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Florida Keys

$57+ 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 12/4. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — EYW
Oct 24 — Oct 311
Fri 10/24
Fri 10/31
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 September 24, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$104
(Kiwi.com)

One-way from

$57
(Cheapflightsfares)

Popular in

March

Cheapest in

September

Average price

$232
Provider with most accurate pricing for Chicago (CHI)-Miami flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Miami flights.
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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. 6% potential increase in price ($18 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 September 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 September 24, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/23. 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.
Mon 10/134:24 pmMDW - MIA
Nonstop3h 02mFrontier
Fri 10/177:20 amMIA - MDW
Nonstop3h 13mFrontier
Deal found 9/23$104
This Kiwi.com deal was found by Cheapflights users on 9/22. 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.
Sun 12/71:35 pmORD - MIA
Nonstop3h 15mSpirit Airlines
Mon 12/810:15 amMIA - ORD
Nonstop3h 15mSpirit Airlines
Deal found 9/22$104
This Kiwi.com deal was found by Cheapflights users on 9/24. 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.
Fri 11/71:35 pmORD - MIA
Nonstop3h 15mSpirit Airlines
Mon 11/1010:15 amMIA - ORD
Nonstop3h 15mSpirit Airlines
Deal found 9/24$105
This Cheapflightsfares deal was found by Cheapflights users on 9/24. 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.
Thu 10/3010:27 amORD - MIA
Nonstop3h 02mSpirit Airlines
Sun 11/27:00 amMIA - ORD
Nonstop3h 22mSpirit Airlines
Deal found 9/24$107
This Booking.com deal was found by Cheapflights users on 9/23. 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 10/189:27 amORD - MIA
Nonstop3h 03mSpirit Airlines
Fri 10/247:00 amMIA - ORD
Nonstop3h 22mSpirit Airlines
Deal found 9/23$108
This Kiwi.com deal was found by Cheapflights users on 9/23. 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.
Mon 10/134:24 pmMDW - MIA
Nonstop3h 02mFrontier
Mon 10/207:20 amMIA - MDW
Nonstop3h 13mFrontier
Deal found 9/23$109
This Kiwi.com deal was found by Cheapflights users on 9/21. 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 12/101:35 pmORD - MIA
Nonstop3h 15mSpirit Airlines
Fri 1/910:15 amMIA - ORD
Nonstop3h 15mSpirit Airlines
Deal found 9/21$109
This Priceline deal was found by Cheapflights users on 9/23. 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.
Mon 10/2010:27 amORD - MIA
Nonstop3h 02mMultiple Airlines
Fri 10/2410:42 amMIA - ORD
1 stop6h 07mMultiple Airlines
Deal found 9/23$110
This Cheapflightsfares deal was found by Cheapflights users on 9/22. 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 10/119:27 amORD - MIA
Nonstop3h 03mSpirit Airlines
Thu 10/167:00 amMIA - ORD
Nonstop3h 22mSpirit Airlines
Deal found 9/22$111
This Cheapflightsfares deal was found by Cheapflights users on 9/24. 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.
Sun 10/1210:27 amORD - MIA
Nonstop3h 02mSpirit Airlines
Fri 10/177:00 amMIA - ORD
Nonstop3h 22mSpirit Airlines
Deal found 9/24$112
This Spirit deal was found by Cheapflights users on 9/24. 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 Spirit is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2310:27 amORD - MIA
Nonstop3h 02mSpirit Airlines
Mon 10/277:00 amMIA - ORD
Nonstop3h 22mSpirit Airlines
Deal found 9/24$113
This Kiwi.com deal was found by Cheapflights users on 9/22. 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.
Mon 10/2010:27 amORD - MIA
Nonstop3h 02mSpirit Airlines
Thu 10/237:00 amMIA - ORD
Nonstop3h 22mSpirit Airlines
Deal found 9/22$114

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 September 24, 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

Tue 11/4

7:35 am-11:49 am

Nonstop3h 14m

Miami

Tue 11/11

12:23 pm-2:52 pm

Nonstop3h 29m

$157

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Mon 12/15

9:00 am-1:05 pm

Nonstop3h 05m

Miami

Tue 12/16

1:05 pm-3:20 pm

Nonstop3h 15m

$157

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Mon 11/3

9:00 am-1:05 pm

Nonstop3h 05m

Miami

Fri 11/7

6:20 am-8:35 am

Nonstop3h 15m

$157

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Wed 10/22

10:54 am-3:11 pm

Nonstop3h 17m

Miami

Tue 10/28

12:23 pm-2:52 pm

Nonstop3h 29m

$167

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Wed 12/10

2:32 pm-9:42 pm

1 stop6h 10m

Miami

Wed 1/7

6:00 am-10:06 am

1 stop5h 06m

$217

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Sat 10/18

6:58 pm-8:15 am

1 stop12h 17m

Key West

Fri 10/24

8:55 am-6:46 pm

1 stop10h 51m

$217

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Wed 11/19

2:30 pm-9:38 pm

1 stop6h 08m

Miami

Wed 12/3

6:00 am-10:20 am

1 stop5h 20m

$217

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Tue 11/18

9:51 am-3:47 pm

1 stop4h 56m

Miami

Wed 12/3

6:00 am-10:20 am

1 stop5h 20m

$217

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Tue 11/18

12:47 pm-8:46 pm

1 stop6h 59m

Miami

Wed 12/3

6:30 pm-11:32 pm

1 stop6h 02m

$217

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Sat 10/18

1:11 pm-9:27 pm

1 stop7h 16m

Miami

Mon 10/20

6:15 pm-10:14 pm

1 stop4h 59m

$217

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/24

Showing 1-10 of 60 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 $489). 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 September 24, 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 September 24, 2025.
Read reviews from past customers who have flown Southwest, United Airlines, and American 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
4,244 reviews

Crew

8.6

Boarding

8.1

Food

7.0

Comfort

8.0

Overall

8.0

Entertainment

7.5

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
4,244 reviews
Southwest
8.0
Very good
4,244 reviews

Crew

8.6

Boarding

8.1

Food

7.0

Comfort

8.0

Overall

8.0

Entertainment

7.5

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
8,928 reviews
Southwest
8.0
Very good
4,244 reviews

Crew

8.6

Boarding

8.1

Food

7.0

Comfort

8.0

Overall

8.0

Entertainment

7.5

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
4,244 reviews

Crew

8.6

Boarding

8.1

Food

7.0

Comfort

8.0

Overall

8.0

Entertainment

7.5

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
8,042 reviews
Southwest
8.0
Very good
4,244 reviews

Crew

8.6

Boarding

8.1

Food

7.0

Comfort

8.0

Overall

8.0

Entertainment

7.5

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.
Frontier
5.8
Fair
3,163 reviews
Southwest
8.0
Very good
4,244 reviews

Crew

8.6

Boarding

8.1

Food

7.0

Comfort

8.0

Overall

8.0

Entertainment

7.5

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.

  • How long is the flight from Chicago to Florida Keys?

    For as low as $157, United Airlines can have you in Florida Keys from Chicago in 3h 05m. The distance between Chicago and Florida Keys is about 1183 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • 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 Frontier ($78), United Airlines ($79), and Southwest ($114).

  • 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 $216. While the most popular route (Chicago O'Hare Intl - Miami) can be booked for $77 on average, our data indicates $362 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 $489). 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

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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 September 24, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$218Average$444FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$252Average$485FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$303Average$441FlexibilityNo cancel feeOn-time71%

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