HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
O'Hare Intl

$162+ 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 9/2. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — ORD
May 4 — May 111
Sun 5/4
Sun 5/11
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Key West to O'Hare Intl with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

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

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 29, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$312
(Mytrip)

One-way from

$162
(American Airlines)

Popular in

March

Cheapest in

December

Average price

$581

Good round-trip deal

$403 or less

Good one-way deal

$269 or less
Provider with most accurate pricing for Key West-Chicago O'Hare Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Key West-Chicago O'Hare Intl flights.
Search Deals
From Key West to Chicago O'Hare Intl
Search Deals
One-way flight from Key West to Chicago O'Hare Intl
Search Deals
Highest demand for flights based on searches. 29% potential increase in price ($177 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($24 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2025
Search Deals
Price to beat on a round-trip flight from 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

Find 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 April 29, 2025.

This Mytrip deal was found by Cheapflights users on 4/28. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/158:53 amEYW - ORD
2 stops32h 32mMultiple Airlines
Wed 5/216:30 amORD - EYW
1 stop8h 26mMultiple Airlines
Deal found 4/28$312
This Delta deal was found by Cheapflights users on 4/28. 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.
Wed 7/96:27 pmEYW - ORD
1 stop6h 42mDelta
Tue 7/157:00 amORD - EYW
1 stop5h 08mDelta
Deal found 4/28$323
This American Airlines deal was found by Cheapflights users on 4/28. 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.
Wed 7/97:51 pmEYW - ORD
1 stop5h 26mAmerican Airlines
Tue 7/155:15 amORD - EYW
2 stops6h 40mAmerican Airlines
Deal found 4/28$328
This United Airlines deal was found by Cheapflights users on 4/28. 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.
Mon 6/26:45 pmEYW - ORD
1 stop26h 22mUnited Airlines
Tue 6/171:04 pmORD - EYW
2 stops28h 01mUnited Airlines
Deal found 4/28$400

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 April 29, 2025.
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

Thu 5/15

8:53 am-4:25 pm

2 stops32h 32m

Chicago O'Hare Intl

Wed 5/21

6:30 am-3:56 pm

1 stop8h 26m

$312

Key WestChicago

EYW - ORD

EYWORD

Key West

Wed 7/9

6:27 pm-12:09 am

1 stop6h 42m

Chicago O'Hare Intl

Tue 7/15

7:00 am-1:08 pm

1 stop5h 08m

$323

Key WestChicago

EYW - ORD

EYWORD

Key West

Wed 7/9

7:51 pm-12:17 am

1 stop5h 26m

Chicago O'Hare Intl

Tue 7/15

5:15 am-12:55 pm

2 stops6h 40m

$328

Key WestChicago

EYW - ORD

EYWORD

Key West

Mon 6/2

6:45 pm-8:07 pm

1 stop26h 22m

Chicago O'Hare Intl

Tue 6/17

1:04 pm-6:05 pm

2 stops28h 01m

$400

Key WestChicago

EYW - ORD

EYWORD

Key West

Tue 9/2

4:56 pm-10:48 pm

1 stop6h 52m

$162

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 6/26

6:45 pm-9:34 am

1 stop15h 49m

$173

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 6/19

2:45 pm-9:19 pm

1 stop7h 34m

$175

Key WestChicago

EYW - ORD

EYWORD

Key West

Wed 5/28

6:25 pm-9:51 am

2 stops16h 26m

$197

Key WestChicago

EYW - ORD

EYWORD

Key West

Fri 5/9

12:02 pm-5:00 pm

3 stops29h 58m

$615

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

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 April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 stars
PricelinePrice Accuracy2 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on 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 eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for 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 month to book a flight from Key West to Chicago O'Hare Intl Airport?

Currently, August 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 March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from 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 April 29, 2025.

It’s typically best to fly out from Key West to Chicago O'Hare Intl Airport at noon. Doing so could potentially save you 30% on the flight price compared to flying in the morning, which is usually more expensive.

Weekly flight availability from Key West to Chicago O'Hare Intl Airport

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 29, 2025.

The most flights from EYW to ORD are scheduled on a Monday (4 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (4 on average).

Rainfall in O'Hare Intl by month

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

In terms of precipitation, rainfall in Chicago O'Hare Intl Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago O'Hare Intl Airport when rainfall is around 1.7 in.

Temperature in O'Hare Intl by month

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

If weather is an important factor for your trip to Chicago O'Hare Intl Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 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 29, 2025.
Alaska Airlines
8.0
Very good
9,961 reviews

Overall

8.0

Food

7.1

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
9,961 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Overall

8.0

Food

7.1

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,936 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Overall

8.0

Food

7.1

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,696 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Overall

8.0

Food

7.1

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Overall

8.0

Food

7.1

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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

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

    Currently priced at $323, Delta will fly you from Key West to Chicago O'Hare Intl Airport and back. In addition to Delta, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from American Airlines and United Airlines - these airlines can fly you to your destination from $328 and $400, respectively. Delta is currently priced 23% 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 American Airlines ($162), United Airlines ($173), and Delta ($197).

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

    Consider Republic Airways (94%), United Airlines (81%) or Air New Zealand (78%) 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 $436 for a flight from Key West to Chicago O'Hare Intl Airport. The cheapest flight overall is $198 while the most popular route, (Key West - Chicago O'Hare Intl) is currently priced at $312.

  • 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.

  • What is the cheapest month to book a flight from Key West to Chicago O'Hare Intl Airport?

    Currently, August 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 March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Key West?

Book flights to Key West if you plan to visit one of these locations
Schaumburg
Hoffman Estates
Rosemont
Beloit
Racine
Skokie
Naperville
Tinley Park
Kenosha
Rockford
Arlington Heights
Elgin
Joliet
Orland Park
Merrillville
Northbrook
Des Plaines
Lake Geneva
Waukegan
Glenview

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Key West to O'Hare Intl

See prices for flight routes from nearby airports that may be better suited for you.
Tampa to O'Hare Intl flights
Orlando to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
Miami to O'Hare Intl flights
Tampa to Midway flights
Jacksonville to O'Hare Intl flights
West Palm Beach to O'Hare Intl flights
Fort Myers to O'Hare Intl flights
Orlando to Midway flights
Miami to Midway flights
Sarasota to O'Hare Intl flights
Jacksonville to Midway flights
Fort Lauderdale to Midway flights
West Palm Beach to Midway flights
Pensacola to O'Hare Intl flights
Panama City to O'Hare Intl flights
Fort Myers to Midway flights
Sarasota to Midway flights
Pensacola to Midway flights
Valparaiso to O'Hare Intl flights
St Petersburg to Rockford flights
Panama City to Midway flights
Tallahassee to O'Hare Intl flights
Gainesville to O'Hare Intl flights
Orlando Sanford Intl to Rockford flights
Valparaiso to Midway flights
Gainesville to Midway flights
Daytona Beach to Midway flights
Daytona Beach to O'Hare Intl flights
Orlando to Rockford flights
Melbourne to O'Hare Intl flights
Key West to Midway flights
Melbourne to Midway flights
Tallahassee to Midway flights
Fort Lauderdale to Rockford flights
Valdosta to O'Hare Intl flights
Punta Gorda to Rockford flights
Fort Myers to Rockford flights
Tampa to Rockford flights
Pensacola to Rockford flights

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 April 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$224Average$394FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$259Average$388FlexibilityNo cancel feeOn-time71%

100% Free

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

Book with Flexibility

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

Travel Smart

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