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 $269. Additional round-trip tickets that might be worth considering are offered by American Airlines and United Airlines, with the lowest prices starting at $328 and $425, respectively. Delta is priced at 28% 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 $207. 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 is the cheapest day to fly from Key West to Chicago?

Travelers seeking maximum savings on their Key West to Chicago flight should consider departing on Thursday at noon when fares are most often at their lowest. Tuesday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

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 cheapest flights from Key West to Chicago?

Looking for the cheapest flight from Key West to Chicago? While on average our users pay $595, our data indicates the cheapest price to be $198. The most popular route (Key West - Chicago O'Hare Intl), is priced around $269.

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 (94%), United Airlines (81%) and Air New Zealand (78%).

What is the cheapest day to fly round-trip from Key West to Chicago?

Wednesday is generally a great day to depart. Flying on this day could help you save up to 197%.

What is the cheapest month to fly from Key West to Chicago?

August can be a great time to fly to Chicago from Key West with a flight ticket averaging about $378. Cheapflights users have found deals in the month of August for as cheap as $250. The most expensive prices can be found in the month of March.

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 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.

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.

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.

$187+ Flights from Key West to Chicago

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Cheap flight deals from Key West to Chicago

Most accurate provider	FlightHub 3 stars
Most trusted provider	eDreams 3 stars
Round-trip from	$269 (Delta)
One-way from	$187 (Mytrip)
Popular in	March
Cheapest in	August
Average price	$386
Good round-trip deal	$609 or less
Good one-way deal	$259 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

Highest demand for flights based on searches. 15% potential increase in price ($68 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 3% potential price decrease ($14 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in April 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 April 17, 2025.

Fri 6/66:25 pmEYW - ORD

1 stop6h 33mDelta

Mon 6/911:20 amORD - EYW

1 stop5h 14mDelta

Deal found 4/16

$269

Wed 7/96:00 pmEYW - MDW

1 stop4h 47mDelta

Tue 7/151:05 pmMDW - EYW

1 stop5h 41mDelta

Deal found 4/17

$269

Wed 7/94:46 pmEYW - ORD

1 stop5h 39mAmerican Airlines

Tue 7/155:15 amORD - EYW

2 stops6h 40mAmerican Airlines

Deal found 4/17

$328

Fri 6/66:45 pmEYW - ORD

1 stop24h 40mUnited Airlines

Mon 6/99:10 pmORD - EYW

2 stops14h 43mUnited Airlines

Deal found 4/16

$425

Best flights from Key West to Chicago
Discover carefully curated flight deals from Key West to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 17, 2025.

Fri 6/66:25 pmEYW - ORD

1 stop6h 33mDelta

Mon 6/911:20 amORD - EYW

1 stop5h 14mDelta

Deal found 4/16

$269

Wed 7/94:46 pmEYW - ORD

1 stop5h 39mAmerican Airlines

Tue 7/155:15 amORD - EYW

2 stops6h 40mAmerican Airlines

Deal found 4/17

$328

Fri 6/66:45 pmEYW - ORD

1 stop24h 40mUnited Airlines

Mon 6/99:10 pmORD - EYW

2 stops14h 43mUnited Airlines

Deal found 4/16

$425

Wed 7/96:00 pmEYW - MDW

1 stop4h 47mDelta

Tue 7/151:05 pmMDW - EYW

1 stop5h 41mDelta

Deal found 4/17

$269

Last-minute flights from Key West to Chicago
Discover last-minute flight deals from Key West to Chicago. Data last updated April 17, 2025 and is based on user searches.

Thu 5/17:00 amEYW - ORD

1 stop6h 05mDelta

Mon 5/57:05 amORD - EYW

1 stop6h 00mDelta

Deal found 4/16

$309

Thu 5/16:13 pmEYW - MDW

1 stop5h 09mDelta

Mon 5/59:52 amMDW - EYW

1 stop6h 25mDelta

Deal found 4/15

$309

Thu 5/112:56 pmEYW - ORD

Nonstop3h 37mAmerican Airlines

Mon 5/58:05 amORD - EYW

Nonstop3h 14mAmerican Airlines

Deal found 4/16

$427

Sat 5/106:45 pmEYW - ORD

1 stop16h 02mUnited Airlines

Sat 5/3111:12 amORD - EYW

1 stop24h 03mUnited Airlines

Deal found 4/16

$453

One-way flights from Key West to Chicago
Search for one-way flight options from Key West to Chicago. Find affordable one-way fares based on user searches. Data last updated April 17, 2025.

Thu 4/249:03 amEYW - ORD

2 stops25h 21mMultiple Airlines

Deal found 4/16

$187

Fri 5/238:45 amEYW - ORD

1 stop25h 54mUnited Airlines

Deal found 4/16

$207

Wed 5/145:30 pmEYW - ORD

2 stops13h 49mAmerican Airlines

Deal found 4/17

$240

Sat 6/76:25 pmEYW - ORD

1 stop5h 52mDelta

Deal found 4/16

$260

Wed 5/77:00 amEYW - MDW

1 stop5h 53mDelta

Deal found 4/16

$420

Tue 6/1711:53 amEYW - ORD

3 stops30h 23mAlaska Airlines

Deal found 4/16

$546

Cheapflights Fare Finder

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

Key WestChicago

EYW - ORD

EYWORD

Key West

Fri 6/6

6:25 pm-11:58 pm

1 stop6h 33m

Chicago O'Hare Intl

Mon 6/9

11:20 am-5:34 pm

1 stop5h 14m

$269

Key WestChicago

EYW - MDW

EYWMDW

Key West

Wed 7/9

6:00 pm-9:47 pm

1 stop4h 47m

Chicago Midway

Tue 7/15

1:05 pm-7:46 pm

1 stop5h 41m

$269

Key WestChicago

EYW - ORD

EYWORD

Key West

Wed 7/9

4:46 pm-9:25 pm

1 stop5h 39m

Chicago O'Hare Intl

Tue 7/15

5:15 am-12:55 pm

2 stops6h 40m

$328

Key WestChicago

EYW - ORD

EYWORD

Key West

Fri 6/6

6:45 pm-6:25 pm

1 stop24h 40m

Chicago O'Hare Intl

Mon 6/9

9:10 pm-12:53 pm

2 stops14h 43m

$425

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 4/24

9:03 am-9:24 am

2 stops25h 21m

$187

Key WestChicago

EYW - ORD

EYWORD

Key West

Fri 5/23

8:45 am-9:39 am

1 stop25h 54m

$207

Key WestChicago

EYW - ORD

EYWORD

Key West

Wed 5/14

5:30 pm-6:19 am

2 stops13h 49m

$240

Key WestChicago

EYW - ORD

EYWORD

Key West

Sat 6/7

6:25 pm-11:17 pm

1 stop5h 52m

$260

Key WestChicago

EYW - MDW

EYWMDW

Key West

Wed 5/7

7:00 am-11:53 am

1 stop5h 53m

$420

Key WestChicago

EYW - ORD

EYWORD

Key West

Tue 6/17

11:53 am-5:16 pm

3 stops30h 23m

$546

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/16

Compare providers for flights from Key West to Chicago

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 April.

Provider	Price Accuracy	Trust Score*
FlightHub	Price Accuracy3 stars	Trust Score*2 stars
eDreams	Price Accuracy3 stars	Trust 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 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 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?

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.

Weekly flight availability from Key West to Chicago

The most flights from EYW to CHI are scheduled on a Monday (4 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (2 on average).

Rainfall in Chicago 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

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

Alaska Airlines

8.0

Very good

9,887 reviews

Reviews

1 / 20

4.0

Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >

Alaska Airlines

8.0

Very good

9,887 reviews

Alaska Airlines

8.0

Very good

9,887 reviews

Reviews

1 / 20

4.0

Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >

Delta

8.0

Very good

7,916 reviews

Alaska Airlines

8.0

Very good

9,887 reviews

Reviews

1 / 20

4.0

Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >

United Airlines

7.4

Good

8,667 reviews

Alaska Airlines

8.0

Very good

9,887 reviews

Reviews

1 / 20

4.0

Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >

American Airlines

7.2

Good

10,000 reviews

Alaska Airlines

8.0

Very good

9,887 reviews

Reviews

1 / 20

4.0

Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >

Related info for your journey

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.
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 $269. Additional round-trip tickets that might be worth considering are offered by American Airlines and United Airlines, with the lowest prices starting at $328 and $425, respectively. Delta is priced at 28% 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 $207. 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 (94%), United Airlines (81%) and Air New Zealand (78%).
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 $595, our data indicates the cheapest price to be $198. The most popular route (Key West - Chicago O'Hare Intl), is priced around $269.
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

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Top 2 airlines flying from Key West to Chicago

Airline	Cheapest	Average	Flexibility	On-time
United Airlines	Cheapest$224	Average$379	FlexibilityNo cancel fee	On-time69%
American Airlines	Cheapest$239	Average$389	FlexibilityNo cancel fee	On-time71%

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$187+ 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 4/24. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Key West to Chicago with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheap flight deals from Key West to Chicago

Most accurate provider

Most trusted provider

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Good round-trip deal

Good one-way deal

Find flight deals from Key West to Chicago

Cheapest flights from Key West to ChicagoExplore 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 April 17, 2025.

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 April 17, 2025.

Cheapflights Fare Finder

Use the filters below to find and compare flights from Key West to Chicago that are best for you.

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 April.

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.

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?

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 April 17, 2025.

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 April 17, 2025.

Rainfall in Chicago by month

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

Temperature in Chicago by month

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

Reviews of airlines servicing Chicago

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?

What are the cheapest airlines flying from Key West to Chicago round-trip?

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

What are the most popular routes from Key West to Chicago?

What are the most reliable airlines from Key West to Chicago?

What are the cheapest flights from Key West to Chicago?

Can I find deals for flights from Key West to Chicago that include hotel bookings?

How can I find direct flights from Key West to Chicago?

Can I find deals for business class flights from Key West to Chicago?

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

Traveling to a place near Key West?

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Alternative routes for Key West to Chicago

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Top 2 airlines flying from Key West to Chicago

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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 April 17, 2025.