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$48+ 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 4/3. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — EYW
Feb 11 — Feb 181
Tue 2/11
Tue 2/18
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 February 6, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$99
(Cheapflightsfares)

One-way from

$48
(Cheapflightsfares)

Popular in

December

Cheapest in

September

Average price

$236
Provider with most accurate pricing for Chicago (CHI)-Miami flight deals.
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From Chicago (CHI) to Florida Keys
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One-way flight from Chicago (CHI) to Florida Keys
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Highest demand for flights based on searches. 17% potential increase in price ($50 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in February 2025
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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 February 6, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 2/6. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/59:08 amORD - MIA
1 stop7h 42mFrontier
Tue 3/1110:45 amMIA - ORD
1 stop6h 53mFrontier
Deal found 2/6$99
This Kiwi.com deal was found by Cheapflights users on 2/5. 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 2/198:33 amORD - MIA
1 stop8h 17mMultiple Airlines
Sat 2/228:05 amMIA - ORD
Nonstop3h 32mMultiple Airlines
Deal found 2/5$100
This eDestinos deal was found by Cheapflights users on 2/6. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/57:25 amMDW - MIA
Nonstop3h 12mFrontier
Wed 3/56:56 pmMIA - MDW
1 stop28h 10mFrontier
Deal found 2/6$100
This Kiwi.com deal was found by Cheapflights users on 2/5. 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 3/59:16 amORD - MIA
1 stop6h 44mSpirit Airlines
Wed 3/129:28 amMIA - ORD
1 stop6h 22mSpirit Airlines
Deal found 2/5$101
This American Airlines deal was found by Cheapflights users on 2/5. 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 2/262:55 pmORD - MIA
Nonstop3h 07mAmerican Airlines
Wed 3/59:41 pmMIA - ORD
Nonstop3h 29mAmerican Airlines
Deal found 2/5$197
This Delta deal was found by Cheapflights users on 2/4. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/259:35 amORD - MIA
1 stop6h 25mDelta
Tue 3/116:00 amMIA - ORD
1 stop5h 12mDelta
Deal found 2/4$217
This Delta deal was found by Cheapflights users on 2/5. 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 3/254:59 pmMDW - MIA
1 stop6h 46mDelta
Wed 3/268:05 amMIA - MDW
1 stop5h 31mDelta
Deal found 2/5$217
This Southwest deal was found by Cheapflights users on 2/5. 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 3/188:35 amMDW - MIA
Nonstop3h 05mSouthwest
Fri 3/217:40 amMIA - MDW
Nonstop3h 15mSouthwest
Deal found 2/5$250
This American Airlines deal was found by Cheapflights users on 2/5. 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 4/18:04 amORD - EYW
Nonstop3h 16mAmerican Airlines
Tue 4/812:52 pmEYW - ORD
Nonstop3h 37mAmerican Airlines
Deal found 2/5$303
This Mytrip deal was found by Cheapflights users on 2/4. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/67:21 pmORD - EYW
1 stop12h 41mMultiple Airlines
Sun 3/95:38 pmEYW - ORD
2 stops23h 49mMultiple Airlines
Deal found 2/4$307
This United Airlines deal was found by Cheapflights users on 2/5. 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 3/114:42 pmORD - EYW
Nonstop3h 21mUnited Airlines
Tue 3/183:59 pmEYW - ORD
Nonstop3h 41mUnited Airlines
Deal found 2/5$309
This Delta deal was found by Cheapflights users on 2/5. 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 2/1812:44 pmMDW - EYW
1 stop6h 27mDelta
Tue 2/256:14 pmEYW - MDW
1 stop5h 06mDelta
Deal found 2/5$318

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 2,558,603 searches. Data last updated February 6, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Wed 3/5

9:08 am-5:50 pm

1 stop7h 42m

Miami

Wed 3/12

6:30 am-5:26 pm

1 stop11h 56m

$99

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Wed 2/19

8:33 am-5:50 pm

1 stop8h 17m

Miami

Fri 2/21

8:05 am-10:37 am

Nonstop3h 32m

$100

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Wed 3/5

7:25 am-11:37 am

Nonstop3h 12m

Miami

Wed 3/5

6:56 pm-10:06 pm

1 stop28h 10m

$100

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Wed 3/5

9:16 am-5:00 pm

1 stop6h 44m

Miami

Wed 3/12

9:28 am-2:50 pm

1 stop6h 22m

$101

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Tue 3/4

7:25 am-11:37 am

Nonstop3h 12m

Miami

Wed 3/5

5:11 pm-11:31 am

2 stops19h 20m

$154

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Wed 3/12

5:35 pm-9:35 pm

Nonstop3h 00m

Miami

Tue 3/18

5:55 pm-8:15 pm

Nonstop3h 20m

$179

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Tue 3/4

10:35 am-2:55 pm

Nonstop3h 20m

Miami

Tue 3/11

7:00 am-9:34 am

Nonstop3h 34m

$188

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Wed 3/5

1:59 pm-6:07 pm

Nonstop3h 08m

Miami

Wed 3/5

9:41 pm-12:10 am

Nonstop3h 29m

$193

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Tue 3/25

4:59 pm-12:45 am

1 stop6h 46m

Miami

Wed 3/26

8:05 am-12:36 pm

1 stop5h 31m

$217

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Tue 2/25

7:05 am-1:46 pm

1 stop5h 41m

Miami

Wed 3/12

10:25 am-4:20 pm

1 stop6h 55m

$217

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/5

Showing 1-10 of 34 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 $520). 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 6, 2025.

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.

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 February 6, 2025.
Read through reviews of airlines operating flights from Chicago to Florida Keys, such as Southwest, Alaska Airlines and Delta. 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
4,549 reviews

Crew

8.7

Boarding

8.2

Comfort

8.1

Food

7.1

Overall

8.1

Entertainment

7.7

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
8.1
Very good
4,549 reviews
Southwest
8.1
Very good
4,549 reviews

Crew

8.7

Boarding

8.2

Comfort

8.1

Food

7.1

Overall

8.1

Entertainment

7.7

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.

Alaska Airlines
8.0
Very good
9,696 reviews
Southwest
8.1
Very good
4,549 reviews

Crew

8.7

Boarding

8.2

Comfort

8.1

Food

7.1

Overall

8.1

Entertainment

7.7

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.

Delta
8.0
Very good
8,396 reviews
Southwest
8.1
Very good
4,549 reviews

Crew

8.7

Boarding

8.2

Comfort

8.1

Food

7.1

Overall

8.1

Entertainment

7.7

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.

JetBlue
7.4
Good
3,128 reviews
Southwest
8.1
Very good
4,549 reviews

Crew

8.7

Boarding

8.2

Comfort

8.1

Food

7.1

Overall

8.1

Entertainment

7.7

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
8,882 reviews
Southwest
8.1
Very good
4,549 reviews

Crew

8.7

Boarding

8.2

Comfort

8.1

Food

7.1

Overall

8.1

Entertainment

7.7

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.

  • 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 ($48), Frontier ($48), and American Airlines ($90).

  • 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 (100%), American Airlines (88%) and Air New Zealand (83%).

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

    Looking at all options, your cheapest flight can be booked for $89. While the most popular route (Chicago O'Hare Intl - Miami) can be booked for $85 on average our data indicates $673 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 $520). 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 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 February 6, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$216Average$427FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$246Average$442FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$260Average$478FlexibilityNo cancel feeOn-time69%
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