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Islamorada

$45+ Cheap flights from Chicago (CHI) to Islamorada, FL

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 3/11. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MIA
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
1 adult, Economy
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The best prices from Chicago to Islamorada are usually found in July or April, booked 28 days in advance, depart on a Thursday or Tuesday and return on a Friday

Cheap flight deals from Chicago to Islamorada

Keep the following information in mind while searching for Chicago to Islamorada flight deals. Data was last updated February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$96
(FlightHub)

One-way from

$45
(FlightHub)

Popular in

December

Cheapest in

July

Average price

$263
Provider with most accurate pricing for Chicago (CHI)-Miami flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Miami flights.
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From Chicago (CHI) to Islamorada
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One-way flight from Chicago (CHI) to Islamorada
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Highest demand for flights based on searches. 16% potential increase in price ($48 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($9 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 Islamorada

Cheapest flights from Chicago to Islamorada
Explore the most affordable flight options available from Chicago to Islamorada. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 20, 2025.

This FlightHub deal was found by Cheapflights users on 2/18. 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.
Mon 3/102:34 pmORD - MIA
Nonstop3h 13mSpirit Airlines
Mon 3/177:42 pmMIA - ORD
Nonstop3h 41mSpirit Airlines
Deal found 2/18$96
This Cheapflightsfares deal was found by Cheapflights users on 2/18. 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.
Sat 3/82:25 pmORD - MIA
1 stop9h 00mFrontier
Mon 3/178:00 amMIA - ORD
1 stop9h 31mFrontier
Deal found 2/18$98
This eDestinos deal was found by Cheapflights users on 2/20. 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 4/82:36 pmMDW - MIA
1 stop7h 39mFrontier
Tue 4/1510:36 amMIA - MDW
1 stop10h 09mFrontier
Deal found 2/20$99
This FlightHub deal was found by Cheapflights users on 2/19. 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.
Sat 3/16:32 pmORD - MIA
1 stop9h 44mMultiple Airlines
Thu 3/611:03 amMIA - ORD
Nonstop3h 44mMultiple Airlines
Deal found 2/19$102
This American Airlines deal was found by Cheapflights users on 2/20. 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.
Sat 3/156:58 pmORD - MIA
Nonstop3h 19mAmerican Airlines
Wed 3/198:26 amMIA - ORD
Nonstop3h 32mAmerican Airlines
Deal found 2/20$199
This Delta deal was found by Cheapflights users on 2/19. 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 3/255:45 amORD - MIA
1 stop7h 00mDelta
Tue 3/256:10 pmMIA - ORD
1 stop6h 46mDelta
Deal found 2/19$217
This Delta deal was found by Cheapflights users on 2/20. 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 4/82:57 pmMDW - MIA
1 stop5h 21mDelta
Tue 4/158:05 amMIA - MDW
1 stop5h 30mDelta
Deal found 2/20$217
This Southwest deal was found by Cheapflights users on 2/20. 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.
Wed 3/123:35 pmMDW - MIA
1 stop6h 15mSouthwest
Tue 3/185:55 pmMIA - MDW
Nonstop3h 20mSouthwest
Deal found 2/20$228

Find flights from Chicago to Islamorada within your budget

Customize your flight search to find flights from Chicago to Islamorada 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 20, 2025.

Fly from

Chicago

Fly to

Islamorada

Route

Depart

Return

Price

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Mon 3/10

2:34 pm-6:47 pm

Nonstop3h 13m

Miami

Mon 3/17

7:42 pm-10:23 pm

Nonstop3h 41m

$96

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sat 3/8

2:25 pm-12:25 am

1 stop9h 00m

Miami

Mon 3/17

8:00 am-4:31 pm

1 stop9h 31m

$98

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Tue 4/8

2:36 pm-11:15 pm

1 stop7h 39m

Miami

Tue 4/15

10:36 am-7:45 pm

1 stop10h 09m

$99

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sat 3/1

6:32 pm-5:16 am

1 stop9h 44m

Miami

Thu 3/6

11:03 am-1:47 pm

Nonstop3h 44m

$102

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sat 3/15

6:58 pm-11:17 pm

Nonstop3h 19m

Miami

Wed 3/19

8:26 am-10:58 am

Nonstop3h 32m

$199

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Tue 3/25

5:45 am-1:45 pm

1 stop7h 00m

Miami

Tue 3/25

6:10 pm-11:56 pm

1 stop6h 46m

$217

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Tue 4/8

2:57 pm-9:18 pm

1 stop5h 21m

Miami

Tue 4/15

8:05 am-12:35 pm

1 stop5h 30m

$217

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Wed 3/12

3:35 pm-10:50 pm

1 stop6h 15m

Miami

Tue 3/18

5:55 pm-8:15 pm

Nonstop3h 20m

$228

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Tue 3/11

5:55 am-4:16 pm

1 stop9h 21m

$45

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Sun 3/9

7:25 am-11:37 am

Nonstop3h 12m

$48

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

Showing 1-10 of 20 results
1
2

Best time to book a flight from Chicago to Islamorada

Have a flexible travel schedule? Discover the best time to fly to Islamorada 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 Islamorada

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

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

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Islamorada. Price data was last updated on February 14, 2025.

The best time to book flights from Chicago to Islamorada is 28 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

What is the cheapest month to book a flight from Chicago to Islamorada?

Currently, September is the cheapest month in which you can book a flight from Chicago to Islamorada (average of $231). Flying from Chicago to Islamorada in March is currently the most expensive (average of $289). 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 I5L?

Find hourly flight availability from Chicago to Islamorada. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 20, 2025.

When flying from Chicago to Islamorada, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

What is the cheapest day to fly from Chicago to Islamorada?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Islamorada. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Chicago to Islamorada flight should consider departing on Tuesday evenings when fares are most often at their lowest. Tuesday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Chicago to Islamorada

Explore weekly flight availability from Chicago to Islamorada. 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 20, 2025.

The most flights from CHI to I5L are scheduled on a Thursday (49 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (20 on average).

Rainfall in Islamorada by month

Plan your trip to Islamorada by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Islamorada 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 Islamorada when rainfall is around 1.6 in.

Temperature in Islamorada by month

Plan your trip to Islamorada by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Islamorada, 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 Islamorada

Get insights into the airlines that provide service to Islamorada. 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 Islamorada. Reviews last updated February 20, 2025.
To help decide which airline to fly from Chicago to Islamorada, see what other customers have to say about Southwest, Delta and United Airlines. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Boarding

8.2

Food

7.1

Comfort

8.1

Overall

8.1

Crew

8.7

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
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Boarding

8.2

Food

7.1

Comfort

8.1

Overall

8.1

Crew

8.7

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
8,220 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Boarding

8.2

Food

7.1

Comfort

8.1

Overall

8.1

Crew

8.7

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
8,766 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Boarding

8.2

Food

7.1

Comfort

8.1

Overall

8.1

Crew

8.7

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.

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Boarding

8.2

Food

7.1

Comfort

8.1

Overall

8.1

Crew

8.7

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.

Sun Country Air
7.0
Good
374 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Boarding

8.2

Food

7.1

Comfort

8.1

Overall

8.1

Crew

8.7

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 Islamorada. 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 Islamorada one-way?

    $45 is the cheapest one-way deal found within the past few days, from Spirit Airlines. You may also be able to find cheap deals on Frontier and Southwest, with prices starting from $48 and $90, respectively.

  • What are the most reliable airlines from Chicago to Islamorada?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Chicago to Islamorada on time: Avianca (86%), United Airlines (85%), Copa Airlines (84%).

  • What are the cheapest flights from Chicago to Islamorada?

    Looking at all options, your cheapest flight can be booked for $44. While the most popular route (Chicago O'Hare Intl - Miami) can be booked for $76 on average our data indicates $776 when flying from Chicago to Islamorada.

  • Can I find deals for flights from Chicago to Islamorada that include hotel bookings?

    Yes. In addition to deals on Chicago to Islamorada flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Islamorada?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Islamorada.

  • Can I find deals for business class flights from Chicago to Islamorada?

    Yes. Cheapflights offers flight deals from Chicago to Islamorada 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 Islamorada?

    Currently, September is the cheapest month in which you can book a flight from Chicago to Islamorada (average of $231). Flying from Chicago to Islamorada in March is currently the most expensive (average of $289). 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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Top 6 airlines flying from Chicago to Islamorada

Discover the top 6 airlines that operate flights from Chicago to Islamorada. 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 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$40Average$171FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$66Average$200FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$158Average$382FlexibilityNo cancel feeOn-time71%
DeltaCheapest$177Average$393FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$178Average$377FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$189Average$395FlexibilityNo cancel feeOn-time63%
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