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Islamorada

$31+ 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 12/4. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MIA
Nov 10 — Nov 171
Sun 11/10
Sun 11/17
1 adult, Economy
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The best prices from Chicago to Islamorada are usually found in July or September, booked 20 days in advance, depart on a Tuesday or Wednesday and return on a Wednesday

Cheap flight deals from Chicago to Islamorada

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Islamorada (I5L). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated November 5, 2024.

Popular in

March

Cheapest in

July

Round-trip from

$108
(Kiwi.com)

One-way from

$31
(eDestinos)
High demand for flights, 26% potential price rise
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Best time to find cheap flights, 22% potential price drop
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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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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 November 5, 2024.

This Kiwi.com deal was found by Cheapflights users on 11/3. 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 12/38:02 pmORD - MIA
Nonstop3h 18mSpirit Airlines
Sat 12/144:38 pmMIA - ORD
Nonstop3h 29mSpirit Airlines
Deal found 11/3$108
This Cheapflightsfares deal was found by Cheapflights users on 11/5. 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.
Sat 11/164:24 pmORD - MIA
1 stop6h 12mFrontier
Sat 11/233:07 pmMIA - ORD
1 stop10h 21mFrontier
Deal found 11/5$109
This FlightHub deal was found by Cheapflights users on 11/4. 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.
Thu 12/57:25 amORD - MIA
1 stop17h 27mMultiple Airlines
Sat 12/74:38 pmMIA - ORD
Nonstop3h 29mMultiple Airlines
Deal found 11/4$111
This FlightHub deal was found by Cheapflights users on 11/4. 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.
Mon 11/118:31 pmMDW - MIA
Nonstop3h 17mFrontier
Mon 11/189:50 pmMIA - MDW
1 stop19h 00mFrontier
Deal found 11/4$113
This eDestinos deal was found by Cheapflights users on 11/4. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/412:57 pmMDW - MIA
2 stops33h 27mMultiple Airlines
Wed 12/119:30 amMIA - MDW
2 stops32h 48mMultiple Airlines
Deal found 11/4$172
This Southwest deal was found by Cheapflights users on 11/4. 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.
Wed 12/47:10 amMDW - MIA
1 stop7h 40mSouthwest
Wed 12/113:40 pmMIA - MDW
Nonstop3h 10mSouthwest
Deal found 11/4$207
This American Airlines deal was found by Cheapflights users on 11/3. 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.
Wed 12/46:50 pmORD - MIA
Nonstop3h 23mAmerican Airlines
Tue 12/101:40 pmMIA - ORD
Nonstop3h 29mAmerican Airlines
Deal found 11/3$212
This Delta deal was found by Cheapflights users on 11/4. 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.
Tue 11/1912:00 pmORD - MIA
1 stop5h 33mDelta
Tue 11/268:05 amMIA - ORD
1 stop5h 45mDelta
Deal found 11/4$255
This United Airlines deal was found by Cheapflights users on 11/4. 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 12/712:45 pmORD - MIA
Nonstop3h 12mUnited Airlines
Mon 12/96:01 pmMIA - ORD
Nonstop3h 24mUnited Airlines
Deal found 11/4$258
This Delta deal was found by Cheapflights users on 11/3. 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.
Tue 11/1210:41 amMDW - MIA
1 stop5h 16mDelta
Tue 11/196:00 amMIA - MDW
1 stop6h 58mDelta
Deal found 11/3$272

Find flights from Chicago to Islamorada within your budget

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 2,554,862 searches. Data last updated November 5, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Tue 12/10

7:33 am-2:56 pm

1 stop6h 23m

$58

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Mon 11/25

5:24 pm-9:43 pm

Nonstop3h 19m

$58

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Tue 11/19

7:10 am-11:26 am

Nonstop3h 16m

$105

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sat 1/25

5:15 pm-12:51 am

1 stop6h 36m

$108

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Wed 2/5

6:00 pm-10:00 pm

Nonstop3h 00m

$111

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Mon 11/18

6:05 am-8:16 am

3 stops49h 11m

$119

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Tue 2/18

5:01 am-12:32 pm

1 stop6h 31m

$62

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sat 2/15

2:57 pm-7:04 pm

Nonstop3h 07m

$159

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Fri 11/15

9:48 am-7:49 pm

1 stop9h 01m

$211

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Wed 11/20

6:49 pm-12:53 am

1 stop5h 04m

$114

Flights are sorted by cheapest first

Deals found on 11/4

Showing 1-10 of 21 results
1
2
3

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.

Travel insights for flights from Chicago to Islamorada

Get recent, data-driven insights about flights from Chicago to Islamorada including ideal travel times, pricing trends, and more.

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 November 1, 2024.

The best time to book flights from Chicago to Islamorada is 20 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.

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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 $218). Flying from Chicago to Islamorada in March is currently the most expensive (average of $287). 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 November 5, 2024.

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 November 3, 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. Friday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

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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 November 5, 2024.

The most flights from CHI to I5L are scheduled on a Monday (43 on average). You will have fewer flight options on Friday, which is when the least amount of flights are scheduled (10 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 November 5, 2024.
To help decide which airline to fly from Chicago to Islamorada, see what other customers have to say about American Airlines, Frontier and Spirit Airlines. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
5,082 reviews

Crew

8.7

Food

7.2

Comfort

8.1

Boarding

8.3

Entertainment

7.7

Overall

8.1

Reviews

1 / 10

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
8.1
Very good
5,082 reviews
Southwest
8.1
Very good
5,082 reviews

Crew

8.7

Food

7.2

Comfort

8.1

Boarding

8.3

Entertainment

7.7

Overall

8.1

Reviews

1 / 10

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
8,830 reviews
Southwest
8.1
Very good
5,082 reviews

Crew

8.7

Food

7.2

Comfort

8.1

Boarding

8.3

Entertainment

7.7

Overall

8.1

Reviews

1 / 10

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
7.5
Good
3,486 reviews
Southwest
8.1
Very good
5,082 reviews

Crew

8.7

Food

7.2

Comfort

8.1

Boarding

8.3

Entertainment

7.7

Overall

8.1

Reviews

1 / 10

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
9,215 reviews
Southwest
8.1
Very good
5,082 reviews

Crew

8.7

Food

7.2

Comfort

8.1

Boarding

8.3

Entertainment

7.7

Overall

8.1

Reviews

1 / 10

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
8.1
Very good
5,082 reviews

Crew

8.7

Food

7.2

Comfort

8.1

Boarding

8.3

Entertainment

7.7

Overall

8.1

Reviews

1 / 10

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.

  • Can I find flights from Chicago to Islamorada for under $200 on Cheapflights?

    Yes, there are multiple flights from Chicago to Islamorada for under $200. The cheapest flight booked recently is on Spirit Airlines for just $108, but on average you can expect to pay $153.

  • Are there nonstop flights from Chicago to Islamorada for under $200 on Cheapflights?

    Cheapflights has at least 5 direct flights from Chicago to Islamorada under $200. A good price for a nonstop flight from Chicago to Islamorada is less than $166.

  • Are there last-minute flights available from Chicago to Islamorada for under $200?

    There are currently 9+ open flights from Chicago to Islamorada within the next 7 days for less than $200.

  • What days are nonstop flights available from Chicago to Islamorada?

    Nonstop flights can be found on the following days: Thursday, Saturday.

  • How many flights depart from Chicago to Islamorada on average per day?

    On average, you can expect to see 11 flights from Chicago to Islamorada a day.
    Morning (6am - Noon) - 36% of flight departures
    Afternoon (Noon - 6pm) - 64% of flight departures

  • How long is the flight from Chicago to Islamorada?

    Spirit Airlines, Frontier, and American Airlines can get you from Chicago to Islamorada in just under 3h 11m. Your travel time can differ by up to 10h 56m. The distance between Chicago and Islamorada is about 1205 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?

    $31 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 $50 and $105, 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: Royal Jordanian (97%), Spirit Airlines (96%), American Airlines (94%).

  • What are the cheapest flights from Chicago to Islamorada?

    Looking at all options, your cheapest flight can be booked for $65. While the most popular route (Chicago O'Hare Intl - Miami) can be booked for $86 on average our data indicates $693 when flying from Chicago to Islamorada.

  • What does ORD to MIA mean?

    ORD stands for Chicago O'Hare Intl Airport, while MIA stands for Miami Airport. These codes are often called IATA codes, a set of identifiers established by IATA (International Air Transport Association) that is widely used by airlines and the aviation industry. Fort Lauderdale Airport (FLL), Key West Airport (EYW), Miami Opa Locka Airport (OPF), Fort Lauderdale Executive Airport (FXE) are other airports near this flight route and their unique identifiers/IATA codes.

  • Can I find deals for flights from Chicago to Islamorada that include extra baggage allowance?

    The amount of baggage you can bring on your Chicago to Islamorada flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Chicago to Islamorada with specific airlines?

    Yes, Cheapflights allows you to browse and filter Chicago to Islamorada flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • 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.

  • Can I find deals for flights from Chicago to Islamorada that allow pets onboard?

    Many airlines flying from Chicago to Islamorada offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Chicago to Islamorada?

    Yes, you can often find last-minute deals on Chicago to Islamorada flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Chicago to Islamorada flight deals updated?

    The Chicago to Islamorada flight deals you see on this page were last updated on 11/5.

  • 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 $218). Flying from Chicago to Islamorada in March is currently the most expensive (average of $287). 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 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 2,554,862 searches. Data last updated November 5, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$29Average$157FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$58Average$142FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$158Average$326FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$159Average$387FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$180Average$403FlexibilityNo cancel feeOn-time69%
DeltaCheapest$215Average$435FlexibilityNo cancel feeOn-timeN/A
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