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O'Hare Intl

$102+ Cheap flights from Key West (EYW) to O'Hare Intl (ORD)

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 2/27. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — ORD
feb. 20 — feb. 271
vie. 2/20
vie. 2/27
1 adult, Economy
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Cheap flight deals from Key West to O'Hare Intl

Cheapest flights from Key West to O'Hare Intl
Explore the most affordable flight options available from Key West to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on enero 21, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 2/410:49 am
EYW
-
ORD
1 stop7h 09m
Multiple Airlines
dom. 2/810:15 am
ORD
-
EYW
1 stop25h 11m
Multiple Airlines
Deal found 1/20$237
This Kiwi.com deal was found by Cheapflights users on 1/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 2/239:49 am
EYW
-
ORD
2 stops26h 58m
Multiple Airlines
lun. 3/25:15 am
ORD
-
EYW
1 stop7h 15m
Multiple Airlines
Deal found 1/20$239
This Kiwi.com deal was found by Cheapflights users on 1/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 2/232:25 pm
EYW
-
ORD
1 stop21h 57m
Spirit Airlines
lun. 3/25:15 am
ORD
-
EYW
1 stop7h 15m
Spirit Airlines
Deal found 1/20$240
This American Airlines deal was found by Cheapflights users on 1/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 4/96:45 pm
EYW
-
ORD
Nonstop3h 52m
American Airlines
lun. 4/131:51 pm
ORD
-
EYW
Nonstop3h 24m
American Airlines
Deal found 1/19$249
This Kiwi.com deal was found by Cheapflights users on 1/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 3/91:06 pm
EYW
-
ORD
1 stop7h 41m
Multiple Airlines
lun. 3/168:15 am
ORD
-
EYW
1 stop27h 06m
Multiple Airlines
Deal found 1/19$253
This United Airlines deal was found by Cheapflights users on 1/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 3/46:35 pm
EYW
-
ORD
1 stop6h 08m
United Airlines
lun. 3/910:39 am
ORD
-
EYW
Nonstop3h 16m
United Airlines
Deal found 1/19$259
This Delta deal was found by Cheapflights users on 1/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 3/45:56 pm
EYW
-
ORD
1 stop7h 00m
Delta
lun. 3/911:10 am
ORD
-
EYW
1 stop7h 31m
Delta
Deal found 1/19$269
This United Airlines deal was found by Cheapflights users on 1/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 2/34:15 pm
EYW
-
ORD
Nonstop3h 33m
United Airlines
sáb. 2/77:10 am
ORD
-
EYW
Nonstop3h 16m
United Airlines
Deal found 1/19$309
This United Airlines deal was found by Cheapflights users on 1/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 3/94:55 pm
EYW
-
ORD
1 stop8h 31m
United Airlines
lun. 3/1610:39 am
ORD
-
EYW
Nonstop3h 16m
United Airlines
Deal found 1/19$316

Find 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 enero 21, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$237
(Kiwi.com)

One-way from

$102
(Super.com)

Popular in

March

Cheapest in

December

Average price

$586

Good round-trip deal

$413 or less

Good one-way deal

$346 or less
Provider with most accurate pricing for Key West-Chicago O'Hare Intl flight deals.
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Provider most trusted by Cheapflights users for Key West-Chicago O'Hare Intl flights.
Search Deals
From Key West to Chicago O'Hare Intl
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One-way flight from Key West to Chicago O'Hare Intl
Search Deals
Highest demand for flights based on searches. 14% potential increase in price ($77 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($24 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals
Price to beat on a round-trip flight from Key West to Chicago O'Hare Intl.
Search Deals
Price to beat on a one-way flight from Key West to Chicago O'Hare Intl.
Search Deals

Cheapflights Fare Finder

 
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 2,558,603 searches. Data last updated enero 21, 2026.
Use the filters below to find and compare flights from Key West to Chicago O'Hare Intl Airport that are best for you.

Fly from

Key West

Fly to

O'Hare Intl

Route

Depart

Return

Price

Key WestChicago

EYW - ORD

EYWORD

Key West

lun. 2/23

9:49 am-11:47 am

2 stops26h 58m

Chicago O'Hare Intl

lun. 3/2

5:15 am-1:30 pm

1 stop7h 15m

$239

Key WestChicago

EYW - ORD

EYWORD

Key West

lun. 2/23

2:25 pm-11:22 am

1 stop21h 57m

Chicago O'Hare Intl

lun. 3/2

5:15 am-1:30 pm

1 stop7h 15m

$240

Key WestChicago

EYW - ORD

EYWORD

Key West

mié. 2/4

10:49 am-11:47 pm

2 stops13h 58m

Chicago O'Hare Intl

dom. 2/8

4:38 pm-9:09 am

1 stop15h 31m

$244

Key WestChicago

EYW - ORD

EYWORD

Key West

jue. 4/9

6:45 pm-9:37 pm

Nonstop3h 52m

Chicago O'Hare Intl

lun. 4/13

1:51 pm-6:15 pm

Nonstop3h 24m

$249

Key WestChicago

EYW - ORD

EYWORD

Key West

lun. 3/9

1:06 pm-7:47 pm

1 stop7h 41m

Chicago O'Hare Intl

lun. 3/16

8:15 am-12:21 pm

1 stop27h 06m

$253

Key WestChicago

EYW - ORD

EYWORD

Key West

mié. 3/4

6:35 pm-11:43 pm

1 stop6h 08m

Chicago O'Hare Intl

lun. 3/9

10:39 am-2:55 pm

Nonstop3h 16m

$259

Key WestChicago

EYW - ORD

EYWORD

Key West

mié. 3/4

5:56 pm-11:56 pm

1 stop7h 00m

Chicago O'Hare Intl

lun. 3/9

11:10 am-7:41 pm

1 stop7h 31m

$269

Key WestChicago

EYW - ORD

EYWORD

Key West

dom. 2/15

2:25 pm-11:24 pm

1 stop9h 59m

$117

Key WestChicago

EYW - ORD

EYWORD

Key West

mié. 3/18

11:51 am-4:55 pm

1 stop6h 04m

$126

Key WestChicago

EYW - ORD

EYWORD

Key West

jue. 3/19

9:46 am-8:00 pm

1 stop11h 14m

$128

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/19

Showing 1-10 of 16 results
1
2

Compare providers for flights from Key West to O'Hare Intl

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 Key West to O'Hare Intl in January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star

*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 Key West-Chicago O'Hare Intl Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Key West-Chicago O'Hare Intl Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Key West-Chicago O'Hare Intl Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Key West-Chicago O'Hare Intl Airport flights, Cheapflights users trust Expedia the most. Expedia 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 Key West-Chicago O'Hare Intl Airport 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 Key West to O'Hare Intl

Have a flexible travel schedule? Discover the best time to fly to O'Hare Intl from Key West 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 Key West to Chicago O'Hare Intl Airport

What is the cheapest time of day to fly from EYW to ORD?

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 enero 21, 2026.

When flying from Key West to Chicago O'Hare Intl Airport, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

The best insider tips for Key West to Chicago O'Hare Intl Airport flights

AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Key West to Chicago O'Hare Intl Airport trip
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on ORD

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more
Terry Ward

Terry Ward

Expert on EYW

Florida-based travel writer and journalist Terry Ward lives in Tampa and has enjoyed watching the city and its hotel offerings grow to match the area's spectacular Gulf of Mexico beaches.

Read more

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 enero 21, 2026.
Peruse reviews from past customers who have flown with United Airlines and American Airlines from Key West to Chicago O'Hare Intl Airport to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
9,191 reviews

Crew

8.1

Overall

7.4

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Food

6.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
United Airlines
7.4
Good
9,191 reviews
United Airlines
7.4
Good
9,191 reviews

Crew

8.1

Overall

7.4

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Food

6.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
American Airlines
7.2
Good
11,174 reviews
United Airlines
7.4
Good
9,191 reviews

Crew

8.1

Overall

7.4

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Food

6.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.

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 5 daily outbound flights to Chicago O'Hare Intl from 2 different airlines.

  • How long is the flight from Key West to Chicago O'Hare Intl Airport?

    A quick flight from Key West to Chicago O'Hare Intl Airport can take about 3h 52m. Spirit Airlines provides one of the quickest options available for as low as $249. Airlines will cover a distance of 1253 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    Currently priced at $249, United Airlines will fly you from Key West to Chicago O'Hare Intl Airport and back. In addition to United Airlines, many other airlines offer competitively priced options for your trip. Check Cheapflights for deals on American Airlines for as low as $289. United Airlines is currently priced 44% below the average price you’ll pay for this route.

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

    Consider United Airlines (85%), Republic Airways (84%) or Air New Zealand (80%) 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 $688 for a flight from Key West to Chicago O'Hare Intl Airport. The cheapest flight overall is $249 while the most popular route, (Key West - Chicago O'Hare Intl) is currently priced at $237.

  • 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 find direct flights from Key West to O'Hare Intl.

  • 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.

See more FAQs

Traveling to a place near Chicago O'Hare Intl Airport?

Book flights to Chicago O'Hare Intl Airport if you plan to visit one of these locations
Schaumburg
Rosemont
Naperville
Gurnee
Elgin
Hoffman Estates
Beloit
Delavan
Oak Brook
Downers Grove
Des Plaines
Elk Grove Village
Skokie
Libertyville
Lake Geneva
Bridgeview
Kenosha
Warrenville
Waukegan
Aurora

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Top 2 airlines flying from Key West to O'Hare Intl

Discover the top 2 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 2,558,603 searches. Data last updated enero 21, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$249Average$367FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$289Average$427FlexibilityNo cancel feeOn-time71%

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