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$45+ Cheap flights from O'Hare Intl (ORD) to Florida Keys

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 2/7. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — EYW
Jan 22 — Jan 291
Thu 1/22
Thu 1/29
1 adult, Economy
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Cheap flight deals from O'Hare Intl to Florida Keys

Cheapest flights from O'Hare Intl to Florida Keys
Explore the most affordable flight options available from O'Hare Intl to Florida Keys. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 23, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 12/23. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:05 pmORD - MIA
Nonstop3h 16mSpirit Airlines
Wed 1/72:35 pmMIA - ORD
Nonstop3h 25mSpirit Airlines
Deal found 12/23$102
This WAYA deal was found by Cheapflights users on 12/23. 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 WAYA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:05 pmORD - MIA
Nonstop3h 16mMultiple Airlines
Wed 1/75:07 pmMIA - ORD
1 stop6h 32mMultiple Airlines
Deal found 12/23$110
This Kiwi.com deal was found by Cheapflights users on 12/23. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:05 pmORD - MIA
Nonstop3h 16mMultiple Airlines
Tue 1/67:09 pmMIA - ORD
1 stop28h 30mMultiple Airlines
Deal found 12/23$116
This Mytrip deal was found by Cheapflights users on 12/22. 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.
Wed 12/316:05 pmORD - MIA
Nonstop3h 16mSpirit Airlines
Wed 1/217:00 amMIA - ORD
2 stops15h 03mSpirit Airlines
Deal found 12/22$123
This Mytrip deal was found by Cheapflights users on 12/21. 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.
Wed 12/316:05 pmORD - MIA
Nonstop3h 16mSpirit Airlines
Thu 2/57:00 amMIA - ORD
2 stops15h 03mSpirit Airlines
Deal found 12/21$136
This Kiwi.com deal was found by Cheapflights users on 12/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:05 pmORD - MIA
Nonstop3h 16mSpirit Airlines
Fri 1/93:48 pmMIA - ORD
Nonstop3h 28mSpirit Airlines
Deal found 12/21$146
This Kiwi.com deal was found by Cheapflights users on 12/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/306:50 amORD - MIA
1 stop14h 09mMultiple Airlines
Sat 1/105:54 amMIA - ORD
Nonstop3h 24mMultiple Airlines
Deal found 12/22$169
This Kiwi.com deal was found by Cheapflights users on 12/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:05 pmORD - MIA
Nonstop3h 16mSpirit Airlines
Thu 1/83:48 pmMIA - ORD
Nonstop3h 28mSpirit Airlines
Deal found 12/21$173
This Kiwi.com deal was found by Cheapflights users on 12/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/315:00 amORD - EYW
2 stops26h 15mMultiple Airlines
Wed 1/74:06 pmEYW - ORD
1 stop24h 22mMultiple Airlines
Deal found 12/21$289
This American Airlines deal was found by Cheapflights users on 12/21. 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.
Wed 12/318:10 amORD - EYW
Nonstop3h 35mAmerican Airlines
Wed 1/712:00 pmEYW - ORD
1 stop5h 20mAmerican Airlines
Deal found 12/21$316
This Kiwi.com deal was found by Cheapflights users on 12/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/3111:23 amORD - EYW
1 stop19h 52mMultiple Airlines
Sun 1/410:37 pmEYW - ORD
2 stops39h 17mMultiple Airlines
Deal found 12/22$340
This United Airlines deal was found by Cheapflights users on 12/22. 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 12/247:55 amORD - EYW
Nonstop3h 39mUnited Airlines
Sat 12/274:08 pmEYW - ORD
Nonstop3h 33mUnited Airlines
Deal found 12/22$342

Find flight deals from O'Hare Intl to Florida Keys

Keep the following information in mind while searching for O'Hare Intl to Florida Keys flight deals. Data was last updated December 23, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$93
(Kiwi.com)

One-way from

$45
(Booking.com)

Popular in

December

Cheapest in

September

Average price

$352
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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From Chicago O'Hare Intl to Florida Keys
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One-way flight from Chicago O'Hare Intl to Florida Keys
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Highest demand for flights based on searches. 9% potential increase in price ($27 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in December 2025
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Cheapflights Fare Finder

 
Customize your flight search to find flights from O'Hare Intl to Florida Keys 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 December 23, 2025.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Florida Keys that are best for you.

Fly from

O'Hare Intl

Fly to

Florida Keys

Route

Depart

Return

Price

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Wed 2/4

7:05 am-3:27 pm

1 stop7h 22m

Miami

Fri 2/6

1:21 pm-6:49 pm

1 stop6h 28m

$217

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Wed 1/28

1:58 pm-10:03 pm

1 stop7h 05m

Miami

Thu 2/5

8:15 am-1:40 pm

1 stop6h 25m

$217

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sun 2/1

1:58 pm-10:03 pm

1 stop7h 05m

Miami

Fri 2/6

10:29 am-4:55 pm

1 stop7h 26m

$217

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Thu 2/5

7:30 am-11:55 am

Nonstop3h 25m

Miami

Tue 2/10

4:19 pm-6:55 pm

Nonstop3h 36m

$227

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Tue 1/27

7:30 am-11:55 am

Nonstop3h 25m

Miami

Tue 1/27

4:19 pm-6:55 pm

Nonstop3h 36m

$237

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Mon 3/16

9:50 am-5:08 pm

1 stop6h 18m

Miami

Wed 3/18

6:00 am-10:00 am

1 stop5h 00m

$249

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Mon 3/16

9:50 am-5:08 pm

1 stop6h 18m

Miami

Tue 3/24

7:02 am-1:38 pm

1 stop7h 36m

$249

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Mon 3/16

7:05 am-3:37 pm

1 stop7h 32m

Miami

Fri 3/20

8:00 am-1:17 pm

1 stop6h 17m

$269

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Mon 3/2

5:00 am-1:06 pm

1 stop7h 06m

Key West

Mon 3/9

6:47 pm-9:33 pm

Nonstop3h 46m

$289

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Sat 1/10

10:50 am-3:17 pm

Nonstop3h 27m

Key West

Thu 1/15

2:25 pm-9:06 pm

1 stop7h 41m

$289

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/22

Showing 1-10 of 43 results
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Best time to book a flight from O'Hare Intl to Florida Keys

Have a flexible travel schedule? Discover the best time to fly to Florida Keys from O'Hare Intl 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 Chicago O'Hare Intl Airport to Florida Keys

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 $249). Flying from Chicago O'Hare Intl Airport to Florida Keys in October 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 ORD to EOA?

Find hourly flight availability from O'Hare Intl to Florida Keys. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 23, 2025.

One of the essential ways to save on airfare from Chicago O'Hare Intl Airport to Florida Keys is to remain as flexible as possible. Flights that are in the evening tend to be the most expensive. A flight in the afternoon could potentially save you up to 50% on airfare.

Weekly flight availability from Chicago O'Hare Intl Airport to Florida Keys

Explore weekly flight availability from O'Hare Intl to Florida Keys. 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 December 23, 2025.

The most flights from ORD to zzEOA are scheduled on a Tuesday (6 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (2 on average).

Reviews of airlines servicing Florida Keys

Get insights into the airlines that provide service to Florida Keys. 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 Florida Keys. Reviews last updated December 23, 2025.
Get a feel of what it's like to fly with Delta, United Airlines, and American Airlines 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
7.9
Good
8,014 reviews

Overall

7.9

Crew

8.5

Food

7.3

Boarding

8.1

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
2.0
Mediocre

Joseph,Aug 2023

MSP - MCO

Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.
Delta
7.9
Good
8,014 reviews
Delta
7.9
Good
8,014 reviews

Overall

7.9

Crew

8.5

Food

7.3

Boarding

8.1

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
2.0
Mediocre

Joseph,Aug 2023

MSP - MCO

Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.
United Airlines
7.4
Good
9,105 reviews
Delta
7.9
Good
8,014 reviews

Overall

7.9

Crew

8.5

Food

7.3

Boarding

8.1

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
2.0
Mediocre

Joseph,Aug 2023

MSP - MCO

Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.
American Airlines
7.2
Good
11,054 reviews
Delta
7.9
Good
8,014 reviews

Overall

7.9

Crew

8.5

Food

7.3

Boarding

8.1

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
2.0
Mediocre

Joseph,Aug 2023

MSP - MCO

Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.
Spirit Airlines
6.3
Okay
8,196 reviews
Delta
7.9
Good
8,014 reviews

Overall

7.9

Crew

8.5

Food

7.3

Boarding

8.1

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
2.0
Mediocre

Joseph,Aug 2023

MSP - MCO

Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.
Frontier
5.8
Fair
3,075 reviews
Delta
7.9
Good
8,014 reviews

Overall

7.9

Crew

8.5

Food

7.3

Boarding

8.1

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
2.0
Mediocre

Joseph,Aug 2023

MSP - MCO

Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.

Related info for your journey

Find useful and relevant information for your journey from O'Hare Intl to Florida Keys. 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 Chicago O'Hare Intl Airport to Florida Keys?

    Departing from Chicago O'Hare Intl Airport to Florida Keys will take you 3h 25m. Airlines will cover a distance of 1198 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    $42 is the cheapest one-way deal found within the past few days, from Spirit Airlines. You may also be able to find cheap deals on Frontier and American Airlines, with prices starting from $55 and $78, respectively.

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

    Consider American Airlines (71%), Envoy Air (71%) or United Airlines (66%) 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 $158. While the most popular route (Chicago O'Hare Intl - Miami) can be booked for $51 on average, our data indicates $354 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 $249). Flying from Chicago O'Hare Intl Airport to Florida Keys in October 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

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Alternative routes for O'Hare Intl to Florida Keys

See prices for flight routes from nearby airports that may be better suited for you.
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Top 4 airlines flying from O'Hare Intl to Florida Keys

Discover the top 4 airlines that operate flights from O'Hare Intl to Florida Keys. 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 December 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$169Average$390FlexibilityNo cancel feeOn-time65%
DeltaCheapest$248Average$363FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$250Average$485FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$324Average$460FlexibilityNo cancel feeOn-time71%

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