HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Florida Keys

$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 8/24. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — EYW
Jun 21 — Jun 281
Sat 6/21
Sat 6/28
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

Keep the following information in mind while searching for O'Hare Intl to Florida Keys flight deals. Data was last updated June 16, 2025.

Round-trip from

$136
(Cheapflightsfares)

One-way from

$69
(United Airlines)

Popular in

March

Cheapest in

September

Average price

$276
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. 12% potential increase in price ($37 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 2025
Search Deals

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 June 16, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 6/13. 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 7/128:09 amORD - MIA
Nonstop3h 14mSpirit Airlines
Thu 7/171:35 pmMIA - ORD
Nonstop3h 36mSpirit Airlines
Deal found 6/13$136
This FlightHub deal was found by Cheapflights users on 6/14. 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.
Tue 7/81:43 pmORD - MIA
Nonstop3h 17mMultiple Airlines
Thu 7/103:00 pmMIA - ORD
1 stop10h 22mMultiple Airlines
Deal found 6/14$139
This American Airlines deal was found by Cheapflights users on 6/14. 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.
Thu 8/146:00 amORD - MIA
Nonstop3h 08mAmerican Airlines
Tue 8/198:10 pmMIA - ORD
Nonstop3h 31mAmerican Airlines
Deal found 6/14$147
This Southwest deal was found by Cheapflights users on 6/15. 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.
Thu 8/71:30 pmORD - MIA
1 stop8h 35mSouthwest
Tue 8/127:10 amMIA - ORD
1 stop5h 40mSouthwest
Deal found 6/15$177
This Cheapflightsfares deal was found by Cheapflights users on 6/14. 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.
Tue 7/15:01 amORD - MIA
1 stop5h 27mFrontier
Fri 7/412:20 pmMIA - ORD
1 stop5h 38mFrontier
Deal found 6/14$188
This Delta deal was found by Cheapflights users on 6/14. 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 7/192:00 pmORD - MIA
1 stop7h 45mDelta
Thu 7/247:23 pmMIA - ORD
1 stop5h 46mDelta
Deal found 6/14$217
This United Airlines deal was found by Cheapflights users on 6/15. 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.
Fri 7/410:50 amORD - MIA
Nonstop3h 20mUnited Airlines
Fri 7/114:16 pmMIA - ORD
Nonstop3h 34mUnited Airlines
Deal found 6/15$240
This American Airlines deal was found by Cheapflights users on 6/14. 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 12/610:05 amORD - EYW
1 stop5h 26mAmerican Airlines
Sat 12/135:24 pmEYW - ORD
1 stop5h 18mAmerican Airlines
Deal found 6/14$323
This Delta deal was found by Cheapflights users on 6/16. 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.
Wed 12/249:55 amORD - EYW
1 stop6h 13mDelta
Wed 12/316:02 pmEYW - ORD
1 stop6h 56mDelta
Deal found 6/16$330
This United Airlines deal was found by Cheapflights users on 6/15. 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.
Fri 7/46:00 amORD - EYW
1 stop6h 12mUnited Airlines
Tue 7/82:12 pmEYW - ORD
1 stop8h 24mUnited Airlines
Deal found 6/15$333
This Mytrip deal was found by Cheapflights users on 6/15. 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 9/275:05 amORD - EYW
2 stops33h 55mMultiple Airlines
Thu 10/210:54 amEYW - ORD
2 stops31h 56mMultiple Airlines
Deal found 6/15$344

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 June 16, 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 7/12

8:09 am-12:23 pm

Nonstop3h 14m

Miami

Thu 7/17

1:35 pm-4:11 pm

Nonstop3h 36m

$136

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Tue 7/8

1:43 pm-6:00 pm

Nonstop3h 17m

Miami

Thu 7/10

3:00 pm-12:22 am

1 stop10h 22m

$139

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Thu 8/14

6:00 am-10:08 am

Nonstop3h 08m

Miami

Tue 8/19

8:10 pm-10:41 pm

Nonstop3h 31m

$147

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Thu 8/7

1:30 pm-11:05 pm

1 stop8h 35m

Miami

Tue 8/12

7:10 am-11:50 am

1 stop5h 40m

$177

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Tue 7/1

5:01 am-11:28 am

1 stop5h 27m

Miami

Fri 7/4

12:20 pm-4:58 pm

1 stop5h 38m

$188

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sat 7/19

2:00 pm-10:45 pm

1 stop7h 45m

Miami

Thu 7/24

7:23 pm-12:09 am

1 stop5h 46m

$217

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Fri 7/4

10:50 am-3:10 pm

Nonstop3h 20m

Miami

Fri 7/11

4:16 pm-6:50 pm

Nonstop3h 34m

$240

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Sat 12/6

10:05 am-4:31 pm

1 stop5h 26m

Key West

Sat 12/13

5:24 pm-9:42 pm

1 stop5h 18m

$323

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Fri 7/4

6:00 am-1:12 pm

1 stop6h 12m

Key West

Tue 7/8

2:12 pm-9:36 pm

1 stop8h 24m

$333

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Thu 8/21

11:15 am-8:12 pm

1 stop7h 57m

Key West

Sun 8/24

6:22 pm-11:56 pm

1 stop6h 34m

$334

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/16

Showing 1-10 of 22 results
1
2
3

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 $493). 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 June 16, 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.

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 June 16, 2025.
See what other customers who have flown with Alaska Airlines, Southwest 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.
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Crew

8.5

Boarding

8.1

Comfort

7.8

Entertainment

7.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Crew

8.5

Boarding

8.1

Comfort

7.8

Entertainment

7.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,278 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Crew

8.5

Boarding

8.1

Comfort

7.8

Entertainment

7.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,963 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Crew

8.5

Boarding

8.1

Comfort

7.8

Entertainment

7.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,801 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Crew

8.5

Boarding

8.1

Comfort

7.8

Entertainment

7.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Crew

8.5

Boarding

8.1

Comfort

7.8

Entertainment

7.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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 United Airlines. You may also be able to find cheap deals on American Airlines and Spirit Airlines, with prices starting from $70 and $72, respectively.

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

    Consider United Airlines (90%), Air New Zealand (90%) or American Airlines (61%) 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 $258. While the most popular route (Chicago O'Hare Intl - Miami) can be booked for $106 on average our data indicates $451 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 $493). 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.

Alternative routes for O'Hare Intl to Florida Keys

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Orlando flights
O'Hare Intl to Fort Lauderdale flights
O'Hare Intl to Miami flights
O'Hare Intl to Tampa flights
O'Hare Intl to Fort Myers flights
Midway to Miami flights
Midway to Orlando flights
O'Hare Intl to West Palm Beach flights
Midway to Fort Lauderdale flights
O'Hare Intl to Sarasota flights
O'Hare Intl to Key West flights
O'Hare Intl to Jacksonville flights
O'Hare Intl to Pensacola flights
Midway to Tampa flights
O'Hare Intl to Panama City flights
Midway to West Palm Beach flights
Midway to Fort Myers flights
Midway to Jacksonville flights
O'Hare Intl to St Petersburg flights
Midway to Key West flights
Midway to Sarasota flights
Midway to Pensacola flights
O'Hare Intl to Melbourne flights
O'Hare Intl to Daytona Beach flights
O'Hare Intl to Valparaiso flights
Midway to Panama City flights
Rockford to Orlando Sanford Intl flights
O'Hare Intl to Gainesville flights
Rockford to St Petersburg flights
O'Hare Intl to Orlando Sanford Intl flights
O'Hare Intl to Tallahassee flights
Midway to Orlando Sanford Intl flights
Midway to Gainesville flights
Midway to Daytona Beach flights
Midway to Valparaiso flights
Midway to Melbourne flights
Midway to Tallahassee flights
O'Hare Intl to Punta Gorda flights
Rockford to Punta Gorda flights
Midway to Punta Gorda flights
Midway to Valdosta flights
O'Hare Intl to Valdosta flights
O'Hare Intl to Destin flights

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 June 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$216Average$336FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$265Average$476FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$283Average$441FlexibilityNo 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.