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$101+ 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 5/14. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — CHI
May 23 — May 301
Sat 5/23
Sat 5/30
1 adult, Economy
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Cheap 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 April 23, 2026.

This Kiwi.com deal was found by Cheapflights users on 4/20. 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.
Thu 5/143:08 pm
EYW
-
ORD
1 stop22h 15m
Multiple Airlines
Sun 5/241:50 pm
ORD
-
EYW
2 stops21h 41m
Multiple Airlines
Deal found 4/20$237
This Kiwi.com deal was found by Cheapflights users on 4/21. 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.
Wed 5/611:46 am
EYW
-
ORD
1 stop22h 41m
Multiple Airlines
Sun 5/108:30 am
ORD
-
EYW
1 stop27h 01m
Multiple Airlines
Deal found 4/21$243
This Kiwi.com deal was found by Cheapflights users on 4/20. 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.
Thu 5/141:57 pm
EYW
-
ORD
1 stop9h 17m
Multiple Airlines
Sun 5/175:30 pm
ORD
-
EYW
1 stop16h 57m
Multiple Airlines
Deal found 4/20$267
This Kiwi.com deal was found by Cheapflights users on 4/22. 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.
Wed 6/311:46 am
EYW
-
ORD
2 stops9h 05m
Multiple Airlines
Sat 6/65:11 pm
ORD
-
EYW
1 stop17h 14m
Multiple Airlines
Deal found 4/22$279
This Kiwi.com deal was found by Cheapflights users on 4/22. 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.
Wed 5/2711:46 am
EYW
-
ORD
2 stops21h 09m
Multiple Airlines
Wed 6/105:25 pm
ORD
-
EYW
1 stop17h 00m
Multiple Airlines
Deal found 4/22$289
This Kiwi.com deal was found by Cheapflights users on 4/18. 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.
Wed 6/311:46 am
EYW
-
ORD
1 stop25h 37m
Multiple Airlines
Wed 6/107:52 am
ORD
-
EYW
2 stops48h 49m
Multiple Airlines
Deal found 4/18$308
This United Airlines deal was found by Cheapflights users on 4/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/144:05 pm
EYW
-
ORD
Nonstop3h 55m
United Airlines
Sun 5/1710:43 am
ORD
-
EYW
Nonstop3h 24m
United Airlines
Deal found 4/20$309
This Kiwi.com deal was found by Cheapflights users on 4/20. 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.
Thu 5/1412:34 pm
EYW
-
MDW
2 stops34h 28m
Multiple Airlines
Sun 5/242:47 pm
MDW
-
EYW
1 stop17h 54m
Multiple Airlines
Deal found 4/20$309
This Kiwi.com deal was found by Cheapflights users on 4/21. 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.
Mon 5/111:11 pm
EYW
-
MDW
2 stops33h 51m
Multiple Airlines
Thu 5/282:47 pm
MDW
-
EYW
1 stop17h 54m
Multiple Airlines
Deal found 4/21$323
This Delta deal was found by Cheapflights users on 4/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/56:23 pm
EYW
-
MDW
1 stop5h 05m
Delta
Sat 5/96:23 am
MDW
-
EYW
1 stop7h 12m
Delta
Deal found 4/20$389
This Kiwi.com deal was found by Cheapflights users on 4/20. 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.
Mon 5/181:11 pm
EYW
-
MDW
2 stops9h 51m
Multiple Airlines
Sun 5/242:47 pm
MDW
-
EYW
1 stop17h 54m
Multiple Airlines
Deal found 4/20$390
This Delta deal was found by Cheapflights users on 4/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/147:30 am
EYW
-
MDW
1 stop5h 26m
Delta
Sun 5/1712:53 pm
MDW
-
EYW
1 stop5h 56m
Delta
Deal found 4/20$489

Find 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 April 23, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$237
(Kiwi.com)

One-way from

$101
(Kiwi.com)

Good round-trip deal

$479 or less

Good one-way deal

$333 or less
Provider with most accurate pricing for Key West-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Key West-Chicago (CHI) flights.
Search Deals
From Key West to Chicago (CHI)
Search Deals
One-way flight from Key West to Chicago (CHI)
Search Deals
Price to beat on a round-trip flight from Key West to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Key West to Chicago (CHI).
Search Deals

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 April 23, 2026.
Use the filters below to find and compare flights from Key West to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Key WestChicago

EYW - ORD

EYWORD

Key West

Wed 6/3

11:46 am-7:51 pm

2 stops9h 05m

Chicago O'Hare Intl

Sat 6/6

5:11 pm-11:25 am

1 stop17h 14m

$279

Key WestChicago

EYW - ORD

EYWORD

Key West

Wed 6/3

11:46 am-12:23 pm

1 stop25h 37m

Chicago O'Hare Intl

Wed 6/10

7:52 am-9:41 am

2 stops48h 49m

$308

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 5/14

4:05 pm-7:00 pm

Nonstop3h 55m

Chicago O'Hare Intl

Sun 5/17

10:43 am-3:07 pm

Nonstop3h 24m

$309

Key WestChicago

EYW - ORD

EYWORD

Key West

Wed 5/27

11:46 am-12:23 pm

1 stop25h 37m

Chicago O'Hare Intl

Wed 6/10

5:25 pm-11:25 am

1 stop17h 00m

$309

Key WestChicago

EYW - ORD

EYWORD

Key West

Tue 7/7

1:01 pm-7:54 pm

1 stop7h 53m

Chicago O'Hare Intl

Tue 7/21

11:22 am-3:46 pm

Nonstop3h 24m

$319

Key WestChicago

EYW - ORD

EYWORD

Key West

Wed 6/3

4:19 pm-7:12 pm

Nonstop3h 53m

Chicago O'Hare Intl

Wed 6/10

6:55 am-4:07 pm

1 stop8h 12m

$319

Key WestChicago

EYW - ORD

EYWORD

Key West

Sat 9/5

6:00 pm-11:57 pm

1 stop6h 57m

Chicago O'Hare Intl

Wed 9/9

1:15 pm-7:45 pm

1 stop5h 30m

$329

Key WestChicago

EYW - ORD

EYWORD

Key West

Sat 9/5

1:07 pm-10:04 pm

1 stop9h 57m

Chicago O'Hare Intl

Wed 9/9

9:59 am-6:27 pm

2 stops7h 28m

$334
Quickest round-trip

Key WestChicago

EYW - ORD

EYWORD

Key West

Wed 5/6

1:08 pm-3:55 pm

Nonstop3h 47m

Chicago O'Hare Intl

Sun 5/10

1:50 pm-6:16 pm

Nonstop3h 26m

$369

Key WestChicago

EYW - ORD

EYWORD

Key West

Mon 5/11

1:11 pm-7:51 pm

2 stops31h 40m

Chicago O'Hare Intl

Thu 5/28

5:11 pm-11:27 am

1 stop17h 16m

$371

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/20

Showing 1-10 of 41 resultsSorted by cheapest first
1
2
3
...
5

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 April.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
ExpediaPrice Accuracy1 starTrust 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 April 23, 2026.

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

Weekly flight availability from Key West to Chicago

Explore weekly flight availability from Key West to Chicago. 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 23, 2026.

The most flights from EYW to CHI are scheduled on a Monday (5 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (4 on average).

The best insider tips for Key West to Chicago 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 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 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 April 23, 2026.
See what other customers who have flown with 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.
American Airlines
7.1
Good
11,659 reviews

Food

6.4

Comfort

7.2

Overall

7.1

Boarding

7.5

Entertainment

6.9

Crew

7.9

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

BNA - ORD

My flight was 8 hours delayed, so I missed my connecting flight to Dublin. I understand it’s not the staff’s fault but the lack of sympathy and apology was appalling. I had been sat in the airport since 4am until 3pm and they did not seem understanding. Not good. Need better customer service.
American Airlines
7.1
Good
11,659 reviews
American Airlines
7.1
Good
11,659 reviews

Food

6.4

Comfort

7.2

Overall

7.1

Boarding

7.5

Entertainment

6.9

Crew

7.9

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

BNA - ORD

My flight was 8 hours delayed, so I missed my connecting flight to Dublin. I understand it’s not the staff’s fault but the lack of sympathy and apology was appalling. I had been sat in the airport since 4am until 3pm and they did not seem understanding. Not good. Need better customer service.

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 4 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 3h 55m. There are 1253 mi between Key West and Chicago. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • 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 $249. Another option worth looking into is American Airlines, starting at $344 round trip.

  • What are the cheapest airlines to fly from Key West to Chicago one-way?

    The cheapest airline one-way is Spirit Airlines, with whom users have recently found tickets for as low as $90. However, be on the lookout for offers from American Airlines and United Airlines, as they are both options that can get you from Key West to Chicago for a low price.

  • 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 Republic Airways (89%), United Airlines (82%) and Air New Zealand (68%).

  • 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 $441, our data indicates the cheapest price to be $188. The most popular route (Key West - Chicago O'Hare Intl), is priced around $243.

  • 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
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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 April 23, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$249Average$315FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$344Average$561FlexibilityNo cancel feeOn-time71%

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