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$90+ 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 12/24. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — CHI
dic. 26 — ene. 21
vie. 12/26
vie. 1/2
1 adult, Economy
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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 noviembre 26, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/24. 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. 12/222:30 pmEYW - ORD
1 stop11h 00mSpirit Airlines
mié. 12/313:26 pmORD - EYW
1 stop18h 54mSpirit Airlines
Deal found 11/24$203
This Mytrip deal was found by Cheapflights users on 11/25. 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.
jue. 12/1112:20 pmEYW - ORD
1 stop8h 41mMultiple Airlines
dom. 12/147:20 amORD - EYW
1 stop7h 24mMultiple Airlines
Deal found 11/25$215
This Kiwi.com deal was found by Cheapflights users on 11/24. 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.
mar. 12/911:45 amEYW - ORD
1 stop25h 54mMultiple Airlines
sáb. 12/131:34 pmORD - EYW
1 stop19h 45mMultiple Airlines
Deal found 11/24$226
This Kiwi.com deal was found by Cheapflights users on 11/24. 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. 12/221:10 pmEYW - ORD
2 stops12h 20mMultiple Airlines
mié. 12/315:00 amORD - EYW
1 stop7h 30mMultiple Airlines
Deal found 11/24$244
This United Airlines deal was found by Cheapflights users on 11/25. 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. 12/174:05 pmEYW - ORD
Nonstop3h 46mUnited Airlines
dom. 12/2110:47 amORD - EYW
Nonstop3h 27mUnited Airlines
Deal found 11/25$249
This Kiwi.com deal was found by Cheapflights users on 11/24. 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. 12/221:10 pmEYW - MDW
1 stop9h 48mMultiple Airlines
mié. 12/313:10 pmMDW - EYW
1 stop16h 05mMultiple Airlines
Deal found 11/24$265
This Kiwi.com deal was found by Cheapflights users on 11/25. 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.
jue. 12/118:55 amEYW - MDW
2 stops10h 13mMultiple Airlines
dom. 12/146:37 pmMDW - EYW
1 stop12h 38mMultiple Airlines
Deal found 11/25$267
This Delta deal was found by Cheapflights users on 11/24. 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.
lun. 12/296:20 pmEYW - ORD
1 stop6h 42mDelta
mar. 1/1312:00 pmORD - EYW
1 stop6h 40mDelta
Deal found 11/24$269
This Delta deal was found by Cheapflights users on 11/24. 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.
lun. 12/2911:47 amEYW - MDW
1 stop5h 33mDelta
mar. 1/1311:21 amMDW - EYW
1 stop7h 19mDelta
Deal found 11/24$269
This FlightHub deal was found by Cheapflights users on 11/25. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/242:30 pmEYW - ORD
1 stop5h 09mSpirit Airlines
mar. 12/305:00 amORD - EYW
1 stop5h 20mSpirit Airlines
Deal found 11/25$271
This Kiwi.com deal was found by Cheapflights users on 11/25. 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. 12/174:31 pmEYW - ORD
1 stop21h 08mMultiple Airlines
dom. 12/216:00 amORD - EYW
2 stops30h 30mMultiple Airlines
Deal found 11/25$289
This Delta deal was found by Cheapflights users on 11/25. 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.
jue. 12/116:10 pmEYW - MDW
1 stop6h 37mDelta
dom. 12/146:00 amMDW - EYW
1 stop4h 43mDelta
Deal found 11/25$329

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 noviembre 26, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$190
(Kiwi.com)

One-way from

$90
(Kiwi.com)

Good round-trip deal

$348 or less

Good one-way deal

$270 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 noviembre 26, 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

lun. 12/22

2:30 pm-12:30 am

1 stop11h 00m

Chicago O'Hare Intl

mié. 12/31

3:26 pm-11:20 am

1 stop18h 54m

$203

Key WestChicago

EYW - ORD

EYWORD

Key West

mié. 2/18

12:38 pm-12:51 pm

1 stop25h 13m

Chicago O'Hare Intl

lun. 2/23

5:15 am-1:30 pm

1 stop7h 15m

$222

Key WestChicago

EYW - ORD

EYWORD

Key West

lun. 1/26

2:25 pm-10:46 pm

2 stops9h 21m

Chicago O'Hare Intl

sáb. 1/31

5:32 pm-11:20 am

1 stop16h 48m

$222

Key WestChicago

EYW - ORD

EYWORD

Key West

lun. 1/5

10:01 pm-12:39 pm

1 stop15h 38m

Chicago O'Hare Intl

dom. 1/11

8:00 am-9:37 pm

1 stop12h 37m

$229

Key WestChicago

EYW - ORD

EYWORD

Key West

lun. 12/22

1:10 pm-12:30 am

2 stops12h 20m

Chicago O'Hare Intl

mié. 12/31

5:00 am-1:30 pm

1 stop7h 30m

$244

Key WestChicago

EYW - ORD

EYWORD

Key West

lun. 12/22

4:10 pm-6:43 pm

Nonstop3h 33m

Chicago O'Hare Intl

mié. 12/31

10:45 am-3:12 pm

Nonstop3h 27m

$249

Key WestChicago

EYW - ORD

EYWORD

Key West

jue. 12/11

9:59 am-12:09 am

2 stops15h 10m

Chicago O'Hare Intl

dom. 12/14

7:20 am-3:44 pm

1 stop7h 24m

$256

Key WestChicago

EYW - ORD

EYWORD

Key West

mié. 12/17

2:47 pm-11:32 pm

1 stop9h 45m

Chicago O'Hare Intl

dom. 12/21

7:55 am-12:34 pm

Nonstop3h 39m

$259

Key WestChicago

EYW - ORD

EYWORD

Key West

mar. 2/17

1:01 pm-11:27 am

2 stops23h 26m

Chicago O'Hare Intl

dom. 2/22

11:42 am-1:30 pm

1 stop24h 48m

$265

Key WestChicago

EYW - MDW

EYWMDW

Key West

lun. 12/22

1:10 pm-9:58 pm

1 stop9h 48m

Chicago Midway

mié. 12/31

3:10 pm-8:15 am

1 stop16h 05m

$265

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/26

Showing 1-10 of 35 results
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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 November.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*1 star
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 flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Key West-Chicago flight deals on Cheapflights vs. eDreams >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 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 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 noviembre 26, 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 33% on your trip compared to booking a flight in the evening.

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 noviembre 26, 2025.

The most flights from EYW to CHI are scheduled on a Monday (5 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (1 on average).

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 noviembre 26, 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
9,050 reviews

Comfort

7.3

Crew

8.1

Overall

7.4

Food

6.6

Entertainment

7.1

Boarding

7.7

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
9,050 reviews
United Airlines
7.4
Good
9,050 reviews

Comfort

7.3

Crew

8.1

Overall

7.4

Food

6.6

Entertainment

7.1

Boarding

7.7

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
11,038 reviews
United Airlines
7.4
Good
9,050 reviews

Comfort

7.3

Crew

8.1

Overall

7.4

Food

6.6

Entertainment

7.1

Boarding

7.7

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 3 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 5h 01m. There are 1238 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 $224. Another option worth looking into is American Airlines, starting at $289 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 (79%), Qatar Airways (79%) and Envoy Air (79%).

  • 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 $583, our data indicates the cheapest price to be $125. The most popular route (Key West - Chicago O'Hare Intl), is priced around $190.

  • 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
Lansing
Hammond
Porter
Benton Harbor
Merrillville

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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 noviembre 26, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$224Average$431FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$289Average$427FlexibilityNo cancel feeOn-time71%

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