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$107+ 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 4/21. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — CHI
Apr 9 — Apr 161
Thu 4/9
Thu 4/16
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 March 10, 2026.

This Kiwi.com deal was found by Cheapflights users on 3/5. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/281:01 pm
EYW
-
ORD
2 stops22h 01m
Multiple Airlines
Sat 5/27:34 pm
ORD
-
EYW
1 stop13h 47m
Multiple Airlines
Deal found 3/5$189
This Kiwi.com deal was found by Cheapflights users on 3/9. 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 4/2911:51 am
EYW
-
MDW
1 stop20h 30m
Multiple Airlines
Sat 5/27:34 pm
MDW
-
EYW
2 stops13h 47m
Multiple Airlines
Deal found 3/9$217
This Kiwi.com deal was found by Cheapflights users on 3/9. 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.
Fri 4/171:06 pm
EYW
-
ORD
1 stop27h 17m
Multiple Airlines
Mon 4/205:48 pm
ORD
-
EYW
1 stop17h 33m
Multiple Airlines
Deal found 3/9$222
This Kiwi.com deal was found by Cheapflights users on 3/9. 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 4/239:46 am
EYW
-
ORD
1 stop12h 44m
Multiple Airlines
Sun 4/266:40 am
ORD
-
EYW
1 stop28h 46m
Multiple Airlines
Deal found 3/9$240
This Delta deal was found by Cheapflights users on 3/9. 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 4/246:23 pm
EYW
-
ORD
1 stop6h 36m
Delta
Sun 4/265:15 am
ORD
-
EYW
1 stop4h 31m
Delta
Deal found 3/9$247
This Kiwi.com deal was found by Cheapflights users on 3/9. 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 4/94:22 pm
EYW
-
ORD
1 stop27h 04m
Multiple Airlines
Sat 4/114:21 pm
ORD
-
EYW
1 stop15h 45m
Multiple Airlines
Deal found 3/9$257
This Kiwi.com deal was found by Cheapflights users on 3/9. 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.
Fri 4/249:49 am
EYW
-
ORD
1 stop9h 31m
Multiple Airlines
Sun 4/2611:28 am
ORD
-
EYW
2 stops20h 41m
Multiple Airlines
Deal found 3/9$260
This American Airlines deal was found by Cheapflights users on 3/6. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/96:46 pm
EYW
-
ORD
Nonstop3h 49m
American Airlines
Mon 4/138:10 am
ORD
-
EYW
Nonstop3h 28m
American Airlines
Deal found 3/6$269
This Super.com deal was found by Cheapflights users on 3/7. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/912:25 pm
EYW
-
ORD
1 stop8h 26m
Spirit Airlines
Mon 4/135:05 am
ORD
-
EYW
1 stop7h 32m
Spirit Airlines
Deal found 3/7$278
This United Airlines deal was found by Cheapflights users on 3/7. 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 4/94:38 pm
EYW
-
ORD
1 stop9h 48m
United Airlines
Mon 4/1310:35 am
ORD
-
EYW
Nonstop3h 16m
United Airlines
Deal found 3/7$279
This Delta deal was found by Cheapflights users on 3/9. 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 4/296:23 pm
EYW
-
MDW
1 stop5h 05m
Delta
Sat 5/211:18 am
MDW
-
EYW
1 stop7h 22m
Delta
Deal found 3/9$313
This Delta deal was found by Cheapflights users on 3/9. 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 4/176:23 pm
EYW
-
MDW
1 stop5h 05m
Delta
Mon 4/206:00 am
MDW
-
EYW
1 stop6h 44m
Delta
Deal found 3/9$333

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 March 10, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$189
(Kiwi.com)

One-way from

$107
(Kiwi.com)

Good round-trip deal

$353 or less

Good one-way deal

$304 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 March 10, 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 - MDW

EYWMDW

Key West

Wed 4/29

11:51 am-7:21 am

1 stop20h 30m

Chicago Midway

Sat 5/2

7:34 pm-10:21 am

2 stops13h 47m

$217

Key WestChicago

EYW - ORD

EYWORD

Key West

Tue 4/28

1:01 pm-6:20 pm

1 stop6h 19m

Chicago O'Hare Intl

Sat 5/2

7:34 pm-10:21 am

1 stop13h 47m

$243

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 4/9

9:46 am-8:03 pm

1 stop11h 17m

Chicago O'Hare Intl

Sat 4/11

9:32 am-10:21 am

1 stop23h 49m

$273

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 4/9

4:38 pm-1:26 am

1 stop9h 48m

Chicago O'Hare Intl

Mon 4/13

10:35 am-2:51 pm

Nonstop3h 16m

$279

Key WestChicago

EYW - ORD

EYWORD

Key West

Wed 4/29

6:46 pm-9:35 pm

Nonstop3h 49m

Chicago O'Hare Intl

Sat 5/2

1:50 pm-6:16 pm

Nonstop3h 26m

$299

Key WestChicago

EYW - MDW

EYWMDW

Key West

Wed 4/29

6:23 pm-10:28 pm

1 stop5h 05m

Chicago Midway

Sat 5/2

11:18 am-7:40 pm

1 stop7h 22m

$313

Key WestChicago

EYW - ORD

EYWORD

Key West

Tue 4/7

12:25 pm-11:17 am

1 stop23h 52m

Chicago O'Hare Intl

Thu 4/30

1:27 pm-1:35 pm

1 stop23h 08m

$346
Quickest round-trip

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 4/23

3:52 pm-6:36 pm

Nonstop3h 44m

Chicago O'Hare Intl

Sun 4/26

10:35 am-2:51 pm

Nonstop3h 16m

$349

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 4/9

2:29 pm-10:00 pm

1 stop8h 31m

Chicago O'Hare Intl

Mon 4/13

3:04 pm-10:58 pm

1 stop6h 54m

$349

Key WestChicago

EYW - ORD

EYWORD

Key West

Wed 4/29

2:35 pm-9:33 pm

1 stop7h 58m

Chicago O'Hare Intl

Sat 5/2

10:43 am-3:07 pm

Nonstop3h 24m

$359

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/5

Showing 1-10 of 47 resultsSorted by cheapest first
1
2
3
...
5
  • 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 month to book a flight from Key West to Chicago?

Currently, December is the cheapest month in which you can book a flight from Key West to Chicago (average of $251). Flying from Key West to Chicago in January is currently the most expensive (average of $884). 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 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 March 10, 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 March 10, 2026.

The most flights from EYW to CHI are scheduled on a Monday (7 on average). You will have fewer flight options on Wednesday, 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 March 10, 2026.
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
9,409 reviews

Boarding

7.7

Crew

8.1

Entertainment

7.1

Comfort

7.3

Food

6.6

Overall

7.4

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
9,409 reviews
United Airlines
7.4
Good
9,409 reviews

Boarding

7.7

Crew

8.1

Entertainment

7.1

Comfort

7.3

Food

6.6

Overall

7.4

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
7.1
Good
11,414 reviews
United Airlines
7.4
Good
9,409 reviews

Boarding

7.7

Crew

8.1

Entertainment

7.1

Comfort

7.3

Food

6.6

Overall

7.4

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 5 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 49m. 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 $309 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 Republic Airways (88%), United Airlines (73%) and Air New Zealand (66%).

  • 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 $422, our data indicates the cheapest price to be $248. The most popular route (Key West - Chicago O'Hare Intl), is priced around $222.

  • 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, December is the cheapest month in which you can book a flight from Key West to Chicago (average of $251). Flying from Key West to Chicago in January is currently the most expensive (average of $884). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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Alternative routes for Key West to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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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 March 10, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$249Average$315FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$309Average$457FlexibilityNo cancel feeOn-time71%

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