What are the cheapest airlines to fly from Chicago to Islamorada one-way?

$29 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on JetBlue and Southwest, with prices starting from $68 and $78, respectively.

Weekly flight availability from Chicago to Islamorada

The most flights from CHI to I5L are scheduled on a Monday (48 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (29 on average).

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.

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).

What are the cheapest flights from Chicago to Islamorada?

Looking at all options, your cheapest flight can be booked for $92. While the most popular route (Chicago O'Hare Intl - Miami) can be booked for $220 on average, our data indicates $973 when flying from Chicago to Islamorada.

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 (75%), Air Canada (70%), Copa Airlines (70%).

What are the most popular airlines that fly from Chicago to Islamorada?

Before booking your flight from Chicago to Islamorada check out the most popular airlines for this route: American Airlines, United Airlines or Frontier.

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.

Find Cheap Flights from Chicago to Islamorada

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Cheapflights Tip: The best prices from Chicago to Islamorada are usually found in January or April, booked 33 days in advance, depart on a Monday or Saturday and return on a Thursday

Find flight deals from Chicago to Islamorada

Most accurate provider	FlightHub 3 stars
Most trusted provider	FlightHub 3 stars
Popular in	July
Cheapest in	January
Average price	$329

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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Highest demand for flights based on searches. 12% potential increase in price ($43 potential increase over avg. RT price).

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Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).

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Average for round-trip flights in September 2026

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Cheapflights Insights

Everything you need to know about your flight from Chicago to Islamorada

Prices

Airlines

What is the cheapest time of day to fly from CHI to I5L?

When flying from Chicago to Islamorada, the time of day you fly usually plays a role in the price. Save by searching for a flight at noon, which can drop the price by up to 14% versus a flight in the evening.

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

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

Reviews of airlines servicing Islamorada

Read reviews from past customers who have flown Southwest,United Airlines, andJetBlue from Chicago to Islamorada. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.

Southwest

8.0

Very good

4,199 reviews

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.

Southwest

8.0

Very good

4,199 reviews

Southwest

8.0

Very good

4,199 reviews

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.

United Airlines

7.4

Good

10,233 reviews

Southwest

8.0

Very good

4,199 reviews

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.

JetBlue

7.1

Good

3,040 reviews

Southwest

8.0

Very good

4,199 reviews

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.

American Airlines

7.0

Good

12,074 reviews

Southwest

8.0

Very good

4,199 reviews

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.

Frontier

5.6

Fair

2,578 reviews

Southwest

8.0

Very good

4,199 reviews

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

What are the cheapest airlines to fly from Chicago to Islamorada one-way?
$29 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on JetBlue and Southwest, with prices starting from $68 and $78, 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 (75%), Air Canada (70%), Copa Airlines (70%).
What are the cheapest flights from Chicago to Islamorada?
Looking at all options, your cheapest flight can be booked for $92. While the most popular route (Chicago O'Hare Intl - Miami) can be booked for $220 on average, our data indicates $973 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.

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Top 7 airlines flying from Chicago to Islamorada

Airline	Cheapest	Average	Flexibility	On-time
Frontier	Cheapest$57	Average$215	FlexibilityNo cancel fee	On-time62%
Allegiant Air	Cheapest$83	Average$129	FlexibilityNo cancel fee	On-time88%
JetBlue	Cheapest$89	Average$258	FlexibilityNo cancel fee	On-time62%
Delta	Cheapest$118	Average$352	FlexibilityNo cancel fee	On-timeN/A
American Airlines	Cheapest$157	Average$379	FlexibilityNo cancel fee	On-time71%
United Airlines	Cheapest$161	Average$367	FlexibilityNo cancel fee	On-time69%
Southwest	Cheapest$203	Average$390	FlexibilityNo cancel fee	On-time63%

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Cheap flights from Chicago (CHI) to Islamorada, FL

Find cheap flights from Chicago to Islamorada with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Find flight deals from Chicago to Islamorada

Most accurate provider

Most trusted provider

Popular in

Cheapest in

Average price

Cheapflights Insights

What is the cheapest time of day to fly from CHI to I5L?

When flying from Chicago to Islamorada, the time of day you fly usually plays a role in the price. Save by searching for a flight at noon, which can drop the price by up to 14% versus a flight in the evening.

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

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

Weekly flight availability from Chicago to Islamorada

The most flights from CHI to I5L are scheduled on a Monday (48 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (29 on average).

Reviews of airlines servicing Islamorada

Read reviews from past customers who have flown Southwest,United Airlines, andJetBlue from Chicago to Islamorada. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.

Related info for your journey

What are the cheapest airlines to fly from Chicago to Islamorada one-way?

What are the most reliable airlines from Chicago to Islamorada?

What are the cheapest flights from Chicago to Islamorada?

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

How can I find direct flights from Chicago to Islamorada?

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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Chicago to Islamorada

See prices for flight routes from nearby airports that may be better suited for you.

Complete your trip

Complete your trip to Islamorada by adding a car rental and/or hotel reservation to your travel itinerary.

Search flights from Chicago to Islamorada by cabin class

Find flights from Chicago to Islamorada, based on your preferred cabin class, be it economy, premium economy, business, or first class.

Chicago and Islamorada flights

Browse other Chicago and Islamorada flight options. Last updated on September 24, 2026.

Other flights from Chicago

Browse through other flights departing from Chicago. Flights are based on user searches made on Cheapflights and were last updated on September 24, 2026.

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Top 7 airlines flying from Chicago to Islamorada

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