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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 3/24. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — EYW
Apr 3 — Apr 101
Fri 4/3
Fri 4/10
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 March 4, 2026.

This Kiwi.com deal was found by Cheapflights users on 3/3. 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 3/99:18 am
ORD
-
MIA
Nonstop3h 18m
Spirit Airlines
Thu 3/126:00 am
MIA
-
ORD
Nonstop3h 25m
Spirit Airlines
Deal found 3/3$92
This CheapOair deal was found by Cheapflights users on 3/3. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/87:23 pm
ORD
-
MIA
Nonstop3h 16m
Multiple Airlines
Fri 3/1312:45 pm
MIA
-
ORD
Nonstop3h 38m
Multiple Airlines
Deal found 3/3$93
This Kiwi.com deal was found by Cheapflights users on 2/28. 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 3/29:18 am
ORD
-
MIA
Nonstop3h 18m
Multiple Airlines
Fri 3/1312:45 pm
MIA
-
ORD
Nonstop3h 38m
Multiple Airlines
Deal found 2/28$94
This Expedia deal was found by Cheapflights users on 3/2. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/183:52 pm
ORD
-
MIA
Nonstop3h 19m
Multiple Airlines
Tue 4/216:30 am
MIA
-
ORD
1 stop11h 41m
Multiple Airlines
Deal found 3/2$95
This Kiwi.com deal was found by Cheapflights users on 3/3. 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 4/910:55 am
ORD
-
MIA
Nonstop3h 05m
Multiple Airlines
Thu 4/169:21 pm
MIA
-
ORD
Nonstop3h 38m
Multiple Airlines
Deal found 3/3$96
This eDestinos deal was found by Cheapflights users on 2/27. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/204:58 pm
ORD
-
MIA
Nonstop3h 19m
Frontier
Thu 4/239:21 pm
MIA
-
ORD
Nonstop3h 38m
Frontier
Deal found 2/27$97
This Kiwi.com deal was found by Cheapflights users on 3/2. 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.
Mon 3/27:23 pm
ORD
-
MIA
Nonstop3h 16m
Spirit Airlines
Thu 3/126:00 am
MIA
-
ORD
Nonstop3h 25m
Spirit Airlines
Deal found 3/2$98
This Kiwi.com deal was found by Cheapflights users on 3/4. 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 5/93:52 pm
ORD
-
MIA
Nonstop3h 19m
Multiple Airlines
Sat 5/164:59 pm
MIA
-
ORD
1 stop5h 13m
Multiple Airlines
Deal found 3/4$99
This Cheapflightsfares deal was found by Cheapflights users on 3/3. 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 5/107:50 am
ORD
-
MIA
Nonstop3h 08m
Spirit Airlines
Sat 5/1611:37 am
MIA
-
ORD
Nonstop3h 28m
Spirit Airlines
Deal found 3/3$100
This Trip.com deal was found by Cheapflights users on 2/28. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/204:58 pm
ORD
-
MIA
Nonstop3h 19m
Frontier
Wed 4/2211:10 am
MIA
-
ORD
1 stop6h 50m
Frontier
Deal found 2/28$101
This Kiwi.com deal was found by Cheapflights users on 3/3. 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 4/253:52 pm
ORD
-
MIA
Nonstop3h 19m
Frontier
Thu 4/303:15 pm
MIA
-
ORD
1 stop10h 37m
Frontier
Deal found 3/3$102
This Cheapflightsfares deal was found by Cheapflights users on 3/2. 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 3/99:05 pm
ORD
-
MIA
Nonstop3h 15m
Frontier
Mon 3/166:00 am
MIA
-
ORD
Nonstop3h 38m
Frontier
Deal found 3/2$103

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 March 4, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$93
(Kiwi.com)

One-way from

$45
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$303
Provider with most accurate pricing for Chicago (CHI)-Miami flight deals.
Search Deals
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. 10% potential increase in price ($31 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 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 March 4, 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

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Mon 3/30

4:51 pm-8:57 pm

Nonstop3h 06m

Miami

Mon 4/6

9:45 pm-8:50 am

1 stop12h 05m

$178

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Mon 5/4

2:40 pm-9:25 pm

1 stop5h 45m

Miami

Sat 5/9

9:30 am-3:30 pm

1 stop7h 00m

$263

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Wed 6/24

11:10 am-5:21 pm

1 stop5h 11m

Miami

Tue 7/7

8:05 am-12:39 pm

1 stop5h 34m

$287

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Sat 4/25

7:00 am-11:24 am

Nonstop3h 24m

Key West

Wed 4/29

4:38 pm-12:45 am

1 stop9h 07m

$339

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Mon 4/20

7:00 am-11:22 am

Nonstop3h 22m

Miami

Tue 4/28

9:00 am-5:05 pm

1 stop9h 05m

$342

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Wed 4/29

7:14 am-3:37 pm

1 stop7h 23m

Key West

Sat 5/2

6:18 pm-11:59 pm

1 stop6h 41m

$345

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Tue 3/17

10:39 am-2:55 pm

Nonstop3h 16m

Key West

Mon 3/23

7:00 am-9:48 am

Nonstop3h 48m

$354

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Tue 7/14

11:10 am-5:21 pm

1 stop5h 11m

Miami

Mon 7/20

6:00 am-10:04 am

1 stop5h 04m

$362

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Tue 7/7

3:05 pm-10:45 am

2 stops18h 40m

Miami

Tue 7/14

6:00 am-1:15 pm

2 stops8h 15m

$365

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Thu 3/19

10:39 am-2:55 pm

Nonstop3h 16m

Key West

Tue 3/24

4:05 pm-6:44 pm

Nonstop3h 39m

$377

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/1

Showing 1-10 of 41 resultsSorted by cheapest first
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2
3
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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 $245). Flying from Chicago O'Hare Intl Airport to Florida Keys in November 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 March 4, 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.

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 March 4, 2026.
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
8,245 reviews

Comfort

7.9

Overall

7.9

Crew

8.5

Entertainment

7.8

Boarding

8.1

Food

7.2

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
8,245 reviews
Delta
7.9
Good
8,245 reviews

Comfort

7.9

Overall

7.9

Crew

8.5

Entertainment

7.8

Boarding

8.1

Food

7.2

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
9,382 reviews
Delta
7.9
Good
8,245 reviews

Comfort

7.9

Overall

7.9

Crew

8.5

Entertainment

7.8

Boarding

8.1

Food

7.2

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
7.1
Good
11,379 reviews
Delta
7.9
Good
8,245 reviews

Comfort

7.9

Overall

7.9

Crew

8.5

Entertainment

7.8

Boarding

8.1

Food

7.2

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
8,490 reviews
Delta
7.9
Good
8,245 reviews

Comfort

7.9

Overall

7.9

Crew

8.5

Entertainment

7.8

Boarding

8.1

Food

7.2

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
5.7
Fair
3,041 reviews
Delta
7.9
Good
8,245 reviews

Comfort

7.9

Overall

7.9

Crew

8.5

Entertainment

7.8

Boarding

8.1

Food

7.2

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 06m. 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 Spirit Airlines and JetBlue, with prices starting from $37 and $68, respectively.

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

    Consider Republic Airways (88%), American Airlines (88%) or Envoy Air (88%) 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 $68 on average, our data indicates $461 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 $245). Flying from Chicago O'Hare Intl Airport to Florida Keys in November 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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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 March 4, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$145Average$385FlexibilityNo cancel feeOn-time65%
DeltaCheapest$248Average$353FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$249Average$436FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$322Average$462FlexibilityNo cancel feeOn-time71%

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