HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Key Largo

$61+ 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 12/9. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MIA
oct. 16 — oct. 231
jue. 10/16
jue. 10/23
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Key Largo with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheapflights Tip: The best prices from Chicago to Key Largo are usually found in September or January, booked 51 days in advance, depart on a Thursday or Monday 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 septiembre 16, 2025.

Round-trip from

$104
(Kiwi.com)

One-way from

$61
(Kiwi.com)

Popular in

March

Cheapest in

September

Average price

$231
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. 6% potential increase in price ($17 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2025
Search Deals

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 septiembre 16, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/2310:27 amORD - MIA
Nonstop3h 02mSpirit Airlines
dom. 10/267:00 amMIA - ORD
Nonstop3h 22mSpirit Airlines
Deal found 9/15$104
This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/910:27 amORD - MIA
Nonstop3h 02mSpirit Airlines
dom. 10/127:00 amMIA - ORD
Nonstop3h 22mSpirit Airlines
Deal found 9/14$107
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/31:35 pmORD - MIA
Nonstop3h 15mSpirit Airlines
dom. 12/1410:15 amMIA - ORD
Nonstop3h 15mSpirit Airlines
Deal found 9/15$108
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/81:35 pmORD - MIA
Nonstop3h 15mSpirit Airlines
mar. 12/910:15 amMIA - ORD
Nonstop3h 15mSpirit Airlines
Deal found 9/15$109
This Priceline deal was found by Cheapflights users on 9/15. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 10/610:27 amORD - MIA
Nonstop3h 02mMultiple Airlines
jue. 10/94:49 pmMIA - ORD
1 stop9h 19mMultiple Airlines
Deal found 9/15$110
This Cheapflightsfares deal was found by Cheapflights users on 9/16. 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.
lun. 10/610:27 amORD - MIA
Nonstop3h 02mSpirit Airlines
sáb. 10/116:00 amMIA - ORD
Nonstop3h 18mSpirit Airlines
Deal found 9/16$111
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 10/510:27 amORD - MIA
Nonstop3h 02mSpirit Airlines
lun. 10/137:00 amMIA - ORD
Nonstop3h 22mSpirit Airlines
Deal found 9/13$113
This Frontier deal was found by Cheapflights users on 9/15. 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.
vie. 10/2412:18 pmMDW - MIA
Nonstop3h 01mFrontier
sáb. 10/2510:34 amMIA - MDW
1 stop7h 39mFrontier
Deal found 9/15$114
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 10/711:13 amORD - MIA
1 stop10h 57mSpirit Airlines
sáb. 10/186:00 amMIA - ORD
Nonstop3h 18mSpirit Airlines
Deal found 9/14$114
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 10/711:13 amORD - MIA
1 stop10h 57mSpirit Airlines
jue. 10/167:00 amMIA - ORD
Nonstop3h 22mSpirit Airlines
Deal found 9/14$115
This Priceline deal was found by Cheapflights users on 9/14. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 10/111:14 pmORD - MIA
1 stop9h 29mMultiple Airlines
sáb. 10/186:00 amMIA - ORD
Nonstop3h 18mMultiple Airlines
Deal found 9/14$116
This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 10/110:27 amORD - MIA
Nonstop3h 12mSpirit Airlines
jue. 10/97:00 amMIA - ORD
Nonstop3h 22mSpirit Airlines
Deal found 9/15$117

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 septiembre 16, 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

mié. 9/24

10:27 am-2:39 pm

Nonstop3h 12m

Miami

sáb. 9/27

7:00 am-9:18 am

Nonstop3h 18m

$158

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

mar. 10/7

10:54 am-3:11 pm

Nonstop3h 17m

Miami

sáb. 10/11

12:27 pm-2:55 pm

Nonstop3h 28m

$177

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

mié. 12/10

9:00 am-1:05 pm

Nonstop3h 05m

Miami

sáb. 12/13

6:25 am-12:25 pm

1 stop7h 00m

$187

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

vie. 10/10

10:54 am-3:11 pm

Nonstop3h 17m

Miami

mar. 10/14

4:17 pm-6:47 pm

Nonstop3h 30m

$200

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

dom. 12/7

1:14 pm-9:42 pm

1 stop7h 28m

Miami

vie. 12/12

8:05 am-12:34 pm

1 stop5h 29m

$217

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

sáb. 10/11

6:10 pm-12:29 am

1 stop5h 19m

Miami

mar. 10/21

6:15 pm-11:58 pm

1 stop6h 43m

$217

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

vie. 10/3

10:54 am-3:11 pm

Nonstop3h 17m

Miami

mar. 10/7

4:17 pm-6:47 pm

Nonstop3h 30m

$222

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

sáb. 12/6

6:22 pm-12:46 am

1 stop5h 24m

Miami

jue. 12/18

8:05 am-1:51 pm

1 stop6h 46m

$227

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

lun. 11/24

9:46 am-3:47 pm

1 stop5h 01m

Miami

jue. 12/4

12:00 pm-4:18 pm

1 stop5h 18m

$227

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

jue. 12/4

5:35 am-12:50 pm

1 stop6h 15m

Miami

mié. 12/10

1:05 pm-3:20 pm

Nonstop3h 15m

$233

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 46 results
1
2
3
...
5

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 September 12, 2025.

The best time to book flights from Chicago to Key Largo is 51 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 septiembre 16, 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 septiembre 16, 2025.

The most flights from CHI to KE9 are scheduled on a Monday (42 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (30 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 septiembre 16, 2025.
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
4,242 reviews

Overall

8.0

Crew

8.6

Boarding

8.1

Comfort

8.0

Food

7.0

Entertainment

7.5

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
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Crew

8.6

Boarding

8.1

Comfort

8.0

Food

7.0

Entertainment

7.5

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
8,924 reviews
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Crew

8.6

Boarding

8.1

Comfort

8.0

Food

7.0

Entertainment

7.5

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
4,242 reviews

Overall

8.0

Crew

8.6

Boarding

8.1

Comfort

8.0

Food

7.0

Entertainment

7.5

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
8,019 reviews
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Crew

8.6

Boarding

8.1

Comfort

8.0

Food

7.0

Entertainment

7.5

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
5.8
Fair
3,174 reviews
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Crew

8.6

Boarding

8.1

Comfort

8.0

Food

7.0

Entertainment

7.5

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 $187, Spirit Airlines can have you in Key Largo from Chicago in 3h 05m. The distance from Chicago to Key Largo is about 1183 mi. Most flights are nonstop.

  • 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 ($64), Frontier ($72), and Southwest ($79).

  • 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: Emirates (88%), United Airlines (86%), Spirit Airlines (82%).

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

    On average you can expect to pay $601 for a flight from Chicago to Key Largo. The cheapest flight overall is $60 while the most popular route, (Chicago O'Hare Intl - Miami) is currently priced at $92.

  • 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Chicago to Key Largo

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Orlando flights
O'Hare Intl to Miami flights
O'Hare Intl to Fort Lauderdale flights
O'Hare Intl to Tampa flights
Midway to Orlando flights
O'Hare Intl to Fort Myers flights
Midway to Miami flights
St. Louis to Orlando flights
O'Hare Intl to West Palm Beach flights
O'Hare Intl to Sarasota flights
Midway to Fort Lauderdale flights
O'Hare Intl to Jacksonville flights
O'Hare Intl to Key West flights
Midway to Tampa flights
St. Louis to Miami flights
Midway to Fort Myers flights
O'Hare Intl to Pensacola flights
St. Louis to Tampa flights
O'Hare Intl to Panama City flights
Midway to West Palm Beach flights
St. Louis to Fort Myers flights
Midway to Jacksonville flights
Moline to Orlando flights
Midway to Key West flights
St. Louis to Jacksonville flights
St. Louis to Fort Lauderdale flights
Midway to Sarasota flights
St. Louis to Key West flights
Peoria to Orlando flights
Midway to Pensacola flights
Midway to Panama City flights
Moline to Tampa flights
St. Louis to Sarasota flights
St. Louis to Pensacola flights
Rockford to Orlando Sanford Intl flights
O'Hare Intl to Daytona Beach flights
O'Hare Intl to Melbourne flights
Rockford to St Petersburg flights
O'Hare Intl to Tallahassee flights
St. Louis to West Palm Beach flights
St. Louis to Panama City flights
Peoria to Tampa flights
O'Hare Intl to Valparaiso flights
Peoria to Fort Myers flights
Moline to Pensacola flights
Moline to Miami flights
Midway to Daytona Beach flights
Bloomington to Orlando flights
O'Hare Intl to Gainesville flights
Midway to Orlando Sanford Intl flights

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 septiembre 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$39Average$187FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$84Average$212FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$127Average$383FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$160Average$366FlexibilityNo cancel feeOn-time71%
DeltaCheapest$176Average$386FlexibilityNo cancel feeOn-timeN/A
Alaska AirlinesCheapest$176Average$215FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$176Average$376FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.