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$59+ 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 12/18. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — EYW
Nov 19 — Nov 261
Tue 11/19
Tue 11/26
1 adult, Economy
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Cheap flight deals from Chicago to Florida Keys

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Florida Keys (zzEOA). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated November 14, 2024.

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 14, 2024.

This FlightHub deal was found by Cheapflights users on 11/14. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/48:02 pmORD - MIA
Nonstop3h 18mMultiple Airlines
Wed 12/118:00 amMIA - ORD
1 stop31h 00mMultiple Airlines
Deal found 11/14$119
This Frontier deal was found by Cheapflights users on 11/12. 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.
Tue 12/175:38 pmORD - MIA
1 stop5h 21mFrontier
Tue 12/244:40 pmMIA - ORD
1 stop8h 19mFrontier
Deal found 11/12$120
This Kiwi.com deal was found by Cheapflights users on 11/14. 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 11/188:31 pmMDW - MIA
Nonstop3h 17mFrontier
Sat 11/2311:42 amMIA - MDW
Nonstop3h 19mFrontier
Deal found 11/14$120
This eDestinos deal was found by Cheapflights users on 11/13. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/38:02 pmORD - MIA
Nonstop3h 18mSpirit Airlines
Thu 12/54:38 pmMIA - ORD
Nonstop3h 29mSpirit Airlines
Deal found 11/13$123
This eDestinos deal was found by Cheapflights users on 11/13. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/236:48 pmMDW - MIA
1 stop14h 12mMultiple Airlines
Mon 11/257:50 amMIA - MDW
1 stop10h 11mMultiple Airlines
Deal found 11/13$210
This Delta deal was found by Cheapflights users on 11/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/75:20 pmORD - MIA
1 stop5h 33mDelta
Wed 12/116:00 amMIA - ORD
1 stop7h 48mDelta
Deal found 11/14$216
This Delta deal was found by Cheapflights users on 11/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/1012:44 pmMDW - MIA
1 stop7h 40mDelta
Tue 12/176:00 amMIA - MDW
1 stop4h 50mDelta
Deal found 11/14$216
This Southwest deal was found by Cheapflights users on 11/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/1511:25 amMDW - MIA
Nonstop3h 05mSouthwest
Wed 1/154:40 pmMIA - MDW
Nonstop3h 15mSouthwest
Deal found 11/14$218
This American Airlines deal was found by Cheapflights users on 11/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/108:15 amORD - MIA
1 stop5h 35mAmerican Airlines
Tue 12/177:00 pmMIA - ORD
Nonstop3h 34mAmerican Airlines
Deal found 11/13$237
This American Airlines deal was found by Cheapflights users on 11/14. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/178:10 amORD - EYW
Nonstop3h 25mAmerican Airlines
Sun 12/228:01 amEYW - ORD
1 stop5h 11mAmerican Airlines
Deal found 11/14$254
This Delta deal was found by Cheapflights users on 11/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/61:59 pmORD - EYW
1 stop5h 35mDelta
Sat 12/146:30 pmEYW - ORD
1 stop6h 28mDelta
Deal found 11/14$263
This Delta deal was found by Cheapflights users on 11/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/256:00 amMDW - EYW
1 stop4h 38mDelta
Wed 12/47:25 amEYW - MDW
1 stop5h 33mDelta
Deal found 11/13$271

Find flights from Chicago to Florida Keys within your budget

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 2,752,363 searches. Data last updated November 14, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Wed 12/4

8:02 pm-12:20 am

Nonstop3h 18m

Miami

Wed 12/11

8:00 am-2:00 pm

1 stop31h 00m

$119

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Fri 12/6

7:25 am-11:38 am

Nonstop3h 13m

Miami

Mon 12/9

8:06 am-1:40 pm

1 stop6h 34m

$120

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Tue 12/3

8:02 pm-12:20 am

Nonstop3h 18m

Miami

Tue 1/28

10:00 am-12:29 pm

Nonstop3h 29m

$123

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Fri 1/24

7:25 am-1:54 am

1 stop17h 29m

Miami

Tue 1/28

7:00 am-1:36 pm

1 stop7h 36m

$129

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Tue 12/10

4:45 pm-9:00 pm

Nonstop3h 15m

Miami

Sat 12/14

6:59 pm-9:34 pm

Nonstop3h 35m

$172

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Tue 1/7

6:10 pm-10:10 pm

Nonstop3h 00m

Miami

Thu 1/9

4:40 pm-6:55 pm

Nonstop3h 15m

$178

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Thu 12/12

12:36 pm-3:07 pm

2 stops25h 31m

Miami

Thu 12/19

5:40 am-12:03 pm

1 stop7h 23m

$214

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sat 12/7

5:55 pm-12:50 am

1 stop5h 55m

Miami

Tue 12/10

8:30 am-12:48 pm

1 stop5h 18m

$216

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Tue 1/7

5:07 pm-12:51 am

1 stop6h 44m

Miami

Thu 1/23

6:00 am-10:12 am

1 stop5h 12m

$216

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Wed 1/29

5:45 am-11:38 am

1 stop4h 53m

Key West

Mon 2/3

6:20 pm-11:59 pm

1 stop6h 39m

$252

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/14

Showing 1-10 of 33 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.

Travel insights for flights from Chicago to Florida Keys

Get recent, data-driven insights about flights from Chicago to Florida Keys including ideal travel times, pricing trends, and more.

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 November 14, 2024.

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 November 14, 2024.

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

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 November 14, 2024.
Read through reviews of airlines operating flights from Chicago to Florida Keys, such as Frontier, Spirit Airlines and American Airlines. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
5,045 reviews

Crew

8.7

Boarding

8.3

Entertainment

7.7

Food

7.2

Comfort

8.1

Overall

8.1

Reviews

1 / 10

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
8.1
Very good
5,045 reviews
Southwest
8.1
Very good
5,045 reviews

Crew

8.7

Boarding

8.3

Entertainment

7.7

Food

7.2

Comfort

8.1

Overall

8.1

Reviews

1 / 10

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.

Alaska Airlines
8.0
Very good
9,439 reviews
Southwest
8.1
Very good
5,045 reviews

Crew

8.7

Boarding

8.3

Entertainment

7.7

Food

7.2

Comfort

8.1

Overall

8.1

Reviews

1 / 10

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.

Delta
8.0
Very good
8,788 reviews
Southwest
8.1
Very good
5,045 reviews

Crew

8.7

Boarding

8.3

Entertainment

7.7

Food

7.2

Comfort

8.1

Overall

8.1

Reviews

1 / 10

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.

JetBlue
7.5
Good
3,447 reviews
Southwest
8.1
Very good
5,045 reviews

Crew

8.7

Boarding

8.3

Entertainment

7.7

Food

7.2

Comfort

8.1

Overall

8.1

Reviews

1 / 10

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
9,194 reviews
Southwest
8.1
Very good
5,045 reviews

Crew

8.7

Boarding

8.3

Entertainment

7.7

Food

7.2

Comfort

8.1

Overall

8.1

Reviews

1 / 10

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.

  • 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 ($59), Frontier ($59), and Southwest ($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 cheapest flights from Chicago to Florida Keys?

    Looking at all options, your cheapest flight can be booked for $118. While the most popular route (Chicago O'Hare Intl - Miami) can be booked for $96 on average our data indicates $467 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.

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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 2,752,363 searches. Data last updated November 14, 2024.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$216Average$432FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$244Average$482FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$275Average$475FlexibilityNo cancel feeOn-time69%
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