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$146+ Cheap flights from Key West (EYW) to Chicago (CHI)

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 11/13. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — CHI
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
1 adult, Economy
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Cheap flight deals from Key West to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Key West (EYW) to Chicago (CHI). 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 August 14, 2025.

Round-trip from

$269
(Delta)

One-way from

$146
(FlightHub)

Popular in

March

Cheapest in

June

Average price

$378

Good round-trip deal

$199 or less

Good one-way deal

$373 or less
From Key West to Chicago (CHI)
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One-way flight from Key West to Chicago (CHI)
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Highest demand for flights based on searches. 16% potential increase in price ($74 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Price to beat on a round-trip flight from Key West to Chicago (CHI).
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Price to beat on a one-way flight from Key West to Chicago (CHI).
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Find flight deals from Key West to Chicago

Cheapest flights from Key West to Chicago
Explore the most affordable flight options available from Key West to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 14, 2025.

This Delta deal was found by Cheapflights users on 8/13. 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.
Thu 9/411:52 amEYW - ORD
1 stop5h 36mDelta
Tue 9/97:05 amORD - EYW
1 stop5h 00mDelta
Deal found 8/13$269
This Delta deal was found by Cheapflights users on 8/13. 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.
Thu 9/47:00 amEYW - MDW
1 stop7h 36mDelta
Tue 9/910:31 amMDW - EYW
1 stop5h 54mDelta
Deal found 8/13$269
This Kiwi.com deal was found by Cheapflights users on 8/13. 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.
Thu 8/284:36 pmEYW - MDW
1 stop21h 43mAllegiant Air
Mon 9/16:35 pmMDW - EYW
1 stop18h 21mAllegiant Air
Deal found 8/13$340
This American Airlines deal was found by Cheapflights users on 8/11. 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.
Sat 11/158:00 amEYW - ORD
1 stop7h 14mAmerican Airlines
Sun 11/168:30 amORD - EYW
Nonstop3h 21mAmerican Airlines
Deal found 8/11$354
This Kiwi.com deal was found by Cheapflights users on 8/12. 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.
Sat 8/163:33 pmEYW - ORD
2 stops43h 52mMultiple Airlines
Sat 8/305:16 pmORD - EYW
1 stop22h 45mMultiple Airlines
Deal found 8/12$367
This Delta deal was found by Cheapflights users on 8/12. 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 8/276:20 pmEYW - ORD
1 stop5h 17mDelta
Sun 8/315:45 amORD - EYW
1 stop6h 20mDelta
Deal found 8/12$374
This Delta deal was found by Cheapflights users on 8/12. 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.
Sat 11/156:00 pmEYW - MDW
1 stop4h 44mDelta
Sun 11/161:05 pmMDW - EYW
1 stop5h 39mDelta
Deal found 8/12$392
This American Airlines deal was found by Cheapflights users on 8/13. 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.
Mon 12/226:05 pmEYW - ORD
Nonstop3h 34mAmerican Airlines
Fri 1/28:05 amORD - EYW
1 stop6h 13mAmerican Airlines
Deal found 8/13$404
This Delta deal was found by Cheapflights users on 8/13. 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 9/36:20 pmEYW - ORD
1 stop5h 17mDelta
Thu 9/117:10 amORD - EYW
2 stops11h 57mDelta
Deal found 8/13$411
This American Airlines deal was found by Cheapflights users on 8/13. 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 9/37:31 pmEYW - ORD
1 stop5h 18mAmerican Airlines
Thu 9/1110:25 amORD - EYW
1 stop7h 34mAmerican Airlines
Deal found 8/13$414
This American Airlines deal was found by Cheapflights users on 8/12. 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 8/271:52 pmEYW - ORD
2 stops8h 19mAmerican Airlines
Sun 8/315:00 amORD - EYW
1 stop6h 58mAmerican Airlines
Deal found 8/12$419
This Delta deal was found by Cheapflights users on 8/13. 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.
Thu 8/142:00 pmEYW - MDW
1 stop4h 47mDelta
Thu 8/2112:43 pmMDW - EYW
1 stop6h 29mDelta
Deal found 8/13$428

Cheapflights Fare Finder

 
Customize your flight search to find flights from Key West to Chicago 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 August 14, 2025.
Use the filters below to find and compare flights from Key West to Chicago that are best for you.

Fly from

Key West

Fly to

Chicago

Route

Depart

Return

Price

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 9/4

11:52 am-4:28 pm

1 stop5h 36m

Chicago O'Hare Intl

Tue 9/9

7:05 am-1:05 pm

1 stop5h 00m

$269

Key WestChicago

EYW - MDW

EYWMDW

Key West

Thu 9/4

7:00 am-1:36 pm

1 stop7h 36m

Chicago Midway

Tue 9/9

10:31 am-5:25 pm

1 stop5h 54m

$269

Key WestChicago

EYW - MDW

EYWMDW

Key West

Thu 8/28

4:36 pm-1:19 pm

1 stop21h 43m

Chicago Midway

Mon 9/1

6:35 pm-1:56 pm

1 stop18h 21m

$340

Key WestChicago

EYW - ORD

EYWORD

Key West

Sat 11/15

8:00 am-2:14 pm

1 stop7h 14m

Chicago O'Hare Intl

Sun 11/16

8:30 am-12:51 pm

Nonstop3h 21m

$354

Key WestChicago

EYW - ORD

EYWORD

Key West

Wed 8/27

6:20 pm-10:37 pm

1 stop5h 17m

Chicago O'Hare Intl

Sun 8/31

5:45 am-1:05 pm

1 stop6h 20m

$374

Key WestChicago

EYW - MDW

EYWMDW

Key West

Sat 11/15

6:00 pm-9:44 pm

1 stop4h 44m

Chicago Midway

Sun 11/16

1:05 pm-7:44 pm

1 stop5h 39m

$392

Key WestChicago

EYW - ORD

EYWORD

Key West

Mon 12/22

6:05 pm-8:39 pm

Nonstop3h 34m

Chicago O'Hare Intl

Fri 1/2

8:05 am-3:18 pm

1 stop6h 13m

$404

Key WestChicago

EYW - ORD

EYWORD

Key West

Wed 9/3

6:20 pm-10:37 pm

1 stop5h 17m

Chicago O'Hare Intl

Thu 9/11

7:10 am-8:07 pm

2 stops11h 57m

$411

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 9/4

11:52 am-4:28 pm

1 stop5h 36m

Chicago O'Hare Intl

Thu 9/11

7:10 am-8:07 pm

2 stops11h 57m

$411

Key WestChicago

EYW - ORD

EYWORD

Key West

Wed 9/3

7:31 pm-11:49 pm

1 stop5h 18m

Chicago O'Hare Intl

Thu 9/11

10:25 am-6:59 pm

1 stop7h 34m

$414

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/13

Showing 1-10 of 38 results
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The best insider tips for Key West to Chicago flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
Cheapflights partnered with top experts to bring you the best recommendations for your Key West to Chicago trip
Airports
EYW

Security lines at EYW are typically short, with waits under 20 minutes. Arrive 1.5 hours before departure to be safe.

Read more about EYWby Terry Ward
ORD

For a quick city transfer from ORD, take the 'L' train. It's often faster than taxis due to Chicago traffic.

Read more about ORDby Ramsey Qubein
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on ORD

Ramsey Qubein

Ramsey Qubein

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

Terry Ward

Terry Ward

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

Best time to book a flight from Key West to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago 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

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

Find hourly flight availability from Key West to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 14, 2025.

A simple way to save on the total cost of your ticket is to fly from Key West to Chicago at noon. If you’re flexible enough to do this you can expect to save up to 30% on your trip compared to booking a flight in the morning.

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated August 14, 2025.
See what other customers who have flown with United Airlines and American Airlines from Key West to Chicago have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
8,922 reviews

Boarding

7.7

Entertainment

7.1

Overall

7.4

Crew

8.1

Food

6.6

Comfort

7.3

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
United Airlines
7.4
Good
8,922 reviews
United Airlines
7.4
Good
8,922 reviews

Boarding

7.7

Entertainment

7.1

Overall

7.4

Crew

8.1

Food

6.6

Comfort

7.3

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
American Airlines
7.2
Good
10,000 reviews
United Airlines
7.4
Good
8,922 reviews

Boarding

7.7

Entertainment

7.1

Overall

7.4

Crew

8.1

Food

6.6

Comfort

7.3

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!

Related info for your journey

Find useful and relevant information for your journey from Key West to Chicago. 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?

    Most people fly from Key West (EYW) if they book a flight from Key West to Chicago. On average, Key West has 0 outbound flights to Chicago per day from 2 airlines. Key West is conveniently located just 2.6 mi from Key West’s city center.

  • What are the cheapest airlines flying from Key West to Chicago round-trip?

    Flying on United Airlines is currently your cheapest option to Chicago, with prices starting at $224. Another option worth looking into is American Airlines, starting at $259 round trip. United Airlines is priced at 41% lower than the current average price of a flight leaving 3 months from now.

  • What are the most popular routes from Key West to Chicago?

    The most popular flight routes from Key West to Chicago are Key West - Chicago O'Hare Intl, Key West - Chicago Midway and Key West - Chicago Greater Rockford.

  • What are the most reliable airlines from Key West to Chicago?

    The top 3 most reliable airlines when flying from Key West to Chicago are Qatar Airways (52%), American Airlines (31%) and Envoy Air (31%).

  • What are the cheapest flights from Key West to Chicago?

    Looking for the cheapest flight from Key West to Chicago? While on average our users pay $359, our data indicates the cheapest price to be $199. The most popular route (Key West - Chicago O'Hare Intl), is priced around $269.

  • Can I find deals for flights from Key West to Chicago that include hotel bookings?

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

  • How can I find direct flights from Key West to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Key West to Chicago.

  • Can I find deals for business class flights from Key West to Chicago?

    Yes. Cheapflights offers flight deals from Key West to Chicago 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?

    Currently, August is the cheapest month in which you can book a flight from Key West to Chicago (average of $245). Flying from Key West to Chicago 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 Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

Browse thousands of different options on Cheapflights for your next trip

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Top 2 airlines flying from Key West to Chicago

Discover the top 2 airlines that operate flights from Key West to Chicago. 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 August 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$224Average$394FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$259Average$378FlexibilityNo cancel feeOn-time71%

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