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Florida Keys

$43+ 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 2/19. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — EYW
Jan 31 — Feb 71
Sat 1/31
Sat 2/7
1 adult, Economy
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Cheap 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 January 1, 2026.

This CheapOair deal was found by Cheapflights users on 12/31. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:05 pmORD - MIA
Nonstop3h 16mSpirit Airlines
Wed 1/72:35 pmMIA - ORD
Nonstop3h 25mSpirit Airlines
Deal found 12/31$249
This American Airlines deal was found by Cheapflights users on 12/31. 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 12/313:04 pmORD - MIA
Nonstop3h 23mAmerican Airlines
Thu 1/110:09 amMIA - ORD
1 stop5h 03mAmerican Airlines
Deal found 12/31$288
This United Airlines deal was found by Cheapflights users on 12/31. 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.
Wed 12/3110:45 amORD - EYW
Nonstop3h 27mUnited Airlines
Thu 1/14:08 pmEYW - ORD
Nonstop3h 33mUnited Airlines
Deal found 12/31$303
This American Airlines deal was found by Cheapflights users on 12/30. 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 12/314:05 pmORD - EYW
1 stop5h 39mAmerican Airlines
Thu 1/18:00 amEYW - ORD
1 stop7h 12mAmerican Airlines
Deal found 12/30$323
This Southwest deal was found by Cheapflights users on 12/31. 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 12/313:45 pmORD - MIA
1 stop5h 05mSouthwest
Thu 1/16:55 amMIA - ORD
1 stop5h 15mSouthwest
Deal found 12/31$327
This United Airlines deal was found by Cheapflights users on 12/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/3110:45 amORD - EYW
Nonstop3h 27mUnited Airlines
Wed 1/74:15 pmEYW - ORD
Nonstop3h 33mUnited Airlines
Deal found 12/30$342
This Kiwi.com deal was found by Cheapflights users on 12/31. 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 12/316:05 pmORD - MIA
Nonstop3h 16mMultiple Airlines
Mon 1/57:10 pmMIA - ORD
1 stop18h 44mMultiple Airlines
Deal found 12/31$354
This American Airlines deal was found by Cheapflights users on 12/31. 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 12/317:26 pmORD - MIA
Nonstop3h 19mAmerican Airlines
Mon 1/58:24 amMIA - ORD
1 stop5h 50mAmerican Airlines
Deal found 12/31$362
This American Airlines deal was found by Cheapflights users on 12/30. 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 12/316:07 amORD - EYW
1 stop8h 26mAmerican Airlines
Tue 1/67:45 pmEYW - ORD
1 stop5h 45mAmerican Airlines
Deal found 12/30$381
This CheapOair deal was found by Cheapflights users on 12/31. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:05 pmORD - MIA
Nonstop3h 16mSpirit Airlines
Mon 1/510:13 amMIA - ORD
1 stop6h 47mSpirit Airlines
Deal found 12/31$407
This United Airlines deal was found by Cheapflights users on 12/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/3010:45 amORD - EYW
Nonstop3h 27mUnited Airlines
Thu 1/112:22 pmEYW - ORD
Nonstop3h 45mUnited Airlines
Deal found 12/30$424
This United Airlines deal was found by Cheapflights users on 12/29. 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.
Tue 12/3010:45 amORD - EYW
Nonstop3h 27mUnited Airlines
Fri 1/24:29 pmEYW - ORD
1 stop7h 08mUnited Airlines
Deal found 12/29$434

Find 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 January 1, 2026.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$88
(CheapOair)

One-way from

$43
(Super.com)

Popular in

December

Cheapest in

September

Average price

$219
Provider with most accurate pricing for Chicago (CHI)-Miami flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Miami flights.
Search Deals
From Chicago (CHI) to Florida Keys
Search Deals
One-way flight from Chicago (CHI) to Florida Keys
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($24 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

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 January 1, 2026.
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

MDW - MIA

MDWMIA

Chicago Midway

Sat 1/31

5:30 pm-9:30 pm

Nonstop3h 00m

Miami

Sat 2/7

6:30 am-8:40 am

Nonstop3h 10m

$157

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Sun 2/8

5:30 pm-9:30 pm

Nonstop3h 00m

Miami

Wed 2/11

2:35 pm-4:50 pm

Nonstop3h 15m

$157

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Fri 1/16

8:43 pm-12:42 am

2 stops26h 59m

Miami

Mon 1/19

5:54 am-8:18 am

Nonstop3h 24m

$185

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Fri 1/30

2:35 pm-8:05 pm

1 stop4h 30m

Miami

Tue 2/3

2:35 pm-4:50 pm

Nonstop3h 15m

$207

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sat 2/7

12:45 pm-10:35 pm

1 stop8h 50m

Miami

Thu 2/12

9:00 am-11:38 am

Nonstop3h 38m

$209

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Sat 2/21

4:13 pm-10:47 pm

1 stop5h 34m

Miami

Wed 2/25

8:15 am-11:59 am

1 stop4h 44m

$217

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Fri 2/20

6:40 pm-12:53 am

1 stop5h 13m

Miami

Fri 2/27

6:00 am-9:54 am

1 stop4h 54m

$217

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sat 1/24

5:59 pm-12:51 am

1 stop5h 52m

Miami

Tue 1/27

10:29 am-4:55 pm

1 stop7h 26m

$217

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sat 2/7

6:03 pm-12:51 am

1 stop5h 48m

Miami

Sat 2/21

6:00 am-10:17 am

1 stop5h 17m

$217

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Wed 1/28

1:58 pm-10:03 pm

1 stop7h 05m

Miami

Thu 2/5

8:15 am-1:40 pm

1 stop6h 25m

$217

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/1

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, January is the cheapest month in which you can book a flight from Chicago to Florida Keys (average of $245). Flying from Chicago to Florida Keys in October is currently the most expensive (average of $323). 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 January 1, 2026.

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 January 1, 2026.
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
4,254 reviews

Entertainment

7.5

Overall

8.0

Boarding

8.1

Crew

8.6

Food

7.0

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
4,254 reviews
Southwest
8.0
Very good
4,254 reviews

Entertainment

7.5

Overall

8.0

Boarding

8.1

Crew

8.6

Food

7.0

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
9,132 reviews
Southwest
8.0
Very good
4,254 reviews

Entertainment

7.5

Overall

8.0

Boarding

8.1

Crew

8.6

Food

7.0

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.
American Airlines
7.2
Good
11,074 reviews
Southwest
8.0
Very good
4,254 reviews

Entertainment

7.5

Overall

8.0

Boarding

8.1

Crew

8.6

Food

7.0

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.
Spirit Airlines
6.3
Okay
8,258 reviews
Southwest
8.0
Very good
4,254 reviews

Entertainment

7.5

Overall

8.0

Boarding

8.1

Crew

8.6

Food

7.0

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.
Frontier
5.7
Fair
3,069 reviews
Southwest
8.0
Very good
4,254 reviews

Entertainment

7.5

Overall

8.0

Boarding

8.1

Crew

8.6

Food

7.0

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.

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

    For as low as $157, Southwest can have you in Florida Keys from Chicago in 3h. 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 ($39), Spirit Airlines ($41), and Southwest ($78).

  • 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 American Airlines (71%), Envoy Air (71%) and United Airlines (66%).

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

    Looking at all options, your cheapest flight can be booked for $158. While the most popular route (Chicago O'Hare Intl - Miami) can be booked for $64 on average, our data indicates $572 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, January is the cheapest month in which you can book a flight from Chicago to Florida Keys (average of $245). Flying from Chicago to Florida Keys in October is currently the most expensive (average of $323). 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 4 airlines flying from Chicago to Florida Keys

Discover the top 4 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 January 1, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$169Average$385FlexibilityNo cancel feeOn-time65%
DeltaCheapest$248Average$398FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$249Average$483FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$323Average$462FlexibilityNo cancel feeOn-time71%

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