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$56+ 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 11/20. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — EYW
Dec 2 — Dec 91
Tue 12/2
Tue 12/9
1 adult, Economy
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Find 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 November 2, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/2. 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 12/3112:39 pmORD - MIA
1 stop5h 51mMultiple Airlines
Wed 1/72:35 pmMIA - ORD
Nonstop3h 25mMultiple Airlines
Deal found 11/2$109
This Cheapflightsfares deal was found by Cheapflights users on 11/2. 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.
Sat 12/66:11 amORD - MIA
1 stop8h 28mFrontier
Sat 12/132:13 pmMIA - ORD
1 stop21h 18mFrontier
Deal found 11/2$110
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 12/32:01 pmORD - MIA
1 stop6h 30mSpirit Airlines
Fri 12/54:08 pmMIA - ORD
Nonstop3h 28mSpirit Airlines
Deal found 11/1$111
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 12/177:41 pmORD - MIA
Nonstop3h 16mSpirit Airlines
Fri 12/262:35 pmMIA - ORD
Nonstop3h 25mSpirit Airlines
Deal found 11/2$112
This Cheapflightsfares deal was found by Cheapflights users on 11/2. 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.
Sun 11/3011:40 amORD - MIA
Nonstop3h 07mSpirit Airlines
Sat 12/64:08 pmMIA - ORD
Nonstop3h 28mSpirit Airlines
Deal found 11/2$115
This Cheapflightsfares deal was found by Cheapflights users on 11/2. 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.
Sat 12/69:14 pmORD - MIA
1 stop10h 09mSpirit Airlines
Thu 12/182:35 pmMIA - ORD
Nonstop3h 25mSpirit Airlines
Deal found 11/2$116
This Cheapflightsfares deal was found by Cheapflights users on 11/2. 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 12/246:05 pmORD - MIA
Nonstop3h 16mSpirit Airlines
Mon 12/292:35 pmMIA - ORD
Nonstop3h 25mSpirit Airlines
Deal found 11/2$117
This Priceline deal was found by Cheapflights users on 11/1. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/910:00 amORD - MIA
1 stop5h 28mMultiple Airlines
Tue 12/162:10 pmMIA - ORD
1 stop6h 59mMultiple Airlines
Deal found 11/1$118
This Kiwi.com deal was found by Cheapflights users on 10/31. 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 1/810:15 amMIA - ORD
Nonstop3h 15mSpirit Airlines
Deal found 10/31$119
This Cheapflightsfares deal was found by Cheapflights users on 11/2. 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.
Mon 12/111:40 amORD - MIA
Nonstop3h 07mSpirit Airlines
Sat 12/62:19 pmMIA - ORD
1 stop8h 52mSpirit Airlines
Deal found 11/2$120
This Cheapflightsfares deal was found by Cheapflights users on 11/2. 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.
Thu 11/203:53 pmORD - MIA
1 stop6h 22mSpirit Airlines
Mon 11/248:10 amMIA - ORD
Nonstop3h 25mSpirit Airlines
Deal found 11/2$121
This Cheapflightsfares deal was found by Cheapflights users on 11/2. 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.
Thu 11/2011:40 amORD - MIA
Nonstop3h 07mSpirit Airlines
Sun 11/238:10 amMIA - ORD
Nonstop3h 25mSpirit Airlines
Deal found 11/2$122

Cheap 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 November 2, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$108
(Spirit)

One-way from

$56
(eDestinos)

Popular in

March

Cheapest in

September

Average price

$292
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
Search Deals
One-way flight from Chicago O'Hare Intl to Florida Keys
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($17 potential increase over avg. RT price).
Search Deals
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 November 2025
Search Deals

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 November 2, 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

Sun 11/23

11:40 am-3:47 pm

Nonstop3h 07m

Miami

Tue 11/25

8:10 am-10:35 am

Nonstop3h 25m

$123

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Thu 12/4

12:39 pm-4:50 pm

Nonstop3h 11m

Miami

Thu 12/11

12:23 pm-2:52 pm

Nonstop3h 29m

$157

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Tue 1/13

1:45 pm-8:05 pm

1 stop5h 20m

Miami

Sat 1/17

6:45 am-11:10 am

1 stop5h 25m

$217

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Thu 12/4

12:39 pm-4:50 pm

Nonstop3h 11m

Miami

Mon 12/8

5:56 pm-8:25 pm

Nonstop3h 29m

$219

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sat 12/6

2:30 pm-9:50 pm

1 stop6h 20m

Miami

Sun 12/7

6:00 am-10:14 am

1 stop5h 14m

$288

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Wed 1/14

1:54 pm-9:37 pm

1 stop6h 43m

Miami

Mon 1/19

7:15 am-1:39 pm

1 stop7h 24m

$288

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Fri 1/23

5:54 pm-12:51 am

1 stop5h 57m

Miami

Sun 1/25

6:00 am-10:08 am

1 stop5h 08m

$288

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Sat 12/13

11:22 am-8:06 pm

1 stop7h 44m

Key West

Thu 12/18

7:40 am-12:10 pm

1 stop5h 30m

$324

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Fri 11/28

11:00 am-3:19 pm

Nonstop3h 19m

Key West

Thu 12/4

4:05 pm-6:51 pm

Nonstop3h 46m

$328

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Sat 11/15

11:17 am-5:23 pm

1 stop5h 06m

Key West

Tue 11/18

7:40 am-12:04 pm

1 stop5h 24m

$329

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/31

Showing 1-10 of 41 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, December is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Florida Keys (average of $229). Flying from Chicago O'Hare Intl Airport to Florida Keys in August is currently the most expensive (average of $336). 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 November 2, 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 morning could potentially save you up to 48% 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 November 2, 2025.

The most flights from ORD to zzEOA are scheduled on a Monday (3 on average). You will have fewer flight options on Tuesday, 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 November 2, 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
7,999 reviews

Overall

7.9

Entertainment

7.9

Food

7.3

Comfort

7.9

Boarding

8.2

Crew

8.5

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
7,999 reviews
Delta
7.9
Good
7,999 reviews

Overall

7.9

Entertainment

7.9

Food

7.3

Comfort

7.9

Boarding

8.2

Crew

8.5

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
8,993 reviews
Delta
7.9
Good
7,999 reviews

Overall

7.9

Entertainment

7.9

Food

7.3

Comfort

7.9

Boarding

8.2

Crew

8.5

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
11,033 reviews
Delta
7.9
Good
7,999 reviews

Overall

7.9

Entertainment

7.9

Food

7.3

Comfort

7.9

Boarding

8.2

Crew

8.5

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
8,121 reviews
Delta
7.9
Good
7,999 reviews

Overall

7.9

Entertainment

7.9

Food

7.3

Comfort

7.9

Boarding

8.2

Crew

8.5

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
3,119 reviews
Delta
7.9
Good
7,999 reviews

Overall

7.9

Entertainment

7.9

Food

7.3

Comfort

7.9

Boarding

8.2

Crew

8.5

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 07m. 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 most reliable airlines from Chicago O'Hare Intl Airport to Florida Keys?

    Consider United Airlines (67%), Air New Zealand (67%) or Republic Airways (67%) 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 $253. While the most popular route (Chicago O'Hare Intl - Miami) can be booked for $63 on average, our data indicates $763 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, December is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Florida Keys (average of $229). Flying from Chicago O'Hare Intl Airport to Florida Keys in August is currently the most expensive (average of $336). 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.

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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 3 airlines flying from O'Hare Intl to Florida Keys

Discover the top 3 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 November 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$218Average$348FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$254Average$489FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$308Average$449FlexibilityNo cancel feeOn-time71%

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