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Islamorada

$69+ 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 11/3. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MIA
Jul 7 — Jul 141
Mon 7/7
Mon 7/14
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Islamorada are usually found in September or July, booked 41 days in advance, depart on a Thursday or Tuesday and return on a Wednesday

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 July 2, 2025.

Round-trip from

$130
(Kiwi.com)

One-way from

$69
(United Airlines)

Popular in

March

Cheapest in

September

Average price

$185
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. 12% potential increase in price ($37 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 2, 2025.

This Kiwi.com deal was found by Cheapflights users on 7/2. 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.
Sat 8/1610:27 amORD - MIA
Nonstop3h 22mSpirit Airlines
Sat 8/237:00 amMIA - ORD
Nonstop3h 22mSpirit Airlines
Deal found 7/2$130
This Priceline deal was found by Cheapflights users on 6/30. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/235:51 amORD - MIA
1 stop6h 21mMultiple Airlines
Fri 8/16:41 pmMIA - ORD
1 stop6h 41mMultiple Airlines
Deal found 6/30$134
This CheapOair deal was found by Cheapflights users on 6/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/812:49 pmMDW - MIA
1 stop8h 40mFrontier
Sun 8/106:00 amMIA - MDW
1 stop15h 54mFrontier
Deal found 6/29$135
This American Airlines deal was found by Cheapflights users on 6/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/307:05 pmORD - MIA
Nonstop3h 19mAmerican Airlines
Sun 9/76:20 amMIA - ORD
Nonstop3h 20mAmerican Airlines
Deal found 6/30$137
This Southwest deal was found by Cheapflights users on 6/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/42:10 pmMDW - MIA
Nonstop3h 00mSouthwest
Sun 9/77:30 amMIA - MDW
Nonstop3h 05mSouthwest
Deal found 6/30$137
This Priceline deal was found by Cheapflights users on 6/30. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/155:01 amORD - MIA
1 stop5h 13mFrontier
Sun 8/173:00 pmMIA - ORD
1 stop10h 22mFrontier
Deal found 6/30$139
This Southwest deal was found by Cheapflights users on 6/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/247:00 amORD - MIA
1 stop9h 35mSouthwest
Wed 8/277:10 amMIA - ORD
1 stop5h 40mSouthwest
Deal found 6/30$157

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 July 2, 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

Sat 8/16

10:27 am-2:49 pm

Nonstop3h 22m

Miami

Sat 8/23

7:00 am-9:22 am

Nonstop3h 22m

$130

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Wed 7/23

5:51 am-1:12 pm

1 stop6h 21m

Miami

Fri 8/1

6:41 pm-12:22 am

1 stop6h 41m

$134

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Fri 8/8

12:49 pm-10:29 pm

1 stop8h 40m

Miami

Sun 8/10

6:00 am-8:54 pm

1 stop15h 54m

$135

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sat 8/30

7:05 pm-11:24 pm

Nonstop3h 19m

Miami

Thu 9/4

2:23 pm-4:54 pm

Nonstop3h 31m

$137

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Thu 9/4

2:10 pm-6:10 pm

Nonstop3h 00m

Miami

Sun 9/7

7:30 am-9:35 am

Nonstop3h 05m

$137

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Fri 8/15

5:01 am-11:14 am

1 stop5h 13m

Miami

Sun 8/17

3:00 pm-12:22 am

1 stop10h 22m

$139

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sun 8/24

7:00 am-5:35 pm

1 stop9h 35m

Miami

Wed 8/27

7:10 am-11:50 am

1 stop5h 40m

$157

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Mon 11/3

10:35 am-2:50 pm

Nonstop3h 15m

$69

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Mon 11/3

9:30 am-1:35 pm

Nonstop3h 05m

$69

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Wed 8/20

3:05 pm-7:17 pm

Nonstop3h 12m

$70

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/30

Showing 1-10 of 15 results
1
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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 June 27, 2025.

The best time to book flights from Chicago to Islamorada is 41 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 July 2, 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 Monday evenings when fares are most often at their lowest. Wednesday 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 July 2, 2025.

The most flights from CHI to I5L are scheduled on a Wednesday (44 on average). You will have fewer flight options on Friday, which is when the least amount of flights are scheduled (11 on average).

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 July 2, 2025.
Read reviews from past customers who have flown Southwest, Delta, and United Airlines 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
4,272 reviews

Crew

8.6

Overall

8.0

Food

7.0

Boarding

8.2

Entertainment

7.6

Comfort

8.0

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
4,272 reviews
Southwest
8.0
Very good
4,272 reviews

Crew

8.6

Overall

8.0

Food

7.0

Boarding

8.2

Entertainment

7.6

Comfort

8.0

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
7,983 reviews
Southwest
8.0
Very good
4,272 reviews

Crew

8.6

Overall

8.0

Food

7.0

Boarding

8.2

Entertainment

7.6

Comfort

8.0

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
8,861 reviews
Southwest
8.0
Very good
4,272 reviews

Crew

8.6

Overall

8.0

Food

7.0

Boarding

8.2

Entertainment

7.6

Comfort

8.0

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
4,272 reviews

Crew

8.6

Overall

8.0

Food

7.0

Boarding

8.2

Entertainment

7.6

Comfort

8.0

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.
Spirit Airlines
6.3
Okay
8,103 reviews
Southwest
8.0
Very good
4,272 reviews

Crew

8.6

Overall

8.0

Food

7.0

Boarding

8.2

Entertainment

7.6

Comfort

8.0

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?

    $69 is the cheapest one-way deal found within the past few days, from United Airlines. You may also be able to find cheap deals on Southwest and American Airlines, with prices starting from $69 and $70, 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: Air Canada (87%), Copa Airlines (87%), Air New Zealand (87%).

  • What are the cheapest flights from Chicago to Islamorada?

    Looking at all options, your cheapest flight can be booked for $71. While the most popular route (Chicago O'Hare Intl - Miami) can be booked for $85 on average our data indicates $684 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.

See more FAQs

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Top 7 airlines flying from Chicago to Islamorada

Discover the top 7 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 July 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$39Average$188FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$80Average$203FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$129Average$403FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$161Average$380FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$176Average$215FlexibilityNo cancel feeOn-time75%
DeltaCheapest$177Average$382FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$195Average$383FlexibilityNo cancel feeOn-time63%

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