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Key Largo

$55+ Cheap flights from Chicago (CHI) to Key Largo, 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 11/15. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MIA
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Key Largo are usually found in September or January, booked 41 days in advance, depart on a Monday or Thursday and return on a Friday

Find flight deals from Chicago to Key Largo

Cheapest flights from Chicago to Key Largo
Explore the most affordable flight options available from Chicago to Key Largo. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 30, 2025.

This CheapOair deal was found by Cheapflights users on 10/27. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/1412:17 pmORD - MIA
Nonstop3h 05mSpirit Airlines
Fri 11/218:10 amMIA - ORD
Nonstop3h 25mSpirit Airlines
Deal found 10/27$106
This Mytrip deal was found by Cheapflights users on 10/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/67:41 pmORD - MIA
Nonstop3h 16mSpirit Airlines
Sat 12/134:08 pmMIA - ORD
Nonstop3h 28mSpirit Airlines
Deal found 10/29$107
This CheapOair deal was found by Cheapflights users on 10/29. 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.
Thu 12/42:16 pmMDW - MIA
Nonstop3h 10mFrontier
Sun 12/78:09 pmMIA - MDW
Nonstop3h 21mFrontier
Deal found 10/29$108
This Priceline deal was found by Cheapflights users on 10/27. 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 12/117:41 pmORD - MIA
Nonstop3h 16mSpirit Airlines
Wed 12/242:35 pmMIA - ORD
Nonstop3h 25mSpirit Airlines
Deal found 10/27$108
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/82:05 pmMDW - MIA
Nonstop3h 00mFrontier
Sat 11/157:05 pmMIA - MDW
Nonstop3h 17mFrontier
Deal found 10/28$110
This CheapOair deal was found by Cheapflights users on 10/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/126:05 pmORD - MIA
1 stop11h 14mFrontier
Mon 11/178:00 amMIA - ORD
1 stop16h 44mFrontier
Deal found 10/28$110
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/112:16 pmMDW - MIA
Nonstop3h 10mFrontier
Wed 12/245:30 amMIA - MDW
1 stop17h 42mFrontier
Deal found 10/29$112
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/2011:40 amORD - MIA
Nonstop3h 07mSpirit Airlines
Wed 11/268:10 amMIA - ORD
Nonstop3h 25mSpirit Airlines
Deal found 10/28$112
This Kissandfly.com deal was found by Cheapflights users on 10/28. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/112:16 pmMDW - MIA
Nonstop3h 10mFrontier
Sun 12/145:30 amMIA - MDW
1 stop13h 42mFrontier
Deal found 10/28$113
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/2511:40 amORD - MIA
Nonstop3h 07mSpirit Airlines
Thu 12/44:08 pmMIA - ORD
Nonstop3h 28mSpirit Airlines
Deal found 10/28$113
This Frontier deal was found by Cheapflights users on 10/28. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/206:05 amMDW - MIA
1 stop10h 04mFrontier
Wed 11/262:44 pmMIA - MDW
Nonstop3h 13mFrontier
Deal found 10/28$114
This Priceline deal was found by Cheapflights users on 10/28. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1112:37 pmORD - MIA
1 stop5h 21mMultiple Airlines
Mon 11/248:10 amMIA - ORD
Nonstop3h 25mMultiple Airlines
Deal found 10/28$114

Cheap flight deals from Chicago to Key Largo

Keep the following information in mind while searching for Chicago to Key Largo flight deals. Data was last updated October 30, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$106
(CheapOair)

One-way from

$55
(Priceline)

Popular in

March

Cheapest in

September

Average price

$267
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 Key Largo
Search Deals
One-way flight from Chicago (CHI) to Key Largo
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($17 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Key Largo 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 October 30, 2025.
Use the filters below to find and compare flights from Chicago to Key Largo that are best for you.

Fly from

Chicago

Fly to

Key Largo

Route

Depart

Return

Price

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Sat 1/17

3:55 pm-9:25 pm

1 stop4h 30m

Miami

Sat 1/24

6:30 am-8:40 am

Nonstop3h 10m

$167

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Mon 1/26

5:33 am-12:14 pm

1 stop5h 41m

Miami

Fri 2/6

7:25 pm-11:57 pm

1 stop5h 32m

$217

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Mon 1/26

10:35 am-5:48 pm

1 stop6h 13m

Miami

Tue 2/3

6:00 am-10:08 am

1 stop5h 08m

$217

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sun 12/7

3:45 pm-10:05 pm

1 stop5h 20m

Miami

Fri 12/12

7:10 am-1:00 pm

1 stop6h 50m

$217

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Mon 1/26

4:34 pm-10:48 pm

1 stop5h 14m

Miami

Wed 2/4

8:05 am-1:18 pm

1 stop6h 13m

$217

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Fri 1/9

5:55 pm-12:51 am

1 stop5h 56m

Miami

Sat 1/17

8:05 am-1:07 pm

1 stop6h 02m

$217

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Thu 1/1

5:31 pm-12:31 am

1 stop6h 00m

Miami

Thu 1/8

12:00 pm-4:43 pm

1 stop5h 43m

$217

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Mon 1/26

5:33 am-12:14 pm

1 stop5h 41m

Miami

Thu 2/5

6:00 am-10:08 am

1 stop5h 08m

$217

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Wed 12/3

6:00 am-1:06 pm

1 stop6h 06m

Miami

Wed 12/3

5:07 pm-11:47 pm

1 stop7h 40m

$217

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Wed 2/11

6:17 pm-12:51 am

1 stop5h 34m

Miami

Wed 2/18

6:00 am-9:56 am

1 stop4h 56m

$217

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

Showing 1-10 of 43 results
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Best time to book a flight from Chicago to Key Largo

Have a flexible travel schedule? Discover the best time to fly to Key Largo 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 Key Largo

How far ahead should I book a flight from Chicago to Key Largo?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Key Largo. Price data was last updated on October 24, 2025.

The best time to book flights from Chicago to Key Largo 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 Key Largo?

Currently, March is the cheapest month in which you can book a flight from Chicago to Key Largo (average of $58). Flying from Chicago to Key Largo 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 KE9?

Find hourly flight availability from Chicago to Key Largo. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 30, 2025.

When flying from Chicago to Key Largo, 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 13% versus a flight at noon.

What is the cheapest day to fly from Chicago to Key Largo?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Key Largo. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Chicago to Key Largo 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.

Reviews of airlines servicing Key Largo

Get insights into the airlines that provide service to Key Largo. 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 Key Largo. Reviews last updated October 30, 2025.
Read through reviews of airlines operating flights from Chicago to Key Largo, such as Southwest, United Airlines, and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,243 reviews

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

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
4,243 reviews
Southwest
8.0
Very good
4,243 reviews

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

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
8,998 reviews
Southwest
8.0
Very good
4,243 reviews

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

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
11,035 reviews
Southwest
8.0
Very good
4,243 reviews

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

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
8,116 reviews
Southwest
8.0
Very good
4,243 reviews

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

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
3,122 reviews
Southwest
8.0
Very good
4,243 reviews

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

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 Key Largo. 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 Key Largo?

    For as low as $167, Southwest can have you in Key Largo from Chicago in 4h 30m. The distance from Chicago to Key Largo is about 1183 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    The cheapest airlines for a one-way flight from Chicago to Key Largo are Spirit Airlines ($64), Southwest ($79), and United Airlines ($79).

  • What are the most reliable airlines from Chicago to Key Largo?

    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 Key Largo on time: Spirit Airlines (88%), United Airlines (86%), Alaska Airlines (82%).

  • What are the cheapest flights from Chicago to Key Largo?

    On average you can expect to pay $655 for a flight from Chicago to Key Largo. The cheapest flight overall is $59 while the most popular route, (Chicago O'Hare Intl - Miami) is currently priced at $84.

  • Can I find deals for flights from Chicago to Key Largo that include hotel bookings?

    Yes. In addition to deals on Chicago to Key Largo flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Key Largo?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Key Largo.

  • Can I find deals for business class flights from Chicago to Key Largo?

    Yes. Cheapflights offers flight deals from Chicago to Key Largo 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 Key Largo?

    Currently, March is the cheapest month in which you can book a flight from Chicago to Key Largo (average of $58). Flying from Chicago to Key Largo 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 7 airlines flying from Chicago to Key Largo

Discover the top 7 airlines that operate flights from Chicago to Key Largo. 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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$58Average$210FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$81Average$221FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$127Average$396FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$153Average$351FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$156Average$417FlexibilityNo cancel feeOn-time63%
Alaska AirlinesCheapest$176Average$215FlexibilityNo cancel feeOn-time75%
DeltaCheapest$176Average$404FlexibilityNo cancel feeOn-timeN/A

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