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$101+ 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 9/10. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — EYW
Aug 27 — Sep 31
Thu 8/27
Thu 9/3
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 July 28, 2026.

This United Airlines deal was found by Cheapflights users on 7/28. 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.
Fri 10/306:12 pm
ORD
-
MIA
Nonstop3h 19m
United Airlines
Tue 11/35:34 pm
MIA
-
ORD
1 stop7h 15m
United Airlines
Deal found 7/28$182
This United Airlines deal was found by Cheapflights users on 7/27. 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.
Sat 11/72:25 pm
ORD
-
MIA
Nonstop3h 20m
United Airlines
Wed 11/115:34 pm
MIA
-
ORD
1 stop7h 15m
United Airlines
Deal found 7/27$184
This United Airlines deal was found by Cheapflights users on 7/28. 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 12/99:00 am
ORD
-
MIA
1 stop7h 35m
United Airlines
Sat 12/126:00 pm
MIA
-
ORD
Nonstop3h 25m
United Airlines
Deal found 7/28$185
This United Airlines deal was found by Cheapflights users on 7/28. 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.
Tue 8/1810:32 am
ORD
-
MIA
Nonstop3h 22m
United Airlines
Sat 8/2211:30 am
MIA
-
ORD
1 stop9h 35m
United Airlines
Deal found 7/28$191
This United Airlines deal was found by Cheapflights users on 7/27. 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 8/266:00 am
ORD
-
MIA
1 stop7h 46m
United Airlines
Wed 9/21:44 pm
MIA
-
ORD
1 stop5h 53m
United Airlines
Deal found 7/27$196
This United Airlines deal was found by Cheapflights users on 7/25. 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.
Sat 11/143:25 pm
ORD
-
MIA
1 stop7h 33m
United Airlines
Mon 11/169:00 am
MIA
-
ORD
Nonstop3h 34m
United Airlines
Deal found 7/25$198
This Kiwi.com deal was found by Cheapflights users on 7/28. 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 8/258:45 am
ORD
-
MIA
1 stop28h 48m
Frontier
Tue 9/18:00 am
MIA
-
ORD
1 stop8h 59m
Frontier
Deal found 7/28$200
This United Airlines deal was found by Cheapflights users on 7/27. 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.
Sat 9/122:16 pm
ORD
-
MIA
1 stop7h 18m
United Airlines
Mon 9/143:57 pm
MIA
-
ORD
Nonstop3h 33m
United Airlines
Deal found 7/27$201
This Kiwi.com deal was found by Cheapflights users on 7/28. 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 8/241:59 pm
ORD
-
MIA
1 stop8h 06m
Frontier
Tue 9/111:10 am
MIA
-
ORD
1 stop9h 58m
Frontier
Deal found 7/28$205
This Kiwi.com deal was found by Cheapflights users on 7/28. 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 8/258:45 am
ORD
-
MIA
1 stop28h 48m
Frontier
Wed 9/211:10 am
MIA
-
ORD
1 stop9h 58m
Frontier
Deal found 7/28$206
This Kiwi.com deal was found by Cheapflights users on 7/28. 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 8/261:59 pm
ORD
-
MIA
1 stop8h 06m
Frontier
Tue 9/111:10 am
MIA
-
ORD
1 stop9h 58m
Frontier
Deal found 7/28$207
This Kiwi.com deal was found by Cheapflights users on 7/25. 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 8/247:05 am
ORD
-
MIA
1 stop8h 16m
Frontier
Mon 8/316:50 am
MIA
-
ORD
1 stop18h 59m
Frontier
Deal found 7/25$208

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 July 28, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$191
(United Airlines)

One-way from

$101
(Kiwi.com)

Popular in

July

Cheapest in

January

Average price

$386
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.
Search Deals
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. 15% potential increase in price ($53 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in July 2026
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 July 28, 2026.
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

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Wed 9/2

6:00 am-2:46 pm

1 stop7h 46m

Miami

Tue 10/6

7:00 am-12:54 pm

1 stop6h 54m

$196

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Wed 9/9

10:25 am-6:52 pm

1 stop7h 27m

Miami

Wed 9/16

5:37 pm-12:28 am

1 stop7h 51m

$211

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sat 10/17

6:14 pm-12:53 am

1 stop5h 39m

Miami

Sat 10/24

8:10 am-2:30 pm

1 stop7h 20m

$227

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Thu 9/10

8:55 am-5:37 pm

1 stop7h 42m

Miami

Mon 9/14

7:40 pm-11:59 pm

1 stop5h 19m

$227
Quickest round-trip

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Mon 8/24

7:30 am-11:54 am

Nonstop3h 24m

Miami

Wed 8/26

3:57 pm-6:30 pm

Nonstop3h 33m

$261

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sat 9/19

7:30 am-11:54 am

Nonstop3h 24m

Miami

Fri 9/25

8:54 am-2:45 pm

1 stop6h 51m

$302

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Thu 8/20

7:30 am-11:54 am

Nonstop3h 24m

Miami

Sun 8/23

3:57 pm-6:30 pm

Nonstop3h 33m

$316

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Wed 8/26

6:00 am-2:46 pm

1 stop7h 46m

Miami

Sun 8/30

3:57 pm-6:30 pm

Nonstop3h 33m

$322

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Wed 9/9

1:51 pm-8:00 pm

1 stop5h 09m

Key West

Wed 9/16

11:42 am-4:37 pm

1 stop5h 55m

$326

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Thu 8/27

11:23 am-7:57 pm

1 stop7h 34m

Key West

Tue 9/1

6:15 pm-11:57 pm

1 stop6h 42m

$339

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/26

Showing 1-10 of 45 resultsSorted by cheapest first
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5

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 $242). Flying from Chicago O'Hare Intl Airport to Florida Keys in June is currently the most expensive (average of $387). 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 July 28, 2026.

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.

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 July 28, 2026.

The most flights from ORD to zzEOA are scheduled on a Monday (3 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (2 on average).

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 40 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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 July 28, 2026.
Get a feel of what it's like to fly with Delta,United Airlines, andAmerican 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
7.8
Good
8,482 reviews

Crew

8.5

Food

7.2

Overall

7.8

Boarding

8.1

Entertainment

7.8

Comfort

7.8

Reviews

1 / 20
4.0
Okay

Joel,May 2026

ATL - JAX

The flight was delivered 50 minutes and taxing took what felt like 20 minutes to takeoff.
Delta
7.8
Good
8,482 reviews
Delta
7.8
Good
8,482 reviews

Crew

8.5

Food

7.2

Overall

7.8

Boarding

8.1

Entertainment

7.8

Comfort

7.8

Reviews

1 / 20
4.0
Okay

Joel,May 2026

ATL - JAX

The flight was delivered 50 minutes and taxing took what felt like 20 minutes to takeoff.
United Airlines
7.4
Good
10,046 reviews
Delta
7.8
Good
8,482 reviews

Crew

8.5

Food

7.2

Overall

7.8

Boarding

8.1

Entertainment

7.8

Comfort

7.8

Reviews

1 / 20
4.0
Okay

Joel,May 2026

ATL - JAX

The flight was delivered 50 minutes and taxing took what felt like 20 minutes to takeoff.
American Airlines
7.1
Good
11,839 reviews
Delta
7.8
Good
8,482 reviews

Crew

8.5

Food

7.2

Overall

7.8

Boarding

8.1

Entertainment

7.8

Comfort

7.8

Reviews

1 / 20
4.0
Okay

Joel,May 2026

ATL - JAX

The flight was delivered 50 minutes and taxing took what felt like 20 minutes to takeoff.
JetBlue
7.1
Good
3,025 reviews
Delta
7.8
Good
8,482 reviews

Crew

8.5

Food

7.2

Overall

7.8

Boarding

8.1

Entertainment

7.8

Comfort

7.8

Reviews

1 / 20
4.0
Okay

Joel,May 2026

ATL - JAX

The flight was delivered 50 minutes and taxing took what felt like 20 minutes to takeoff.
Frontier
5.6
Fair
2,753 reviews
Delta
7.8
Good
8,482 reviews

Crew

8.5

Food

7.2

Overall

7.8

Boarding

8.1

Entertainment

7.8

Comfort

7.8

Reviews

1 / 20
4.0
Okay

Joel,May 2026

ATL - JAX

The flight was delivered 50 minutes and taxing took what felt like 20 minutes to takeoff.

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 5h 39m. 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?

    $36 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 $78, respectively.

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

    Consider Republic Airways (96%), United Airlines (94%) or American Airlines (90%) 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 $261. While the most popular route (Chicago O'Hare Intl - Miami) can be booked for $171 on average, our data indicates $380 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 $242). Flying from Chicago O'Hare Intl Airport to Florida Keys in June is currently the most expensive (average of $387). 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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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 July 28, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$206Average$418FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$249Average$413FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$308Average$475FlexibilityNo cancel feeOn-time71%

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