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Key Largo

$68+ 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 6/23. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MIA
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Key Largo are usually found in July or September, booked 41 days in advance, depart on a Thursday or Tuesday and return on a Thursday

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 June 12, 2025.

Round-trip from

$136
(Kiwi.com)

One-way from

$68
(Booking.com)

Popular in

March

Cheapest in

July

Average price

$276
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. 12% potential increase in price ($37 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 12, 2025.

This Kiwi.com deal was found by Cheapflights users on 6/11. 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 6/301:43 pmORD - MIA
Nonstop3h 17mSpirit Airlines
Sat 7/191:35 pmMIA - ORD
Nonstop3h 36mSpirit Airlines
Deal found 6/11$136
This CheapOair deal was found by Cheapflights users on 6/10. 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 9/1112:48 pmMDW - MIA
1 stop9h 10mFrontier
Mon 9/156:42 pmMIA - MDW
1 stop5h 43mFrontier
Deal found 6/10$145
This American Airlines deal was found by Cheapflights users on 6/11. 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 11/1210:06 amORD - MIA
Nonstop3h 09mAmerican Airlines
Wed 11/123:17 pmMIA - ORD
Nonstop3h 27mAmerican Airlines
Deal found 6/11$152
This Southwest deal was found by Cheapflights users on 6/10. 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 9/222:10 pmMDW - MIA
Nonstop3h 00mSouthwest
Sat 9/274:05 pmMIA - MDW
Nonstop3h 10mSouthwest
Deal found 6/10$157
This Kiwi.com deal was found by Cheapflights users on 6/10. 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 9/26:45 amORD - MIA
Nonstop3h 13mMultiple Airlines
Thu 9/115:45 amMIA - ORD
1 stop5h 41mMultiple Airlines
Deal found 6/10$168
This Delta deal was found by Cheapflights users on 6/11. 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.
Sat 7/262:00 pmORD - MIA
1 stop7h 45mDelta
Sat 8/27:23 pmMIA - ORD
1 stop5h 46mDelta
Deal found 6/11$217
This Delta deal was found by Cheapflights users on 6/11. 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.
Sat 7/124:22 pmMDW - MIA
1 stop7h 27mDelta
Tue 7/1512:46 pmMIA - MDW
1 stop6h 54mDelta
Deal found 6/11$217
This United Airlines deal was found by Cheapflights users on 6/12. 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.
Wed 9/310:55 amORD - MIA
Nonstop3h 17mUnited Airlines
Wed 9/104:16 pmMIA - ORD
Nonstop3h 30mUnited Airlines
Deal found 6/12$237
This Southwest deal was found by Cheapflights users on 6/11. 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.
Sun 8/177:00 amORD - MIA
1 stop9h 35mSouthwest
Thu 8/217:10 amMIA - ORD
2 stops10h 15mSouthwest
Deal found 6/11$244
This Frontier deal was found by Cheapflights users on 6/11. 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.
Sun 8/175:01 amORD - MIA
1 stop5h 13mFrontier
Sun 8/247:40 amMIA - ORD
1 stop11h 48mFrontier
Deal found 6/11$274

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 June 12, 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

Mon 6/30

1:43 pm-6:00 pm

Nonstop3h 17m

Miami

Sat 7/19

1:35 pm-4:11 pm

Nonstop3h 36m

$136

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Thu 9/11

12:48 pm-10:58 pm

1 stop9h 10m

Miami

Mon 9/15

6:42 pm-11:25 pm

1 stop5h 43m

$145

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Wed 11/12

10:06 am-2:15 pm

Nonstop3h 09m

Miami

Wed 11/12

3:17 pm-5:44 pm

Nonstop3h 27m

$152

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Mon 9/22

2:10 pm-6:10 pm

Nonstop3h 00m

Miami

Sat 9/27

4:05 pm-6:15 pm

Nonstop3h 10m

$157

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Tue 9/2

6:45 am-10:58 am

Nonstop3h 13m

Miami

Thu 9/11

5:45 am-10:26 am

1 stop5h 41m

$168

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sat 7/26

2:00 pm-10:45 pm

1 stop7h 45m

Miami

Sat 8/2

8:11 am-12:50 pm

1 stop5h 39m

$217

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Sat 7/12

4:22 pm-12:49 am

1 stop7h 27m

Miami

Tue 7/15

12:46 pm-6:40 pm

1 stop6h 54m

$217

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sun 8/17

5:01 am-11:14 am

1 stop5h 13m

Miami

Sun 8/24

7:40 am-6:28 pm

1 stop11h 48m

$274

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Mon 6/23

1:43 pm-6:00 pm

Nonstop3h 17m

$68

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Tue 11/18

7:35 am-11:49 am

Nonstop3h 14m

$79

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/9

Showing 1-10 of 19 results
1
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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 June 9, 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 $228). 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 June 12, 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 Tuesday evenings when fares are most often at their lowest. Tuesday 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 June 12, 2025.

The most flights from CHI to KE9 are scheduled on a Monday (44 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (30 on average).

Rainfall in Key Largo by month

Plan your trip to Key Largo by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Key Largo 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 Key Largo when rainfall is around 1.6 in.

Temperature in Key Largo by month

Plan your trip to Key Largo by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Key Largo, 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 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 June 12, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta and United Airlines from Chicago to Key Largo to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Boarding

8.2

Entertainment

7.6

Overall

8.0

Comfort

8.0

Crew

8.6

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
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Boarding

8.2

Entertainment

7.6

Overall

8.0

Comfort

8.0

Crew

8.6

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
7,950 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Boarding

8.2

Entertainment

7.6

Overall

8.0

Comfort

8.0

Crew

8.6

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
8,790 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Boarding

8.2

Entertainment

7.6

Overall

8.0

Comfort

8.0

Crew

8.6

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
4,287 reviews

Food

7.1

Boarding

8.2

Entertainment

7.6

Overall

8.0

Comfort

8.0

Crew

8.6

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
8,052 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Boarding

8.2

Entertainment

7.6

Overall

8.0

Comfort

8.0

Crew

8.6

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 ($68), Southwest ($79), and American Airlines ($80).

  • 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: ANA (91%), Finnair (88%), Air Canada (87%).

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

    On average you can expect to pay $661 for a flight from Chicago to Key Largo. The cheapest flight overall is $66 while the most popular route, (Chicago O'Hare Intl - Miami) is currently priced at $85.

  • 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 $228). 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.

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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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$39Average$176FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$76Average$198FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$134Average$391FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$159Average$382FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$176Average$215FlexibilityNo cancel feeOn-time75%
DeltaCheapest$177Average$370FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$204Average$387FlexibilityNo cancel feeOn-time63%

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