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Key Largo

$67+ 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 9/7. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MIA
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Key Largo are usually found in September or August, booked 41 days in advance, depart on a Thursday or Friday and return on a Friday

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 July 31, 2025.

Round-trip from

$133
(FlightHub)

One-way from

$67
(FlightHub)

Popular in

March

Cheapest in

September

Average price

$230
From Chicago (CHI) to Key Largo
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One-way flight from Chicago (CHI) to Key Largo
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Highest demand for flights based on searches. 11% potential increase in price ($33 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% 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 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 July 31, 2025.

This FlightHub deal was found by Cheapflights users on 7/31. 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.
Sat 9/611:12 amORD - MIA
1 stop11h 05mSpirit Airlines
Thu 9/117:00 amMIA - ORD
Nonstop3h 18mSpirit Airlines
Deal found 7/31$133
This American Airlines deal was found by Cheapflights users on 7/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/68:10 amORD - MIA
Nonstop3h 11mAmerican Airlines
Mon 9/87:59 pmMIA - ORD
Nonstop3h 27mAmerican Airlines
Deal found 7/29$137
This Southwest deal was found by Cheapflights users on 7/30. 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.
Mon 12/159:00 amMDW - MIA
Nonstop3h 05mSouthwest
Wed 12/171:05 pmMIA - MDW
Nonstop3h 15mSouthwest
Deal found 7/30$137
This Frontier deal was found by Cheapflights users on 7/29. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2310:03 pmMDW - MIA
Nonstop3h 00mFrontier
Mon 10/276:53 pmMIA - MDW
Nonstop3h 15mFrontier
Deal found 7/29$144
This Kiwi.com deal was found by Cheapflights users on 7/29. 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.
Sat 8/236:00 amORD - MIA
1 stop5h 29mMultiple Airlines
Sat 8/307:00 amMIA - ORD
Nonstop3h 22mMultiple Airlines
Deal found 7/29$154
This Southwest deal was found by Cheapflights users on 7/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/191:30 pmORD - MIA
1 stop8h 35mSouthwest
Sun 9/287:00 amMIA - ORD
1 stop7h 05mSouthwest
Deal found 7/29$157
This Delta deal was found by Cheapflights users on 7/31. 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 9/3010:35 amMDW - MIA
1 stop6h 58mDelta
Wed 10/812:20 pmMIA - MDW
1 stop7h 05mDelta
Deal found 7/31$217

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 July 31, 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

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sat 9/6

11:12 am-11:17 pm

1 stop11h 05m

Miami

Thu 9/11

7:00 am-9:18 am

Nonstop3h 18m

$133

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sat 9/6

7:05 am-11:09 am

Nonstop3h 04m

Miami

Mon 9/8

7:00 pm-9:22 pm

Nonstop3h 22m

$137

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Mon 12/15

9:00 am-1:05 pm

Nonstop3h 05m

Miami

Wed 12/17

1:05 pm-3:20 pm

Nonstop3h 15m

$137

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Thu 10/23

10:03 pm-2:03 am

Nonstop3h 00m

Miami

Mon 10/27

6:53 pm-9:08 pm

Nonstop3h 15m

$144

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sat 8/23

6:00 am-12:29 pm

1 stop5h 29m

Miami

Sat 8/30

7:00 am-9:22 am

Nonstop3h 22m

$154

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Fri 9/19

7:00 am-3:15 pm

1 stop7h 15m

Miami

Mon 9/22

6:05 am-12:45 pm

1 stop7h 40m

$157

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Tue 9/30

10:35 am-6:33 pm

1 stop6h 58m

Miami

Wed 10/8

12:20 pm-6:25 pm

1 stop7h 05m

$217

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sun 9/7

10:27 am-2:39 pm

Nonstop3h 12m

$67

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sat 11/15

2:02 pm-6:17 pm

Nonstop3h 15m

$69

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Mon 9/15

2:10 pm-6:10 pm

Nonstop3h 00m

$69

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

Showing 1-10 of 16 results
1
2

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 July 25, 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, September is the cheapest month in which you can book a flight from Chicago to Key Largo (average of $232). Flying from Chicago to Key Largo 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 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 July 31, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago to Key Largo as you normally would.

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 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 Key Largo

Explore weekly flight availability from Chicago to Key Largo. 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 31, 2025.

The most flights from CHI to KE9 are scheduled on a Thursday (44 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (28 on average).

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 July 31, 2025.
Read through reviews of airlines operating flights from Chicago to Key Largo, such as Southwest, Delta, and United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

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
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

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
7,981 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

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
8,900 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

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
4,246 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

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
8,049 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

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 Key Largo. 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 Key Largo one-way?

    The cheapest airlines for a one-way flight from Chicago to Key Largo are Spirit Airlines ($67), American Airlines ($69), and Southwest ($69).

  • 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 (84%), Air Canada (84%), Copa Airlines (84%).

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

    On average you can expect to pay $750 for a flight from Chicago to Key Largo. The cheapest flight overall is $57 while the most popular route, (Chicago O'Hare Intl - Miami) is currently priced at $90.

  • 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, September is the cheapest month in which you can book a flight from Chicago to Key Largo (average of $232). Flying from Chicago to Key Largo 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 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 July 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$39Average$185FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$85Average$206FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$127Average$393FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$158Average$378FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$176Average$215FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$176Average$375FlexibilityNo cancel feeOn-time63%
DeltaCheapest$177Average$376FlexibilityNo cancel feeOn-timeN/A

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