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Florida Keys

$66+ 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 5/20. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — EYW
May 6 — May 131
Tue 5/6
Tue 5/13
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 May 1, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$136
(Cheapflightsfares)

One-way from

$66
(eDestinos)

Popular in

December

Cheapest in

July

Average price

$208
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. 13% potential increase in price ($39 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 May 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 May 1, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 4/30. 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 5/179:55 amORD - MIA
Nonstop3h 15mSpirit Airlines
Sat 5/243:15 pmMIA - ORD
Nonstop3h 26mSpirit Airlines
Deal found 4/30$136
This Kiwi.com deal was found by Cheapflights users on 4/30. 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 6/29:55 amORD - MIA
Nonstop3h 15mMultiple Airlines
Sun 6/85:30 amMIA - ORD
1 stop5h 52mMultiple Airlines
Deal found 4/30$150
This American Airlines deal was found by Cheapflights users on 4/30. 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 6/46:55 amORD - MIA
1 stop4h 45mAmerican Airlines
Wed 6/42:18 pmMIA - ORD
1 stop6h 17mAmerican Airlines
Deal found 4/30$184
This Southwest deal was found by Cheapflights users on 4/30. 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.
Wed 6/45:10 pmMDW - MIA
Nonstop2h 55mSouthwest
Sat 6/75:45 amMIA - MDW
Nonstop3h 05mSouthwest
Deal found 4/30$197
This Kiwi.com deal was found by Cheapflights users on 4/30. 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.
Sat 11/83:59 pmMDW - MIA
Nonstop3h 02mFrontier
Sat 11/1512:47 pmMIA - MDW
Nonstop3h 17mFrontier
Deal found 4/30$212
This Delta deal was found by Cheapflights users on 4/30. 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 5/244:15 pmMDW - MIA
1 stop7h 22mDelta
Sat 5/315:35 amMIA - MDW
1 stop5h 05mDelta
Deal found 4/30$217
This Delta deal was found by Cheapflights users on 4/30. 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 6/216:15 pmORD - MIA
1 stop5h 42mDelta
Tue 6/245:30 amMIA - ORD
1 stop5h 39mDelta
Deal found 4/30$217
This Frontier deal was found by Cheapflights users on 4/30. 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 5/86:00 amORD - MIA
1 stop8h 00mFrontier
Thu 5/156:00 amMIA - ORD
1 stop8h 34mFrontier
Deal found 4/30$218
This American Airlines deal was found by Cheapflights users on 5/1. 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.
Sun 5/2510:34 amORD - EYW
1 stop5h 06mAmerican Airlines
Tue 6/35:30 pmEYW - ORD
1 stop6h 18mAmerican Airlines
Deal found 5/1$322
This Delta deal was found by Cheapflights users on 4/30. 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 7/512:44 pmMDW - EYW
1 stop5h 55mDelta
Wed 7/97:00 amEYW - MDW
1 stop5h 53mDelta
Deal found 4/30$323
This Delta deal was found by Cheapflights users on 4/30. 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 6/149:40 amORD - EYW
1 stop6h 54mDelta
Tue 6/176:29 pmEYW - ORD
1 stop6h 28mDelta
Deal found 4/30$323
This United Airlines deal was found by Cheapflights users on 5/1. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/810:55 amORD - EYW
Nonstop3h 11mUnited Airlines
Sat 11/154:05 pmEYW - ORD
Nonstop3h 25mUnited Airlines
Deal found 5/1$324

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 May 1, 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 5/17

9:55 am-2:10 pm

Nonstop3h 15m

Miami

Sat 5/24

3:15 pm-5:41 pm

Nonstop3h 26m

$136

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Mon 6/2

9:55 am-2:10 pm

Nonstop3h 15m

Miami

Sun 6/8

5:30 am-10:22 am

1 stop5h 52m

$150

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Wed 6/4

6:55 am-12:40 pm

1 stop4h 45m

Miami

Wed 6/4

2:18 pm-7:35 pm

1 stop6h 17m

$184

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Wed 6/4

5:10 pm-9:05 pm

Nonstop2h 55m

Miami

Sat 6/7

5:45 am-7:50 am

Nonstop3h 05m

$197

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Sat 5/24

4:15 pm-12:37 am

1 stop7h 22m

Miami

Sat 5/31

5:35 am-9:40 am

1 stop5h 05m

$217

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sat 6/21

6:15 pm-12:57 am

1 stop5h 42m

Miami

Tue 6/24

5:30 am-10:09 am

1 stop5h 39m

$217

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Thu 6/5

2:58 pm-11:50 pm

1 stop7h 52m

Miami

Mon 6/9

7:25 am-8:56 pm

1 stop14h 31m

$218

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Sat 5/31

6:10 am-10:09 pm

1 stop14h 59m

Miami

Sun 6/1

10:59 pm-10:16 pm

1 stop24h 17m

$260

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Wed 5/14

12:40 pm-9:30 pm

1 stop7h 50m

Miami

Sat 5/17

6:50 am-4:45 pm

2 stops10h 55m

$278

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Sun 5/25

10:34 am-4:40 pm

1 stop5h 06m

Key West

Tue 6/3

5:30 pm-10:48 pm

1 stop6h 18m

$322

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

Showing 1-10 of 32 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 $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 May 1, 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 May 1, 2025.
Read through reviews of airlines operating flights from Chicago to Florida Keys, such as Alaska Airlines, Southwest and Delta. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
9,972 reviews

Boarding

8.1

Entertainment

7.1

Crew

8.5

Overall

8.0

Food

7.1

Comfort

7.9

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
9,972 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Boarding

8.1

Entertainment

7.1

Crew

8.5

Overall

8.0

Food

7.1

Comfort

7.9

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
4,293 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Boarding

8.1

Entertainment

7.1

Crew

8.5

Overall

8.0

Food

7.1

Comfort

7.9

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
7,934 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Boarding

8.1

Entertainment

7.1

Crew

8.5

Overall

8.0

Food

7.1

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Avelo Airlines
7.5
Good
Alaska Airlines
8.0
Very good
9,972 reviews

Boarding

8.1

Entertainment

7.1

Crew

8.5

Overall

8.0

Food

7.1

Comfort

7.9

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
8,696 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Boarding

8.1

Entertainment

7.1

Crew

8.5

Overall

8.0

Food

7.1

Comfort

7.9

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 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 ($66), Frontier ($85), and American Airlines ($90).

  • 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 (84%), Republic Airways (79%) and Air New Zealand (76%).

  • What are the cheapest flights from Chicago to Florida Keys?

    Looking at all options, your cheapest flight can be booked for $227. While the most popular route (Chicago O'Hare Intl - Miami) can be booked for $75 on average our data indicates $462 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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$216Average$375FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$262Average$467FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$263Average$433FlexibilityNo cancel feeOn-time71%

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