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Islamorada

$62+ 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 4/8. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MIA
Apr 6 — Apr 131
Sun 4/6
Sun 4/13
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Islamorada are usually found in July or September, booked 28 days in advance, depart on a Thursday or Friday 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 April 1, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$111
(Gotogate)

One-way from

$63
(Cheapflightsfares)

Popular in

December

Cheapest in

July

Average price

$201
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. 15% potential increase in price ($43 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 April 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 April 1, 2025.

This Gotogate deal was found by Cheapflights users on 3/31. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/139:55 amORD - MIA
Nonstop3h 15mSpirit Airlines
Tue 5/203:15 pmMIA - ORD
Nonstop3h 26mSpirit Airlines
Deal found 3/31$111
This Frontier deal was found by Cheapflights users on 3/31. 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 4/86:00 amMDW - MIA
Nonstop3h 08mFrontier
Tue 4/1511:03 amMIA - MDW
Nonstop3h 28mFrontier
Deal found 3/31$133
This Kiwi.com deal was found by Cheapflights users on 4/1. 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 5/149:55 amORD - MIA
Nonstop3h 15mMultiple Airlines
Sun 5/187:12 amMIA - ORD
1 stop9h 45mMultiple Airlines
Deal found 4/1$148
This Southwest deal was found by Cheapflights users on 3/31. 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 5/48:40 pmMDW - MIA
Nonstop3h 00mSouthwest
Sat 5/105:05 amMIA - MDW
Nonstop3h 10mSouthwest
Deal found 3/31$177
This American Airlines deal was found by Cheapflights users on 3/31. 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 5/37:17 pmORD - MIA
Nonstop3h 12mAmerican Airlines
Tue 5/612:20 pmMIA - ORD
Nonstop3h 32mAmerican Airlines
Deal found 3/31$178
This United Airlines deal was found by Cheapflights users on 3/30. 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.
Sat 5/37:30 amORD - MIA
Nonstop3h 18mUnited Airlines
Fri 5/94:08 pmMIA - ORD
Nonstop3h 35mUnited Airlines
Deal found 3/30$197
This Frontier deal was found by Cheapflights users on 3/31. 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.
Fri 4/255:23 pmORD - MIA
1 stop10h 58mFrontier
Thu 5/13:55 pmMIA - ORD
1 stop8h 16mFrontier
Deal found 3/31$198
This JetBlue Airways deal was found by Cheapflights users on 3/31. 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 Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/31:13 pmORD - MIA
1 stop8h 24mJetBlue
Tue 5/62:30 pmMIA - ORD
1 stop8h 24mJetBlue
Deal found 3/31$217
This Delta deal was found by Cheapflights users on 3/31. 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.
Wed 5/1412:48 pmMDW - MIA
1 stop5h 44mDelta
Wed 5/218:40 amMIA - MDW
1 stop4h 48mDelta
Deal found 3/31$217
This Delta deal was found by Cheapflights users on 4/1. 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 5/245:15 pmORD - MIA
1 stop5h 31mDelta
Tue 5/277:30 pmMIA - ORD
1 stop5h 28mDelta
Deal found 4/1$227

Cheapflights Fare Finder

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 April 1, 2025.
Use the filters below to find and compare flights from Chicago to Islamorada that are best for you.

Fly from

Chicago

Fly to

Islamorada

Route

Depart

Return

Price

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Tue 5/13

9:55 am-2:10 pm

Nonstop3h 15m

Miami

Tue 5/20

3:15 pm-5:41 pm

Nonstop3h 26m

$111

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Tue 4/15

6:00 am-10:08 am

Nonstop3h 08m

Miami

Sat 4/19

12:25 pm-3:00 pm

Nonstop3h 35m

$144

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Wed 4/30

6:51 am-10:57 am

Nonstop3h 06m

Miami

Fri 5/2

6:00 am-1:20 pm

1 stop8h 20m

$150

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Sun 5/4

8:40 pm-12:40 am

Nonstop3h 00m

Miami

Sat 5/10

5:05 am-7:15 am

Nonstop3h 10m

$177

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sat 5/3

7:17 pm-11:29 pm

Nonstop3h 12m

Miami

Tue 5/6

12:20 pm-2:52 pm

Nonstop3h 32m

$178

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sat 5/3

7:30 am-11:48 am

Nonstop3h 18m

Miami

Fri 5/9

4:08 pm-6:43 pm

Nonstop3h 35m

$197

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Fri 4/25

5:23 pm-5:21 am

1 stop10h 58m

Miami

Thu 5/1

3:55 pm-11:11 pm

1 stop8h 16m

$198

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sat 5/3

1:13 pm-10:37 pm

1 stop8h 24m

Miami

Tue 5/6

2:30 pm-9:54 pm

1 stop8h 24m

$217

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Wed 5/14

12:48 pm-6:25 pm

1 stop4h 37m

Miami

Wed 5/21

5:35 am-9:40 am

1 stop5h 05m

$217

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sat 5/24

5:15 pm-11:46 pm

1 stop5h 31m

Miami

Tue 5/27

7:30 pm-11:58 pm

1 stop5h 28m

$227

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/1

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.

Cheapflights Insights

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

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 March 28, 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 $229). 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 April 1, 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 April 1, 2025.

The most flights from CHI to I5L are scheduled on a Wednesday (49 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (32 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 April 1, 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
8.0
Very good
4,277 reviews

Overall

8.0

Comfort

8.0

Boarding

8.2

Crew

8.7

Entertainment

7.6

Food

7.1

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
8.0
Very good
4,277 reviews
Southwest
8.0
Very good
4,277 reviews

Overall

8.0

Comfort

8.0

Boarding

8.2

Crew

8.7

Entertainment

7.6

Food

7.1

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
7,898 reviews
Southwest
8.0
Very good
4,277 reviews

Overall

8.0

Comfort

8.0

Boarding

8.2

Crew

8.7

Entertainment

7.6

Food

7.1

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
8,615 reviews
Southwest
8.0
Very good
4,277 reviews

Overall

8.0

Comfort

8.0

Boarding

8.2

Crew

8.7

Entertainment

7.6

Food

7.1

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
7.3
Good
2,924 reviews
Southwest
8.0
Very good
4,277 reviews

Overall

8.0

Comfort

8.0

Boarding

8.2

Crew

8.7

Entertainment

7.6

Food

7.1

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
8.0
Very good
4,277 reviews

Overall

8.0

Comfort

8.0

Boarding

8.2

Crew

8.7

Entertainment

7.6

Food

7.1

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?

    $63 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 United Airlines, with prices starting from $63 and $89, 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 (89%), Air New Zealand (88%), United Airlines (87%).

  • What are the cheapest flights from Chicago to Islamorada?

    Looking at all options, your cheapest flight can be booked for $61. While the most popular route (Chicago O'Hare Intl - Miami) can be booked for $86 on average our data indicates $963 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 $229). 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 April 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$39Average$164FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$67Average$185FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$158Average$386FlexibilityNo cancel feeOn-time71%
DeltaCheapest$177Average$385FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$179Average$395FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$195Average$390FlexibilityNo cancel feeOn-time63%

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