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Cheap flights from Chicago (CHI) to Key West (EYW) from $174

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 6/5. 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 4 — Jun 111
From?
To?
Tue 6/4
Tue 6/11
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 May 30, 2024.

Popular in

March

Cheapest in

August

Round-trip from

$374

One-way from

$225
High demand for flights, 14% potential price rise
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Best time to find cheap flights, 32% potential price drop
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From Chicago (CHI) to Key West
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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 26%.

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 $454 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 United Airlines flights from Chicago to Key West

Explore cheap flight options specifically provided by United Airlines for the route between Chicago and Key West. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,784,634 searches. Data last updated May 30, 2024.
Find some of the cheapest United Airlines flights traveling from Chicago to Key West. Deals update often to give you more flight options matching your criteria
Wed 6/56:00 amORD - EYW
1 stop7h 09mUnited Airlines
Wed 6/123:20 pmEYW - ORD
1 stop8h 55mUnited Airlines
Deal found 5/29$364
Tue 7/306:00 amORD - EYW
1 stop7h 09mUnited Airlines
Fri 8/211:20 amEYW - ORD
1 stop23h 01mUnited Airlines
Deal found 5/29$366
Sat 11/211:15 amORD - EYW
1 stop22h 40mUnited Airlines
Tue 11/58:10 pmEYW - ORD
2 stops27h 50mUnited Airlines
Deal found 5/29$374
Sun 10/2710:40 amORD - EYW
Nonstop3h 10mUnited Airlines
Fri 11/111:45 amEYW - ORD
1 stop23h 02mUnited Airlines
Deal found 5/29$376
Sun 10/2710:40 amORD - EYW
Nonstop3h 10mUnited Airlines
Fri 11/18:10 pmEYW - ORD
2 stops27h 50mUnited Airlines
Deal found 5/29$393
Mon 8/126:00 amORD - EYW
1 stop7h 09mUnited Airlines
Fri 8/1611:20 amEYW - ORD
1 stop23h 01mUnited Airlines
Deal found 5/29$411
Sun 11/1710:40 amORD - EYW
Nonstop3h 10mUnited Airlines
Sun 11/248:10 pmEYW - ORD
1 stop14h 31mUnited Airlines
Deal found 5/29$416
Mon 9/1610:55 amORD - EYW
1 stop26h 30mUnited Airlines
Thu 9/1911:30 amEYW - ORD
1 stop23h 21mUnited Airlines
Deal found 5/29$422
Fri 11/2210:40 amORD - EYW
Nonstop3h 10mUnited Airlines
Wed 11/274:00 pmEYW - ORD
Nonstop3h 24mUnited Airlines
Deal found 5/29$424

Cheap Delta flights from Chicago to Key West

Explore cheap flight options specifically provided by Delta for the route between Chicago and Key West. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,784,634 searches. Data last updated May 30, 2024.
Take a gander at the lowest prices we've found on Delta flights from Chicago to Key West. Check back soon if you're not seeing flights that suit your needs.
Wed 9/412:35 pmMDW - EYW
1 stop6h 03mDelta
Tue 9/107:00 amEYW - MDW
1 stop5h 58mDelta
Deal found 5/30$232
Wed 9/412:35 pmMDW - EYW
1 stop6h 03mDelta
Tue 9/107:00 amEYW - MDW
1 stop5h 58mDelta
Deal found 5/29$248
Sat 7/69:15 amORD - EYW
1 stop6h 50mDelta
Thu 7/112:30 pmEYW - ORD
1 stop7h 37mDelta
Deal found 5/29$268
Wed 8/2110:28 amMDW - EYW
1 stop5h 40mDelta
Thu 8/296:03 pmEYW - MDW
1 stop4h 43mDelta
Deal found 5/30$303
Fri 8/2310:28 amMDW - EYW
1 stop5h 40mDelta
Mon 8/267:23 amEYW - MDW
1 stop5h 21mDelta
Deal found 5/29$323
Fri 7/56:00 amMDW - EYW
1 stop6h 22mDelta
Thu 7/116:03 pmEYW - MDW
1 stop4h 43mDelta
Deal found 5/29$327
Fri 7/1912:22 pmORD - EYW
1 stop6h 16mDelta
Tue 7/236:03 pmEYW - ORD
1 stop6h 51mDelta
Deal found 5/29$343
Fri 7/1910:28 amMDW - EYW
1 stop5h 40mDelta
Tue 7/236:03 pmEYW - MDW
1 stop4h 43mDelta
Deal found 5/29$358
Sat 7/276:00 amMDW - EYW
1 stop4h 47mDelta
Sat 8/36:03 pmEYW - MDW
1 stop4h 43mDelta
Deal found 5/30$398

Cheap Chicago to Key West flights in May & June 2024

Find cheap flight options from Chicago to Key West specifically for the months of May and June 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 2,784,634 searches. Prices were last updated on May 30, 2024.
These are some of the most attractive deals on flights from Chicago to Key West in 2024. Check back soon for alternative fares.
Fri 6/149:45 amORD - EYW
1 stop5h 44mAmerican Airlines
Mon 6/172:25 pmEYW - ORD
1 stop8h 03mAmerican Airlines
Deal found 5/29$347
Tue 6/188:30 amORD - EYW
1 stop6h 59mAmerican Airlines
Tue 6/253:10 pmEYW - ORD
2 stops7h 27mAmerican Airlines
Deal found 5/30$350
Thu 6/278:04 pmORD - EYW
1 stop11h 58mMultiple Airlines
Thu 7/42:43 pmEYW - ORD
2 stops20h 18mMultiple Airlines
Deal found 5/28$352
Tue 6/185:30 amORD - EYW
2 stops8h 10mAmerican Airlines
Tue 6/253:10 pmEYW - ORD
2 stops7h 27mAmerican Airlines
Deal found 5/30$355
Wed 6/56:00 amORD - EYW
1 stop7h 09mUnited Airlines
Wed 6/123:20 pmEYW - ORD
1 stop8h 55mUnited Airlines
Deal found 5/29$364
Wed 6/125:30 amORD - EYW
1 stop5h 36mAmerican Airlines
Tue 6/184:59 pmEYW - ORD
1 stop7h 59mAmerican Airlines
Deal found 5/30$365
Wed 6/59:45 amORD - EYW
2 stops8h 14mAmerican Airlines
Wed 6/1212:46 pmEYW - ORD
1 stop7h 44mAmerican Airlines
Deal found 5/29$370
Thu 6/275:18 pmORD - EYW
3 stops21h 50mMultiple Airlines
Thu 7/42:43 pmEYW - ORD
2 stops20h 18mMultiple Airlines
Deal found 5/28$371
Wed 6/127:05 amORD - EYW
2 stops9h 11mAmerican Airlines
Tue 6/183:10 pmEYW - ORD
2 stops7h 27mAmerican Airlines
Deal found 5/30$375

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 2,784,634 searches. Data last updated May 30, 2024.
These are some of the most attractive deals on flights from Chicago to Key West in 2024. Check back soon for alternative fares.
Sun 9/18:24 amORD - EYW
1 stop5h 26mAmerican Airlines
Thu 9/55:13 pmEYW - ORD
1 stop7h 44mAmerican Airlines
Deal found 5/30$197
Wed 9/412:35 pmMDW - EYW
1 stop6h 03mDelta
Tue 9/107:00 amEYW - MDW
1 stop5h 58mDelta
Deal found 5/30$232
Wed 9/412:22 pmORD - EYW
1 stop6h 16mDelta
Tue 9/107:00 amEYW - ORD
1 stop6h 04mDelta
Deal found 5/30$232
Wed 9/412:35 pmMDW - EYW
1 stop6h 03mDelta
Tue 9/107:00 amEYW - MDW
1 stop5h 58mDelta
Deal found 5/29$248
Wed 8/146:00 amORD - EYW
1 stop6h 35mDelta
Mon 8/196:03 pmEYW - ORD
1 stop6h 51mDelta
Deal found 5/29$248
Wed 7/316:16 pmORD - EYW
1 stop13h 55mMultiple Airlines
Wed 8/74:57 pmEYW - ORD
2 stops17h 17mMultiple Airlines
Deal found 5/30$258
Sat 7/69:15 amORD - EYW
1 stop6h 50mDelta
Thu 7/112:30 pmEYW - ORD
1 stop7h 37mDelta
Deal found 5/29$268
Wed 7/315:37 pmORD - EYW
2 stops14h 34mMultiple Airlines
Wed 8/74:57 pmEYW - ORD
2 stops17h 17mMultiple Airlines
Deal found 5/30$270
Mon 7/16:02 amORD - EYW
1 stop5h 59mAmerican Airlines
Fri 7/54:24 pmEYW - ORD
1 stop5h 56mAmerican Airlines
Deal found 5/29$272

Non-stop flights to Key West from Chicago

Discover non-stop flight options from Chicago to Key West. Find direct flights with no layovers, providing a convenient travel experience. Explore non-stop flight options based on user searches, and compare prices and availability for your desired travel dates. Over the last 7 days, Cheapflights users made 2,784,634 searches. Data last updated May 30, 2024.
Take a look at some of the direct flights traveling from Chicago to Key West in the near future. Search for alternative flights from Chicago to Key West by utilizing the search form above.
Fri 11/2210:40 amORD - EYW
Nonstop3h 10mUnited Airlines
Wed 11/274:00 pmEYW - ORD
Nonstop3h 24mUnited Airlines
Deal found 5/29$424
Fri 11/110:40 amORD - EYW
Nonstop3h 10mUnited Airlines
Mon 11/44:00 pmEYW - ORD
Nonstop3h 24mUnited Airlines
Deal found 5/29$439
Fri 11/810:40 amORD - EYW
Nonstop3h 10mUnited Airlines
Sun 11/104:00 pmEYW - ORD
Nonstop3h 24mUnited Airlines
Deal found 5/30$450
Fri 11/810:40 amORD - EYW
Nonstop3h 10mUnited Airlines
Sun 11/104:00 pmEYW - ORD
Nonstop3h 24mUnited Airlines
Deal found 5/29$452
Sun 11/1710:40 amORD - EYW
Nonstop3h 10mUnited Airlines
Sun 11/244:00 pmEYW - ORD
Nonstop3h 24mUnited Airlines
Deal found 5/29$473
Sun 10/2710:40 amORD - EYW
Nonstop3h 10mUnited Airlines
Fri 11/14:00 pmEYW - ORD
Nonstop3h 24mUnited Airlines
Deal found 5/29$489
Fri 11/110:40 amORD - EYW
Nonstop3h 10mUnited Airlines
Sun 11/34:00 pmEYW - ORD
Nonstop3h 24mUnited Airlines
Deal found 5/30$538
Sat 11/210:40 amORD - EYW
Nonstop3h 10mUnited Airlines
Tue 11/54:00 pmEYW - ORD
Nonstop3h 24mUnited Airlines
Deal found 5/29$539
Fri 11/110:40 amORD - EYW
Nonstop3h 10mUnited Airlines
Tue 11/54:00 pmEYW - ORD
Nonstop3h 24mUnited Airlines
Deal found 5/29$588

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 2,784,634 searches. Data last updated May 30, 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.
Wed 6/56:00 amORD - EYW
1 stop7h 09mUnited Airlines
Wed 6/123:20 pmEYW - ORD
1 stop8h 55mUnited Airlines
Deal found 5/29$364
Wed 6/59:45 amORD - EYW
2 stops8h 14mAmerican Airlines
Wed 6/1212:46 pmEYW - ORD
1 stop7h 44mAmerican Airlines
Deal found 5/29$370
Fri 6/75:30 amORD - EYW
1 stop5h 36mAmerican Airlines
Mon 6/105:04 pmEYW - ORD
1 stop6h 30mAmerican Airlines
Deal found 5/30$387
Thu 6/67:00 amORD - EYW
1 stop8h 24mAmerican Airlines
Sat 6/812:05 pmEYW - ORD
1 stop6h 34mAmerican Airlines
Deal found 5/29$388
Thu 6/65:30 amORD - EYW
2 stops7h 25mAmerican Airlines
Sat 6/82:38 pmEYW - ORD
1 stop8h 56mAmerican Airlines
Deal found 5/29$392
Fri 6/75:07 amORD - EYW
2 stops7h 59mAmerican Airlines
Mon 6/105:04 pmEYW - ORD
1 stop6h 30mAmerican Airlines
Deal found 5/30$393
Wed 6/56:15 amORD - EYW
1 stop4h 51mAmerican Airlines
Tue 6/112:40 pmEYW - ORD
1 stop7h 57mAmerican Airlines
Deal found 5/30$435
Wed 6/59:45 amORD - EYW
2 stops8h 14mAmerican Airlines
Tue 6/114:59 pmEYW - ORD
1 stop7h 59mAmerican Airlines
Deal found 5/30$440
Thu 6/65:30 amORD - EYW
2 stops7h 25mAmerican Airlines
Sat 6/85:47 pmEYW - ORD
2 stops7h 11mAmerican Airlines
Deal found 5/29$445

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 2,784,634 searches. Data last updated May 30, 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.
Wed 6/511:01 amORD - EYW
3 stops25h 45mMultiple Airlines
Deal found 5/29$174
Wed 8/286:20 pmORD - EYW
1 stop19h 05mUnited Airlines
Deal found 5/29$178
Wed 8/2811:20 amORD - EYW
1 stop23h 40mUnited Airlines
Deal found 5/29$190
Wed 8/286:20 pmORD - EYW
1 stop19h 05mUnited Airlines
Deal found 5/30$207
Sun 6/97:40 pmMDW - EYW
2 stops17h 31mAllegiant Air
Deal found 5/29$211
Wed 8/2812:59 pmORD - EYW
2 stops24h 26mUnited Airlines
Deal found 5/30$212
Wed 6/56:40 pmORD - EYW
1 stop18h 45mUnited Airlines
Deal found 5/29$214
Thu 8/85:37 pmORD - EYW
2 stops14h 24mMultiple Airlines
Deal found 5/29$220
Wed 6/56:40 pmORD - EYW
2 stops18h 06mMultiple Airlines
Deal found 5/29$224

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 2,784,634 searches. Data last updated May 30, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$197 - $366

Route

Depart

Return

Price

Chicago O'Hare IntlKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Sun 9/1

1 stop5h 26m

Key West

Thu 9/5

1 stop7h 44m

$197

Chicago MidwayKey West

MDW - EYW

MDWEYW

Chicago Midway

Wed 9/4

1 stop6h 03m

Key West

Tue 9/10

1 stop5h 58m

$232

Chicago O'Hare IntlKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Wed 9/4

1 stop6h 16m

Key West

Tue 9/10

1 stop8h 12m

$232

Chicago MidwayKey West

MDW - EYW

MDWEYW

Chicago Midway

Wed 9/4

1 stop6h 03m

Key West

Tue 9/10

1 stop5h 58m

$248

Chicago O'Hare IntlKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Mon 9/9

1 stop6h 07m

Key West

Sat 9/14

1 stop8h 12m

$248

Chicago O'Hare IntlKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Wed 7/31

1 stop13h 55m

Key West

Wed 8/7

2 stops17h 17m

$258

Chicago O'Hare IntlKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Wed 7/31

2 stops14h 34m

Key West

Wed 8/7

2 stops17h 17m

$270

Chicago O'Hare IntlKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Mon 7/1

1 stop5h 59m

Key West

Fri 7/5

1 stop5h 56m

$272

Chicago O'Hare IntlKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Tue 7/30

1 stop7h 09m

Key West

Fri 8/2

1 stop23h 01m

$366

Flights are sorted by cheapest first

Deals found on 5/30

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 24, 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 May 26, 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

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 May 30, 2024.
To help decide which airline to fly from Chicago to Key West, see what other customers have to say about United Airlines, Delta and American 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.
Delta
8.0
Very good
10,457 reviews
Check prices

Entertainment

8.0

Comfort

7.9

Food

7.4

Boarding

8.2

Overall

8.0

Crew

8.6

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
10,457 reviews
Delta
8.0
Very good
10,457 reviews
Check prices

Entertainment

8.0

Comfort

7.9

Food

7.4

Boarding

8.2

Overall

8.0

Crew

8.6

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
1,002 reviews
Delta
8.0
Very good
10,457 reviews
Check prices

Entertainment

8.0

Comfort

7.9

Food

7.4

Boarding

8.2

Overall

8.0

Crew

8.6

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
10,777 reviews
Delta
8.0
Very good
10,457 reviews
Check prices

Entertainment

8.0

Comfort

7.9

Food

7.4

Boarding

8.2

Overall

8.0

Crew

8.6

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
14,284 reviews
Delta
8.0
Very good
10,457 reviews
Check prices

Entertainment

8.0

Comfort

7.9

Food

7.4

Boarding

8.2

Overall

8.0

Crew

8.6

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 $200 on Cheapflights?

    Yes, there are multiple flights from Chicago to Key West for under $200. The cheapest flight booked recently is on American Airlines for just $197, but on average you can expect to pay $284.

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

    Cheapflights has at least 15 direct flights from Chicago to Key West under $500. A good price for a nonstop flight from Chicago to Key West is less than $649.

  • 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 American Airlines. Our recent data shows that you can find tickets from as low as $197 on this airline. An additional option worth looking into is Delta, starting at $232. American Airlines is currently priced 56% 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 $178. 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 (87%), American Airlines (74%), Envoy Air( 74%).

  • 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 $463, our data indicates the cheapest price to be $325. The most popular route (Chicago O'Hare Intl - Key West), is priced around $216.

  • 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 5/30.

  • 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, January is the cheapest month in which you can book a flight from Chicago to Key West (average of $374). Flying from Chicago to Key West in March is currently the most expensive (average of $504). 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.

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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 2,784,634 searches. Data last updated May 30, 2024.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$226Average$458FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
DeltaCheapest$226Average$462FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
United AirlinesCheapest$246Average$468FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Alaska AirlinesCheapest$438Average$467FlexibilityNo cancel feeOn-time75%
Search Alaska Airlines flights
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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.
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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 May 30, 2024.
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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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