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$69+ 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 9/7. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — EYW
Jul 8 — Jul 151
Tue 7/8
Tue 7/15
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 July 3, 2025.

Round-trip from

$129
(Booking.com)

One-way from

$69
(American Airlines)

Popular in

March

Cheapest in

September

Average price

$185
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. 12% potential increase in price ($37 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 3, 2025.

This Booking.com deal was found by Cheapflights users on 7/2. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/1610:27 amORD - MIA
Nonstop3h 22mSpirit Airlines
Sat 8/237:00 amMIA - ORD
Nonstop3h 22mSpirit Airlines
Deal found 7/2$129
This FlightHub deal was found by Cheapflights users on 7/2. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2211:44 amORD - MIA
1 stop17h 46mMultiple Airlines
Tue 8/267:00 amMIA - ORD
Nonstop3h 22mMultiple Airlines
Deal found 7/2$134
This American Airlines deal was found by Cheapflights users on 7/2. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/307:05 pmORD - MIA
Nonstop3h 19mAmerican Airlines
Fri 9/123:50 pmMIA - ORD
Nonstop3h 23mAmerican Airlines
Deal found 7/2$137
This Priceline deal was found by Cheapflights users on 7/2. 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 7/315:01 amORD - MIA
1 stop5h 13mFrontier
Sun 8/33:00 pmMIA - ORD
1 stop10h 22mFrontier
Deal found 7/2$142
This United Airlines deal was found by Cheapflights users on 7/2. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/107:01 amORD - MIA
Nonstop3h 17mUnited Airlines
Wed 8/1312:20 pmMIA - ORD
Nonstop3h 35mUnited Airlines
Deal found 7/2$153
This Southwest deal was found by Cheapflights users on 7/3. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/247:30 amORD - MIA
1 stop7h 35mSouthwest
Wed 8/276:55 amMIA - ORD
1 stop7h 10mSouthwest
Deal found 7/3$157
This American Airlines deal was found by Cheapflights users on 7/3. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/25:00 amORD - EYW
1 stop7h 50mAmerican Airlines
Wed 8/61:13 pmEYW - ORD
1 stop6h 16mAmerican Airlines
Deal found 7/3$323
This Mytrip deal was found by Cheapflights users on 7/3. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/175:16 pmORD - EYW
2 stops22h 25mMultiple Airlines
Sun 8/244:36 pmEYW - ORD
2 stops24h 34mMultiple Airlines
Deal found 7/3$339
This Delta deal was found by Cheapflights users on 7/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/121:35 pmORD - EYW
1 stop5h 14mDelta
Tue 7/226:27 pmEYW - ORD
1 stop6h 42mDelta
Deal found 7/3$340
This United Airlines deal was found by Cheapflights users on 7/1. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/166:00 amORD - EYW
1 stop6h 12mUnited Airlines
Sat 7/262:08 pmEYW - ORD
1 stop8h 33mUnited Airlines
Deal found 7/1$383

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 3, 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

Sat 8/16

10:27 am-2:49 pm

Nonstop3h 22m

Miami

Sat 8/23

7:00 am-9:22 am

Nonstop3h 22m

$129

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Fri 8/22

11:44 am-6:30 am

1 stop17h 46m

Miami

Tue 8/26

7:00 am-9:22 am

Nonstop3h 22m

$134

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sat 8/30

7:05 pm-11:24 pm

Nonstop3h 19m

Miami

Fri 9/12

3:50 pm-6:13 pm

Nonstop3h 23m

$137

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Thu 7/31

5:01 am-11:14 am

1 stop5h 13m

Miami

Sun 8/3

3:00 pm-12:22 am

1 stop10h 22m

$142

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sun 8/10

7:01 am-11:18 am

Nonstop3h 17m

Miami

Wed 8/13

12:20 pm-2:55 pm

Nonstop3h 35m

$153

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sun 8/24

7:30 am-4:05 pm

1 stop7h 35m

Miami

Wed 8/27

6:55 am-1:05 pm

1 stop7h 10m

$157

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Sat 8/2

5:00 am-1:50 pm

1 stop7h 50m

Key West

Wed 8/6

1:13 pm-6:29 pm

1 stop6h 16m

$323

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Thu 7/31

11:20 am-7:49 pm

1 stop7h 29m

Key West

Tue 8/5

11:48 am-6:49 pm

1 stop8h 01m

$337

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Sun 8/17

5:16 pm-4:41 pm

2 stops22h 25m

Key West

Sun 8/24

4:36 pm-4:10 pm

2 stops24h 34m

$339

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Wed 7/16

6:00 am-1:12 pm

1 stop6h 12m

Key West

Sat 7/26

2:08 pm-9:41 pm

1 stop8h 33m

$383

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/3

Showing 1-10 of 19 results
1
2

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 $492). 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 3, 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 July 3, 2025.
Get a feel of what it's like to fly with Southwest, Delta, and United 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
4,266 reviews

Overall

8.0

Comfort

8.0

Food

7.0

Crew

8.6

Boarding

8.2

Entertainment

7.6

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
4,266 reviews
Southwest
8.0
Very good
4,266 reviews

Overall

8.0

Comfort

8.0

Food

7.0

Crew

8.6

Boarding

8.2

Entertainment

7.6

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.
Delta
8.0
Very good
7,982 reviews
Southwest
8.0
Very good
4,266 reviews

Overall

8.0

Comfort

8.0

Food

7.0

Crew

8.6

Boarding

8.2

Entertainment

7.6

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
8,861 reviews
Southwest
8.0
Very good
4,266 reviews

Overall

8.0

Comfort

8.0

Food

7.0

Crew

8.6

Boarding

8.2

Entertainment

7.6

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
4,266 reviews

Overall

8.0

Comfort

8.0

Food

7.0

Crew

8.6

Boarding

8.2

Entertainment

7.6

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
8,086 reviews
Southwest
8.0
Very good
4,266 reviews

Overall

8.0

Comfort

8.0

Food

7.0

Crew

8.6

Boarding

8.2

Entertainment

7.6

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.

  • What are the cheapest airlines to fly from Chicago O'Hare Intl Airport to Florida Keys one-way?

    $69 is the cheapest one-way deal found within the past few days, from American Airlines. You may also be able to find cheap deals on Frontier and Spirit Airlines, with prices starting from $71 and $72, respectively.

  • 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 $303. While the most popular route (Chicago O'Hare Intl - Miami) can be booked for $87 on average our data indicates $523 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 $492). 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 July 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$216Average$337FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$264Average$477FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$285Average$439FlexibilityNo cancel feeOn-time71%

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