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$117+ 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 4/17. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — CHI
abr. 2 — abr. 91
mié. 4/2
mié. 4/9
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 marzo 28, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$289
(United Airlines)

One-way from

$117
(Mytrip)

Popular in

July

Cheapest in

August

Average price

$473

Good round-trip deal

$419 or less

Good one-way deal

$338 or less
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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Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in March 2025
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Price to beat on a round-trip flight from Key West to Chicago (CHI).
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Price to beat on a one-way flight from Key West to Chicago (CHI).
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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 marzo 28, 2025.

This United Airlines deal was found by Cheapflights users on 3/27. 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.
vie. 4/114:04 pmEYW - ORD
Nonstop3h 35mUnited Airlines
mar. 4/1510:59 amORD - EYW
Nonstop3h 05mUnited Airlines
Deal found 3/27$289
This American Airlines deal was found by Cheapflights users on 3/26. 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.
jue. 5/12:17 pmEYW - ORD
1 stop7h 23mAmerican Airlines
lun. 5/58:05 amORD - EYW
Nonstop3h 14mAmerican Airlines
Deal found 3/26$319
This Delta deal was found by Cheapflights users on 3/26. 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. 5/13:00 pmEYW - ORD
1 stop6h 50mDelta
lun. 5/57:05 amORD - EYW
1 stop6h 00mDelta
Deal found 3/26$329
This Delta deal was found by Cheapflights users on 3/26. 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. 5/17:00 amEYW - MDW
1 stop6h 03mDelta
lun. 5/56:04 amMDW - EYW
1 stop7h 01mDelta
Deal found 3/26$329
This Mytrip deal was found by Cheapflights users on 3/27. 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. 3/274:23 pmEYW - ORD
3 stops32h 36mMultiple Airlines
lun. 3/316:45 amORD - EYW
1 stop25h 32mMultiple Airlines
Deal found 3/27$801

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 marzo 28, 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

vie. 4/11

4:04 pm-6:39 pm

Nonstop3h 35m

Chicago O'Hare Intl

mar. 4/15

10:59 am-3:04 pm

Nonstop3h 05m

$289

Key WestChicago

EYW - ORD

EYWORD

Key West

vie. 5/2

3:06 pm-9:21 pm

1 stop7h 15m

Chicago O'Hare Intl

lun. 5/5

8:05 am-12:19 pm

Nonstop3h 14m

$319

Key WestChicago

EYW - MDW

EYWMDW

Key West

jue. 5/1

7:00 am-12:03 pm

1 stop6h 03m

Chicago Midway

lun. 5/5

6:04 am-2:05 pm

1 stop7h 01m

$329

Key WestChicago

EYW - ORD

EYWORD

Key West

jue. 6/19

7:10 am-5:55 pm

2 stops11h 45m

Chicago O'Hare Intl

dom. 6/22

9:00 am-7:40 pm

2 stops9h 40m

$1,333

Key WestChicago

EYW - RFD

EYWRFD

Key West

jue. 4/17

9:03 am-8:08 am

1 stop24h 05m

$117

Key WestChicago

EYW - ORD

EYWORD

Key West

jue. 4/17

12:56 pm-3:33 pm

Nonstop3h 37m

$159

Key WestChicago

EYW - ORD

EYWORD

Key West

jue. 4/17

9:03 am-6:13 pm

2 stops10h 10m

$161

Key WestChicago

EYW - MDW

EYWMDW

Key West

jue. 4/17

6:13 pm-10:22 pm

1 stop5h 09m

$200

Key WestChicago

EYW - MDW

EYWMDW

Key West

dom. 6/8

8:53 am-2:03 pm

2 stops30h 10m

$205

Key WestChicago

EYW - ORD

EYWORD

Key West

sáb. 6/7

6:25 pm-11:17 pm

1 stop5h 52m

$240

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/27

Showing 1-10 of 11 results
1
2

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 March.
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.

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 $323). 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 marzo 28, 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 30% 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 marzo 28, 2025.
Delta
8.0
Very good
7,896 reviews

Crew

8.5

Food

7.3

Entertainment

7.9

Overall

8.0

Comfort

8.0

Boarding

8.2

Reviews

1 / 20
2.0
Mediocre

Santiago,Apr 2024

MCO - ATL

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Delta
8.0
Very good
7,896 reviews
Delta
8.0
Very good
7,896 reviews

Crew

8.5

Food

7.3

Entertainment

7.9

Overall

8.0

Comfort

8.0

Boarding

8.2

Reviews

1 / 20
2.0
Mediocre

Santiago,Apr 2024

MCO - ATL

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
United Airlines
7.4
Good
8,603 reviews
Delta
8.0
Very good
7,896 reviews

Crew

8.5

Food

7.3

Entertainment

7.9

Overall

8.0

Comfort

8.0

Boarding

8.2

Reviews

1 / 20
2.0
Mediocre

Santiago,Apr 2024

MCO - ATL

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Allegiant Air
7.3
Good
731 reviews
Delta
8.0
Very good
7,896 reviews

Crew

8.5

Food

7.3

Entertainment

7.9

Overall

8.0

Comfort

8.0

Boarding

8.2

Reviews

1 / 20
2.0
Mediocre

Santiago,Apr 2024

MCO - ATL

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,896 reviews

Crew

8.5

Food

7.3

Entertainment

7.9

Overall

8.0

Comfort

8.0

Boarding

8.2

Reviews

1 / 20
2.0
Mediocre

Santiago,Apr 2024

MCO - ATL

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

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 United Airlines is currently your cheapest option to Chicago, with prices starting at $289. Additional round-trip tickets that might be worth considering are offered by American Airlines and Delta, with the lowest prices starting at $319 and $329, respectively. United Airlines is priced at 25% 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 Allegiant Air, with whom users have recently found tickets for as low as $117. However, be on the lookout for offers from American Airlines and Delta, 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%), Air New Zealand (86%) and United Airlines (84%).

  • 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 $509, our data indicates the cheapest price to be $259. The most popular route (Key West - Chicago O'Hare Intl), is priced around $289.

  • 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 $323). 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
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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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 marzo 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$224Average$379FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$239Average$388FlexibilityNo cancel feeOn-time71%
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