Florida Keys

$105+ 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 8/5. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — EYW
Jul 9 — Jul 161
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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 June 9, 2026.

This American Airlines deal was found by Cheapflights users on 6/9. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/42:50 pm
ORD
-
MIA
Nonstop3h 12m
American Airlines
Tue 11/105:05 pm
MIA
-
ORD
Nonstop3h 28m
American Airlines
Deal found 6/9$207
This Southwest deal was found by Cheapflights users on 6/8. 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.
Tue 8/189:25 am
MDW
-
MIA
Nonstop3h 00m
Southwest
Tue 8/254:00 pm
MIA
-
MDW
Nonstop3h 05m
Southwest
Deal found 6/8$209
This American Airlines deal was found by Cheapflights users on 6/8. 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.
Tue 8/45:00 am
ORD
-
MIA
Nonstop3h 09m
American Airlines
Tue 8/113:09 pm
MIA
-
ORD
Nonstop3h 42m
American Airlines
Deal found 6/8$209
This American Airlines deal was found by Cheapflights users on 6/8. 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 11/252:50 pm
ORD
-
MIA
Nonstop3h 12m
American Airlines
Wed 12/28:35 pm
MIA
-
ORD
Nonstop3h 22m
American Airlines
Deal found 6/8$213
This United Airlines deal was found by Cheapflights users on 6/8. 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 8/256:00 am
ORD
-
MIA
1 stop7h 46m
United Airlines
Tue 9/294:01 pm
MIA
-
ORD
Nonstop3h 31m
United Airlines
Deal found 6/8$215
This Kiwi.com deal was found by Cheapflights users on 6/6. 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.
Tue 7/215:46 pm
ORD
-
MIA
1 stop29h 45m
Frontier
Tue 7/286:30 am
MIA
-
ORD
1 stop19h 19m
Frontier
Deal found 6/6$221
This Super.com deal was found by Cheapflights users on 6/8. 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.
Wed 7/156:05 am
MDW
-
MIA
1 stop6h 48m
Frontier
Wed 7/225:28 pm
MIA
-
MDW
1 stop5h 35m
Frontier
Deal found 6/8$227
This Delta deal was found by Cheapflights users on 6/8. 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.
Wed 11/48:15 am
ORD
-
MIA
1 stop5h 14m
Delta
Tue 11/1011:45 am
MIA
-
ORD
1 stop5h 52m
Delta
Deal found 6/8$227
This Kiwi.com deal was found by Cheapflights users on 6/4. 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 8/226:00 am
MDW
-
MIA
1 stop6h 29m
Frontier
Sat 8/298:10 am
MIA
-
MDW
1 stop15h 01m
Frontier
Deal found 6/4$228
This Cheapflightsfares deal was found by Cheapflights users on 6/9. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/19:48 pm
ORD
-
MIA
1 stop31h 06m
Frontier
Tue 7/76:30 am
MIA
-
ORD
1 stop19h 19m
Frontier
Deal found 6/9$228
This Frontier deal was found by Cheapflights users on 6/8. 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.
Wed 7/16:00 am
MDW
-
MIA
1 stop9h 31m
Frontier
Wed 7/1511:19 am
MIA
-
MDW
1 stop11h 44m
Frontier
Deal found 6/8$229
This Frontier deal was found by Cheapflights users on 6/8. 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.
Wed 7/11:29 pm
ORD
-
MIA
1 stop8h 34m
Frontier
Wed 7/1511:19 am
MIA
-
ORD
1 stop9h 34m
Frontier
Deal found 6/8$229

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 June 9, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$207
(American Airlines)

One-way from

$105
(Southwest)

Popular in

June

Cheapest in

September

Average price

$359
Provider with most accurate pricing for Chicago (CHI)-Miami flight deals.
Provider most trusted by Cheapflights users for Chicago (CHI)-Miami flights.
From Chicago (CHI) to Florida Keys
One-way flight from Chicago (CHI) to Florida Keys
Highest demand for flights based on searches. 13% potential increase in price ($43 potential increase over avg. RT price).
Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
Average for round-trip flights in June 2026

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 June 9, 2026.
Use the filters below to find and compare flights from Chicago to Florida Keys that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Tue 7/14

10:33 am-2:57 pm

Nonstop3h 24m

Miami

Wed 7/22

4:10 pm-6:53 pm

Nonstop3h 43m

$239

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Thu 8/13

8:00 am-12:10 pm

Nonstop3h 10m

Miami

Tue 8/18

4:00 pm-6:05 pm

Nonstop3h 05m

$253

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Thu 8/13

7:30 am-11:54 am

Nonstop3h 24m

Miami

Tue 8/18

5:01 pm-11:26 pm

1 stop7h 25m

$263

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sat 10/17

4:00 pm-11:43 pm

1 stop6h 43m

Miami

Sat 10/24

4:01 pm-6:32 pm

Nonstop3h 31m

$289

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Tue 7/7

10:33 am-2:57 pm

Nonstop3h 24m

Miami

Tue 7/14

1:10 pm-8:32 pm

1 stop8h 22m

$293

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Thu 7/16

7:00 am-11:24 am

Nonstop3h 24m

Miami

Tue 7/21

5:32 pm-8:13 pm

Nonstop3h 41m

$311

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Wed 6/24

11:45 am-3:45 pm

Nonstop3h 00m

Miami

Tue 7/14

11:45 am-3:55 pm

1 stop5h 10m

$318

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sat 7/25

7:00 am-11:24 am

Nonstop3h 24m

Miami

Sat 8/1

5:32 pm-8:13 pm

Nonstop3h 41m

$327

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Mon 8/17

6:40 am-1:00 pm

1 stop5h 20m

Key West

Mon 8/24

6:15 pm-12:02 am

1 stop6h 47m

$329

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Wed 8/19

6:05 am-1:00 pm

1 stop5h 55m

Key West

Wed 8/26

6:15 pm-10:36 pm

1 stop5h 21m

$339

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/4

Showing 1-10 of 60 resultsSorted by cheapest first
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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, October is the cheapest month in which you can book a flight from Chicago to Florida Keys (average of $221). Flying from Chicago to Florida Keys in December is currently the most expensive (average of $404). 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 June 9, 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 June 9, 2026.

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

How far ahead should I book a flight from Chicago to Florida Keys?

The price you pay for your flight from Chicago to Florida Keys may vary depending on when you book. For the best chance of a lower fare, look to book 32 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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 June 9, 2026.
Read reviews from past customers who have flown Southwest,Delta, andUnited 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.

Comfort

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Overall

7.9

Boarding

8.1

Reviews

1 / 20
6.0
Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.

Comfort

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Overall

7.9

Boarding

8.1

Reviews

1 / 20
6.0
Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.

Comfort

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Overall

7.9

Boarding

8.1

Reviews

1 / 20
6.0
Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.

Comfort

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Overall

7.9

Boarding

8.1

Reviews

1 / 20
6.0
Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.

Comfort

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Overall

7.9

Boarding

8.1

Reviews

1 / 20
6.0
Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.

Comfort

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Overall

7.9

Boarding

8.1

Reviews

1 / 20
6.0
Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.

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 $253, United Airlines can have you in Florida Keys from Chicago in 3h 10m. 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 ($32), JetBlue ($68), and American Airlines ($78).

  • What are the most popular routes 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 (97%), Air New Zealand (91%) and United Airlines (89%).

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

    Looking at all options, your cheapest flight can be booked for $188. While the most popular route (Chicago O'Hare Intl - Miami) can be booked for $239 on average, our data indicates $360 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, October is the cheapest month in which you can book a flight from Chicago to Florida Keys (average of $221). Flying from Chicago to Florida Keys in December is currently the most expensive (average of $404). 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.

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 June 9, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$206Average$438FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$249Average$414FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$308Average$476FlexibilityNo cancel feeOn-time71%

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