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Florida Keys

$68+ Cheap flights from Chicago (CHI) 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.
CHI — EYW
jun. 23 — jun. 301
lun. 6/23
lun. 6/30
1 adult, Economy
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Cheap flight deals from Chicago to Florida Keys

Keep the following information in mind while searching for Chicago to Florida Keys flight deals. Data was last updated junio 18, 2025.

Round-trip from

$135
(Cheapflightsfares)

One-way from

$68
(American Airlines)

Popular in

March

Cheapest in

September

Average price

$276
From Chicago (CHI) to Florida Keys
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One-way flight from Chicago (CHI) 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 June 2025
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Find flight deals from Chicago to Florida Keys

Cheapest flights from Chicago to Florida Keys
Explore the most affordable flight options available from Chicago to Florida Keys. Find the lowest fares from popular airlines and budget airlines, with prices last updated on junio 18, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 6/17. 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.
jue. 9/183:11 pmORD - MIA
Nonstop3h 15mSpirit Airlines
mié. 9/248:21 pmMIA - ORD
Nonstop3h 26mSpirit Airlines
Deal found 6/17$135
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.
jue. 8/2110:55 amORD - MIA
Nonstop3h 17mUnited Airlines
mar. 8/264:16 pmMIA - ORD
Nonstop3h 30mUnited Airlines
Deal found 6/15$137
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 9/42:10 pmMDW - MIA
Nonstop3h 00mSouthwest
dom. 9/77:30 amMIA - MDW
Nonstop3h 05mSouthwest
Deal found 6/16$137
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 7/81:43 pmORD - MIA
Nonstop3h 17mMultiple Airlines
jue. 7/103:00 pmMIA - ORD
1 stop10h 22mMultiple Airlines
Deal found 6/16$139
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 8/146:00 amORD - MIA
Nonstop3h 08mAmerican Airlines
mar. 8/196:55 pmMIA - ORD
Nonstop3h 30mAmerican Airlines
Deal found 6/15$147
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 9/47:00 amORD - MIA
1 stop7h 15mSouthwest
dom. 9/77:15 amMIA - ORD
1 stop5h 35mSouthwest
Deal found 6/16$157
This Cheapflightsfares deal was found by Cheapflights users on 6/17. 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.
mié. 6/255:01 amORD - MIA
1 stop11h 14mFrontier
jue. 6/266:00 amMIA - ORD
1 stop18h 28mFrontier
Deal found 6/17$188
This KAYAK 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 10/1910:03 pmMDW - MIA
Nonstop3h 00mFrontier
dom. 10/266:53 pmMIA - MDW
Nonstop3h 15mFrontier
Deal found 6/15$193
This Delta deal was found by Cheapflights users on 6/17. 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.
mié. 7/1611:01 amORD - MIA
1 stop5h 09mDelta
mié. 7/238:11 amMIA - ORD
1 stop5h 39mDelta
Deal found 6/17$217
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.
sáb. 8/301:08 pmMDW - MIA
1 stop7h 22mDelta
jue. 9/48:10 amMIA - MDW
1 stop5h 18mDelta
Deal found 6/16$222
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 7/129:40 amORD - MIA
1 stop9h 04mJetBlue
lun. 7/148:39 pmMIA - ORD
1 stop12h 16mJetBlue
Deal found 6/16$284
This American Airlines deal was found by Cheapflights users on 6/17. 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.
mié. 12/248:05 amORD - EYW
1 stop7h 39mAmerican Airlines
mar. 12/307:35 pmEYW - ORD
1 stop5h 21mAmerican Airlines
Deal found 6/17$323

Cheapflights Fare Finder

Customize your flight search to find flights from Chicago 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 junio 18, 2025.
Use the filters below to find and compare flights from Chicago to Florida Keys that are best for you.

Fly from

Chicago

Fly to

Florida Keys

Route

Depart

Return

Price

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

mar. 6/24

1:43 pm-6:00 pm

Nonstop3h 17m

Miami

mié. 7/9

1:35 pm-4:11 pm

Nonstop3h 36m

$135

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

jue. 8/21

10:55 am-3:12 pm

Nonstop3h 17m

Miami

mar. 8/26

4:16 pm-6:46 pm

Nonstop3h 30m

$137

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

jue. 9/4

2:10 pm-6:10 pm

Nonstop3h 00m

Miami

dom. 9/7

7:30 am-9:35 am

Nonstop3h 05m

$137

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

mar. 7/8

1:43 pm-6:00 pm

Nonstop3h 17m

Miami

jue. 7/10

3:00 pm-12:22 am

1 stop10h 22m

$139

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

jue. 8/14

6:00 am-10:08 am

Nonstop3h 08m

Miami

mar. 8/19

6:55 pm-9:25 pm

Nonstop3h 30m

$147

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

jue. 9/4

7:00 am-3:15 pm

1 stop7h 15m

Miami

dom. 9/7

7:15 am-11:50 am

1 stop5h 35m

$157

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

mié. 6/25

5:01 am-5:15 pm

1 stop11h 14m

Miami

dom. 6/29

6:00 am-11:43 pm

1 stop18h 43m

$188

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

mié. 7/16

11:01 am-5:10 pm

1 stop5h 09m

Miami

mié. 7/23

8:11 am-12:50 pm

1 stop5h 39m

$217

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

sáb. 8/30

1:08 pm-9:30 pm

1 stop7h 22m

Miami

jue. 9/4

8:10 am-12:28 pm

1 stop5h 18m

$222

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

sáb. 7/12

9:40 am-7:44 pm

1 stop9h 04m

Miami

lun. 7/14

8:39 pm-7:55 am

1 stop12h 16m

$284

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/17

Showing 1-10 of 34 results
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Best time to book a flight from Chicago to Florida Keys

Have a flexible travel schedule? Discover the best time to fly to Florida Keys from Chicago 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 to Florida Keys

What is the cheapest month to book a flight from Chicago to Florida Keys?

Currently, August is the cheapest month in which you can book a flight from Chicago to Florida Keys (average of $328). Flying from Chicago 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 CHI to EOA?

Find hourly flight availability from Chicago 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 junio 18, 2025.

When flying from Chicago 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 junio 18, 2025.
Read through reviews of airlines operating flights from Chicago to Florida Keys, such as Southwest, Delta and United Airlines. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,280 reviews

Overall

8.0

Crew

8.6

Food

7.1

Boarding

8.2

Entertainment

7.6

Comfort

8.0

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
4,280 reviews
Southwest
8.0
Very good
4,280 reviews

Overall

8.0

Crew

8.6

Food

7.1

Boarding

8.2

Entertainment

7.6

Comfort

8.0

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
7,964 reviews
Southwest
8.0
Very good
4,280 reviews

Overall

8.0

Crew

8.6

Food

7.1

Boarding

8.2

Entertainment

7.6

Comfort

8.0

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
8,809 reviews
Southwest
8.0
Very good
4,280 reviews

Overall

8.0

Crew

8.6

Food

7.1

Boarding

8.2

Entertainment

7.6

Comfort

8.0

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.
JetBlue
7.3
Good
2,924 reviews
Southwest
8.0
Very good
4,280 reviews

Overall

8.0

Crew

8.6

Food

7.1

Boarding

8.2

Entertainment

7.6

Comfort

8.0

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.
Allegiant Air
7.3
Good
722 reviews
Southwest
8.0
Very good
4,280 reviews

Overall

8.0

Crew

8.6

Food

7.1

Boarding

8.2

Entertainment

7.6

Comfort

8.0

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 Chicago 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 to Florida Keys one-way?

    The cheapest airlines for a one-way flight from Chicago to Florida Keys are American Airlines ($68), United Airlines ($69), and Southwest ($69).

  • What are the most popular routes from Chicago to Florida Keys?

    While some choose either Chicago Midway - Miami or Chicago O'Hare Intl - Key West, Chicago O'Hare Intl - Miami is the most popular route from Chicago to Florida Keys.

  • What are the most reliable airlines from Chicago to Florida Keys?

    The top 3 most reliable airlines when flying from Chicago to Florida Keys are United Airlines (90%), Air New Zealand (90%) and American Airlines (61%).

  • What are the cheapest flights from Chicago 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 $104 on average our data indicates $451 when flying from Chicago to Florida Keys.

  • Can I find deals for flights from Chicago to Florida Keys that include hotel bookings?

    Yes. In addition to deals on Chicago to Florida Keys flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Florida Keys?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Florida Keys.

  • Can I find deals for business class flights from Chicago to Florida Keys?

    Yes. Cheapflights offers flight deals from Chicago 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 to Florida Keys?

    Currently, August is the cheapest month in which you can book a flight from Chicago to Florida Keys (average of $328). Flying from Chicago 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

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Alternative routes for Chicago 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 Chicago to Florida Keys

Discover the top 3 airlines that operate flights from Chicago 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 junio 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$216Average$387FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$265Average$476FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$283Average$441FlexibilityNo cancel feeOn-time71%

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