Airlines

7.2

Good

10,000 reviews

Delta

8.0

Very good

7,929 reviews

Reviews

1 / 20

2.0

Mediocre

Joseph,Aug 2023

MSP - MCO

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 is 1 daily inbound flight from Chicago from 3 different airlines.
What are the cheapest airlines flying from Chicago to Key West round-trip?
Our cheapest airline available from Chicago to Key West is Delta. Our recent data shows that you can find tickets from as low as $323 on this airline. Additional options worth looking into are American Airlines and United Airlines, starting at $328 and $335 round-trip. Delta 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 United Airlines, with whom users have recently found tickets for as low as $173. However, be on the lookout for offers from American 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: United Airlines (84%), Republic Airways (79%), Air New Zealand( 76%).
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 $462, our data indicates the cheapest price to be $227. The most popular route (Chicago O'Hare Intl - Key West), is priced around $245.
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

Alternative routes for Chicago to Key West

O'Hare Intl to Orlando flights

O'Hare Intl to Miami flights

O'Hare Intl to Fort Lauderdale flights

O'Hare Intl to Tampa flights

Midway to Orlando flights

O'Hare Intl to Fort Myers flights

Midway to Miami flights

O'Hare Intl to Sarasota flights

O'Hare Intl to Pensacola flights

St. Louis to Orlando flights

O'Hare Intl to Jacksonville flights

St. Louis to Miami flights

Midway to Tampa flights

O'Hare Intl to West Palm Beach flights

Midway to Fort Lauderdale flights

O'Hare Intl to Panama City flights

O'Hare Intl to Key West flights

St. Louis to Tampa flights

Midway to West Palm Beach flights

Midway to Fort Myers flights

O'Hare Intl to Valparaiso flights

Midway to Jacksonville flights

St. Louis to Pensacola flights

Midway to Pensacola flights

Peoria to Orlando flights

Midway to Sarasota flights

St. Louis to Fort Lauderdale flights

Midway to Panama City flights

Moline to Orlando flights

Moline to Tampa flights

Midway to Key West flights

St. Louis to Sarasota flights

St. Louis to Panama City flights

Rockford to Orlando Sanford Intl flights

St. Louis to Fort Myers flights

St. Louis to Key West flights

Moline to Fort Myers flights

St. Louis to West Palm Beach flights

Moline to Key West flights

O'Hare Intl to Daytona Beach flights

Rockford to St Petersburg flights

St. Louis to Jacksonville flights

O'Hare Intl to Gainesville flights

Peoria to Fort Lauderdale flights

Moline to Sarasota flights

Springfield to Orlando flights

Moline to Pensacola flights

Moline to Miami flights

Peoria to Fort Myers flights

O'Hare Intl to St Petersburg flights

Other flights to Key West

Top 3 airlines flying from Chicago to Key West

Airline	Cheapest	Average	Flexibility	On-time
Delta	Cheapest$216	Average$375	FlexibilityNo cancel fee	On-timeN/A
United Airlines	Cheapest$262	Average$467	FlexibilityNo cancel fee	On-time69%
American Airlines	Cheapest$263	Average$433	FlexibilityNo cancel fee	On-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.

$173+ 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 6/1. 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 April 29, 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 April 29, 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 April.

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 April 25, 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 April 29, 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

100% Free

Book with Flexibility

Travel Smart

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 April 29, 2025.