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Florida Keys

$61+ 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 12/9. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — EYW
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
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 September 17, 2025.

Round-trip from

$104
(Kiwi.com)

One-way from

$61
(Kiwi.com)

Popular in

March

Cheapest in

September

Average price

$231
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. 6% potential increase in price ($17 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 September 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 September 17, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
Thu 10/3010:27 amORD - MIA
Nonstop3h 02mSpirit Airlines
Sun 11/27:00 amMIA - ORD
Nonstop3h 22mSpirit Airlines
Deal found 9/16$104
This Cheapflightsfares deal was found by Cheapflights users on 9/16. 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 10/610:27 amORD - MIA
Nonstop3h 02mSpirit Airlines
Sat 10/116:00 amMIA - ORD
Nonstop3h 18mSpirit Airlines
Deal found 9/16$105
This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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 10/910:27 amORD - MIA
Nonstop3h 02mSpirit Airlines
Sun 10/127:00 amMIA - ORD
Nonstop3h 22mSpirit Airlines
Deal found 9/15$107
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 12/31:35 pmORD - MIA
Nonstop3h 15mSpirit Airlines
Fri 12/1210:15 amMIA - ORD
Nonstop3h 15mSpirit Airlines
Deal found 9/15$108
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 12/81:35 pmORD - MIA
Nonstop3h 15mSpirit Airlines
Tue 12/910:15 amMIA - ORD
Nonstop3h 15mSpirit Airlines
Deal found 9/15$109
This Priceline deal was found by Cheapflights users on 9/15. 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.
Mon 10/610:27 amORD - MIA
Nonstop3h 02mMultiple Airlines
Thu 10/94:49 pmMIA - ORD
1 stop9h 19mMultiple Airlines
Deal found 9/15$110
This Cheapflightsfares deal was found by Cheapflights users on 9/16. 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 10/110:27 amORD - MIA
Nonstop3h 12mSpirit Airlines
Sat 10/47:00 amMIA - ORD
Nonstop3h 18mSpirit Airlines
Deal found 9/16$112
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 10/510:27 amORD - MIA
Nonstop3h 02mSpirit Airlines
Thu 10/167:00 amMIA - ORD
Nonstop3h 22mSpirit Airlines
Deal found 9/14$113
This Priceline deal was found by Cheapflights users on 9/15. 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.
Sat 10/111:14 pmORD - MIA
1 stop9h 29mMultiple Airlines
Sat 10/186:00 amMIA - ORD
Nonstop3h 18mMultiple Airlines
Deal found 9/15$116
This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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 10/110:27 amORD - MIA
Nonstop3h 12mSpirit Airlines
Thu 10/97:00 amMIA - ORD
Nonstop3h 22mSpirit Airlines
Deal found 9/15$117
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 10/510:27 amORD - MIA
Nonstop3h 02mSpirit Airlines
Mon 10/137:00 amMIA - ORD
Nonstop3h 22mSpirit Airlines
Deal found 9/14$118
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 9/2910:27 amORD - MIA
Nonstop3h 12mSpirit Airlines
Wed 10/17:00 amMIA - ORD
Nonstop3h 18mSpirit Airlines
Deal found 9/15$119

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 September 17, 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

Fri 10/3

10:27 am-2:39 pm

Nonstop3h 12m

Miami

Sun 10/5

7:00 am-9:22 am

Nonstop3h 22m

$148

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Wed 10/22

6:00 am-2:17 pm

1 stop7h 17m

Miami

Wed 10/29

7:00 am-9:29 am

Nonstop3h 29m

$197

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sat 11/15

1:45 pm-9:40 pm

2 stops6h 55m

Miami

Sun 12/7

6:55 am-11:10 am

1 stop5h 15m

$222

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Fri 10/3

10:54 am-3:11 pm

Nonstop3h 17m

Miami

Tue 10/7

4:17 pm-6:47 pm

Nonstop3h 30m

$222

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Fri 12/12

5:05 am-1:30 pm

1 stop7h 25m

Key West

Mon 12/15

2:25 pm-11:42 pm

1 stop10h 17m

$223

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sat 12/6

6:22 pm-12:46 am

1 stop5h 24m

Miami

Thu 12/18

8:05 am-1:51 pm

1 stop6h 46m

$227

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Tue 12/16

2:32 pm-9:42 pm

1 stop6h 10m

Miami

Tue 12/23

6:23 pm-11:58 pm

1 stop6h 35m

$227

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Mon 11/24

9:46 am-3:47 pm

1 stop5h 01m

Miami

Thu 12/4

12:00 pm-4:18 pm

1 stop5h 18m

$227

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sat 10/18

7:30 am-11:47 am

Nonstop3h 17m

Miami

Sat 10/18

4:17 pm-6:47 pm

Nonstop3h 30m

$257

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Tue 9/30

5:30 am-1:28 pm

1 stop6h 58m

Miami

Wed 10/1

6:00 am-10:10 am

1 stop5h 10m

$257

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 40 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 $491). 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 September 17, 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 September 17, 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
4,242 reviews

Overall

8.0

Boarding

8.1

Food

7.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

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
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Boarding

8.1

Food

7.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

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
8,926 reviews
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Boarding

8.1

Food

7.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

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
4,242 reviews

Overall

8.0

Boarding

8.1

Food

7.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

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
8,023 reviews
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Boarding

8.1

Food

7.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

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
3,173 reviews
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Boarding

8.1

Food

7.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

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. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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 $216. While the most popular route (Chicago O'Hare Intl - Miami) can be booked for $85 on average, our data indicates $374 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 $491). 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 September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$218Average$345FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$258Average$485FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$303Average$440FlexibilityNo cancel feeOn-time71%

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