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Florida Keys

$64+ 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 9/29. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — EYW
Aug 25 — Sep 11
Mon 8/25
Mon 9/1
1 adult, Economy
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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 August 20, 2025.

Round-trip from

$121
(Cheapflightsfares)

One-way from

$64
(FlightHub)

Popular in

March

Cheapest in

September

Average price

$237
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 August 2025
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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 August 20, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 8/20. 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.
Fri 9/1210:27 amORD - MIA
Nonstop3h 12mSpirit Airlines
Mon 9/157:00 amMIA - ORD
Nonstop3h 18mSpirit Airlines
Deal found 8/20$121
This Cheapflightsfares deal was found by Cheapflights users on 8/19. 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 9/811:13 amORD - MIA
1 stop11h 04mSpirit Airlines
Wed 9/177:00 amMIA - ORD
Nonstop3h 18mSpirit Airlines
Deal found 8/19$123
This Cheapflightsfares deal was found by Cheapflights users on 8/20. 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 9/410:27 amORD - MIA
Nonstop3h 12mSpirit Airlines
Mon 9/87:00 amMIA - ORD
Nonstop3h 18mSpirit Airlines
Deal found 8/20$124
This Kiwi.com deal was found by Cheapflights users on 8/19. 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.
Fri 9/1910:27 amORD - MIA
Nonstop3h 12mMultiple Airlines
Mon 9/296:59 pmMIA - ORD
1 stop6h 11mMultiple Airlines
Deal found 8/19$125
This Priceline deal was found by Cheapflights users on 8/19. 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.
Wed 10/811:00 amORD - MIA
1 stop6h 45mMultiple Airlines
Sat 10/116:00 amMIA - ORD
Nonstop3h 18mMultiple Airlines
Deal found 8/19$126
This Kiwi.com deal was found by Cheapflights users on 8/18. 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 10/2211:00 amORD - MIA
1 stop6h 45mMultiple Airlines
Fri 10/247:00 amMIA - ORD
Nonstop3h 22mMultiple Airlines
Deal found 8/18$127
This Kiwi.com deal was found by Cheapflights users on 8/19. 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.
Sat 10/189:24 pmORD - MIA
1 stop11h 17mSpirit Airlines
Thu 10/237:00 amMIA - ORD
Nonstop3h 22mSpirit Airlines
Deal found 8/19$128
This Kiwi.com deal was found by Cheapflights users on 8/18. 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.
Mon 9/1510:27 amORD - MIA
Nonstop3h 12mMultiple Airlines
Thu 9/184:00 pmMIA - ORD
1 stop8h 20mMultiple Airlines
Deal found 8/18$129
This Kiwi.com deal was found by Cheapflights users on 8/18. 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.
Fri 10/2411:51 amORD - MIA
1 stop7h 56mMultiple Airlines
Sun 10/267:00 amMIA - ORD
Nonstop3h 22mMultiple Airlines
Deal found 8/18$130
This Kiwi.com deal was found by Cheapflights users on 8/18. 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.
Sun 9/1410:27 amORD - MIA
Nonstop3h 12mSpirit Airlines
Tue 9/237:00 amMIA - ORD
Nonstop3h 18mSpirit Airlines
Deal found 8/18$131
This SmartFares deal was found by Cheapflights users on 8/18. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/210:27 amORD - MIA
Nonstop3h 12mSpirit Airlines
Thu 10/97:00 amMIA - ORD
Nonstop3h 22mSpirit Airlines
Deal found 8/18$132
This Kiwi.com deal was found by Cheapflights users on 8/18. 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.
Mon 9/1511:36 amORD - MIA
1 stop9h 02mMultiple Airlines
Sat 9/277:00 amMIA - ORD
Nonstop3h 18mMultiple Airlines
Deal found 8/18$133

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 August 20, 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 11/9

2:02 pm-6:17 pm

Nonstop3h 15m

Miami

Tue 11/18

12:23 pm-2:52 pm

Nonstop3h 29m

$137

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Mon 9/22

10:54 am-3:10 pm

Nonstop3h 16m

Miami

Fri 9/26

12:27 pm-2:55 pm

Nonstop3h 28m

$137

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Fri 9/12

10:27 am-2:39 pm

Nonstop3h 12m

Miami

Sun 9/14

7:00 am-9:18 am

Nonstop3h 18m

$138

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Thu 9/11

6:21 pm-8:29 am

1 stop13h 08m

Miami

Mon 9/15

7:00 am-9:18 am

Nonstop3h 18m

$138

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Wed 2/4

7:35 am-9:59 pm

1 stop13h 24m

Miami

Wed 2/11

10:15 am-12:30 pm

Nonstop3h 15m

$146

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Wed 1/28

1:35 pm-5:50 pm

Nonstop3h 15m

Miami

Mon 2/2

10:15 am-12:30 pm

Nonstop3h 15m

$156

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Fri 9/19

1:30 pm-11:05 pm

1 stop8h 35m

Miami

Fri 9/26

4:10 pm-11:05 pm

1 stop7h 55m

$157

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Fri 9/19

1:30 pm-11:05 pm

1 stop8h 35m

Miami

Tue 9/30

7:45 am-12:45 pm

1 stop6h 00m

$157

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sat 9/27

1:30 pm-8:35 pm

1 stop6h 05m

Miami

Tue 10/7

6:55 am-1:05 pm

1 stop7h 10m

$157

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Thu 10/2

7:00 am-6:15 pm

1 stop10h 15m

Miami

Sat 10/4

6:00 am-11:50 am

1 stop6h 50m

$157

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/20

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, August is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Florida Keys (average of $328). Flying from Chicago O'Hare Intl Airport to Florida Keys in March is currently the most expensive (average of $492). 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 August 20, 2025.

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 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 August 20, 2025.
Get a feel of what it's like to fly with Southwest, 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.
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Food

7.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Food

7.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
United Airlines
7.4
Good
8,928 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Food

7.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Food

7.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Spirit Airlines
6.3
Okay
8,039 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Food

7.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Frontier
5.8
Fair
3,207 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Food

7.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

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 12m. Airlines will cover a distance of 1198 mi. Generally, flights for this route are nonstop.

  • 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 $249. While the most popular route (Chicago O'Hare Intl - Miami) can be booked for $73 on average our data indicates $414 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, August is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Florida Keys (average of $328). Flying from Chicago O'Hare Intl Airport to Florida Keys in March is currently the most expensive (average of $492). 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 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 August 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$216Average$333FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$261Average$479FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$295Average$440FlexibilityNo cancel feeOn-time71%

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