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Cheap flights from O'Hare Intl (ORD) to Florida Keys

ORD — EYW
Nov 29 — Dec 61
Sun 11/29
Sun 12/6
1 adult, Economy
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Find flight deals from O'Hare Intl to Florida Keys

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Popular in

July

Cheapest in

January

Average price

$379
Provider with most accurate pricing for Chicago (CHI)-Miami flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Miami flights.
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Highest demand for flights based on searches. 9% potential increase in price ($33 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in October 2026
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Cheapflights Insights

Everything you need to know about your flight from Chicago O'Hare Intl Airport to Florida Keys

How far ahead should I book a flight from Chicago O'Hare Intl Airport to Florida Keys?

The price you pay for your flight from Chicago O'Hare Intl Airport to Florida Keys may vary depending on when you book. For the best chance of a lower fare, look to book 26 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to Florida Keys?

Currently, January is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Florida Keys (average of $248). Flying from Chicago O'Hare Intl Airport to Florida Keys in December is currently the most expensive (average of $395). 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 ORD to EOA?

When flying from Chicago O'Hare Intl Airport to Florida Keys, 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 Florida Keys

Get a feel of what it's like to fly with Delta,United Airlines, andJetBlue from Chicago O'Hare Intl Airport to Florida Keys by reading reviews from past customers. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.8
Good
8,694 reviews

Food

7.2

Entertainment

7.8

Crew

8.5

Overall

7.8

Boarding

8.1

Comfort

7.8

Reviews

1 / 20
4.0
Okay

Jennifer,Sep 2026

ORD - LGA

The flight crew was 30 minutes late to an am flight and then that caused a delay
Delta
7.8
Good
8,694 reviews
Delta
7.8
Good
8,694 reviews

Food

7.2

Entertainment

7.8

Crew

8.5

Overall

7.8

Boarding

8.1

Comfort

7.8

Reviews

1 / 20
4.0
Okay

Jennifer,Sep 2026

ORD - LGA

The flight crew was 30 minutes late to an am flight and then that caused a delay
United Airlines
7.3
Good
10,452 reviews
Delta
7.8
Good
8,694 reviews

Food

7.2

Entertainment

7.8

Crew

8.5

Overall

7.8

Boarding

8.1

Comfort

7.8

Reviews

1 / 20
4.0
Okay

Jennifer,Sep 2026

ORD - LGA

The flight crew was 30 minutes late to an am flight and then that caused a delay
JetBlue
7.1
Good
3,075 reviews
Delta
7.8
Good
8,694 reviews

Food

7.2

Entertainment

7.8

Crew

8.5

Overall

7.8

Boarding

8.1

Comfort

7.8

Reviews

1 / 20
4.0
Okay

Jennifer,Sep 2026

ORD - LGA

The flight crew was 30 minutes late to an am flight and then that caused a delay
American Airlines
7.0
Good
12,210 reviews
Delta
7.8
Good
8,694 reviews

Food

7.2

Entertainment

7.8

Crew

8.5

Overall

7.8

Boarding

8.1

Comfort

7.8

Reviews

1 / 20
4.0
Okay

Jennifer,Sep 2026

ORD - LGA

The flight crew was 30 minutes late to an am flight and then that caused a delay
Frontier
5.5
Fair
2,516 reviews
Delta
7.8
Good
8,694 reviews

Food

7.2

Entertainment

7.8

Crew

8.5

Overall

7.8

Boarding

8.1

Comfort

7.8

Reviews

1 / 20
4.0
Okay

Jennifer,Sep 2026

ORD - LGA

The flight crew was 30 minutes late to an am flight and then that caused a delay

Related info for your journey

  • What are the cheapest airlines to fly from Chicago O'Hare Intl Airport to Florida Keys one-way?

    $29 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on JetBlue and American Airlines, with prices starting from $68 and $85, respectively.

  • What are the most reliable airlines from Chicago O'Hare Intl Airport to Florida Keys?

    Consider American Airlines (92%), Envoy Air (92%) or United Airlines (33%) when booking your flight. These represent the most reliable airlines when flying from Chicago O'Hare Intl Airport to Florida Keys.

  • What are the cheapest flights from Chicago O'Hare Intl Airport to Florida Keys?

    Looking at all options, your cheapest flight can be booked for $268. While the most popular route (Chicago O'Hare Intl - Miami) can be booked for $113 on average, our data indicates $486 when flying from Chicago O'Hare Intl Airport to Florida Keys.

  • Can I find deals for flights from O'Hare Intl to Florida Keys that include hotel bookings?

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

  • How can I find direct flights from O'Hare Intl to Florida Keys?

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

  • Can I find deals for business class flights from O'Hare Intl to Florida Keys?

    Yes. Cheapflights offers flight deals from O'Hare Intl to Florida Keys 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 Chicago O'Hare Intl Airport to Florida Keys?

    Currently, January is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Florida Keys (average of $248). Flying from Chicago O'Hare Intl Airport to Florida Keys in December is currently the most expensive (average of $395). 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

Browse thousands of different options on Cheapflights for your next trip

Top 2 airlines flying from O'Hare Intl to Florida Keys

AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$249Average$415FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$305Average$471FlexibilityNo cancel feeOn-time71%

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