Cheap flights from Key West (EYW) to O'Hare Intl (ORD) from $104

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 7/23. 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.
EYW — ORD
Apr 21 — Apr 281

The best prices from Key West to Chicago O'Hare Intl are usually found in September or August, booked 41 days in advance, depart on a Wednesday or Thursday and return on a Tuesday

Cheap flight deals from Key West to O'Hare Intl

Discover tips and strategies to find the most affordable flight options for your journey from Key West (EYW) to O'Hare Intl (ORD). 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 April 16, 2024.

Popular in

June

Cheapest in

September

Round-trip from

$222

One-way from

$104
High demand for flights, 30% potential price rise
Best time to find cheap flights, 32% potential price drop
From Key West to Chicago O'Hare Intl
One-way flight from Key West to Chicago O'Hare Intl

What is the cheapest day to fly round-trip from Key West to Chicago O'Hare Intl Airport?

It’s generally more expensive to depart on a Tuesday, if you have to leave on this day you can still search on Cheapflights to find great options that meet your needs.

What is the cheapest month to fly from Key West to Chicago O'Hare Intl Airport?

Our data shows that October tends to be the cheapest month to fly to Chicago O'Hare Intl Airport from Key West. Users have commonly found prices around $376 for the month, but tickets can be as low as $227. Due to multiple factors, prepare for potentially higher prices in March.

When is the cheapest time to fly from Key West to Chicago O'Hare Intl Airport (EYW - ORD)?

It’s typically best to fly out from Key West to Chicago O'Hare Intl Airport in the evening. Doing so could potentially save you 50% on the flight price compared to flying in the afternoon, which is usually more expensive.

Cheap Delta flights from Key West to O'Hare Intl

Explore cheap flight options specifically provided by Delta for the route between Key West and O'Hare Intl. 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 3,185,007 searches. Data last updated April 16, 2024.
Take a peek at the cheapest Delta flights we've detected traveling from Key West to Chicago. Make sure to double check the flight details before booking.
Fri 5/33:02 pmEYW - ORD
1 stop8h 21mDelta
Tue 5/79:32 amORD - EYW
1 stop6h 40mDelta
Deal found 4/15$247
Fri 5/33:02 pmEYW - ORD
1 stop8h 21mDelta
Tue 5/79:32 amORD - EYW
1 stop6h 40mDelta
Deal found 4/14$268
Tue 6/47:05 amEYW - ORD
2 stops14h 50mDelta
Tue 6/259:15 amORD - EYW
1 stop6h 50mDelta
Deal found 4/14$422
Sun 6/27:05 amEYW - ORD
1 stop17h 49mDelta
Tue 6/259:15 amORD - EYW
1 stop6h 50mDelta
Deal found 4/14$437
Thu 6/66:10 pmEYW - ORD
1 stop6h 44mDelta
Sat 6/297:10 amORD - EYW
2 stops11h 30mDelta
Deal found 4/14$442
Tue 6/46:10 pmEYW - ORD
1 stop6h 44mDelta
Fri 6/286:00 amORD - EYW
1 stop10h 05mDelta
Deal found 4/14$449
Thu 6/66:10 pmEYW - ORD
1 stop6h 44mDelta
Fri 6/286:00 amORD - EYW
1 stop10h 05mDelta
Deal found 4/14$469
Sun 6/27:05 amEYW - ORD
1 stop17h 49mDelta
Wed 6/267:05 amORD - EYW
1 stop9h 00mDelta
Deal found 4/14$516
Mon 6/36:10 pmEYW - ORD
1 stop6h 44mDelta
Tue 6/256:00 amORD - EYW
1 stop4h 44mDelta
Deal found 4/14$728

Cheap United Airlines flights from Key West to O'Hare Intl

Explore cheap flight options specifically provided by United Airlines for the route between Key West and O'Hare Intl. 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 3,185,007 searches. Data last updated April 16, 2024.
Take a gander at the lowest prices we've found on United Airlines flights from Key West to Chicago. Check back soon if you're not seeing flights that suit your needs.
Fri 5/34:05 pmEYW - ORD
2 stops8h 25mUnited Airlines
Tue 5/77:00 amORD - EYW
1 stop9h 24mUnited Airlines
Deal found 4/14$482
Fri 6/72:55 pmEYW - ORD
1 stop6h 30mUnited Airlines
Thu 6/277:40 amORD - EYW
1 stop6h 45mUnited Airlines
Deal found 4/14$607

Cheap Key West to O'Hare Intl flights in April & May 2024

Find cheap flight options from Key West to O'Hare Intl specifically for the months of April and May 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 3,185,007 searches. Prices were last updated on April 16, 2024.
Listed are some of the best fares we've found on flights departing from Key West to Chicago in 2024. Check back soon for alternative fares.
Fri 5/105:09 pmEYW - ORD
1 stop5h 20mAmerican Airlines
Tue 5/145:15 amORD - EYW
1 stop4h 46mAmerican Airlines
Deal found 4/15$229
Wed 5/225:09 pmEYW - ORD
1 stop7h 50mAmerican Airlines
Wed 6/127:00 amORD - EYW
1 stop8h 24mAmerican Airlines
Deal found 4/15$230
Fri 5/175:09 pmEYW - ORD
1 stop5h 20mAmerican Airlines
Mon 5/207:30 amORD - EYW
1 stop7h 38mAmerican Airlines
Deal found 4/14$245
Fri 5/33:02 pmEYW - ORD
1 stop8h 21mDelta
Tue 5/79:32 amORD - EYW
1 stop6h 40mDelta
Deal found 4/15$247
Fri 5/175:55 pmEYW - ORD
2 stops23h 40mMultiple Airlines
Mon 5/205:00 amORD - EYW
1 stop8h 40mMultiple Airlines
Deal found 4/14$266
Fri 5/33:02 pmEYW - ORD
1 stop8h 21mDelta
Tue 5/79:32 amORD - EYW
1 stop6h 40mDelta
Deal found 4/14$268
Fri 5/1011:45 amEYW - ORD
1 stop6h 55mMultiple Airlines
Tue 5/149:25 pmORD - EYW
2 stops16h 00mMultiple Airlines
Deal found 4/15$289
Fri 5/1011:45 amEYW - ORD
1 stop12h 44mMultiple Airlines
Tue 5/145:36 pmORD - EYW
3 stops19h 49mMultiple Airlines
Deal found 4/15$333
Wed 5/225:09 pmEYW - ORD
1 stop7h 50mAmerican Airlines
Wed 6/128:10 amORD - EYW
2 stops7h 19mAmerican Airlines
Deal found 4/15$342

Key West to O'Hare Intl 2024 flight deals

Discover exclusive flight deals for travel between Key West and O'Hare Intl in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 3,185,007 searches. Data last updated April 16, 2024.
Listed are some of the best fares we've found on flights departing from Key West to Chicago in 2024. Check back soon for alternative fares.
Tue 6/412:49 pmEYW - ORD
1 stop7h 32mAmerican Airlines
Tue 6/257:00 amORD - EYW
1 stop8h 12mAmerican Airlines
Deal found 4/14$212
Fri 5/105:09 pmEYW - ORD
1 stop5h 20mAmerican Airlines
Tue 5/145:15 amORD - EYW
1 stop4h 46mAmerican Airlines
Deal found 4/15$229
Wed 5/225:09 pmEYW - ORD
1 stop7h 50mAmerican Airlines
Wed 6/127:00 amORD - EYW
1 stop8h 24mAmerican Airlines
Deal found 4/15$230
Fri 5/175:09 pmEYW - ORD
1 stop5h 20mAmerican Airlines
Mon 5/207:30 amORD - EYW
1 stop7h 38mAmerican Airlines
Deal found 4/14$245
Fri 5/33:02 pmEYW - ORD
1 stop8h 21mDelta
Tue 5/79:32 amORD - EYW
1 stop6h 40mDelta
Deal found 4/15$247
Fri 5/175:55 pmEYW - ORD
2 stops23h 40mMultiple Airlines
Mon 5/205:00 amORD - EYW
1 stop8h 40mMultiple Airlines
Deal found 4/14$266
Fri 5/33:02 pmEYW - ORD
1 stop8h 21mDelta
Tue 5/79:32 amORD - EYW
1 stop6h 40mDelta
Deal found 4/14$268
Wed 6/53:25 pmEYW - ORD
1 stop6h 47mAmerican Airlines
Wed 6/265:30 amORD - EYW
1 stop5h 36mAmerican Airlines
Deal found 4/14$275
Wed 6/511:30 amEYW - ORD
1 stop7h 06mMultiple Airlines
Tue 6/258:13 amORD - EYW
1 stop10h 22mMultiple Airlines
Deal found 4/14$278

One-way flights to O'Hare Intl from Key West

Search for one-way flight options from Key West to O'Hare Intl. Find affordable one-way fares based on user searches. Compare prices and availability to plan your one-way journey according to your preferred dates and budget. Over the last 7 days, Cheapflights users made 3,185,007 searches. Data last updated April 16, 2024.
Take a look at some of the one-way flights we've detected from Key West to Chicago. Users can also find round-trip Key West to Chicago flights by using the search form above.
Tue 7/232:44 pmEYW - ORD
1 stop7h 57mDelta
Deal found 4/15$104
Mon 4/295:28 pmEYW - ORD
1 stop6h 58mMultiple Airlines
Deal found 4/15$143
Mon 4/2911:45 amEYW - ORD
2 stops21h 52mMultiple Airlines
Deal found 4/15$179
Thu 4/2511:30 amEYW - ORD
2 stops10h 35mMultiple Airlines
Deal found 4/15$201
Mon 4/2911:45 amEYW - ORD
3 stops31h 58mMultiple Airlines
Deal found 4/15$202
Sun 4/2811:45 amEYW - ORD
1 stop22h 38mMultiple Airlines
Deal found 4/15$205
Mon 4/228:10 pmEYW - ORD
1 stop13h 27mMultiple Airlines
Deal found 4/15$207
Thu 4/2511:30 amEYW - ORD
1 stop13h 50mMultiple Airlines
Deal found 4/15$210
Sun 4/2811:45 amEYW - ORD
2 stops30h 42mMultiple Airlines
Deal found 4/15$214

Find flights from Key West to O'Hare Intl within your budget

Customize your flight search to find flights from Key West to O'Hare Intl that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 3,185,007 searches. Data last updated April 16, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$212 - $482

Route

Depart

Return

Price

Key WestChicago O'Hare Intl

EYW - ORD

EYWORD

Key West

Tue 6/4

1 stop7h 32m

Chicago O'Hare Intl

Tue 6/25

1 stop8h 12m

$212

Key WestChicago O'Hare Intl

EYW - ORD

EYWORD

Key West

Fri 5/10

1 stop5h 20m

Chicago O'Hare Intl

Tue 5/14

1 stop4h 46m

$229

Key WestChicago O'Hare Intl

EYW - ORD

EYWORD

Key West

Wed 5/22

1 stop7h 50m

Chicago O'Hare Intl

Wed 6/12

1 stop8h 24m

$230

Key WestChicago O'Hare Intl

EYW - ORD

EYWORD

Key West

Fri 5/17

1 stop5h 20m

Chicago O'Hare Intl

Mon 5/20

1 stop7h 38m

$245

Key WestChicago O'Hare Intl

EYW - ORD

EYWORD

Key West

Fri 5/3

1 stop8h 21m

Chicago O'Hare Intl

Tue 5/7

1 stop6h 40m

$247

Key WestChicago O'Hare Intl

EYW - ORD

EYWORD

Key West

Fri 5/17

2 stops23h 40m

Chicago O'Hare Intl

Mon 5/20

1 stop8h 40m

$266

Key WestChicago O'Hare Intl

EYW - ORD

EYWORD

Key West

Fri 5/3

1 stop8h 21m

Chicago O'Hare Intl

Tue 5/7

1 stop6h 40m

$268

Key WestChicago O'Hare Intl

EYW - ORD

EYWORD

Key West

Wed 6/5

1 stop7h 06m

Chicago O'Hare Intl

Tue 6/25

1 stop10h 22m

$278

Key WestChicago O'Hare Intl

EYW - ORD

EYWORD

Key West

Fri 5/3

2 stops8h 25m

Chicago O'Hare Intl

Tue 5/7

1 stop9h 24m

$482

Flights are sorted by cheapest first

Deals found on 4/14

When is the best time to book a flight from Key West to Chicago O'Hare Intl Airport?

Use this chart to determine the optimal time to book a round-trip flight from Key West to O'Hare Intl. Price data was last updated on January 28, 2024.
The best time to book flights from Key West to Chicago O'Hare Intl Airport is 39 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

When is the cheapest time to fly from Key West to Chicago O'Hare Intl Airport?

Use this chart to determine the cheapest time to fly round-trip from Key West to O'Hare Intl. Price data was last updated on April 14, 2024.
Morning
Noon
Afternoon
Evening
All times are departure.
Travelers seeking maximum savings on their Key West to Chicago O'Hare Intl Airport flight should consider departing on Wednesday evenings when fares are most often at their lowest. Saturday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
Search Deals

Average price of flights to O'Hare Intl by month

Plan your trip from Key West to O'Hare Intl by taking into account the cheapest months to travel. The average price of a one-way flight from Key West to O'Hare Intl is currently $185 while a round-trip flight costs $273. Price data was last updated on April 14, 2024.

Currently, February is the cheapest month in which you can book a flight from Key West to Chicago O'Hare Intl Airport (average of $245). Flying from Key West to Chicago O'Hare Intl Airport in June is currently the most expensive (average of $357). 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.

January

$248

February

$245

March

$280

April

$276

May

$283

June

$357

July

$336

August

$276

September

$258

October

$248

November

$270

December

$248

Temperature and rainfall in O'Hare Intl by month

Plan your trip to O'Hare Intl by taking into account the average temperature and rainfall totals by month.

CHI

Temperature

23 - 73.4 °F

Reviews of airlines servicing O'Hare Intl

Get insights into the airlines that provide service to O'Hare Intl. 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 O'Hare Intl. Reviews last updated April 16, 2024.
Peruse reviews from past customers who have flown with Delta, United Airlines and American Airlines from Key West to Chicago to help guide your decision. 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.
8.1
Very good
11,123 reviews

Overall

8.1

Food

7.5

Comfort

7.9

Boarding

8.2

Crew

8.6

Entertainment

8.0

Reviews

1 / 10

Although I adhered to 17.7 lbs for carry-on and complied with dimensions of personal item for ITA, I felt very restricted compared to other travelers.

8.1
Very good
11,123 reviews
8.1
Very good
11,123 reviews

Overall

8.1

Food

7.5

Comfort

7.9

Boarding

8.2

Crew

8.6

Entertainment

8.0

Reviews

1 / 10

Although I adhered to 17.7 lbs for carry-on and complied with dimensions of personal item for ITA, I felt very restricted compared to other travelers.

7.4
Good
11,360 reviews
8.1
Very good
11,123 reviews

Overall

8.1

Food

7.5

Comfort

7.9

Boarding

8.2

Crew

8.6

Entertainment

8.0

Reviews

1 / 10

Although I adhered to 17.7 lbs for carry-on and complied with dimensions of personal item for ITA, I felt very restricted compared to other travelers.

7.3
Good
14,952 reviews
8.1
Very good
11,123 reviews

Overall

8.1

Food

7.5

Comfort

7.9

Boarding

8.2

Crew

8.6

Entertainment

8.0

Reviews

1 / 10

Although I adhered to 17.7 lbs for carry-on and complied with dimensions of personal item for ITA, I felt very restricted compared to other travelers.

Related info for your journey

Find useful and relevant information for your journey from Key West to O'Hare Intl. 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 from for flights from Key West to Chicago O'Hare Intl?

    Located just 2.6 mi from the city center, Key West is the airport most travelers will use when flying to Chicago O'Hare Intl from Key West. Booking flights from Key West (EYW) to Chicago O'Hare Intl should be relatively easy as there are 3 daily outbound flights to Chicago O'Hare Intl from 3 different airlines.

  • Can I find flights from Key West to Chicago O'Hare Intl Airport for under $300 on Cheapflights?

    Yes, there are multiple flights from Key West to Chicago O'Hare Intl Airport for under $300. The cheapest flight booked recently is on American Airlines for just $212, but on average you can expect to pay $295.

  • What are the cheapest airlines flying from Key West to Chicago O'Hare Intl Airport round-trip?

    Currently priced at $212, American Airlines will fly you from Key West to Chicago O'Hare Intl Airport and back. In addition to American Airlines, many other airlines offer competitively priced options for your trip. Check Cheapflights for deals on Delta for as low as $247. American Airlines is currently priced 50% below the average price you’ll pay for this route.

  • What are the cheapest airlines to fly from Key West to Chicago O'Hare Intl Airport one-way?

    The cheapest airlines for a one-way flight from Key West to Chicago O'Hare Intl Airport are Delta ($104), United Airlines ($277), and American Airlines ($334).

  • What are the most popular airlines that fly from Key West to Chicago O'Hare Intl Airport?

  • What are the most reliable airlines from Key West to Chicago O'Hare Intl Airport?

    Consider United Airlines (62%), Air New Zealand (60%) or American Airlines (58%) when booking your flight. These represent the most reliable airlines when flying from Key West to Chicago O'Hare Intl Airport.

  • What are the cheapest flights from Key West to Chicago O'Hare Intl Airport?

    On average you can expect to pay $565 for a flight from Key West to Chicago O'Hare Intl Airport. The cheapest flight overall is $193 while the most popular route, (Key West - Chicago O'Hare Intl) is currently priced at $247.

  • What does EYW to ORD mean?

    These are just IATA (International Air Transport Association) codes. They are used in aviation to identify and differentiate airports. That’s why a Key West Airport to Chicago O'Hare Intl Airport flight would often be abbreviated as a EYW to ORD flight.

  • Can I find deals for flights from Key West to O'Hare Intl that include extra baggage allowance?

    The amount of baggage you can bring 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 Key West to O'Hare Intl with specific airlines?

    Yes, Cheapflights allows you to browse and filter 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 Key West to O'Hare Intl that include hotel bookings?

    Yes. In addition to deals on Key West to O'Hare Intl flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Key West to O'Hare Intl?

    After entering your origin and destination, apply the non-stop filter on the search result page to see available direct flights.

  • Can I find deals for business class flights from Key West to O'Hare Intl?

    Yes. Cheapflights offers flight deals from Key West to O'Hare Intl 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 Key West to O'Hare Intl that allow pets onboard?

    Many airlines do 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 Key West to O'Hare Intl?

    Yes, you can often find last-minute deals on Key West to O'Hare Intl 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 Key West to Chicago O'Hare Intl Airport flight deals updated?

    The Key West to Chicago O'Hare Intl Airport flight deals you see on this page were last updated on 4/15.

See more FAQs

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Top 3 airlines flying from Key West to O'Hare Intl

Discover the top 3 airlines that operate flights from Key West to O'Hare Intl. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 3,185,007 searches. Data last updated April 16, 2024.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$225Average$374FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
DeltaCheapest$311Average$441FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
United AirlinesCheapest$320Average$582FlexibilityNo cancel feeOn-time69%
Search United Airlines flights

Search flights from Key West to O'Hare Intl by cabin class

Find flights from Key West to O'Hare Intl, based on your preferred cabin class, be it economy, premium economy, business, or first class.

Hourly flight availability from Key West to O'Hare Intl

Find hourly flight availability from Key West to O'Hare Intl. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 16, 2024.
0%of flight departuresEarly morningMidnight to 6 am
0%of flight departuresMorning6 am to noon
100%of flight departuresAfternoonNoon to 6 pm
0%of flight departuresEvening6 pm to midnight
Midnight
6 AM
Noon
6 PM

Weekly flight availability from Key West to O'Hare Intl

Explore weekly flight availability from Key West to O'Hare Intl. 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 April 16, 2024.
Sunday3daily flights
Monday3daily flights
Tuesday3daily flights
Wednesday3daily flights
Thursday3daily flights
Friday3daily flights
Saturday3daily flights

Fly with Cheapflights

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

How does Cheapflights help users find flights from Key West to O'Hare Intl?

When you search for this flight from Key West to O'Hare Intl, 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 Key West to O'Hare Intl?

Cheapflights taps into our reliable network of hundreds of airlines and travel agencies to find the best deals for flights from Key West to O'Hare Intl for you. Better yet — we are completely free to use.

Can Cheapflights find flights from Key West to O'Hare Intl with no change fees?

Yes! Cheapflights helps users easily find flights from Key West to O'Hare Intl with no change fees.

Can Cheapflights notify me if prices for flights from Key West to O'Hare Intl become cheaper?

Yes! Start tracking prices for Key West to O'Hare Intl 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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