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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 3/11. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — EYW
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
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 February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$96
(FlightHub)

One-way from

$45
(FlightHub)

Popular in

December

Cheapest in

July

Average price

$263
Provider with most accurate pricing for Chicago (CHI)-Miami flight deals.
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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. 16% potential increase in price ($48 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in February 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 February 20, 2025.

This FlightHub deal was found by Cheapflights users on 2/18. 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.
Mon 3/102:34 pmORD - MIA
Nonstop3h 13mSpirit Airlines
Mon 3/177:42 pmMIA - ORD
Nonstop3h 41mSpirit Airlines
Deal found 2/18$96
This Cheapflightsfares deal was found by Cheapflights users on 2/18. 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 3/82:25 pmORD - MIA
1 stop9h 00mFrontier
Mon 3/178:00 amMIA - ORD
1 stop9h 31mFrontier
Deal found 2/18$98
This FlightHub deal was found by Cheapflights users on 2/19. 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.
Sat 3/16:32 pmORD - MIA
1 stop9h 44mMultiple Airlines
Thu 3/611:03 amMIA - ORD
Nonstop3h 44mMultiple Airlines
Deal found 2/19$102
This American Airlines deal was found by Cheapflights users on 2/20. 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 3/156:58 pmORD - MIA
Nonstop3h 19mAmerican Airlines
Wed 3/198:26 amMIA - ORD
Nonstop3h 32mAmerican Airlines
Deal found 2/20$199
This Delta deal was found by Cheapflights users on 2/19. 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.
Tue 3/255:45 amORD - MIA
1 stop7h 00mDelta
Tue 3/256:10 pmMIA - ORD
1 stop6h 46mDelta
Deal found 2/19$217
This Mytrip deal was found by Cheapflights users on 2/19. 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.
Fri 3/287:10 pmORD - EYW
1 stop18h 15mMultiple Airlines
Thu 4/38:53 amEYW - ORD
2 stops25h 52mMultiple Airlines
Deal found 2/19$306
This American Airlines deal was found by Cheapflights users on 2/19. 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.
Fri 5/168:10 amORD - EYW
1 stop7h 42mAmerican Airlines
Wed 5/2112:49 pmEYW - ORD
Nonstop3h 39mAmerican Airlines
Deal found 2/19$312
This Delta deal was found by Cheapflights users on 2/19. 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.
Tue 3/182:55 pmORD - EYW
1 stop4h 35mDelta
Wed 3/267:00 amEYW - ORD
2 stops14h 38mDelta
Deal found 2/19$317
This United Airlines deal was found by Cheapflights users on 2/19. 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.
Thu 3/134:42 pmORD - EYW
Nonstop3h 21mUnited Airlines
Mon 3/1710:19 amEYW - ORD
Nonstop3h 50mUnited Airlines
Deal found 2/19$338

Find flights from O'Hare Intl to Florida Keys within your budget

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 February 20, 2025.

Fly from

O'Hare Intl

Fly to

Florida Keys

Route

Depart

Return

Price

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Mon 3/10

2:34 pm-6:47 pm

Nonstop3h 13m

Miami

Mon 3/17

7:42 pm-10:23 pm

Nonstop3h 41m

$96

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sat 3/8

2:25 pm-12:25 am

1 stop9h 00m

Miami

Mon 3/17

8:00 am-4:31 pm

1 stop9h 31m

$98

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sat 3/1

6:32 pm-5:16 am

1 stop9h 44m

Miami

Thu 3/6

11:03 am-1:47 pm

Nonstop3h 44m

$102

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sat 3/15

6:58 pm-11:17 pm

Nonstop3h 19m

Miami

Wed 3/19

8:26 am-10:58 am

Nonstop3h 32m

$199

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Tue 3/25

5:45 am-1:45 pm

1 stop7h 00m

Miami

Tue 3/25

6:10 pm-11:56 pm

1 stop6h 46m

$217

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Fri 3/28

7:10 pm-2:25 pm

1 stop18h 15m

Key West

Thu 4/3

8:53 am-9:45 am

2 stops25h 52m

$306

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Fri 5/16

8:10 am-4:52 pm

1 stop7h 42m

Key West

Wed 5/21

12:49 pm-3:28 pm

Nonstop3h 39m

$312

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Tue 3/18

2:55 pm-8:30 pm

1 stop4h 35m

Key West

Wed 3/26

7:00 am-8:38 pm

2 stops14h 38m

$317

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Thu 3/13

4:42 pm-9:03 pm

Nonstop3h 21m

Key West

Mon 3/17

10:19 am-1:09 pm

Nonstop3h 50m

$338

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Tue 3/11

5:55 am-4:16 pm

1 stop9h 21m

$45

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

Showing 1-10 of 22 results
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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.

Travel insights for flights from O'Hare Intl to Florida Keys

Get recent, data-driven insights about flights from O'Hare Intl to Florida Keys including ideal travel times, pricing trends, and more.

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 $510). 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 February 20, 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.

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 February 20, 2025.

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

Rainfall in Florida Keys by month

Plan your trip to Florida Keys by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Florida Keys ranges from 1.6 - 9.9 inches per month. September is typically the wettest month, when rainfall can reach 9.9 in. January is typically the driest time to visit Florida Keys when rainfall is around 1.6 in.

Temperature in Florida Keys by month

Plan your trip to Florida Keys by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Florida Keys, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 84.2 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 68.0 F).

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 February 20, 2025.
See what other customers who have flown with Southwest, Alaska Airlines and Delta from Chicago to Florida Keys have to say. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Boarding

8.2

Comfort

8.1

Overall

8.1

Crew

8.7

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
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Boarding

8.2

Comfort

8.1

Overall

8.1

Crew

8.7

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.

Alaska Airlines
8.0
Very good
9,697 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Boarding

8.2

Comfort

8.1

Overall

8.1

Crew

8.7

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
8,219 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Boarding

8.2

Comfort

8.1

Overall

8.1

Crew

8.7

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
8,765 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Boarding

8.2

Comfort

8.1

Overall

8.1

Crew

8.7

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
8.1
Very good
4,411 reviews

Food

7.1

Boarding

8.2

Comfort

8.1

Overall

8.1

Crew

8.7

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?

    $45 is the cheapest one-way deal found within the past few days, from Spirit Airlines. You may also be able to find cheap deals on Frontier and United Airlines, with prices starting from $50 and $100, respectively.

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

    Consider Air New Zealand (83%), United Airlines (77%) or American Airlines (72%) 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 $89. While the most popular route (Chicago O'Hare Intl - Miami) can be booked for $76 on average our data indicates $431 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 $510). 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.

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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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$216Average$288FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$247Average$437FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$254Average$469FlexibilityNo cancel feeOn-time69%
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