HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$122+ 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 7/15. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — CHI
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Key West to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 June 12, 2025.

Round-trip from

$337
(Mytrip)

One-way from

$122
(Trip.com)

Popular in

March

Cheapest in

June

Average price

$268

Good round-trip deal

$427 or less

Good one-way deal

$293 or less
From Key West to Chicago (CHI)
Search Deals
One-way flight from Key West to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 17% potential increase in price ($78 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 2025
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

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 June 12, 2025.

This Delta deal was found by Cheapflights users on 6/12. 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 10/16:00 pmEYW - ORD
1 stop6h 53mDelta
Wed 10/86:00 amORD - EYW
1 stop6h 08mDelta
Deal found 6/12$289
This American Airlines deal was found by Cheapflights users on 6/12. 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 10/17:31 pmEYW - ORD
1 stop5h 17mAmerican Airlines
Wed 10/85:15 amORD - EYW
2 stops6h 45mAmerican Airlines
Deal found 6/12$328
This Mytrip deal was found by Cheapflights users on 6/11. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/2910:02 amEYW - ORD
1 stop10h 24mMultiple Airlines
Wed 7/304:36 pmORD - EYW
1 stop23h 09mMultiple Airlines
Deal found 6/11$337
This United Airlines deal was found by Cheapflights users on 6/10. 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.
Fri 8/86:45 pmEYW - ORD
1 stop24h 38mUnited Airlines
Sun 8/1010:45 amORD - EYW
2 stops20h 15mUnited Airlines
Deal found 6/10$378
This Delta deal was found by Cheapflights users on 6/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/97:00 amEYW - MDW
1 stop5h 58mDelta
Mon 7/1412:43 pmMDW - EYW
1 stop6h 06mDelta
Deal found 6/11$484

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 June 12, 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

Tue 7/29

10:02 am-7:26 pm

1 stop10h 24m

Chicago O'Hare Intl

Wed 7/30

4:36 pm-4:45 pm

1 stop23h 09m

$337

Key WestChicago

EYW - ORD

EYWORD

Key West

Fri 8/8

6:27 pm-12:09 am

1 stop6h 42m

Chicago O'Hare Intl

Sun 8/10

9:50 am-5:32 pm

1 stop6h 42m

$344

Key WestChicago

EYW - ORD

EYWORD

Key West

Wed 7/30

2:31 pm-9:00 pm

1 stop7h 29m

Chicago O'Hare Intl

Sun 8/3

6:00 am-4:12 pm

1 stop9h 12m

$364

Key WestChicago

EYW - ORD

EYWORD

Key West

Fri 8/8

6:45 pm-6:23 pm

1 stop24h 38m

Chicago O'Hare Intl

Sun 8/10

10:45 am-8:00 am

2 stops20h 15m

$378

Key WestChicago

EYW - MDW

EYWMDW

Key West

Wed 7/9

7:00 am-11:58 am

1 stop5h 58m

Chicago Midway

Mon 7/14

12:43 pm-7:49 pm

1 stop6h 06m

$484

Key WestChicago

EYW - ORD

EYWORD

Key West

Tue 7/15

6:45 pm-3:42 pm

1 stop21h 57m

$122

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 7/17

6:27 pm-12:09 am

1 stop6h 42m

$264

Key WestChicago

EYW - MDW

EYWMDW

Key West

Tue 7/22

7:00 am-11:58 am

1 stop5h 58m

$264

Key WestChicago

EYW - ORD

EYWORD

Key West

Mon 6/30

1:42 pm-7:49 am

2 stops19h 07m

$265

Key WestChicago

EYW - ORD

EYWORD

Key West

Sun 7/20

7:51 pm-7:33 am

2 stops12h 42m

$400

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

Showing 1-10 of 11 results
1
2

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 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.

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 June 12, 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 31% on your trip compared to booking a flight in the morning.

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 June 12, 2025.
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Overall

8.0

Boarding

8.1

Comfort

7.8

Food

7.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Overall

8.0

Boarding

8.1

Comfort

7.8

Food

7.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,946 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Overall

8.0

Boarding

8.1

Comfort

7.8

Food

7.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,790 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Overall

8.0

Boarding

8.1

Comfort

7.8

Food

7.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Overall

8.0

Boarding

8.1

Comfort

7.8

Food

7.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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 Delta is currently your cheapest option to Chicago, with prices starting at $344. Additional round-trip tickets that might be worth considering are offered by American Airlines and United Airlines, with the lowest prices starting at $364 and $378, respectively. Delta is priced at 9% lower than the current average price of a flight leaving 3 months from now.

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

    The cheapest airline one-way is Delta, with whom users have recently found tickets for as low as $264. However, be on the lookout for offers from United Airlines and American 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 United Airlines (69%), Air New Zealand (69%) and American Airlines (59%).

  • 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 $513, our data indicates the cheapest price to be $141. The most popular route (Key West - Chicago O'Hare Intl), is priced around $256.

  • 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 Key West?

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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Key West to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Fort Lauderdale to O'Hare Intl flights
Orlando to O'Hare Intl flights
Miami to O'Hare Intl flights
Tampa to O'Hare Intl flights
Jacksonville to O'Hare Intl flights
Orlando to Midway flights
West Palm Beach to O'Hare Intl flights
Tampa to Midway flights
Fort Myers to O'Hare Intl flights
Miami to Midway flights
Sarasota to O'Hare Intl flights
Fort Lauderdale to Midway flights
West Palm Beach to Midway flights
Pensacola to O'Hare Intl flights
Orlando to St. Louis flights
Jacksonville to Midway flights
Miami to St. Louis flights
Tampa to St. Louis flights
Fort Lauderdale to St. Louis flights
Sarasota to Midway flights
Fort Myers to St. Louis flights
Fort Myers to Midway flights
Pensacola to Midway flights
Jacksonville to St. Louis flights
West Palm Beach to St. Louis flights
St Petersburg to Rockford flights
Daytona Beach to Midway flights
Panama City to O'Hare Intl flights
Tallahassee to O'Hare Intl flights
Daytona Beach to O'Hare Intl flights
Melbourne to O'Hare Intl flights
Pensacola to St. Louis flights
Sarasota to St. Louis flights
Orlando to Moline flights
Orlando Sanford Intl to Rockford flights
Tallahassee to Midway flights
Valparaiso to O'Hare Intl flights
Fort Lauderdale to Moline flights
Tampa to Moline flights
Melbourne to Midway flights
Valparaiso to Midway flights
Gainesville to O'Hare Intl flights
Jacksonville to Moline flights
Sarasota to Moline flights
Orlando to Peoria flights
Key West to O'Hare Intl flights
Gainesville to Midway flights
Miami to Moline flights
Pensacola to Moline flights
Jacksonville to Peoria flights

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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$224Average$394FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$289Average$423FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.