Key Largo

$45+ 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 4/18. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MIA
Apr 17 — Apr 241
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Cheapflights Tip: The best prices from Chicago to Key Largo are usually found in September or October, booked 41 days in advance, depart on a Monday or Sunday and return on a Thursday

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 March 18, 2026.

This Super.com deal was found by Cheapflights users on 3/13. 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.
Mon 4/204:58 pm
ORD
-
MIA
Nonstop3h 19m
Frontier
Thu 4/239:21 pm
MIA
-
ORD
Nonstop3h 38m
Frontier
Deal found 3/13$99
This Frontier deal was found by Cheapflights users on 3/15. 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 4/193:52 pm
ORD
-
MIA
Nonstop3h 19m
Frontier
Thu 4/239:21 pm
MIA
-
ORD
Nonstop3h 38m
Frontier
Deal found 3/15$100
This Cheapflightsfares deal was found by Cheapflights users on 3/16. 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.
Sun 4/124:51 pm
ORD
-
MIA
Nonstop3h 06m
Spirit Airlines
Sat 4/184:59 pm
MIA
-
ORD
1 stop5h 13m
Spirit Airlines
Deal found 3/16$101
This CheapOair deal was found by Cheapflights users on 3/17. 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.
Mon 4/134:51 pm
ORD
-
MIA
Nonstop3h 06m
Spirit Airlines
Sat 4/184:59 pm
MIA
-
ORD
1 stop5h 13m
Spirit Airlines
Deal found 3/17$102
This Super.com deal was found by Cheapflights users on 3/15. 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.
Sat 5/23:52 pm
ORD
-
MIA
Nonstop3h 19m
Frontier
Sun 5/107:00 am
MIA
-
ORD
Nonstop3h 37m
Frontier
Deal found 3/15$103
This Expedia deal was found by Cheapflights users on 3/16. 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 4/253:52 pm
ORD
-
MIA
Nonstop3h 19m
Multiple Airlines
Sun 5/310:41 am
MIA
-
ORD
Nonstop3h 24m
Multiple Airlines
Deal found 3/16$104
This Cheapflightsfares deal was found by Cheapflights users on 3/17. 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.
Wed 4/84:51 pm
ORD
-
MIA
Nonstop3h 06m
Spirit Airlines
Mon 4/139:45 pm
MIA
-
ORD
1 stop12h 05m
Spirit Airlines
Deal found 3/17$105
This Priceline deal was found by Cheapflights users on 3/13. 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 4/149:45 am
ORD
-
MIA
1 stop9h 59m
Multiple Airlines
Thu 4/169:21 pm
MIA
-
ORD
Nonstop3h 38m
Multiple Airlines
Deal found 3/13$106
This Booking.com deal was found by Cheapflights users on 3/17. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/710:55 am
ORD
-
MIA
Nonstop3h 05m
Spirit Airlines
Mon 4/139:45 pm
MIA
-
ORD
1 stop12h 05m
Spirit Airlines
Deal found 3/17$107
This Trip.com deal was found by Cheapflights users on 3/16. 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.
Sat 4/116:30 am
MDW
-
MIA
Nonstop3h 10m
Frontier
Wed 4/151:10 pm
MIA
-
MDW
1 stop7h 21m
Frontier
Deal found 3/16$107
This CheapOair deal was found by Cheapflights users on 3/18. 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 4/114:51 pm
ORD
-
MIA
Nonstop3h 06m
Spirit Airlines
Sat 4/184:59 pm
MIA
-
ORD
1 stop5h 13m
Spirit Airlines
Deal found 3/18$108
This Trip.com deal was found by Cheapflights users on 3/14. 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.
Sat 4/46:30 am
MDW
-
MIA
Nonstop3h 10m
Multiple Airlines
Tue 4/143:12 pm
MIA
-
MDW
1 stop8h 02m
Multiple Airlines
Deal found 3/14$108

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 March 18, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$99
(Super.com)

One-way from

$45
(Frontier)

Popular in

December

Cheapest in

September

Average price

$318
Provider with most accurate pricing for Chicago (CHI)-Miami flight deals.
Provider most trusted by Cheapflights users for Chicago (CHI)-Miami flights.
From Chicago (CHI) to Key Largo
One-way flight from Chicago (CHI) to Key Largo
Highest demand for flights based on searches. 10% potential increase in price ($33 potential increase over avg. RT price).
Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
Average for round-trip flights in March 2026

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 March 18, 2026.
Use the filters below to find and compare flights from Chicago to Key Largo that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Thu 3/26

10:55 am-3:00 pm

Nonstop3h 05m

Miami

Sat 3/28

6:00 am-8:25 am

Nonstop3h 25m

$225

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Sat 4/25

7:50 am-11:50 am

Nonstop3h 00m

Miami

Thu 4/30

5:30 am-10:25 am

1 stop5h 55m

$247

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Thu 4/30

6:50 pm-10:50 pm

Nonstop3h 00m

Miami

Thu 5/7

6:20 am-12:00 pm

1 stop6h 40m

$247

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Fri 5/8

6:50 pm-10:50 pm

Nonstop3h 00m

Miami

Sun 5/10

6:10 am-12:00 pm

2 stops6h 50m

$252
Quickest round-trip

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Sun 5/17

6:45 pm-10:45 pm

Nonstop3h 00m

Miami

Fri 5/22

6:05 am-8:20 am

Nonstop3h 15m

$272

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Sat 5/2

3:45 pm-7:40 pm

Nonstop2h 55m

Miami

Mon 5/4

6:40 am-12:05 pm

1 stop6h 25m

$297

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Mon 4/6

5:25 am-1:20 pm

1 stop6h 55m

Miami

Thu 4/16

6:40 am-1:10 pm

2 stops7h 30m

$302

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Tue 4/14

7:55 am-11:55 am

Nonstop3h 00m

Miami

Wed 4/15

12:10 pm-8:20 pm

1 stop9h 10m

$307

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Fri 5/1

4:35 pm-10:00 pm

1 stop4h 25m

Miami

Mon 5/4

6:05 am-8:20 am

Nonstop3h 15m

$317

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Wed 4/8

3:00 pm-8:40 pm

1 stop4h 40m

Miami

Sat 4/11

8:25 am-1:10 pm

1 stop5h 45m

$327

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/13

Showing 1-10 of 43 resultsSorted by cheapest first
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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 13, 2026.

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, 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 March 18, 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 14% versus a flight in the afternoon.

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 March 14, 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 March 18, 2026.

The most flights from CHI to KE9 are scheduled on a Monday (59 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (49 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 March 18, 2026.
Read through reviews of airlines operating flights from Chicago to Key Largo, such as Southwest,United Airlines, andAmerican Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.

Entertainment

7.5

Overall

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Comfort

8.0

Reviews

1 / 20
6.0
Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.

Entertainment

7.5

Overall

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Comfort

8.0

Reviews

1 / 20
6.0
Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.

Entertainment

7.5

Overall

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Comfort

8.0

Reviews

1 / 20
6.0
Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.

Entertainment

7.5

Overall

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Comfort

8.0

Reviews

1 / 20
6.0
Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.

Entertainment

7.5

Overall

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Comfort

8.0

Reviews

1 / 20
6.0
Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.

Entertainment

7.5

Overall

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Comfort

8.0

Reviews

1 / 20
6.0
Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.

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 $247, Spirit Airlines can have you in Key Largo from Chicago in 3h. 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 Frontier ($36), Spirit Airlines ($37), 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: Atlas Air (83%), GOL (77%), Aer Lingus (73%).

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

    On average you can expect to pay $550 for a flight from Chicago to Key Largo. The cheapest flight overall is $43 while the most popular route, (Chicago O'Hare Intl - Miami) is currently priced at $80.

  • 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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Alternative routes for Chicago to Key Largo

See prices for flight routes from nearby airports that may be better suited for you.

Top 9 airlines flying from Chicago to Key Largo

Discover the top 9 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 March 18, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$56Average$182FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$70Average$226FlexibilityNo cancel feeOn-time65%
Allegiant AirCheapest$84Average$146FlexibilityNo cancel feeOn-time88%
JetBlueCheapest$89Average$234FlexibilityNo cancel feeOn-time62%
DeltaCheapest$108Average$376FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$119Average$377FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$156Average$356FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$176Average$249FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$176Average$361FlexibilityNo cancel feeOn-time63%

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