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$110+ 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 1/8. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — CHI
Dec 23 — Dec 301
Mon 12/23
Mon 12/30
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 December 18, 2024.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$268
(Delta)

One-way from

$110
(Mytrip)

Popular in

February

Cheapest in

August

Average price

$379
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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High demand for flights, 6% potential price rise
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Best time to find cheap flights, 1% potential price drop
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Average for round-trip flights in December 2024
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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 December 18, 2024.

This American Airlines deal was found by Cheapflights users on 12/17. 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 12/241:07 pmEYW - ORD
Nonstop3h 31mAmerican Airlines
Sat 1/1110:28 amORD - EYW
1 stop7h 39mAmerican Airlines
Deal found 12/17$254
This United Airlines deal was found by Cheapflights users on 12/17. 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.
Tue 12/2412:26 pmEYW - ORD
Nonstop3h 29mUnited Airlines
Tue 12/3111:02 amORD - EYW
Nonstop3h 11mUnited Airlines
Deal found 12/17$279
This Delta deal was found by Cheapflights users on 12/17. 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 12/182:19 pmEYW - ORD
1 stop7h 46mDelta
Wed 1/15:45 amORD - EYW
1 stop5h 22mDelta
Deal found 12/17$628
This Delta deal was found by Cheapflights users on 12/17. 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 12/243:50 pmEYW - MDW
1 stop7h 16mDelta
Mon 12/306:00 amMDW - EYW
1 stop5h 07mDelta
Deal found 12/17$647

Find flights from Key West to Chicago within your budget

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 December 18, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

Key WestChicago

EYW - ORD

EYWORD

Key West

Wed 1/22

6:16 pm-11:59 pm

1 stop6h 43m

Chicago O'Hare Intl

Tue 1/28

11:05 am-5:21 pm

1 stop5h 16m

$268

Key WestChicago

EYW - ORD

EYWORD

Key West

Wed 1/22

3:09 pm-7:26 pm

1 stop5h 17m

Chicago O'Hare Intl

Wed 1/29

8:10 am-12:34 pm

Nonstop3h 24m

$279

Key WestChicago

EYW - ORD

EYWORD

Key West

Sun 1/19

4:50 pm-12:15 am

1 stop8h 25m

Chicago O'Hare Intl

Mon 1/27

10:35 am-2:49 pm

Nonstop3h 14m

$314

Key WestChicago

EYW - MDW

EYWMDW

Key West

Wed 1/8

6:16 pm-10:20 pm

1 stop5h 04m

Chicago Midway

Sat 1/11

10:57 am-5:21 pm

1 stop5h 24m

$478

Key WestChicago

EYW - ORD

EYWORD

Key West

Wed 1/8

10:52 am-8:49 pm

1 stop10h 57m

$110

Key WestChicago

EYW - ORD

EYWORD

Key West

Wed 2/19

4:07 pm-6:49 pm

Nonstop3h 42m

$140

Key WestChicago

EYW - MDW

EYWMDW

Key West

Wed 3/12

2:00 pm-9:51 pm

1 stop8h 51m

$157

Key WestChicago

EYW - ORD

EYWORD

Key West

Sat 2/1

3:03 pm-6:49 pm

1 stop4h 46m

$178

Key WestChicago

EYW - ORD

EYWORD

Key West

Sat 12/28

12:55 pm-6:09 pm

1 stop6h 14m

$278

Key WestChicago

EYW - MDW

EYWMDW

Key West

Tue 2/25

7:00 am-11:59 am

1 stop5h 59m

$283

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/18

Showing 1-10 of 11 results
1
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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 December.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
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 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.

Travel insights for flights from Key West to Chicago

Get recent, data-driven insights about flights from Key West to Chicago including ideal travel times, pricing trends, and more.

What is the cheapest month to book a flight from Key West to Chicago?

Currently, September is the cheapest month in which you can book a flight from Key West to Chicago (average of $232). Flying from Key West to Chicago in June is currently the most expensive (average of $308). 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 December 18, 2024.

A simple way to save on the total cost of your ticket is to fly from Key West to Chicago in the morning. If you’re flexible enough to do this you can expect to save up to 6% on your trip compared to booking a flight in the afternoon.

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 December 18, 2024.
Read reviews from past customers who have flown American Airlines, Delta and United Airlines from Key West to Chicago. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
9,552 reviews

Crew

8.5

Food

7.2

Entertainment

7.1

Overall

8.0

Boarding

8.2

Comfort

7.9

Reviews

1 / 10

Things were good, crew was good. It was just the flight itself was very rough. Lots of turbulence, probably one of the shakiest flights I've been on. Kids throwing up, kids crying everywhere because of it.

Alaska Airlines
8.0
Very good
9,552 reviews
Alaska Airlines
8.0
Very good
9,552 reviews

Crew

8.5

Food

7.2

Entertainment

7.1

Overall

8.0

Boarding

8.2

Comfort

7.9

Reviews

1 / 10

Things were good, crew was good. It was just the flight itself was very rough. Lots of turbulence, probably one of the shakiest flights I've been on. Kids throwing up, kids crying everywhere because of it.

Delta
8.0
Very good
8,604 reviews
Alaska Airlines
8.0
Very good
9,552 reviews

Crew

8.5

Food

7.2

Entertainment

7.1

Overall

8.0

Boarding

8.2

Comfort

7.9

Reviews

1 / 10

Things were good, crew was good. It was just the flight itself was very rough. Lots of turbulence, probably one of the shakiest flights I've been on. Kids throwing up, kids crying everywhere because of it.

United Airlines
7.4
Good
9,059 reviews
Alaska Airlines
8.0
Very good
9,552 reviews

Crew

8.5

Food

7.2

Entertainment

7.1

Overall

8.0

Boarding

8.2

Comfort

7.9

Reviews

1 / 10

Things were good, crew was good. It was just the flight itself was very rough. Lots of turbulence, probably one of the shakiest flights I've been on. Kids throwing up, kids crying everywhere because of it.

American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
9,552 reviews

Crew

8.5

Food

7.2

Entertainment

7.1

Overall

8.0

Boarding

8.2

Comfort

7.9

Reviews

1 / 10

Things were good, crew was good. It was just the flight itself was very rough. Lots of turbulence, probably one of the shakiest flights I've been on. Kids throwing up, kids crying everywhere because of it.

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 1 outbound flight 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 $268. Additional round-trip tickets that might be worth considering are offered by American Airlines and United Airlines, with the lowest prices starting at $279 and $314, respectively. Delta is priced at 32% 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 United Airlines, with whom users have recently found tickets for as low as $140. However, be on the lookout for offers from Delta 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 Republic Airways (100%), American Airlines (93%) and Qatar Airways (87%).

  • 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 $336, our data indicates the cheapest price to be $134. The most popular route (Key West - Chicago O'Hare Intl), is priced around $314.

  • 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, September is the cheapest month in which you can book a flight from Key West to Chicago (average of $232). Flying from Key West to Chicago in June is currently the most expensive (average of $308). 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.

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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 December 18, 2024.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$211Average$419FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$224Average$394FlexibilityNo cancel feeOn-time69%
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