HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Florida Keys

$56+ 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 12/8. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — EYW
Dez 12 — Dez 191
Fr 12/12
Fr 12/19
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Florida Keys with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 November 12, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/9. 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.
Sa 12/132:59 pmMDW - MIA
Nonstop3h 10mFrontier
Sa 12/2010:19 pmMIA - MDW
1 stop24h 53mFrontier
Deal found 11/9$113
This Kiwi.com deal was found by Cheapflights users on 11/10. 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.
Do 11/2711:40 amORD - MIA
Nonstop3h 07mMultiple Airlines
Di 12/25:30 amMIA - ORD
1 stop14h 16mMultiple Airlines
Deal found 11/10$113
This CheapOair deal was found by Cheapflights users on 11/11. 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.
So 12/142:59 pmMDW - MIA
Nonstop3h 10mFrontier
Sa 12/205:30 amMIA - MDW
1 stop8h 51mFrontier
Deal found 11/11$114
This Expedia deal was found by Cheapflights users on 11/10. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mi 12/38:00 amORD - MIA
1 stop7h 28mMultiple Airlines
Sa 12/64:08 pmMIA - ORD
Nonstop3h 28mMultiple Airlines
Deal found 11/10$114
This Super.com deal was found by Cheapflights users on 11/10. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
So 12/142:59 pmMDW - MIA
Nonstop3h 10mFrontier
Mi 12/2412:10 pmMIA - MDW
Nonstop3h 27mFrontier
Deal found 11/10$115
This Kiwi.com deal was found by Cheapflights users on 11/10. 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.
Mi 12/38:00 amORD - MIA
1 stop7h 28mMultiple Airlines
Di 12/232:35 pmMIA - ORD
Nonstop3h 25mMultiple Airlines
Deal found 11/10$115
This Kiwi.com deal was found by Cheapflights users on 11/9. 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.
So 12/72:59 pmMDW - MIA
Nonstop3h 10mFrontier
Fr 12/127:09 pmMIA - MDW
1 stop27h 13mFrontier
Deal found 11/9$116
This Cheapflightsfares deal was found by Cheapflights users on 11/10. 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.
Sa 12/69:14 pmORD - MIA
1 stop10h 09mSpirit Airlines
Do 12/182:35 pmMIA - ORD
Nonstop3h 25mSpirit Airlines
Deal found 11/10$116
This CheapOair deal was found by Cheapflights users on 11/11. 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.
Sa 12/132:59 pmMDW - MIA
Nonstop3h 10mFrontier
So 12/146:00 amMIA - MDW
1 stop30h 08mFrontier
Deal found 11/11$117
This Cheapflightsfares deal was found by Cheapflights users on 11/10. 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.
Mi 12/177:41 pmORD - MIA
Nonstop3h 16mSpirit Airlines
So 12/212:35 pmMIA - ORD
Nonstop3h 25mSpirit Airlines
Deal found 11/10$117
This FlightHub deal was found by Cheapflights users on 11/11. 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.
Sa 12/66:11 amORD - MIA
1 stop8h 28mMultiple Airlines
Sa 12/134:08 pmMIA - ORD
Nonstop3h 28mMultiple Airlines
Deal found 11/11$118
This Kiwi.com deal was found by Cheapflights users on 11/11. 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.
Mo 12/2212:39 pmORD - MIA
1 stop7h 30mMultiple Airlines
Mi 12/242:35 pmMIA - ORD
Nonstop3h 25mMultiple Airlines
Deal found 11/11$119

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 November 12, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$113
(Kiwi.com)

One-way from

$56
(eDestinos)

Popular in

December

Cheapest in

September

Average price

$311
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. 6% potential increase in price ($18 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
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 November 12, 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

MDW - MIA

MDWMIA

Chicago Midway

Di 1/27

5:30 pm-9:30 pm

Nonstop3h 00m

Miami

Do 1/29

6:55 am-11:15 am

1 stop5h 20m

$167

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Do 1/29

3:15 pm-10:00 pm

1 stop5h 45m

Miami

Sa 2/7

7:35 am-11:35 am

1 stop5h 00m

$177

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Mo 11/24

6:00 am-1:02 pm

1 stop6h 02m

Miami

Do 12/4

4:55 pm-11:47 pm

1 stop7h 52m

$217

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Mi 1/28

5:33 am-12:14 pm

1 stop5h 41m

Miami

Do 2/5

1:21 pm-6:49 pm

1 stop6h 28m

$217

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Di 12/2

5:13 pm-12:46 am

1 stop6h 33m

Miami

Mi 12/3

8:10 am-12:34 pm

1 stop5h 24m

$228

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Mo 11/24

1:04 pm-8:46 pm

1 stop6h 42m

Miami

Di 12/2

12:36 pm-4:45 pm

1 stop5h 09m

$228

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Sa 1/24

6:40 am-2:50 pm

1 stop7h 10m

Miami

Fr 1/30

7:15 am-1:55 pm

2 stops7h 40m

$243

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Mo 1/5

7:45 am-12:10 pm

Nonstop3h 25m

Miami

Mi 1/7

9:00 am-11:34 am

Nonstop3h 34m

$255

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Mo 11/24

2:02 pm-6:17 pm

Nonstop3h 15m

Miami

Fr 11/28

7:00 am-9:30 am

Nonstop3h 30m

$258

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Di 1/20

5:30 pm-9:30 pm

Nonstop3h 00m

Miami

Mo 1/26

7:15 am-2:55 pm

1 stop8h 40m

$270

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/10

Showing 1-10 of 60 results
1
2
3
...
6

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, December is the cheapest month in which you can book a flight from Chicago to Florida Keys (average of $134). Flying from Chicago to Florida Keys in August is currently the most expensive (average of $336). 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 November 12, 2025.

It’s typically best to fly out from Chicago to Florida Keys in the afternoon. Doing so could potentially save you 48% on the flight price compared to flying in the evening, which is usually more expensive.

Weekly flight availability from Chicago to Florida Keys

Explore weekly flight availability from Chicago to Florida Keys. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated November 12, 2025.

The most flights from CHI to zzEOA are scheduled on a Monday (3 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (2 on average).

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 November 12, 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
4,236 reviews

Overall

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Crew

8.6

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
4,236 reviews
Southwest
8.0
Very good
4,236 reviews

Overall

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Crew

8.6

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
9,013 reviews
Southwest
8.0
Very good
4,236 reviews

Overall

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Crew

8.6

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.
American Airlines
7.2
Good
11,049 reviews
Southwest
8.0
Very good
4,236 reviews

Overall

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Crew

8.6

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.
Spirit Airlines
6.3
Okay
8,137 reviews
Southwest
8.0
Very good
4,236 reviews

Overall

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Crew

8.6

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.
Frontier
5.8
Fair
3,112 reviews
Southwest
8.0
Very good
4,236 reviews

Overall

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Crew

8.6

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.

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

    For as low as $167, 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 Spirit Airlines ($63), Southwest ($79), and United Airlines ($79).

  • 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 (67%), Air New Zealand (67%) and Republic Airways (67%).

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

    Looking at all options, your cheapest flight can be booked for $253. While the most popular route (Chicago O'Hare Intl - Miami) can be booked for $62 on average, our data indicates $612 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, December is the cheapest month in which you can book a flight from Chicago to Florida Keys (average of $134). Flying from Chicago to Florida Keys in August is currently the most expensive (average of $336). 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

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Chicago to Florida Keys

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Orlando flights
O'Hare Intl to Miami flights
O'Hare Intl to Fort Lauderdale flights
O'Hare Intl to Tampa flights
O'Hare Intl to Fort Myers flights
Midway to Miami flights
Midway to Orlando flights
Midway to Tampa flights
O'Hare Intl to Sarasota flights
O'Hare Intl to West Palm Beach flights
Midway to Fort Lauderdale flights
O'Hare Intl to Key West flights
St. Louis to Orlando flights
O'Hare Intl to Jacksonville flights
St. Louis to Miami flights
Midway to Fort Myers flights
St. Louis to Fort Lauderdale flights
O'Hare Intl to Pensacola flights
Midway to West Palm Beach flights
O'Hare Intl to Panama City flights
St. Louis to Tampa flights
Midway to Key West flights
Midway to Sarasota flights
Moline to Orlando flights
St. Louis to Key West flights
St. Louis to Fort Myers flights
St. Louis to Jacksonville flights
Rockford to Orlando Sanford Intl flights
Midway to Jacksonville flights
Rockford to St Petersburg flights
Moline to Tampa flights
St. Louis to Sarasota flights
Midway to Pensacola flights
Peoria to Orlando flights
Midway to Panama City flights
St. Louis to Pensacola flights
Rockford to Punta Gorda flights
Peoria to Fort Lauderdale flights
O'Hare Intl to Valparaiso flights
Peoria to Miami flights
Moline to Fort Myers flights
St. Louis to West Palm Beach flights
Moline to Fort Lauderdale flights
O'Hare Intl to Daytona Beach flights
Moline to West Palm Beach flights
O'Hare Intl to Melbourne flights
O'Hare Intl to Tallahassee flights
St. Louis to Panama City flights
Peoria to Fort Myers flights
Midway to Melbourne flights

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 November 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$218Average$445FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$255Average$490FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$314Average$452FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.