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Florida Keys

$67+ 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 9/1. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — EYW
Aug 9 — Aug 161
Sat 8/9
Sat 8/16
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 August 4, 2025.

Round-trip from

$131
(Mytrip)

One-way from

$67
(FlightHub)

Popular in

March

Cheapest in

September

Average price

$206
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. 11% potential increase in price ($33 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in August 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 August 4, 2025.

This Mytrip deal was found by Cheapflights users on 8/4. 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 9/68:56 pmORD - MIA
1 stop11h 05mSpirit Airlines
Mon 9/87:00 amMIA - ORD
Nonstop3h 18mSpirit Airlines
Deal found 8/4$131
This American Airlines deal was found by Cheapflights users on 8/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/307:05 amORD - MIA
Nonstop3h 04mAmerican Airlines
Sat 10/49:26 pmMIA - ORD
Nonstop3h 23mAmerican Airlines
Deal found 8/1$137
This Southwest deal was found by Cheapflights users on 8/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/82:10 pmMDW - MIA
Nonstop3h 00mSouthwest
Sat 9/134:05 pmMIA - MDW
Nonstop3h 10mSouthwest
Deal found 8/2$137
This Southwest deal was found by Cheapflights users on 8/4. 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 9/182:55 pmORD - MIA
1 stop4h 50mSouthwest
Mon 9/227:10 amMIA - ORD
1 stop5h 40mSouthwest
Deal found 8/4$152
This Kiwi.com deal was found by Cheapflights users on 8/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/310:27 amORD - MIA
Nonstop3h 22mMultiple Airlines
Fri 9/56:59 pmMIA - ORD
1 stop6h 11mMultiple Airlines
Deal found 8/1$154
This Frontier deal was found by Cheapflights users on 8/2. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2310:03 pmMDW - MIA
Nonstop3h 00mFrontier
Mon 10/276:53 pmMIA - MDW
Nonstop3h 15mFrontier
Deal found 8/2$155
This Delta deal was found by Cheapflights users on 8/4. 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 9/64:25 pmMDW - MIA
1 stop6h 59mDelta
Thu 9/114:25 pmMIA - MDW
1 stop6h 11mDelta
Deal found 8/4$217
This Delta deal was found by Cheapflights users on 8/3. 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.
Mon 8/256:00 amMDW - EYW
1 stop6h 05mDelta
Wed 9/37:00 amEYW - MDW
1 stop7h 36mDelta
Deal found 8/3$269
This Delta deal was found by Cheapflights users on 8/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/315:45 amORD - EYW
1 stop6h 20mDelta
Sat 9/67:00 amEYW - ORD
1 stop6h 17mDelta
Deal found 8/2$269
This Mytrip deal was found by Cheapflights users on 8/1. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/137:00 amORD - EYW
1 stop11h 46mMultiple Airlines
Sun 11/162:25 pmEYW - ORD
1 stop10h 17mMultiple Airlines
Deal found 8/1$288
This FlightHub deal was found by Cheapflights users on 8/2. 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.
Thu 11/65:05 amORD - EYW
1 stop7h 25mSpirit Airlines
Mon 11/102:25 pmEYW - ORD
1 stop10h 17mSpirit Airlines
Deal found 8/2$303
This American Airlines deal was found by Cheapflights users on 8/2. 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.
Wed 12/248:05 amORD - EYW
1 stop6h 22mAmerican Airlines
Tue 12/306:05 pmEYW - ORD
Nonstop3h 34mAmerican Airlines
Deal found 8/2$313

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 August 4, 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

Sat 9/6

8:56 pm-9:01 am

1 stop11h 05m

Miami

Mon 9/8

7:00 am-9:18 am

Nonstop3h 18m

$131

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Mon 9/8

2:10 pm-6:10 pm

Nonstop3h 00m

Miami

Sat 9/13

4:05 pm-6:15 pm

Nonstop3h 10m

$137

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Tue 9/30

7:05 am-11:09 am

Nonstop3h 04m

Miami

Sat 10/4

9:26 pm-11:49 pm

Nonstop3h 23m

$137

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Thu 9/18

1:30 pm-11:05 pm

1 stop8h 35m

Miami

Mon 9/22

7:10 am-11:50 am

1 stop5h 40m

$152

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Wed 9/3

10:27 am-2:49 pm

Nonstop3h 22m

Miami

Sun 9/7

4:01 pm-11:20 pm

1 stop8h 19m

$154

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Thu 10/23

10:03 pm-2:03 am

Nonstop3h 00m

Miami

Mon 10/27

6:53 pm-9:08 pm

Nonstop3h 15m

$155

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Sat 9/6

4:25 pm-12:24 am

1 stop6h 59m

Miami

Thu 9/11

4:25 pm-9:36 pm

1 stop6h 11m

$217

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Mon 8/25

6:00 am-1:05 pm

1 stop6h 05m

Key West

Wed 9/3

7:00 am-1:36 pm

1 stop7h 36m

$269

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Sun 8/31

5:45 am-1:05 pm

1 stop6h 20m

Key West

Sat 9/6

7:00 am-12:17 pm

1 stop6h 17m

$269

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Tue 9/16

5:46 pm-9:12 am

1 stop14h 26m

Key West

Fri 9/19

8:47 am-9:58 pm

1 stop14h 11m

$303

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/2

Showing 1-10 of 26 results
1
2
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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 $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 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 August 4, 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.

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 August 4, 2025.
Read reviews from past customers who have flown Southwest, Delta, and United Airlines from Chicago to Florida Keys. 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
4,246 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.5

Food

7.0

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
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.5

Food

7.0

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
7,987 reviews
Southwest
8.0
Very good
4,246 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.5

Food

7.0

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
8,912 reviews
Southwest
8.0
Very good
4,246 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.5

Food

7.0

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.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,246 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.5

Food

7.0

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.
Sun Country Air
6.9
Okay
334 reviews
Southwest
8.0
Very good
4,246 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.5

Food

7.0

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 Spirit Airlines ($67), American 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 cheapest flights from Chicago to Florida Keys?

    Looking at all options, your cheapest flight can be booked for $293. While the most popular route (Chicago O'Hare Intl - Miami) can be booked for $85 on average our data indicates $473 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 $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 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 August 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$216Average$427FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$264Average$480FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$287Average$439FlexibilityNo cancel feeOn-time71%

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