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Cheap flights from Chicago (CHI) to Key West (EYW) from $91

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 7/2. 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 7 — Jun 141
From?
To?
Fri 6/7
Fri 6/14
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 2, 2024.

Popular in

March

Cheapest in

August

Round-trip from

$374

One-way from

$108
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 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 $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 American Airlines flights from Chicago to Key West

Explore cheap flight options specifically provided by American 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 2,807,690 searches. Data last updated June 2, 2024.
Find some of the cheapest American Airlines flights traveling from Chicago to Key West. Deals update often to give you more flight options matching your criteria
Fri 9/610:15 amORD - EYW
1 stop5h 28mAmerican Airlines
Mon 9/92:56 pmEYW - ORD
1 stop7h 37mAmerican Airlines
Deal found 6/2$273
Fri 9/610:15 amORD - EYW
1 stop5h 28mAmerican Airlines
Mon 9/911:59 amEYW - ORD
2 stops6h 40mAmerican Airlines
Deal found 6/2$278
Sat 9/78:40 amORD - EYW
2 stops7h 49mAmerican Airlines
Sat 9/146:01 pmEYW - ORD
2 stops6h 56mAmerican Airlines
Deal found 6/1$283
Sun 8/45:28 amORD - EYW
1 stop5h 36mAmerican Airlines
Tue 8/204:50 pmEYW - ORD
1 stop5h 33mAmerican Airlines
Deal found 5/31$345
Thu 9/127:25 amORD - EYW
1 stop5h 49mAmerican Airlines
Sun 9/152:56 pmEYW - ORD
1 stop7h 37mAmerican Airlines
Deal found 6/1$348
Sat 10/58:40 amORD - EYW
2 stops7h 49mAmerican Airlines
Tue 10/81:31 pmEYW - ORD
1 stop6h 37mAmerican Airlines
Deal found 6/1$353
Fri 9/610:15 amORD - EYW
1 stop5h 28mAmerican Airlines
Fri 9/131:46 pmEYW - ORD
2 stops6h 29mAmerican Airlines
Deal found 6/1$358
Wed 9/46:35 amORD - EYW
2 stops9h 54mAmerican Airlines
Sun 9/82:56 pmEYW - ORD
2 stops10h 01mAmerican Airlines
Deal found 6/1$363
Thu 9/128:25 amORD - EYW
1 stop5h 00mAmerican Airlines
Tue 9/171:46 pmEYW - ORD
2 stops6h 29mAmerican Airlines
Deal found 6/1$423

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 2,807,690 searches. Data last updated June 2, 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 9/46:00 amMDW - EYW
1 stop6h 35mDelta
Tue 9/107:25 amEYW - MDW
1 stop5h 32mDelta
Deal found 6/1$232
Fri 8/910:28 amMDW - EYW
1 stop5h 40mDelta
Wed 8/146:03 pmEYW - MDW
1 stop4h 43mDelta
Deal found 6/2$248
Wed 8/2110:28 amMDW - EYW
1 stop5h 40mDelta
Thu 8/296:03 pmEYW - MDW
1 stop4h 43mDelta
Deal found 6/1$268
Wed 7/1712:35 pmMDW - EYW
1 stop6h 03mDelta
Wed 7/246:03 pmEYW - MDW
1 stop4h 43mDelta
Deal found 6/2$288
Tue 7/96:00 amMDW - EYW
1 stop6h 35mDelta
Sat 7/136:03 pmEYW - MDW
1 stop4h 43mDelta
Deal found 6/1$303
Fri 7/1912:35 pmMDW - EYW
1 stop6h 03mDelta
Wed 7/246:03 pmEYW - MDW
1 stop4h 43mDelta
Deal found 6/2$323
Fri 7/1912:22 pmORD - EYW
1 stop6h 16mDelta
Tue 7/236:03 pmEYW - ORD
1 stop6h 51mDelta
Deal found 6/1$343
Fri 7/1910:28 amMDW - EYW
1 stop5h 40mDelta
Thu 7/256:03 pmEYW - MDW
1 stop4h 43mDelta
Deal found 6/2$358
Wed 7/2412:35 pmMDW - EYW
1 stop6h 03mDelta
Wed 7/316:03 pmEYW - MDW
1 stop4h 43mDelta
Deal found 6/2$363

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 2,807,690 searches. Prices were last updated on June 2, 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 6/1412:00 pmORD - EYW
1 stop5h 59mAmerican Airlines
Mon 6/172:25 pmEYW - ORD
1 stop8h 03mAmerican Airlines
Deal found 6/1$348
Thu 6/136:45 amORD - EYW
1 stop6h 10mAmerican Airlines
Thu 6/204:59 pmEYW - ORD
1 stop5h 38mAmerican Airlines
Deal found 6/1$368
Thu 6/135:30 amORD - EYW
2 stops7h 25mAmerican Airlines
Thu 6/205:04 pmEYW - ORD
1 stop6h 30mAmerican Airlines
Deal found 6/1$423
Mon 6/175:30 amORD - EYW
1 stop5h 36mAmerican Airlines
Fri 6/285:04 pmEYW - ORD
1 stop6h 30mAmerican Airlines
Deal found 6/1$428
Tue 6/186:31 amORD - EYW
2 stops11h 28mAmerican Airlines
Fri 6/285:04 pmEYW - ORD
1 stop6h 30mAmerican Airlines
Deal found 6/1$433
Thu 6/612:00 pmORD - EYW
1 stop5h 59mAmerican Airlines
Sat 6/84:52 pmEYW - ORD
1 stop7h 49mAmerican Airlines
Deal found 6/1$438
Thu 6/68:34 amORD - EYW
1 stop6h 50mAmerican Airlines
Sat 6/85:47 pmEYW - ORD
2 stops7h 11mAmerican Airlines
Deal found 6/1$443
Thu 6/69:45 amORD - EYW
2 stops8h 14mAmerican Airlines
Tue 6/1111:15 amEYW - ORD
2 stops9h 15mAmerican Airlines
Deal found 6/2$448
Tue 6/186:40 pmORD - EYW
1 stop18h 55mUnited Airlines
Sat 6/299:00 amEYW - ORD
2 stops15h 15mUnited Airlines
Deal found 6/1$450

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 2,807,690 searches. Data last updated June 2, 2024.
These are some of the most attractive deals on flights from Chicago to Key West in 2024. Check back soon for alternative fares.
Sat 9/79:23 amORD - EYW
1 stop6h 45mDelta
Thu 9/126:16 pmEYW - ORD
1 stop6h 40mDelta
Deal found 6/1$232
Sat 8/1712:35 pmMDW - EYW
1 stop6h 03mDelta
Wed 8/216:03 pmEYW - MDW
1 stop4h 43mDelta
Deal found 6/1$248
Fri 9/69:22 amORD - EYW
1 stop6h 46mDelta
Sat 9/147:25 amEYW - ORD
1 stop6h 09mDelta
Deal found 6/1$248
Wed 8/2112:35 pmMDW - EYW
1 stop6h 03mDelta
Thu 8/296:03 pmEYW - MDW
1 stop4h 43mDelta
Deal found 6/2$268
Thu 7/256:00 amORD - EYW
1 stop6h 35mDelta
Wed 7/316:03 pmEYW - ORD
1 stop6h 51mDelta
Deal found 6/2$268
Fri 9/610:15 amORD - EYW
1 stop5h 28mAmerican Airlines
Mon 9/92:56 pmEYW - ORD
1 stop7h 37mAmerican Airlines
Deal found 6/2$273
Fri 9/610:15 amORD - EYW
1 stop5h 28mAmerican Airlines
Mon 9/911:59 amEYW - ORD
2 stops6h 40mAmerican Airlines
Deal found 6/2$278
Sat 9/78:40 amORD - EYW
2 stops7h 49mAmerican Airlines
Sat 9/146:01 pmEYW - ORD
2 stops6h 56mAmerican Airlines
Deal found 6/1$283
Wed 7/176:00 amORD - EYW
1 stop6h 35mDelta
Wed 7/246:03 pmEYW - ORD
1 stop6h 51mDelta
Deal found 6/2$288

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 2,807,690 searches. Data last updated June 2, 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.
Sun 11/1710:40 amORD - EYW
Nonstop3h 10mUnited Airlines
Sun 11/244:00 pmEYW - ORD
Nonstop3h 24mUnited Airlines
Deal found 6/2$473
Fri 11/110:40 amORD - EYW
Nonstop3h 10mUnited Airlines
Mon 11/44:00 pmEYW - ORD
Nonstop3h 24mUnited Airlines
Deal found 6/1$538
Sat 11/210:40 amORD - EYW
Nonstop3h 10mUnited Airlines
Tue 11/54:00 pmEYW - ORD
Nonstop3h 24mUnited Airlines
Deal found 6/2$539
Fri 11/110:40 amORD - EYW
Nonstop3h 10mUnited Airlines
Tue 11/54:00 pmEYW - ORD
Nonstop3h 24mUnited Airlines
Deal found 6/1$588
Wed 11/68:15 amORD - EYW
Nonstop3h 12mAmerican Airlines
Tue 11/121:46 pmEYW - ORD
Nonstop3h 29mAmerican Airlines
Deal found 6/1$689
Thu 11/710:40 amORD - EYW
Nonstop3h 10mUnited Airlines
Mon 11/114:00 pmEYW - ORD
Nonstop3h 24mUnited Airlines
Deal found 6/2$693
Fri 11/2910:40 amORD - EYW
Nonstop3h 10mUnited Airlines
Mon 12/24:00 pmEYW - ORD
Nonstop3h 24mUnited Airlines
Deal found 6/2$850
Tue 11/268:15 amORD - EYW
Nonstop3h 12mAmerican Airlines
Sat 11/301:46 pmEYW - ORD
Nonstop3h 29mAmerican Airlines
Deal found 6/1$854
Sat 11/2310:40 amORD - EYW
Nonstop3h 10mUnited Airlines
Thu 11/284:00 pmEYW - ORD
Nonstop3h 24mUnited Airlines
Deal found 6/1$865

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 2,807,690 searches. Data last updated June 2, 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 6/116:40 pmORD - EYW
1 stop18h 55mUnited Airlines
Sat 6/159:00 amEYW - ORD
2 stops15h 20mUnited Airlines
Deal found 6/1$531
Sun 6/96:00 amORD - EYW
1 stop7h 09mUnited Airlines
Fri 6/1411:20 amEYW - ORD
1 stop23h 01mUnited Airlines
Deal found 6/1$532
Tue 6/112:25 pmORD - EYW
2 stops23h 10mUnited Airlines
Sat 6/159:00 amEYW - ORD
2 stops15h 20mUnited Airlines
Deal found 6/1$536
Sun 6/96:00 amORD - EYW
1 stop7h 09mUnited Airlines
Fri 6/1411:20 amEYW - ORD
2 stops27h 50mUnited Airlines
Deal found 6/1$537
Tue 6/116:40 pmORD - EYW
1 stop18h 55mUnited Airlines
Sat 6/159:00 amEYW - ORD
1 stop25h 36mUnited Airlines
Deal found 6/1$556
Fri 6/77:00 amORD - EYW
1 stop6h 40mUnited Airlines
Sun 6/911:45 amEYW - ORD
1 stop22h 36mUnited Airlines
Deal found 6/1$667
Tue 6/116:00 amMDW - EYW
1 stop6h 20mDelta
Sat 6/156:00 pmEYW - MDW
1 stop4h 46mDelta
Deal found 6/1$668
Fri 6/78:34 amORD - EYW
1 stop6h 50mAmerican Airlines
Sun 6/97:29 pmEYW - ORD
1 stop5h 24mAmerican Airlines
Deal found 6/1$673
Sun 6/912:32 pmORD - EYW
3 stops26h 36mMultiple Airlines
Fri 6/149:57 amEYW - ORD
2 stops25h 04mMultiple Airlines
Deal found 6/1$677

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 2,807,690 searches. Data last updated June 2, 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.
Tue 7/23:21 pmORD - EYW
1 stop24h 14mMultiple Airlines
Deal found 6/1$91
Thu 7/412:00 pmORD - EYW
1 stop6h 38mDelta
Deal found 6/1$108
Tue 7/211:02 amORD - EYW
2 stops28h 33mMultiple Airlines
Deal found 6/1$148
Wed 8/286:20 pmORD - EYW
1 stop19h 25mUnited Airlines
Deal found 6/1$207
Wed 8/2812:59 pmORD - EYW
2 stops24h 46mUnited Airlines
Deal found 6/1$212
Thu 7/47:05 amORD - EYW
2 stops10h 54mAmerican Airlines
Deal found 6/1$218
Mon 9/166:10 pmORD - EYW
1 stop21h 55mUnited Airlines
Deal found 6/1$219
Mon 9/27:24 amORD - EYW
1 stop8h 41mUnited Airlines
Deal found 6/2$220
Tue 6/186:40 pmORD - EYW
1 stop18h 55mUnited Airlines
Deal found 6/1$227

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 2,807,690 searches. Data last updated June 2, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$232 - $354

Route

Depart

Return

Price

Chicago MidwayKey West

MDW - EYW

MDWEYW

Chicago Midway

Wed 9/4

1 stop6h 35m

Key West

Tue 9/10

1 stop5h 32m

$232

Chicago O'Hare IntlKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Sat 9/7

1 stop6h 45m

Key West

Thu 9/12

1 stop6h 40m

$232

Chicago MidwayKey West

MDW - EYW

MDWEYW

Chicago Midway

Fri 8/9

1 stop5h 40m

Key West

Wed 8/14

1 stop4h 43m

$248

Chicago O'Hare IntlKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Fri 9/6

1 stop6h 46m

Key West

Thu 9/12

1 stop6h 40m

$248

Chicago O'Hare IntlKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Fri 9/6

1 stop5h 28m

Key West

Mon 9/9

1 stop7h 37m

$273

Chicago O'Hare IntlKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Fri 9/6

1 stop5h 28m

Key West

Mon 9/9

2 stops6h 40m

$278

Chicago O'Hare IntlKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Sat 9/7

2 stops7h 49m

Key West

Sat 9/14

2 stops6h 56m

$283

Chicago O'Hare IntlKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Sat 8/10

1 stop13h 05m

Key West

Sat 8/17

2 stops15h 53m

$336

Chicago O'Hare IntlKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Fri 11/15

Nonstop3h 10m

Key West

Tue 11/19

Nonstop3h 24m

$354

Flights are sorted by cheapest first

Deals found on 6/1

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

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 2, 2024.
To help decide which airline to fly from Chicago to Key West, see what other customers have to say about American 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.
Delta
8.0
Very good
10,402 reviews
Check prices

Comfort

7.9

Food

7.4

Crew

8.6

Boarding

8.2

Entertainment

8.0

Overall

8.0

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
10,402 reviews
Delta
8.0
Very good
10,402 reviews
Check prices

Comfort

7.9

Food

7.4

Crew

8.6

Boarding

8.2

Entertainment

8.0

Overall

8.0

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
10,755 reviews
Delta
8.0
Very good
10,402 reviews
Check prices

Comfort

7.9

Food

7.4

Crew

8.6

Boarding

8.2

Entertainment

8.0

Overall

8.0

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
14,260 reviews
Delta
8.0
Very good
10,402 reviews
Check prices

Comfort

7.9

Food

7.4

Crew

8.6

Boarding

8.2

Entertainment

8.0

Overall

8.0

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 $232, but on average you can expect to pay $293.

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

    Cheapflights has at least 12 direct flights from Chicago to Key West under $500. A good price for a nonstop flight from Chicago to Key West is less than $778.

  • Are there last-minute flights available from Chicago to Key West for under $600?

    There are currently 17+ open flights from Chicago to Key West within the next 7 days for less than $600.

  • 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 $232 on this airline. Additional options worth looking into are American Airlines and United Airlines, starting at $273 and $354 round-trip. Delta is currently priced 48% 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 Delta, with whom users have recently found tickets for as low as $108. However, be on the lookout for offers from United Airlines and American Airlines, 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 $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 6/2.

  • 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 2,807,690 searches. Data last updated June 2, 2024.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$226Average$461FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
DeltaCheapest$226Average$460FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
United AirlinesCheapest$247Average$469FlexibilityNo 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 June 2, 2024.
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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.

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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.

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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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