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$108+ 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 11/9. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — CHI
Oct 15 — Oct 221
From?
To?
Tue 10/15
Tue 10/22
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 October 10, 2024.

Popular in

November

Cheapest in

August

Round-trip from

$209
(United Airlines)

One-way from

$108
(Delta)
High demand for flights, 25% potential price rise
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Best time to find cheap flights, 26% potential price drop
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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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Cheap Key West to Chicago flights in October & November 2024

Find cheap flight options from Key West to Chicago specifically for the months of October and November 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 2,713,696 searches. Prices were last updated on October 10, 2024.
These are some of the best deals we've found on flights to Chicago in 2024 at this time. Check back soon for alternative fares.
This United Airlines deal was found by Cheapflights users on 10/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/94:05 pmEYW - ORD
Nonstop3h 21mUnited Airlines
Fri 11/1510:55 amORD - EYW
Nonstop3h 06mUnited Airlines
Deal found 10/9$209
This American Airlines deal was found by Cheapflights users on 10/9. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/2612:55 pmEYW - ORD
Nonstop3h 31mAmerican Airlines
Fri 11/298:14 amORD - EYW
Nonstop3h 18mAmerican Airlines
Deal found 10/9$269
This Delta deal was found by Cheapflights users on 10/9. 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.
Sat 11/96:20 pmEYW - ORD
1 stop6h 37mDelta
Fri 11/1512:00 pmORD - EYW
1 stop7h 30mDelta
Deal found 10/9$287
This Delta deal was found by Cheapflights users on 10/9. 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.
Sat 11/97:25 amEYW - MDW
1 stop6h 49mDelta
Fri 11/156:00 amMDW - EYW
1 stop6h 18mDelta
Deal found 10/9$488

Key West to Chicago 2024 flight deals

Discover exclusive flight deals for travel between Key West and Chicago in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 2,713,696 searches. Data last updated October 10, 2024.
These are some of the best deals we've found on flights to Chicago in 2024 at this time. Check back soon for alternative fares.
This United Airlines deal was found by Cheapflights users on 10/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/94:05 pmEYW - ORD
Nonstop3h 21mUnited Airlines
Fri 11/1510:55 amORD - EYW
Nonstop3h 06mUnited Airlines
Deal found 10/9$209
This Delta deal was found by Cheapflights users on 10/9. 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.
Tue 12/241:02 pmEYW - ORD
1 stop7h 13mDelta
Sat 1/1111:30 amORD - EYW
1 stop7h 16mDelta
Deal found 10/9$242
This American Airlines deal was found by Cheapflights users on 10/9. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/2612:55 pmEYW - ORD
Nonstop3h 31mAmerican Airlines
Fri 11/298:14 amORD - EYW
Nonstop3h 18mAmerican Airlines
Deal found 10/9$269
This Delta deal was found by Cheapflights users on 10/9. 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.
Sat 11/97:25 amEYW - MDW
1 stop6h 49mDelta
Fri 11/156:00 amMDW - EYW
1 stop6h 18mDelta
Deal found 10/9$488

Key West to Chicago flights leaving soon

Find last-minute flight options from Key West to Chicago for spontaneous travel. Discover available flights and compare prices based on user searches. Secure great deals and offers for spontaneous trips with quick booking options. Over the last 7 days, Cheapflights users made 2,713,696 searches. Data last updated October 10, 2024.
Book one of these great deals on flights from Key West to Chicago. To prevent any unwanted surprises, users should verify their flight info before booking.
This Delta deal was found by Cheapflights users on 10/9. 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.
Sat 10/1212:38 pmEYW - ORD
1 stop5h 00mDelta
Sat 10/1912:06 pmORD - EYW
1 stop7h 12mDelta
Deal found 10/9$473
This United Airlines deal was found by Cheapflights users on 10/10. 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.
Wed 10/162:00 pmEYW - ORD
2 stops10h 37mUnited Airlines
Sun 10/206:00 amORD - EYW
1 stop6h 46mUnited Airlines
Deal found 10/10$558
This American Airlines deal was found by Cheapflights users on 10/9. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/123:46 pmEYW - ORD
2 stops7h 13mAmerican Airlines
Sat 10/195:05 amORD - EYW
1 stop8h 23mAmerican Airlines
Deal found 10/9$583

One-way flights to Chicago from Key West

Search for one-way flight options from Key West to Chicago. Find affordable one-way fares based on user searches. Compare prices and availability to plan your one-way journey according to your preferred dates and budget. Over the last 7 days, Cheapflights users made 2,713,696 searches. Data last updated October 10, 2024.
Take a look at some of the best available options we've come across on one-way flights from Key West to Chicago. For those needing a return trip from Key West, there is a search form available above.
This Delta deal was found by Cheapflights users on 10/8. 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.
Sat 11/96:20 pmEYW - ORD
1 stop6h 37mDelta
Deal found 10/8$108
This Mytrip deal was found by Cheapflights users on 10/10. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/115:12 pmEYW - ORD
1 stop15h 28mMultiple Airlines
Deal found 10/10$111
This American Airlines deal was found by Cheapflights users on 10/9. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/91:06 pmEYW - ORD
Nonstop3h 31mAmerican Airlines
Deal found 10/9$115
This Delta deal was found by Cheapflights users on 10/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/106:00 pmEYW - MDW
1 stop4h 49mDelta
Deal found 10/10$124
This United Airlines deal was found by Cheapflights users on 10/8. 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 12/104:05 pmEYW - ORD
Nonstop3h 21mUnited Airlines
Deal found 10/8$135
This Trip.com deal was found by Cheapflights users on 10/9. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/226:00 pmEYW - MDW
1 stop7h 18mMultiple Airlines
Deal found 10/9$258
This Mytrip deal was found by Cheapflights users on 10/9. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/224:23 pmEYW - RFD
2 stops18h 17mAllegiant Air
Deal found 10/9$262
This Alaska Airlines deal was found by Cheapflights users on 10/10. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/1111:10 amEYW - ORD
3 stops33h 28mAlaska Airlines
Deal found 10/10$813

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 2,713,696 searches. Data last updated October 10, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$209 - $488

Route

Depart

Return

Price

Key WestChicago O'Hare Intl

EYW - ORD

EYWORD

Key West

Sat 11/9

Nonstop3h 21m

Chicago O'Hare Intl

Fri 11/15

Nonstop3h 06m

$209

Key WestChicago O'Hare Intl

EYW - ORD

EYWORD

Key West

Tue 12/24

1 stop7h 13m

Chicago O'Hare Intl

Sat 1/11

1 stop7h 16m

$242

Key WestChicago O'Hare Intl

EYW - ORD

EYWORD

Key West

Tue 11/26

Nonstop3h 31m

Chicago O'Hare Intl

Fri 11/29

Nonstop3h 18m

$269

Key WestChicago Midway

EYW - MDW

EYWMDW

Key West

Sat 11/9

1 stop6h 49m

Chicago Midway

Fri 11/15

1 stop6h 18m

$488

Flights are sorted by cheapest first

Deals found on 10/9

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 October 10, 2024.

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 36% on your trip compared to booking a flight in the evening.

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 October 10, 2024.
Read reviews from past customers who have flown United Airlines, Delta and American 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
9,392 reviews

Boarding

8.2

Overall

8.0

Food

7.2

Comfort

7.9

Crew

8.6

Entertainment

7.1

Reviews

1 / 10

It was the first time I have flown Alaska and I don’t think I can recommend it to others. It was so hot on the plane, food was preordered but I never received it.

Alaska Airlines
8.0
Very good
9,392 reviews
Alaska Airlines
8.0
Very good
9,392 reviews

Boarding

8.2

Overall

8.0

Food

7.2

Comfort

7.9

Crew

8.6

Entertainment

7.1

Reviews

1 / 10

It was the first time I have flown Alaska and I don’t think I can recommend it to others. It was so hot on the plane, food was preordered but I never received it.

Delta
8.0
Very good
8,963 reviews
Alaska Airlines
8.0
Very good
9,392 reviews

Boarding

8.2

Overall

8.0

Food

7.2

Comfort

7.9

Crew

8.6

Entertainment

7.1

Reviews

1 / 10

It was the first time I have flown Alaska and I don’t think I can recommend it to others. It was so hot on the plane, food was preordered but I never received it.

United Airlines
7.4
Good
9,366 reviews
Alaska Airlines
8.0
Very good
9,392 reviews

Boarding

8.2

Overall

8.0

Food

7.2

Comfort

7.9

Crew

8.6

Entertainment

7.1

Reviews

1 / 10

It was the first time I have flown Alaska and I don’t think I can recommend it to others. It was so hot on the plane, food was preordered but I never received it.

Allegiant Air
7.4
Good
875 reviews
Alaska Airlines
8.0
Very good
9,392 reviews

Boarding

8.2

Overall

8.0

Food

7.2

Comfort

7.9

Crew

8.6

Entertainment

7.1

Reviews

1 / 10

It was the first time I have flown Alaska and I don’t think I can recommend it to others. It was so hot on the plane, food was preordered but I never received it.

American Airlines
7.3
Good
10,000 reviews
Alaska Airlines
8.0
Very good
9,392 reviews

Boarding

8.2

Overall

8.0

Food

7.2

Comfort

7.9

Crew

8.6

Entertainment

7.1

Reviews

1 / 10

It was the first time I have flown Alaska and I don’t think I can recommend it to others. It was so hot on the plane, food was preordered but I never received 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 0 outbound flights to Chicago per day from 3 airlines. Key West is conveniently located just 2.6 mi from Key West’s city center.

  • Can I find flights from Key West to Chicago for under $300 on Cheapflights?

    Yes, there are multiple flights from Key West to Chicago for under $300. The cheapest flight booked recently is on United Airlines for just $209, but on average you can expect to pay $302.

  • Are there nonstop flights from Key West to Chicago for under $300 on Cheapflights?

    Cheapflights has at least 2 direct flights from Key West to Chicago under $300. A good price for a nonstop flight from Key West to Chicago is less than $239.

  • Are there last-minute flights available from Key West to Chicago for under $500?

    There are currently 3+ open flights from Key West to Chicago within the next 7 days for less than $500.

  • 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 $209. Additional round-trip tickets that might be worth considering are offered by Delta and American Airlines, with the lowest prices starting at $242 and $269, respectively. United Airlines is priced at 47% 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 $108. However, be on the lookout for offers from American Airlines and United 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 cheapest flights from Key West to Chicago?

    Looking for the cheapest flight from Key West to Chicago? While on average our users pay $298, our data indicates the cheapest price to be $114. The most popular route (Key West - Chicago O'Hare Intl), is priced around $209.

  • What does EYW to ORD mean?

    EYW and ORD are unique codes to identify airports used in the aviation industry. They are defined by IATA (International Air Transport Association) and are commonly called IATA codes. EYW to ORD refers to a flight route from Key West Airport to Chicago O'Hare Intl Airport. This flight route has multiple associated airports, so we think it might be helpful to learn the name and codes of them as well. They are Chicago Midway Airport (MDW), Chicago Greater Rockford Airport (RFD).

  • Can I find deals for flights from Key West to Chicago that include extra baggage allowance?

    The amount of baggage you can bring on your Key West to Chicago flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Key West to Chicago with specific airlines?

    Yes, Cheapflights allows you to browse and filter Key West to Chicago flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • 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.

  • Can I find deals for flights from Key West to Chicago that allow pets onboard?

    Many airlines flying from Key West to Chicago offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Key West to Chicago?

    Yes, you can often find last-minute deals on Key West to Chicago flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Key West to Chicago flight deals updated?

    The Key West to Chicago flight deals you see on this page were last updated on 10/9.

  • 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.

See more FAQs

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Top 3 airlines flying from Key West to Chicago

Discover the top 3 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 2,713,696 searches. Data last updated October 10, 2024.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$211Average$457FlexibilityNo cancel feeOn-time71%
DeltaCheapest$278Average$441FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$313Average$518FlexibilityNo cancel feeOn-time69%
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