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Islamorada

$54+ 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 2/27. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MIA
Jan 26 — Feb 21
Sun 1/26
Sun 2/2
1 adult, Economy
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The best prices from Chicago to Islamorada are usually found in September or April, booked 28 days in advance, depart on a Tuesday or Wednesday and return on a Friday

Cheap flight deals from Chicago to Islamorada

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Islamorada (I5L). 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 January 21, 2025.

Round-trip from

$105
(eDestinos)

One-way from

$54
(Cheapflightsfares)

Popular in

December

Cheapest in

September

Average price

$245
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. 17% potential increase in price ($51 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 January 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 January 21, 2025.

This FlightHub deal was found by Cheapflights users on 1/21. 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 2/198:33 amORD - MIA
1 stop8h 17mMultiple Airlines
Sat 2/228:05 amMIA - ORD
Nonstop3h 32mMultiple Airlines
Deal found 1/21$107
This FlightHub deal was found by Cheapflights users on 1/20. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/197:25 amMDW - MIA
Nonstop3h 12mFrontier
Sat 2/226:25 amMIA - MDW
1 stop18h 52mFrontier
Deal found 1/20$107
This Cheapflightsfares deal was found by Cheapflights users on 1/21. 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 2/227:25 amORD - MIA
1 stop14h 55mFrontier
Thu 2/271:29 pmMIA - ORD
1 stop8h 22mFrontier
Deal found 1/21$108
This Cheapflightsfares deal was found by Cheapflights users on 1/20. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/22:02 pmORD - MIA
Nonstop3h 14mSpirit Airlines
Tue 2/410:00 amMIA - ORD
Nonstop3h 29mSpirit Airlines
Deal found 1/20$109
This American Airlines deal was found by Cheapflights users on 1/21. 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.
Sun 2/231:59 pmORD - MIA
Nonstop3h 11mAmerican Airlines
Tue 2/258:27 amMIA - ORD
Nonstop3h 30mAmerican Airlines
Deal found 1/21$157
This United Airlines deal was found by Cheapflights users on 1/21. 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 2/182:06 pmORD - MIA
Nonstop3h 20mUnited Airlines
Tue 2/257:00 amMIA - ORD
Nonstop3h 34mUnited Airlines
Deal found 1/21$177
This Delta deal was found by Cheapflights users on 1/21. 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 2/182:08 pmMDW - MIA
1 stop6h 34mDelta
Thu 2/206:00 amMIA - MDW
1 stop5h 12mDelta
Deal found 1/21$217
This Delta deal was found by Cheapflights users on 1/20. 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.
Sat 2/85:10 pmORD - MIA
1 stop6h 41mDelta
Wed 2/121:34 pmMIA - ORD
1 stop4h 51mDelta
Deal found 1/20$237
This Southwest deal was found by Cheapflights users on 1/20. 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.
Mon 2/36:10 pmMDW - MIA
Nonstop3h 00mSouthwest
Wed 2/54:40 pmMIA - MDW
Nonstop3h 15mSouthwest
Deal found 1/20$237
This JetBlue deal was found by Cheapflights users on 1/21. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/311:24 pmORD - MIA
1 stop9h 27mJetBlue
Tue 4/87:00 amMIA - ORD
1 stop6h 27mJetBlue
Deal found 1/21$255

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 January 21, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Mon 2/10

2:02 pm-6:16 pm

Nonstop3h 14m

Miami

Tue 2/25

9:42 pm-7:28 am

1 stop10h 46m

$105

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Tue 2/18

7:25 am-11:37 am

Nonstop3h 12m

Miami

Tue 2/25

9:42 pm-7:07 am

1 stop10h 25m

$105

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Wed 5/7

7:00 am-11:14 am

Nonstop3h 14m

Miami

Sat 5/10

7:21 pm-9:30 pm

Nonstop3h 09m

$106

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sat 2/22

7:25 am-11:20 pm

1 stop14h 55m

Miami

Tue 2/25

9:42 pm-7:28 am

1 stop10h 46m

$108

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sun 2/23

7:00 am-11:10 am

Nonstop3h 10m

Miami

Wed 2/26

9:12 am-11:40 am

Nonstop3h 28m

$157

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Wed 4/2

10:37 am-6:44 pm

1 stop7h 07m

Miami

Tue 4/8

7:00 am-12:27 pm

1 stop6h 27m

$197

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Tue 2/18

2:08 pm-9:42 pm

1 stop6h 34m

Miami

Thu 2/27

6:00 am-11:59 am

1 stop6h 59m

$217

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sat 2/8

5:10 pm-12:51 am

1 stop6h 41m

Miami

Wed 2/12

1:34 pm-5:25 pm

1 stop4h 51m

$237

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Fri 1/31

12:45 pm-5:06 pm

Nonstop3h 21m

Miami

Tue 2/25

7:00 am-9:34 am

Nonstop3h 34m

$252

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Tue 2/18

6:20 am-3:50 pm

1 stop8h 30m

Miami

Thu 2/20

1:25 pm-8:30 pm

2 stops8h 05m

$262

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/21

Showing 1-10 of 23 results
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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 January 17, 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 $230). 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 January 21, 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. Thursday 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 January 21, 2025.

The most flights from CHI to I5L are scheduled on a Monday (43 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (24 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 January 21, 2025.
To help decide which airline to fly from Chicago to Islamorada, see what other customers have to say about Frontier, 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
4,662 reviews

Comfort

8.1

Crew

8.7

Food

7.2

Boarding

8.2

Entertainment

7.7

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
4,662 reviews
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Crew

8.7

Food

7.2

Boarding

8.2

Entertainment

7.7

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
8,521 reviews
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Crew

8.7

Food

7.2

Boarding

8.2

Entertainment

7.7

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
7.4
Good
3,201 reviews
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Crew

8.7

Food

7.2

Boarding

8.2

Entertainment

7.7

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
8,985 reviews
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Crew

8.7

Food

7.2

Boarding

8.2

Entertainment

7.7

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.

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Crew

8.7

Food

7.2

Boarding

8.2

Entertainment

7.7

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 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?

    $54 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on Spirit Airlines and United Airlines, with prices starting from $65 and $79, 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 (87%), United Airlines (86%), Copa Airlines (81%).

  • What are the cheapest flights from Chicago to Islamorada?

    Looking at all options, your cheapest flight can be booked for $62. While the most popular route (Chicago O'Hare Intl - Miami) can be booked for $85 on average our data indicates $733 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 $230). 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 January 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$29Average$185FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$68Average$189FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$158Average$387FlexibilityNo cancel feeOn-time71%
DeltaCheapest$177Average$427FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$179Average$385FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$188Average$396FlexibilityNo cancel feeOn-time63%
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