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Key Largo

$42+ 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 3/4. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MIA
Mar 2 — Mar 91
Mon 3/2
Mon 3/9
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 86 days in advance, depart on a Monday or Sunday and return on a Friday

Cheap 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 January 31, 2026.

This CheapOair deal was found by Cheapflights users on 1/30. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/39:18 am
ORD
-
MIA
1 stop10h 33m
Spirit Airlines
Thu 3/53:50 pm
MIA
-
ORD
Nonstop3h 28m
Spirit Airlines
Deal found 1/30$86
This CheapOair deal was found by Cheapflights users on 1/29. 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.
Wed 2/189:18 am
ORD
-
MIA
Nonstop3h 18m
Spirit Airlines
Wed 2/257:12 am
MIA
-
ORD
Nonstop3h 27m
Spirit Airlines
Deal found 1/29$87
This Expedia deal was found by Cheapflights users on 1/31. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/227:23 pm
ORD
-
MIA
Nonstop3h 16m
Spirit Airlines
Tue 2/247:12 am
MIA
-
ORD
Nonstop3h 27m
Spirit Airlines
Deal found 1/31$88
This Trip.com deal was found by Cheapflights users on 1/29. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/96:00 am
MDW
-
MIA
Nonstop3h 13m
Frontier
Sat 3/1411:13 am
MIA
-
MDW
Nonstop3h 28m
Frontier
Deal found 1/29$88
This Expedia deal was found by Cheapflights users on 1/29. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/2111:48 am
ORD
-
MIA
Nonstop3h 15m
Multiple Airlines
Tue 2/247:12 am
MIA
-
ORD
Nonstop3h 27m
Multiple Airlines
Deal found 1/29$89
This Expedia deal was found by Cheapflights users on 1/30. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/28:59 am
ORD
-
MIA
1 stop10h 52m
Multiple Airlines
Fri 3/61:00 pm
MIA
-
ORD
Nonstop3h 38m
Multiple Airlines
Deal found 1/30$90
This Expedia deal was found by Cheapflights users on 1/29. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/16:57 pm
ORD
-
MIA
Nonstop3h 17m
Spirit Airlines
Tue 2/35:54 am
MIA
-
ORD
Nonstop3h 24m
Spirit Airlines
Deal found 1/29$91
This Kiwi.com deal was found by Cheapflights users on 1/31. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/76:57 pm
ORD
-
MIA
Nonstop3h 17m
Spirit Airlines
Thu 3/126:00 am
MIA
-
ORD
Nonstop3h 25m
Spirit Airlines
Deal found 1/31$92
This CheapOair deal was found by Cheapflights users on 1/30. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/218:59 am
ORD
-
MIA
1 stop10h 52m
Spirit Airlines
Wed 2/257:12 am
MIA
-
ORD
Nonstop3h 27m
Spirit Airlines
Deal found 1/30$93
This Expedia deal was found by Cheapflights users on 1/31. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/29:23 am
ORD
-
MIA
Nonstop3h 18m
Spirit Airlines
Tue 2/35:54 am
MIA
-
ORD
Nonstop3h 24m
Spirit Airlines
Deal found 1/31$94
This Expedia deal was found by Cheapflights users on 1/31. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/76:57 pm
ORD
-
MIA
Nonstop3h 17m
Spirit Airlines
Mon 2/95:54 am
MIA
-
ORD
Nonstop3h 24m
Spirit Airlines
Deal found 1/31$95
This Super.com deal was found by Cheapflights users on 1/31. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/226:15 am
MDW
-
MIA
Nonstop3h 13m
Frontier
Tue 2/2412:25 pm
MIA
-
MDW
1 stop7h 42m
Frontier
Deal found 1/31$95

Find 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 January 31, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$86
(Cheapflightsfares)

One-way from

$42
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$238
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. 9% potential increase in price ($28 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
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 January 31, 2026.
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 2/23

7:30 am-11:47 am

Nonstop3h 17m

Miami

Fri 2/27

9:00 am-11:38 am

Nonstop3h 38m

$197

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Mon 2/23

9:40 am-1:45 pm

Nonstop3h 05m

Miami

Tue 2/24

2:35 pm-4:50 pm

Nonstop3h 15m

$197

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Tue 3/3

5:30 pm-9:30 pm

Nonstop3h 00m

Miami

Sat 3/7

6:25 am-8:40 am

Nonstop3h 15m

$212

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Sat 2/28

4:13 pm-12:53 am

1 stop7h 40m

Miami

Fri 3/6

6:00 am-9:54 am

1 stop4h 54m

$217

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Mon 2/23

12:45 pm-6:21 pm

1 stop4h 36m

Miami

Tue 3/3

8:15 am-11:59 am

1 stop4h 44m

$217

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Mon 2/23

12:45 pm-8:44 pm

1 stop6h 59m

Miami

Fri 2/27

6:00 am-9:54 am

1 stop4h 54m

$217

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Wed 2/18

5:30 pm-9:30 pm

Nonstop3h 00m

Miami

Tue 2/24

2:35 pm-4:50 pm

Nonstop3h 15m

$227

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Mon 2/23

7:30 am-11:47 am

Nonstop3h 17m

Miami

Tue 2/24

9:00 am-11:38 am

Nonstop3h 38m

$247

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Wed 3/18

5:30 am-12:08 pm

1 stop5h 38m

Miami

Fri 3/20

12:00 pm-6:34 pm

1 stop7h 34m

$258

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Sun 3/1

4:55 pm-11:15 pm

1 stop5h 20m

Miami

Sat 3/7

6:40 pm-10:40 pm

1 stop5h 00m

$258

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/31

Showing 1-10 of 45 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 January 30, 2026.

The best time to book flights from Chicago to Key Largo is 86 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, October is the cheapest month in which you can book a flight from Chicago to Key Largo (average of $49). Flying from Chicago to Key Largo in July is currently the most expensive (average of $118). 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 January 31, 2026.

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 evening, which can drop the price by up to 12% 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 January 31, 2026.

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.

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 January 31, 2026.

The most flights from CHI to KE9 are scheduled on a Friday (50 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (26 on average).

How much does it cost to fly round-trip from Chicago to Key Largo?

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 January 31, 2026.
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
4,267 reviews

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Crew

8.6

Overall

8.0

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
4,267 reviews
Southwest
8.0
Very good
4,267 reviews

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Crew

8.6

Overall

8.0

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
9,219 reviews
Southwest
8.0
Very good
4,267 reviews

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Crew

8.6

Overall

8.0

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
11,213 reviews
Southwest
8.0
Very good
4,267 reviews

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Crew

8.6

Overall

8.0

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
8,396 reviews
Southwest
8.0
Very good
4,267 reviews

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Crew

8.6

Overall

8.0

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.
Frontier
5.7
Fair
3,054 reviews
Southwest
8.0
Very good
4,267 reviews

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Crew

8.6

Overall

8.0

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.

  • How long is the flight from Chicago to Key Largo?

    For as low as $197, United Airlines can have you in Key Largo from Chicago in 3h 05m. 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 ($38), Frontier ($44), and JetBlue ($68).

  • 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 (81%), Alaska Airlines (77%), Air New Zealand (77%).

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

    On average you can expect to pay $647 for a flight from Chicago to Key Largo. The cheapest flight overall is $51 while the most popular route, (Chicago O'Hare Intl - Miami) is currently priced at $54.

  • 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, October is the cheapest month in which you can book a flight from Chicago to Key Largo (average of $49). Flying from Chicago to Key Largo in July is currently the most expensive (average of $118). 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 8 airlines flying from Chicago to Key Largo

Discover the top 8 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 January 31, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$39Average$177FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$71Average$222FlexibilityNo cancel feeOn-time65%
Allegiant AirCheapest$83Average$150FlexibilityNo cancel feeOn-time88%
DeltaCheapest$108Average$375FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$119Average$384FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$153Average$346FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$166Average$376FlexibilityNo cancel feeOn-time63%
Alaska AirlinesCheapest$176Average$249FlexibilityNo cancel feeOn-time75%

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