HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Florida Keys

$66+ 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 5/14. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — EYW
May 31 — Jun 71
Sun 5/31
Sun 6/7
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from O'Hare Intl to Florida Keys with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 May 1, 2026.

This Kiwi.com deal was found by Cheapflights users on 4/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/119:20 am
ORD
-
MIA
Nonstop3h 08m
Multiple Airlines
Thu 5/142:17 pm
MIA
-
ORD
Nonstop3h 37m
Multiple Airlines
Deal found 4/27$135
This Kiwi.com deal was found by Cheapflights users on 4/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/271:50 pm
ORD
-
MIA
1 stop7h 57m
Frontier
Wed 6/311:23 am
MIA
-
ORD
1 stop9h 28m
Frontier
Deal found 4/27$136
This Priceline deal was found by Cheapflights users on 4/26. 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 5/145:49 pm
ORD
-
MIA
Nonstop3h 18m
Multiple Airlines
Thu 5/219:30 pm
MIA
-
ORD
Nonstop3h 26m
Multiple Airlines
Deal found 4/26$137
This Cheapflightsfares deal was found by Cheapflights users on 4/27. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/47:10 am
ORD
-
MIA
Nonstop3h 13m
Spirit Airlines
Thu 7/99:44 am
MIA
-
ORD
Nonstop3h 19m
Spirit Airlines
Deal found 4/27$139
This Kiwi.com deal was found by Cheapflights users on 4/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/14:05 pm
ORD
-
MIA
1 stop7h 39m
Frontier
Tue 6/95:26 pm
MIA
-
ORD
1 stop15h 37m
Frontier
Deal found 4/30$140
This Kiwi.com deal was found by Cheapflights users on 4/28. 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.
Thu 5/145:49 pm
ORD
-
MIA
Nonstop3h 18m
Multiple Airlines
Fri 5/159:30 pm
MIA
-
ORD
Nonstop3h 26m
Multiple Airlines
Deal found 4/28$141
This Kiwi.com deal was found by Cheapflights users on 4/28. 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 5/196:55 am
ORD
-
MIA
1 stop8h 32m
Frontier
Wed 5/2711:23 am
MIA
-
ORD
1 stop9h 18m
Frontier
Deal found 4/28$145
This Kiwi.com deal was found by Cheapflights users on 4/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/145:49 pm
ORD
-
MIA
Nonstop3h 18m
Frontier
Tue 5/265:22 pm
MIA
-
ORD
1 stop15h 33m
Frontier
Deal found 4/27$146
This CheapOair deal was found by Cheapflights users on 4/26. 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.
Thu 5/145:49 pm
ORD
-
MIA
Nonstop3h 18m
Frontier
Tue 5/1911:23 am
MIA
-
ORD
1 stop9h 28m
Frontier
Deal found 4/26$147
This Cheapflightsfares deal was found by Cheapflights users on 4/30. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/117:10 am
ORD
-
MIA
Nonstop3h 13m
Spirit Airlines
Fri 7/179:44 am
MIA
-
ORD
Nonstop3h 19m
Spirit Airlines
Deal found 4/30$149
This American Airlines deal was found by Cheapflights users on 4/27. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/211:46 am
ORD
-
EYW
Nonstop3h 27m
American Airlines
Tue 6/911:28 am
EYW
-
ORD
1 stop7h 16m
American Airlines
Deal found 4/27$319
This Kiwi.com deal was found by Cheapflights users on 4/26. 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 5/165:30 pm
ORD
-
EYW
1 stop16h 55m
Multiple Airlines
Wed 5/2011:46 am
EYW
-
ORD
2 stops12h 29m
Multiple Airlines
Deal found 4/26$321

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 May 1, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$135
(Kiwi.com)

One-way from

$66
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$280
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. 9% potential increase in price ($29 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 May 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 May 1, 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

Tue 5/26

6:05 pm-10:27 pm

Nonstop3h 22m

Miami

Tue 6/2

12:30 pm-3:13 pm

Nonstop3h 43m

$199

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Tue 6/2

6:05 pm-10:27 pm

Nonstop3h 22m

Miami

Wed 6/3

4:53 pm-12:45 am

1 stop8h 52m

$209

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Mon 5/25

7:00 am-11:24 am

Nonstop3h 24m

Miami

Wed 5/27

12:30 pm-3:13 pm

Nonstop3h 43m

$210
Quickest round-trip

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Mon 5/18

7:14 am-11:37 am

Nonstop3h 23m

Miami

Wed 5/20

12:10 pm-2:50 pm

Nonstop3h 40m

$210

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Wed 6/17

7:00 am-11:24 am

Nonstop3h 24m

Miami

Tue 6/30

4:53 pm-12:45 am

1 stop8h 52m

$299

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Thu 5/28

6:05 pm-10:27 pm

Nonstop3h 22m

Miami

Mon 6/1

5:24 pm-8:08 pm

Nonstop3h 44m

$311

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sat 7/4

7:00 am-11:24 am

Nonstop3h 24m

Miami

Wed 7/8

12:30 pm-3:13 pm

Nonstop3h 43m

$317

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Sat 5/30

5:30 am-2:09 pm

1 stop7h 39m

Key West

Wed 6/3

2:03 pm-8:26 pm

1 stop7h 23m

$329

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Fri 7/17

6:35 am-1:29 pm

1 stop5h 54m

Key West

Sun 7/19

6:18 pm-11:53 pm

1 stop6h 35m

$354

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Wed 7/29

6:35 am-1:29 pm

1 stop5h 54m

Key West

Sat 8/1

7:50 am-12:27 pm

1 stop5h 37m

$354

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

Showing 1-10 of 41 resultsSorted by cheapest first
1
2
3
...
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

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.

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 $72). Flying from Chicago O'Hare Intl Airport to Florida Keys in July is currently the most expensive (average of $599). 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 May 1, 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 May 1, 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 (3 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 May 1, 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
8,464 reviews

Comfort

7.9

Food

7.2

Boarding

8.1

Overall

7.9

Entertainment

7.8

Crew

8.5

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
8,464 reviews
Delta
7.9
Good
8,464 reviews

Comfort

7.9

Food

7.2

Boarding

8.1

Overall

7.9

Entertainment

7.8

Crew

8.5

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
9,675 reviews
Delta
7.9
Good
8,464 reviews

Comfort

7.9

Food

7.2

Boarding

8.1

Overall

7.9

Entertainment

7.8

Crew

8.5

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
11,684 reviews
Delta
7.9
Good
8,464 reviews

Comfort

7.9

Food

7.2

Boarding

8.1

Overall

7.9

Entertainment

7.8

Crew

8.5

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
8,637 reviews
Delta
7.9
Good
8,464 reviews

Comfort

7.9

Food

7.2

Boarding

8.1

Overall

7.9

Entertainment

7.8

Crew

8.5

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
2,970 reviews
Delta
7.9
Good
8,464 reviews

Comfort

7.9

Food

7.2

Boarding

8.1

Overall

7.9

Entertainment

7.8

Crew

8.5

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 22m. 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 (85%), United Airlines (82%) or American Airlines (81%) 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 $265. While the most popular route (Chicago O'Hare Intl - Miami) can be booked for $149 on average, our data indicates $407 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 $72). Flying from Chicago O'Hare Intl Airport to Florida Keys in July is currently the most expensive (average of $599). 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

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 May 1, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$145Average$376FlexibilityNo cancel feeOn-time65%
DeltaCheapest$206Average$360FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$249Average$419FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$311Average$469FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.