HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Florida Keys

$41+ 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 3/3. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — EYW
Mar 19 — Mar 261
Thu 3/19
Thu 3/26
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.

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 February 17, 2026.

This Kiwi.com deal was found by Cheapflights users on 2/14. 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 3/99:05 pm
ORD
-
MIA
Nonstop3h 15m
Multiple Airlines
Wed 3/186:00 am
MIA
-
ORD
Nonstop3h 25m
Multiple Airlines
Deal found 2/14$81
This Frontier deal was found by Cheapflights users on 2/16. 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.
Mon 4/133:15 pm
ORD
-
MIA
Nonstop3h 19m
Frontier
Mon 4/203:27 pm
MIA
-
ORD
Nonstop3h 38m
Frontier
Deal found 2/16$82
This Super.com deal was found by Cheapflights users on 2/13. 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.
Fri 2/2710:48 am
ORD
-
MIA
Nonstop3h 15m
Frontier
Sat 2/288:00 am
MIA
-
ORD
Nonstop3h 38m
Frontier
Deal found 2/13$83
This Cheapflightsfares deal was found by Cheapflights users on 2/13. 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 3/57:23 pm
ORD
-
MIA
Nonstop3h 16m
Spirit Airlines
Sat 3/146:00 am
MIA
-
ORD
Nonstop3h 25m
Spirit Airlines
Deal found 2/13$84
This Kiwi.com deal was found by Cheapflights users on 2/13. 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 3/87:23 pm
ORD
-
MIA
Nonstop3h 16m
Spirit Airlines
Thu 3/124:06 pm
MIA
-
ORD
Nonstop3h 25m
Spirit Airlines
Deal found 2/13$85
This Super.com deal was found by Cheapflights users on 2/16. 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.
Sat 2/2111:48 am
ORD
-
MIA
Nonstop3h 15m
Frontier
Sat 2/288:00 am
MIA
-
ORD
Nonstop3h 38m
Frontier
Deal found 2/16$86
This Kiwi.com deal was found by Cheapflights users on 2/14. 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 3/16:15 am
MDW
-
MIA
Nonstop3h 13m
Frontier
Fri 3/611:13 am
MIA
-
MDW
Nonstop3h 28m
Frontier
Deal found 2/14$86
This Cheapflightsfares deal was found by Cheapflights users on 2/16. 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.
Mon 2/239:18 am
ORD
-
MIA
Nonstop3h 18m
Spirit Airlines
Fri 2/277:12 am
MIA
-
ORD
Nonstop3h 27m
Spirit Airlines
Deal found 2/16$87
This Cheapflightsfares deal was found by Cheapflights users on 2/13. 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 5/73:52 pm
ORD
-
MIA
Nonstop3h 19m
Frontier
Sun 5/109:21 pm
MIA
-
ORD
Nonstop3h 38m
Frontier
Deal found 2/13$88
This Frontier deal was found by Cheapflights users on 2/14. 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.
Sun 3/16:15 am
MDW
-
MIA
Nonstop3h 13m
Frontier
Thu 3/511:28 am
MIA
-
MDW
Nonstop3h 28m
Frontier
Deal found 2/14$88
This Priceline deal was found by Cheapflights users on 2/16. 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 3/211:33 am
ORD
-
MIA
Nonstop3h 15m
Multiple Airlines
Fri 3/67:12 am
MIA
-
ORD
Nonstop3h 27m
Multiple Airlines
Deal found 2/16$89
This Frontier deal was found by Cheapflights users on 2/12. 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 2/266:15 am
MDW
-
MIA
Nonstop3h 13m
Frontier
Thu 3/511:28 am
MIA
-
MDW
Nonstop3h 28m
Frontier
Deal found 2/12$89

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 February 17, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$81
(Kiwi.com)

One-way from

$41
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$265
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. 10% potential increase in price ($31 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 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 February 17, 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

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Wed 4/29

10:45 am-3:05 pm

Nonstop3h 20m

Miami

Mon 5/4

7:25 pm-10:05 pm

Nonstop3h 40m

$154

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Mon 5/11

6:50 pm-10:50 pm

Nonstop3h 00m

Miami

Wed 5/13

6:40 am-8:50 am

Nonstop3h 10m

$177

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Wed 5/6

10:35 am-2:57 pm

Nonstop3h 22m

Miami

Mon 5/11

7:25 pm-10:05 pm

Nonstop3h 40m

$177

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Tue 4/21

10:45 am-3:05 pm

Nonstop3h 20m

Miami

Wed 4/22

4:13 pm-6:52 pm

Nonstop3h 39m

$191

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Thu 3/5

6:15 am-10:28 am

Nonstop3h 13m

Miami

Mon 3/9

12:12 pm-11:20 pm

1 stop12h 08m

$202

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Wed 3/18

4:51 pm-8:57 pm

Nonstop3h 06m

Miami

Sun 3/22

6:00 am-8:25 am

Nonstop3h 25m

$205

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Wed 4/1

7:40 am-11:40 am

Nonstop3h 00m

Miami

Wed 4/8

6:40 am-8:50 am

Nonstop3h 10m

$208

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Mon 3/2

1:10 pm-5:29 pm

Nonstop3h 19m

Miami

Fri 3/6

5:36 pm-8:20 pm

Nonstop3h 44m

$211

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Mon 3/23

6:00 am-10:13 am

Nonstop3h 13m

Miami

Fri 3/27

3:12 pm-10:19 pm

1 stop8h 07m

$216

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Tue 3/17

9:50 am-3:37 pm

1 stop4h 47m

Miami

Wed 3/25

6:00 am-10:00 am

1 stop5h 00m

$217

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/16

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, 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 $324). 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 February 17, 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.

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 February 17, 2026.

The most flights from CHI to zzEOA are scheduled on a Wednesday (6 on average). You will have fewer flight options on Tuesday, 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 February 17, 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
4,289 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Comfort

8.0

Food

7.0

Overall

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
4,289 reviews
Southwest
8.0
Very good
4,289 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Comfort

8.0

Food

7.0

Overall

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
9,308 reviews
Southwest
8.0
Very good
4,289 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Comfort

8.0

Food

7.0

Overall

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
11,294 reviews
Southwest
8.0
Very good
4,289 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Comfort

8.0

Food

7.0

Overall

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
8,464 reviews
Southwest
8.0
Very good
4,289 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Comfort

8.0

Food

7.0

Overall

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
3,048 reviews
Southwest
8.0
Very good
4,289 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Comfort

8.0

Food

7.0

Overall

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 $177, United Airlines can have you in Florida Keys from Chicago in 3h. The distance between Chicago and Florida Keys is about 1183 mi. Most flights are nonstop.

  • 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 ($36), Spirit Airlines ($37), and JetBlue ($68).

  • 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 Republic Airways (93%), United Airlines (88%) and Air New Zealand (82%).

  • 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 $67 on average, our data indicates $374 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 $324). 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 Fort Lauderdale flights
O'Hare Intl to Orlando flights
O'Hare Intl to Miami flights
O'Hare Intl to Tampa flights
O'Hare Intl to Fort Myers flights
Midway to Miami flights
Midway to Orlando flights
O'Hare Intl to West Palm Beach flights
Midway to Fort Lauderdale flights
O'Hare Intl to Sarasota flights
St. Louis to Orlando flights
Midway to Fort Myers flights
Midway to Tampa flights
O'Hare Intl to Pensacola flights
O'Hare Intl to Jacksonville flights
O'Hare Intl to Key West flights
St. Louis to Miami flights
St. Louis to Fort Lauderdale flights
O'Hare Intl to Panama City flights
St. Louis to Tampa flights
Midway to West Palm Beach flights
St. Louis to Fort Myers flights
Midway to Jacksonville flights
Midway to Sarasota flights
Moline to Orlando flights
Moline to Tampa flights
Midway to Pensacola flights
Midway to Key West flights
Rockford to St Petersburg flights
Peoria to Orlando flights
St. Louis to West Palm Beach flights
Rockford to Orlando Sanford Intl flights
Midway to Panama City flights
St. Louis to Panama City flights
St. Louis to Pensacola flights
St. Louis to Key West flights
Moline to Fort Myers flights
O'Hare Intl to Valparaiso flights
St. Louis to Sarasota flights
O'Hare Intl to Daytona Beach flights
Bloomington to Orlando flights
Rockford to Punta Gorda flights
O'Hare Intl to Melbourne flights
St. Louis to Jacksonville flights
Peoria to Fort Myers flights
Peoria to Tampa flights
Moline to Fort Lauderdale flights
Moline to Miami flights
Peoria to Pensacola flights
Midway to Punta Gorda flights

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 February 17, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$145Average$390FlexibilityNo cancel feeOn-time65%
DeltaCheapest$248Average$426FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$249Average$424FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$322Average$459FlexibilityNo 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.