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Cheap flights from Florida Keys to Chicago (CHI)

EYW — CHI
Jul 8 — Jul 151
Wed 7/8
Wed 7/15
1 adult, Economy
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Find flight deals from Florida Keys to Chicago

Keep the following information in mind while searching for Florida Keys to Chicago flight deals. Data was last updated June 8, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$191
(Kiwi.com)

One-way from

$90
(Kiwi.com)
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 Florida Keys to Chicago (CHI)
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One-way flight from Florida Keys to Chicago (CHI)
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Cheapflights Insights

Everything you need to know about your flight from Florida Keys to Chicago

How far ahead should I book a flight from Florida Keys to Chicago?

To ensure you get the cheapest price possible for a flight from Florida Keys to Chicago, you should look to book at least 53 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

What is the cheapest month to book a flight from Florida Keys to Chicago?

Currently, March is the cheapest month in which you can book a flight from Florida Keys to Chicago (average of $27). Flying from Florida Keys to Chicago in July is currently the most expensive (average of $96). 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 EOA to CHI?

Find hourly flight availability from Florida Keys 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 8, 2026.

When flying from Florida Keys to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 8, 2026.
Get a feel of what it's like to fly with Southwest,United Airlines, andAmerican Airlines from Florida Keys to Chicago by reading reviews from past customers. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
7.9
Good
4,246 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Overall

7.9

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
7.9
Good
4,246 reviews
Southwest
7.9
Good
4,246 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Overall

7.9

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
United Airlines
7.4
Good
9,785 reviews
Southwest
7.9
Good
4,246 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Overall

7.9

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
American Airlines
7.1
Good
11,642 reviews
Southwest
7.9
Good
4,246 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Overall

7.9

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Frontier
5.6
Fair
2,904 reviews
Southwest
7.9
Good
4,246 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Overall

7.9

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Related info for your journey

Find useful and relevant information for your journey from Florida Keys to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Florida Keys to Chicago?

    United Airlines, Delta, and Southwest can get you from Florida Keys to Chicago in just under 5h 32m. Your travel time can differ by up to 1h 53m. The distance between Florida Keys and Chicago is about 1198 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Florida Keys to Chicago one-way?

    To fly one-way, consider booking your trip with Frontier, which is currently one of the cheapest options available, starting at $44. JetBlue flights start at $71 while deals on Southwest start at $79 one-way.

  • What are the most popular routes from Florida Keys to Chicago?

    When deciding which route to take from Florida Keys to Chicago consider Miami - Chicago O'Hare Intl, Miami - Chicago Midway or Key West - Chicago O'Hare Intl as they are the most popular.

  • What are the most reliable airlines from Florida Keys to Chicago?

    Before booking your flight to Chicago from Florida Keys, check out the most reliable airlines to get you to your destination on time: Republic Airways (96%), Air New Zealand (87%), United Airlines( 85%).

  • What are the cheapest flights from Florida Keys to Chicago?

    Looking for the cheapest flight from Florida Keys to Chicago? While on average our users pay $469, our data indicates the cheapest price to be $228. The most popular route (Miami - Chicago O'Hare Intl), is priced around $239.

  • Can I find deals for flights from Florida Keys to Chicago that include hotel bookings?

    Yes. In addition to deals on Florida Keys to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Florida Keys to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Florida Keys to Chicago.

  • Can I find deals for business class flights from Florida Keys to Chicago?

    Yes. Cheapflights offers flight deals from Florida Keys 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 Florida Keys to Chicago?

    Currently, March is the cheapest month in which you can book a flight from Florida Keys to Chicago (average of $27). Flying from Florida Keys to Chicago in July is currently the most expensive (average of $96). 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 Chicago?

Book flights to Chicago if you plan to visit one of these locations
Benton Harbor
Lansing
Merrillville
Hammond
Porter

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Alternative routes for Florida Keys to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Top airline flying from Florida Keys to Chicago

Discover the top airline that operate flights from Florida Keys 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 8, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$344Average$460FlexibilityNo cancel feeOn-time71%

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