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$49+ 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 4/6. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — EYW
May 3 — May 101
Sun 5/3
Sun 5/10
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 April 3, 2026.

This Kiwi.com deal was found by Cheapflights users on 3/31. 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.
Tue 4/214:03 pm
ORD
-
MIA
1 stop6h 48m
Spirit Airlines
Sat 4/2511:37 am
MIA
-
ORD
Nonstop3h 28m
Spirit Airlines
Deal found 3/31$99
This Cheapflightsfares deal was found by Cheapflights users on 3/31. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/114:51 pm
ORD
-
MIA
Nonstop3h 06m
Spirit Airlines
Sat 4/184:59 pm
MIA
-
ORD
1 stop5h 13m
Spirit Airlines
Deal found 3/31$100
This Priceline deal was found by Cheapflights users on 4/2. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/75:45 pm
ORD
-
MIA
Nonstop3h 18m
Multiple Airlines
Mon 5/119:30 pm
MIA
-
ORD
Nonstop3h 26m
Multiple Airlines
Deal found 4/2$101
This CheapOair deal was found by Cheapflights users on 3/29. 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.
Mon 4/2011:28 am
ORD
-
MIA
1 stop10h 03m
Multiple Airlines
Thu 4/309:21 pm
MIA
-
ORD
Nonstop3h 38m
Multiple Airlines
Deal found 3/29$102
This Cheapflightsfares deal was found by Cheapflights users on 4/1. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/1310:55 am
ORD
-
MIA
Nonstop3h 05m
Spirit Airlines
Sat 4/1811:37 am
MIA
-
ORD
Nonstop3h 28m
Spirit Airlines
Deal found 4/1$103
This CheapOair deal was found by Cheapflights users on 4/1. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/134:51 pm
ORD
-
MIA
Nonstop3h 06m
Spirit Airlines
Thu 4/1610:41 am
MIA
-
ORD
Nonstop3h 24m
Spirit Airlines
Deal found 4/1$104
This Cheapflightsfares deal was found by Cheapflights users on 3/29. 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 4/163:52 pm
ORD
-
MIA
Nonstop3h 19m
Frontier
Mon 4/2010:17 pm
MIA
-
ORD
Nonstop3h 38m
Frontier
Deal found 3/29$105
This Expedia deal was found by Cheapflights users on 3/31. 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 Expedia 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
Multiple Airlines
Tue 4/286:30 am
MIA
-
ORD
1 stop11h 41m
Multiple Airlines
Deal found 3/31$106
This Mytrip deal was found by Cheapflights users on 3/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/186:40 am
ORD
-
MIA
Nonstop3h 02m
Spirit Airlines
Sat 4/258:00 am
MIA
-
ORD
1 stop14h 12m
Spirit Airlines
Deal found 3/30$107
This CheapOair deal was found by Cheapflights users on 3/31. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/63:15 pm
ORD
-
MIA
Nonstop3h 19m
Multiple Airlines
Thu 4/97:20 am
MIA
-
ORD
Nonstop3h 30m
Multiple Airlines
Deal found 3/31$108
This Cheapflightsfares deal was found by Cheapflights users on 4/3. 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.
Fri 5/17:50 am
ORD
-
MIA
Nonstop3h 08m
Spirit Airlines
Fri 5/89:30 pm
MIA
-
ORD
Nonstop3h 26m
Spirit Airlines
Deal found 4/3$109
This Kiwi.com deal was found by Cheapflights users on 4/1. 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.
Sun 5/108:30 am
ORD
-
EYW
1 stop27h 01m
Multiple Airlines
Thu 5/1412:05 pm
EYW
-
ORD
1 stop12h 08m
Multiple Airlines
Deal found 4/1$314

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 April 3, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$99
(Kiwi.com)

One-way from

$49
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$257
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. 10% potential increase in price ($32 potential increase over avg. RT price).
Search Deals
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 April 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 April 3, 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

Sat 5/2

1:55 pm-10:05 pm

2 stops7h 10m

Miami

Sat 5/9

6:15 am-3:30 pm

2 stops10h 15m

$187

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sat 5/23

1:55 pm-11:15 pm

2 stops8h 20m

Miami

Sat 5/30

6:15 am-1:10 pm

1 stop7h 55m

$214
Quickest round-trip

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sat 4/25

8:50 am-1:08 pm

Nonstop3h 18m

Miami

Tue 4/28

12:24 pm-3:03 pm

Nonstop3h 39m

$221

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sat 4/25

7:00 am-11:22 am

Nonstop3h 22m

Miami

Wed 4/29

12:24 pm-3:03 pm

Nonstop3h 39m

$221

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Thu 5/14

3:05 pm-10:00 pm

1 stop5h 55m

Miami

Mon 5/18

5:30 am-3:30 pm

2 stops11h 00m

$246

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Mon 5/4

2:40 pm-10:00 pm

2 stops6h 20m

Miami

Thu 5/7

6:20 am-3:30 pm

2 stops10h 10m

$251

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Fri 5/8

2:40 pm-10:00 pm

2 stops6h 20m

Miami

Mon 5/11

5:30 am-3:30 pm

2 stops11h 00m

$269

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Tue 4/21

8:15 am-3:35 pm

1 stop6h 20m

Miami

Wed 4/29

4:43 pm-9:25 pm

1 stop5h 42m

$298

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Tue 5/12

10:35 am-2:57 pm

Nonstop3h 22m

Miami

Mon 5/18

7:40 pm-10:20 pm

Nonstop3h 40m

$300

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Sat 9/19

1:15 pm-7:45 pm

1 stop5h 30m

Key West

Fri 9/25

2:35 pm-9:45 pm

1 stop8h 10m

$329

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/3

Showing 1-10 of 42 resultsSorted by cheapest first
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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, January is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Florida Keys (average of $246). 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 April 3, 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 April 3, 2026.

The most flights from ORD to zzEOA are scheduled on a Monday (4 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 April 3, 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
7.9
Good
8,383 reviews

Boarding

8.1

Food

7.2

Crew

8.5

Entertainment

7.8

Overall

7.9

Comfort

7.9

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
8,383 reviews
Delta
7.9
Good
8,383 reviews

Boarding

8.1

Food

7.2

Crew

8.5

Entertainment

7.8

Overall

7.9

Comfort

7.9

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
9,542 reviews
Delta
7.9
Good
8,383 reviews

Boarding

8.1

Food

7.2

Crew

8.5

Entertainment

7.8

Overall

7.9

Comfort

7.9

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
11,554 reviews
Delta
7.9
Good
8,383 reviews

Boarding

8.1

Food

7.2

Crew

8.5

Entertainment

7.8

Overall

7.9

Comfort

7.9

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
8,583 reviews
Delta
7.9
Good
8,383 reviews

Boarding

8.1

Food

7.2

Crew

8.5

Entertainment

7.8

Overall

7.9

Comfort

7.9

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
3,000 reviews
Delta
7.9
Good
8,383 reviews

Boarding

8.1

Food

7.2

Crew

8.5

Entertainment

7.8

Overall

7.9

Comfort

7.9

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 18m. 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 United Airlines (84%), American Airlines (83%) or Envoy Air (83%) 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 $67 on average, our data indicates $405 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 $246). 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

Browse thousands of different options on Cheapflights for your next trip

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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 April 3, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$145Average$376FlexibilityNo cancel feeOn-time65%
DeltaCheapest$248Average$353FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$249Average$427FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$309Average$465FlexibilityNo cancel feeOn-time71%

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