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$102+ 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 12/11. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — CHI
Nov 5 — Nov 121
Wed 11/5
Wed 11/12
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 October 6, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$247
(Kiwi.com)

One-way from

$102
(Kiwi.com)

Good round-trip deal

$424 or less

Good one-way deal

$294 or less
Provider with most accurate pricing for Key West-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Key West-Chicago (CHI) flights.
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From Key West to Chicago (CHI)
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One-way flight from Key West to Chicago (CHI)
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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 October 6, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/6. 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.
Tue 10/2111:45 amEYW - ORD
1 stop23h 23mMultiple Airlines
Sat 10/256:58 pmORD - EYW
1 stop12h 17mMultiple Airlines
Deal found 10/6$247
This Delta deal was found by Cheapflights users on 10/4. 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.
Fri 10/3112:22 pmEYW - ORD
1 stop7h 27mDelta
Mon 11/35:20 amORD - EYW
1 stop6h 42mDelta
Deal found 10/4$269
This Kiwi.com deal was found by Cheapflights users on 10/4. 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 12/118:55 amEYW - ORD
1 stop10h 49mMultiple Airlines
Thu 12/1110:05 pmORD - EYW
2 stops14h 25mMultiple Airlines
Deal found 10/4$284
This Delta deal was found by Cheapflights users on 10/4. 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.
Mon 11/246:18 pmEYW - ORD
1 stop6h 44mDelta
Sat 11/295:23 amORD - EYW
1 stop5h 08mDelta
Deal found 10/4$289
This American Airlines deal was found by Cheapflights users on 10/4. 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.
Tue 11/251:21 pmEYW - ORD
Nonstop3h 40mAmerican Airlines
Tue 12/28:45 amORD - EYW
Nonstop3h 19mAmerican Airlines
Deal found 10/4$303
This Kiwi.com deal was found by Cheapflights users on 10/4. 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.
Tue 11/2510:59 amEYW - ORD
1 stop27h 24mMultiple Airlines
Tue 12/212:32 pmORD - EYW
1 stop20h 35mMultiple Airlines
Deal found 10/4$310
This Kiwi.com deal was found by Cheapflights users on 10/4. 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.
Tue 11/2510:25 amEYW - MDW
1 stop27h 56mMultiple Airlines
Tue 12/25:56 pmMDW - EYW
2 stops37h 19mMultiple Airlines
Deal found 10/4$326
This Delta deal was found by Cheapflights users on 10/6. 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.
Tue 10/216:17 pmEYW - MDW
1 stop4h 57mDelta
Sat 10/2510:35 amMDW - EYW
1 stop5h 46mDelta
Deal found 10/6$329
This Delta deal was found by Cheapflights users on 10/6. 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 11/17:40 amEYW - ORD
1 stop5h 36mDelta
Wed 11/511:23 amORD - EYW
1 stop4h 58mDelta
Deal found 10/6$340
This American Airlines deal was found by Cheapflights users on 10/3. 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 11/15:10 pmEYW - ORD
1 stop7h 40mAmerican Airlines
Wed 11/51:45 pmORD - EYW
1 stop7h 03mAmerican Airlines
Deal found 10/3$347
This Delta deal was found by Cheapflights users on 10/6. 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 11/16:17 pmEYW - MDW
1 stop4h 57mDelta
Wed 11/510:40 amMDW - EYW
1 stop5h 41mDelta
Deal found 10/6$360
This Delta deal was found by Cheapflights users on 10/5. 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 10/87:40 amEYW - MDW
1 stop5h 18mDelta
Sat 10/1110:35 amMDW - EYW
1 stop5h 46mDelta
Deal found 10/5$435

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 October 6, 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

Fri 10/31

8:55 am-9:33 pm

1 stop13h 38m

Chicago O'Hare Intl

Mon 11/3

11:24 am-11:05 am

2 stops22h 41m

$256

Key WestChicago

EYW - ORD

EYWORD

Key West

Tue 10/21

11:45 am-1:47 pm

2 stops27h 02m

Chicago O'Hare Intl

Sat 10/25

6:58 pm-8:15 am

1 stop12h 17m

$256

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 12/11

8:55 am-5:04 pm

1 stop9h 09m

Chicago O'Hare Intl

Thu 12/11

7:49 pm-8:15 am

1 stop11h 26m

$256

Key WestChicago

EYW - ORD

EYWORD

Key West

Tue 11/25

6:18 pm-12:02 am

1 stop6h 44m

Chicago O'Hare Intl

Tue 12/2

1:20 pm-8:06 pm

1 stop5h 46m

$269

Key WestChicago

EYW - ORD

EYWORD

Key West

Fri 10/31

12:22 pm-6:49 pm

1 stop7h 27m

Chicago O'Hare Intl

Mon 11/3

5:20 am-1:02 pm

1 stop6h 42m

$269

Key WestChicago

EYW - ORD

EYWORD

Key West

Mon 11/24

6:18 pm-12:02 am

1 stop6h 44m

Chicago O'Hare Intl

Sat 11/29

5:23 am-11:31 am

1 stop5h 08m

$289

Key WestChicago

EYW - ORD

EYWORD

Key West

Tue 11/25

1:21 pm-4:01 pm

Nonstop3h 40m

Chicago O'Hare Intl

Tue 12/2

8:45 am-1:04 pm

Nonstop3h 19m

$303

Key WestChicago

EYW - MDW

EYWMDW

Key West

Tue 11/25

10:25 am-1:21 pm

1 stop27h 56m

Chicago Midway

Tue 12/2

5:56 pm-8:15 am

2 stops37h 19m

$326

Key WestChicago

EYW - ORD

EYWORD

Key West

Tue 11/25

10:59 am-9:17 am

2 stops23h 18m

Chicago O'Hare Intl

Tue 12/2

12:32 pm-10:07 am

1 stop20h 35m

$335

Key WestChicago

EYW - ORD

EYWORD

Key West

Sat 11/1

7:40 am-12:16 pm

1 stop5h 36m

Chicago O'Hare Intl

Wed 11/5

11:23 am-5:21 pm

1 stop4h 58m

$340

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/4

Showing 1-10 of 29 results
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2
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Compare providers for flights from Key West to Chicago

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 Chicago in October.
ProviderPrice AccuracyTrust Score*
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice 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 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 flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Key West-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Key West-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub 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 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 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 October 6, 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 37% on your trip compared to booking a flight in the evening.

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

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 October 6, 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
8,957 reviews

Entertainment

7.1

Boarding

7.7

Food

6.6

Overall

7.4

Crew

8.1

Comfort

7.3

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
8,957 reviews
United Airlines
7.4
Good
8,957 reviews

Entertainment

7.1

Boarding

7.7

Food

6.6

Overall

7.4

Crew

8.1

Comfort

7.3

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
11,040 reviews
United Airlines
7.4
Good
8,957 reviews

Entertainment

7.1

Boarding

7.7

Food

6.6

Overall

7.4

Crew

8.1

Comfort

7.3

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 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.

  • How long is the flight from Key West to Chicago?

    Departing from Key West to Chicago will take you 6h 44m. There are 1253 mi between Key West and Chicago.

  • 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.

  • 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 American Airlines (100%), Qatar Airways (100%) and Envoy Air (100%).

  • 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 $367, our data indicates the cheapest price to be $178. The most popular route (Key West - Chicago O'Hare Intl), is priced around $249.

  • 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.

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
Porter
Benton Harbor
Chesterton

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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 October 6, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$224Average$499FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$259Average$398FlexibilityNo cancel feeOn-time71%

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