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Islamorada

$53+ 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 4/1. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MIA
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Islamorada are usually found in September or January, booked 69 days in advance, depart on a Monday or Thursday and return on a Friday

Cheap 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 December 18, 2025.

This Super.com deal was found by Cheapflights users on 12/17. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:05 pmORD - MIA
Nonstop3h 16mSpirit Airlines
Wed 1/710:13 amMIA - ORD
1 stop6h 47mSpirit Airlines
Deal found 12/17$102
This Kiwi.com deal was found by Cheapflights users on 12/16. 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 12/316:05 pmORD - MIA
Nonstop3h 16mSpirit Airlines
Fri 1/93:48 pmMIA - ORD
Nonstop3h 28mSpirit Airlines
Deal found 12/16$106
This Super.com deal was found by Cheapflights users on 12/15. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/313:32 pmMDW - MIA
Nonstop3h 10mFrontier
Wed 1/75:07 pmMIA - MDW
1 stop6h 10mFrontier
Deal found 12/15$108
This Kiwi.com deal was found by Cheapflights users on 12/16. 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 12/316:05 pmORD - MIA
Nonstop3h 16mSpirit Airlines
Sat 1/105:54 amMIA - ORD
Nonstop3h 24mSpirit Airlines
Deal found 12/16$119
This Kiwi.com deal was found by Cheapflights users on 12/17. 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 12/316:05 amORD - MIA
1 stop12h 25mMultiple Airlines
Fri 1/95:54 amMIA - ORD
Nonstop3h 24mMultiple Airlines
Deal found 12/17$138
This Kiwi.com deal was found by Cheapflights users on 12/17. 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 12/316:05 amORD - MIA
1 stop12h 25mMultiple Airlines
Wed 1/710:13 amMIA - ORD
1 stop6h 47mMultiple Airlines
Deal found 12/17$147
This Mytrip deal was found by Cheapflights users on 12/15. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:05 pmORD - MIA
Nonstop3h 16mSpirit Airlines
Tue 1/69:59 pmMIA - ORD
2 stops23h 05mSpirit Airlines
Deal found 12/15$162
This Priceline deal was found by Cheapflights users on 12/15. 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.
Tue 12/167:41 pmORD - MIA
Nonstop3h 16mSpirit Airlines
Sat 1/105:54 amMIA - ORD
Nonstop3h 24mSpirit Airlines
Deal found 12/15$163
This Kiwi.com deal was found by Cheapflights users on 12/17. 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.
Tue 12/306:50 amORD - MIA
1 stop14h 09mMultiple Airlines
Wed 1/215:54 amMIA - ORD
Nonstop3h 24mMultiple Airlines
Deal found 12/17$168
This CheapOair deal was found by Cheapflights users on 12/16. 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.
Wed 12/246:12 amMDW - MIA
1 stop12h 18mFrontier
Fri 1/911:43 amMIA - MDW
Nonstop3h 23mFrontier
Deal found 12/16$192
This Kiwi.com deal was found by Cheapflights users on 12/17. 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 12/313:32 pmMDW - MIA
Nonstop3h 10mMultiple Airlines
Tue 1/68:00 amMIA - MDW
1 stop15h 17mMultiple Airlines
Deal found 12/17$199
This CheapOair deal was found by Cheapflights users on 12/16. 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.
Tue 12/306:14 amMDW - MIA
1 stop12h 16mFrontier
Wed 1/711:43 amMIA - MDW
Nonstop3h 23mFrontier
Deal found 12/16$203

Find flight deals from Chicago to Islamorada

Keep the following information in mind while searching for Chicago to Islamorada flight deals. Data was last updated December 18, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$99
(CheapOair)

One-way from

$53
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$346
Provider with most accurate pricing for Chicago (CHI)-Miami flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Miami flights.
Search Deals
From Chicago (CHI) to Islamorada
Search Deals
One-way flight from Chicago (CHI) to Islamorada
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($26 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 December 18, 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

Mon 5/4

6:34 pm-10:51 pm

Nonstop3h 17m

Miami

Thu 5/7

3:47 pm-6:15 pm

Nonstop3h 28m

$108

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Wed 5/6

6:34 pm-10:51 pm

Nonstop3h 17m

Miami

Sun 5/10

7:35 am-6:40 pm

1 stop12h 05m

$196

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Wed 1/14

11:39 am-5:46 pm

1 stop5h 07m

Miami

Sun 1/18

4:44 pm-7:09 pm

Nonstop3h 25m

$202

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Tue 2/17

12:45 pm-9:59 pm

1 stop8h 14m

Miami

Tue 2/24

9:00 am-11:38 am

Nonstop3h 38m

$209

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Thu 4/16

7:41 am-3:04 pm

1 stop6h 23m

Miami

Thu 4/23

7:35 am-6:40 pm

1 stop12h 05m

$209

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Tue 1/20

10:35 am-5:45 pm

1 stop6h 10m

Miami

Tue 1/27

12:00 pm-4:55 pm

1 stop5h 55m

$217

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sat 2/7

6:03 pm-12:51 am

1 stop5h 48m

Miami

Thu 2/19

6:00 am-10:08 am

1 stop5h 08m

$217

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Sun 2/15

4:13 pm-12:53 am

1 stop7h 40m

Miami

Fri 2/20

6:00 am-9:56 am

1 stop4h 56m

$217

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Sat 1/31

4:30 pm-12:51 am

1 stop7h 21m

Miami

Sat 2/7

8:05 am-12:46 pm

1 stop5h 41m

$217

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Sat 2/21

11:01 am-6:21 pm

1 stop6h 20m

Miami

Sat 2/28

6:00 am-10:16 am

1 stop5h 16m

$217

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/17

Showing 1-10 of 41 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 December 12, 2025.

The best time to book flights from Chicago to Islamorada is 69 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, October is the cheapest month in which you can book a flight from Chicago to Islamorada (average of $45). Flying from Chicago to Islamorada in June is currently the most expensive (average of $117). 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 December 18, 2025.

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 in the morning, which can drop the price by up to 18% versus a flight in the evening.

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 Wednesday at noon when fares are most often at their lowest. Friday at noon 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 December 18, 2025.

The most flights from CHI to I5L are scheduled on a Thursday (53 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (15 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 December 18, 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
7.9
Good
4,250 reviews

Food

7.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Overall

7.9

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
7.9
Good
4,250 reviews
Southwest
7.9
Good
4,250 reviews

Food

7.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Overall

7.9

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
9,091 reviews
Southwest
7.9
Good
4,250 reviews

Food

7.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Overall

7.9

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
11,054 reviews
Southwest
7.9
Good
4,250 reviews

Food

7.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Overall

7.9

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
8,190 reviews
Southwest
7.9
Good
4,250 reviews

Food

7.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Overall

7.9

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.
Frontier
5.8
Fair
3,081 reviews
Southwest
7.9
Good
4,250 reviews

Food

7.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Overall

7.9

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.

  • How long is the flight from Chicago to Islamorada?

    Spirit Airlines, Frontier, and United Airlines can get you from Chicago to Islamorada in just under 3h 17m. Your travel time can differ by up to 4h 57m. The distance between Chicago and Islamorada is about 1198 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    $39 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 $42 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: ANA (100%), Emirates (88%), Spirit Airlines (81%).

  • What are the cheapest flights from Chicago to Islamorada?

    Looking at all options, your cheapest flight can be booked for $54. While the most popular route (Chicago O'Hare Intl - Miami) can be booked for $50 on average, our data indicates $767 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, October is the cheapest month in which you can book a flight from Chicago to Islamorada (average of $45). Flying from Chicago to Islamorada in June is currently the most expensive (average of $117). 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 9 airlines flying from Chicago to Islamorada

Discover the top 9 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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$39Average$194FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$85Average$230FlexibilityNo cancel feeOn-time65%
DeltaCheapest$125Average$382FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$127Average$400FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$130Average$302FlexibilityNo cancel feeOn-time62%
Allegiant AirCheapest$150Average$254FlexibilityNo cancel feeOn-time88%
American AirlinesCheapest$153Average$348FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$166Average$379FlexibilityNo cancel feeOn-time63%
Alaska AirlinesCheapest$176Average$215FlexibilityNo cancel feeOn-time75%

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