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Islamorada

$60+ 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 10/30. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MIA
Sep 2 — Sep 91
Tue 9/2
Tue 9/9
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Islamorada are usually found in September or October, booked 41 days in advance, depart on a Thursday or Monday 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 August 28, 2025.

Round-trip from

$113
(Priceline)

One-way from

$60
(Frontier)

Popular in

March

Cheapest in

September

Average price

$246
From Chicago (CHI) to Islamorada
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One-way flight from Chicago (CHI) to Islamorada
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($25 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in August 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 August 28, 2025.

This Trip.com deal was found by Cheapflights users on 8/28. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/146:10 amORD - MIA
1 stop13h 11mMultiple Airlines
Fri 9/197:00 amMIA - ORD
Nonstop3h 18mMultiple Airlines
Deal found 8/28$114
This FlightHub deal was found by Cheapflights users on 8/27. 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 9/1010:27 amORD - MIA
Nonstop3h 12mMultiple Airlines
Thu 9/184:00 pmMIA - ORD
1 stop8h 20mMultiple Airlines
Deal found 8/27$115
This Priceline deal was found by Cheapflights users on 8/26. 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 10/158:05 amMDW - MIA
1 stop9h 40mFrontier
Sat 11/87:05 pmMIA - MDW
Nonstop3h 17mFrontier
Deal found 8/26$116
This Cheapflightsfares deal was found by Cheapflights users on 8/28. 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 9/1410:27 amORD - MIA
Nonstop3h 12mSpirit Airlines
Sat 9/207:00 amMIA - ORD
Nonstop3h 18mSpirit Airlines
Deal found 8/28$116
This CheapOair deal was found by Cheapflights users on 8/26. 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.
Mon 10/2010:33 amMDW - MIA
Nonstop3h 00mFrontier
Thu 10/238:50 amMIA - MDW
1 stop9h 23mFrontier
Deal found 8/26$117
This Gotogate deal was found by Cheapflights users on 8/27. 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.
Thu 9/2510:27 amORD - MIA
Nonstop3h 12mMultiple Airlines
Sun 9/286:00 amMIA - ORD
1 stop28h 37mMultiple Airlines
Deal found 8/27$117
This CheapOair deal was found by Cheapflights users on 8/26. 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.
Sun 11/95:40 amMDW - MIA
1 stop11h 08mFrontier
Sat 11/157:05 pmMIA - MDW
Nonstop3h 17mFrontier
Deal found 8/26$118
This FlightHub deal was found by Cheapflights users on 8/27. 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.
Sun 10/1910:27 amORD - MIA
Nonstop3h 02mSpirit Airlines
Mon 10/207:00 amMIA - ORD
Nonstop3h 22mSpirit Airlines
Deal found 8/27$118
This Priceline deal was found by Cheapflights users on 8/27. 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.
Thu 10/98:25 amMDW - MIA
1 stop10h 29mFrontier
Mon 10/139:26 pmMIA - MDW
Nonstop3h 20mFrontier
Deal found 8/27$119
This FlightHub deal was found by Cheapflights users on 8/28. 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.
Sun 11/91:35 pmORD - MIA
Nonstop3h 15mMultiple Airlines
Sat 11/156:35 pmMIA - ORD
1 stop5h 54mMultiple Airlines
Deal found 8/28$119
This CheapOair deal was found by Cheapflights users on 8/26. 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.
Sat 11/12:05 pmMDW - MIA
Nonstop3h 00mFrontier
Mon 11/1010:30 amMIA - MDW
1 stop7h 45mFrontier
Deal found 8/26$120
This Kiwi.com deal was found by Cheapflights users on 8/26. 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.
Mon 10/275:50 pmORD - MIA
1 stop5h 44mMultiple Airlines
Tue 11/47:00 amMIA - ORD
Nonstop3h 22mMultiple Airlines
Deal found 8/26$120

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 August 28, 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

Sun 9/14

6:10 am-8:21 pm

1 stop13h 11m

Miami

Fri 9/19

7:00 am-9:18 am

Nonstop3h 18m

$114

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Fri 11/7

1:36 pm-2:23 pm

1 stop23h 47m

Miami

Sun 11/16

10:15 am-12:30 pm

Nonstop3h 15m

$115

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Fri 9/19

6:11 pm-10:42 pm

1 stop27h 31m

Miami

Mon 9/22

7:00 am-9:18 am

Nonstop3h 18m

$115

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Tue 9/9

10:27 am-2:39 pm

Nonstop3h 12m

Miami

Tue 9/16

7:00 am-9:18 am

Nonstop3h 18m

$116

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Mon 9/15

10:27 am-2:39 pm

Nonstop3h 12m

Miami

Sat 9/20

7:00 am-9:18 am

Nonstop3h 18m

$116

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Mon 9/8

10:27 am-2:39 pm

Nonstop3h 12m

Miami

Wed 9/17

7:00 am-9:18 am

Nonstop3h 18m

$116

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Thu 10/2

6:11 pm-2:55 pm

1 stop19h 44m

Miami

Tue 10/7

7:00 am-9:22 am

Nonstop3h 22m

$116

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Fri 9/19

10:27 am-2:39 pm

Nonstop3h 12m

Miami

Mon 9/22

7:00 am-9:18 am

Nonstop3h 18m

$116

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Mon 10/20

10:33 am-2:33 pm

Nonstop3h 00m

Miami

Thu 10/23

8:50 am-5:13 pm

1 stop9h 23m

$117

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Tue 10/21

8:05 am-2:32 pm

1 stop5h 27m

Miami

Mon 10/27

9:00 am-11:17 am

Nonstop3h 17m

$117

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/27

Showing 1-10 of 38 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 August 22, 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 $232). 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 August 28, 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 August 28, 2025.

The most flights from CHI to I5L are scheduled on a Monday (38 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (19 on average).

How much does it cost to fly round-trip from Chicago to Islamorada?

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 August 28, 2025.
Read reviews from past customers who have flown Southwest, United Airlines, and American 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
4,242 reviews

Comfort

8.0

Boarding

8.1

Crew

8.6

Overall

8.0

Food

7.0

Entertainment

7.5

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
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Boarding

8.1

Crew

8.6

Overall

8.0

Food

7.0

Entertainment

7.5

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
8,944 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Boarding

8.1

Crew

8.6

Overall

8.0

Food

7.0

Entertainment

7.5

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
4,242 reviews

Comfort

8.0

Boarding

8.1

Crew

8.6

Overall

8.0

Food

7.0

Entertainment

7.5

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
8,028 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Boarding

8.1

Crew

8.6

Overall

8.0

Food

7.0

Entertainment

7.5

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.
Frontier
5.8
Fair
3,204 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Boarding

8.1

Crew

8.6

Overall

8.0

Food

7.0

Entertainment

7.5

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.

  • How long is the flight from Chicago to Islamorada?

    Spirit Airlines and Frontier can get you from Chicago to Islamorada in just under 3h. Your travel time will be generally consistent. The distance between Chicago and Islamorada is about 1183 mi. Generally, flights for this route are nonstop.

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

    $60 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 Southwest, with prices starting from $62 and $69, 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: United Airlines (90%), Spirit Airlines (83%), Air Canada (79%).

  • What are the cheapest flights from Chicago to Islamorada?

    Looking at all options, your cheapest flight can be booked for $55. While the most popular route (Chicago O'Hare Intl - Miami) can be booked for $81 on average our data indicates $595 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 $232). 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 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 August 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$39Average$188FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$85Average$214FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$127Average$383FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$158Average$366FlexibilityNo cancel feeOn-time71%
DeltaCheapest$176Average$392FlexibilityNo cancel feeOn-timeN/A
Alaska AirlinesCheapest$176Average$215FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$176Average$368FlexibilityNo cancel feeOn-time63%

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