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Key Largo

$63+ 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 4/8. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MIA
Apr 7 — Apr 141
Mon 4/7
Mon 4/14
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 28 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 April 2, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$112
(Kiwi.com)

One-way from

$63
(Cheapflightsfares)

Popular in

December

Cheapest in

July

Average price

$201
Provider with most accurate pricing for Chicago (CHI)-Miami flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Miami flights.
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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. 15% potential increase in price ($43 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 2, 2025.

This Gotogate deal was found by Cheapflights users on 3/31. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/139:55 amORD - MIA
Nonstop3h 15mSpirit Airlines
Tue 5/203:15 pmMIA - ORD
Nonstop3h 26mSpirit Airlines
Deal found 3/31$111
This Cheapflightsfares deal was found by Cheapflights users on 4/1. 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.
Tue 4/86:00 amMDW - MIA
Nonstop3h 08mFrontier
Tue 4/1511:03 amMIA - MDW
Nonstop3h 28mFrontier
Deal found 4/1$132
This Kiwi.com deal was found by Cheapflights users on 4/1. 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 4/306:51 amORD - MIA
Nonstop3h 06mMultiple Airlines
Mon 5/57:30 amMIA - ORD
1 stop11h 59mMultiple Airlines
Deal found 4/1$150
This Southwest deal was found by Cheapflights users on 3/31. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/48:40 pmMDW - MIA
Nonstop3h 00mSouthwest
Sat 5/105:05 amMIA - MDW
Nonstop3h 10mSouthwest
Deal found 3/31$177
This American Airlines deal was found by Cheapflights users on 4/1. 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 5/35:24 pmORD - MIA
Nonstop3h 06mAmerican Airlines
Tue 5/64:55 pmMIA - ORD
Nonstop3h 26mAmerican Airlines
Deal found 4/1$178
This United Airlines deal was found by Cheapflights users on 3/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/37:30 amORD - MIA
Nonstop3h 18mUnited Airlines
Fri 5/94:08 pmMIA - ORD
Nonstop3h 35mUnited Airlines
Deal found 3/30$197
This Cheapflightsfares deal was found by Cheapflights users on 4/1. 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.
Thu 5/18:00 amORD - MIA
1 stop26h 11mFrontier
Sun 5/46:00 amMIA - ORD
1 stop18h 41mFrontier
Deal found 4/1$198
This Delta deal was found by Cheapflights users on 4/1. 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 5/1311:03 amORD - MIA
1 stop6h 22mDelta
Wed 5/1410:37 amMIA - ORD
1 stop7h 10mDelta
Deal found 4/1$217
This Delta deal was found by Cheapflights users on 4/1. 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 5/136:00 amMDW - MIA
1 stop6h 15mDelta
Wed 5/2110:37 amMIA - MDW
1 stop5h 43mDelta
Deal found 4/1$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 April 2, 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

Tue 5/13

9:55 am-2:10 pm

Nonstop3h 15m

Miami

Tue 5/20

3:15 pm-5:41 pm

Nonstop3h 26m

$111

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Tue 4/8

6:00 am-10:08 am

Nonstop3h 08m

Miami

Tue 4/15

11:03 am-1:31 pm

Nonstop3h 28m

$132

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Wed 4/30

6:51 am-10:57 am

Nonstop3h 06m

Miami

Mon 5/5

7:30 am-6:29 pm

1 stop11h 59m

$150

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Sun 5/4

8:40 pm-12:40 am

Nonstop3h 00m

Miami

Sat 5/10

5:05 am-7:15 am

Nonstop3h 10m

$177

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sat 5/3

5:24 pm-9:30 pm

Nonstop3h 06m

Miami

Tue 5/6

4:55 pm-7:21 pm

Nonstop3h 26m

$178

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sat 5/3

7:30 am-11:48 am

Nonstop3h 18m

Miami

Fri 5/9

4:08 pm-6:43 pm

Nonstop3h 35m

$197

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Thu 5/1

8:00 am-11:11 am

1 stop26h 11m

Miami

Sun 5/4

6:00 am-11:41 pm

1 stop18h 41m

$198

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Tue 5/13

11:03 am-6:25 pm

1 stop6h 22m

Miami

Wed 5/14

10:37 am-4:47 pm

1 stop7h 10m

$217

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Tue 5/13

10:25 am-4:51 pm

1 stop5h 26m

Miami

Tue 5/20

5:35 am-11:53 am

1 stop7h 18m

$217

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Tue 4/8

4:32 pm-8:45 pm

Nonstop3h 13m

$63

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/1

Showing 1-10 of 21 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 March 28, 2025.

The best time to book flights from Chicago to Key Largo is 28 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 $229). 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 April 2, 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 April 2, 2025.

The most flights from CHI to KE9 are scheduled on a Tuesday (46 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (11 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 April 2, 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
4,272 reviews

Crew

8.6

Entertainment

7.6

Comfort

8.0

Food

7.1

Boarding

8.2

Overall

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
8.0
Very good
4,272 reviews
Southwest
8.0
Very good
4,272 reviews

Crew

8.6

Entertainment

7.6

Comfort

8.0

Food

7.1

Boarding

8.2

Overall

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.
Delta
8.0
Very good
7,898 reviews
Southwest
8.0
Very good
4,272 reviews

Crew

8.6

Entertainment

7.6

Comfort

8.0

Food

7.1

Boarding

8.2

Overall

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
8,615 reviews
Southwest
8.0
Very good
4,272 reviews

Crew

8.6

Entertainment

7.6

Comfort

8.0

Food

7.1

Boarding

8.2

Overall

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
10,000 reviews
Southwest
8.0
Very good
4,272 reviews

Crew

8.6

Entertainment

7.6

Comfort

8.0

Food

7.1

Boarding

8.2

Overall

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
7,886 reviews
Southwest
8.0
Very good
4,272 reviews

Crew

8.6

Entertainment

7.6

Comfort

8.0

Food

7.1

Boarding

8.2

Overall

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 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 ($63), Frontier ($63), and United Airlines ($89).

  • 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: Avianca (89%), Air New Zealand (88%), United Airlines (87%).

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

    On average you can expect to pay $963 for a flight from Chicago to Key Largo. The cheapest flight overall is $61 while the most popular route, (Chicago O'Hare Intl - Miami) is currently priced at $95.

  • 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 $229). 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 6 airlines flying from Chicago to Key Largo

Discover the top 6 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 April 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$39Average$164FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$67Average$185FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$158Average$386FlexibilityNo cancel feeOn-time71%
DeltaCheapest$177Average$385FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$179Average$395FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$195Average$390FlexibilityNo cancel feeOn-time63%

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