$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 5/6. Fares are subject to change and may not be available on all flights or dates of travel.
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 July or September, booked 39 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 24, 2025.
Most accurate provider | Mytrip 3 stars |
|---|---|
Most trusted provider | Mytrip 3 stars |
Round-trip from | $131 (Booking.com) |
One-way from | $68 (Cheapflightsfares) |
Popular in | December |
Cheapest in | July |
Average price | $272 |
Find flight deals from Chicago to Key Largo
Cheapest flights from Chicago to Key LargoExplore 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 24, 2025.
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 24, 2025.
This Booking.com deal was found by Cheapflights users on 4/23. 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.
This Kiwi.com deal was found by Cheapflights users on 4/23. 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.
This Southwest deal was found by Cheapflights users on 4/23. 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.
This American Airlines deal was found by Cheapflights users on 4/23. 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.
This Frontier deal was found by Cheapflights users on 4/23. 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.
This JetBlue deal was found by Cheapflights users on 4/23. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Delta deal was found by Cheapflights users on 4/23. 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.
This eDestinos deal was found by Cheapflights users on 4/23. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Delta deal was found by Cheapflights users on 4/23. 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.
This United Airlines deal was found by Cheapflights users on 4/23. 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.
This Kissandfly.com deal was found by Cheapflights users on 4/23. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight 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 April 24, 2025.
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
ChicagoMiami
ORD - MIA
ORDMIA
Chicago O'Hare Intl
Wed 6/11
5:51 am-1:06 pm
1 stop6h 15m
Miami
Tue 6/17
7:20 pm-9:56 pm
Nonstop3h 36m
ChicagoMiami
ORD - MIA
ORDMIA
Chicago O'Hare Intl
Wed 5/7
9:55 am-2:10 pm
Nonstop3h 15m
Miami
Sun 5/11
7:12 am-3:57 pm
1 stop9h 45m
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Tue 7/1
9:45 am-1:50 pm
Nonstop3h 05m
Miami
Sat 7/5
5:45 am-7:50 am
Nonstop3h 05m
ChicagoMiami
ORD - MIA
ORDMIA
Chicago O'Hare Intl
Sat 5/24
4:50 pm-8:58 pm
Nonstop3h 08m
Miami
Tue 5/27
8:20 pm-10:48 pm
Nonstop3h 28m
ChicagoMiami
ORD - MIA
ORDMIA
Chicago O'Hare Intl
Thu 5/29
2:58 pm-11:43 pm
1 stop7h 45m
Miami
Sun 6/1
10:59 pm-10:37 am
1 stop12h 38m
ChicagoMiami
ORD - MIA
ORDMIA
Chicago O'Hare Intl
Wed 6/11
9:49 am-6:17 pm
1 stop7h 28m
Miami
Sat 6/14
5:30 am-12:29 pm
1 stop7h 59m
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Wed 6/11
9:24 am-5:10 pm
1 stop6h 46m
Miami
Wed 6/18
8:11 am-12:29 pm
1 stop5h 18m
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Mon 5/12
6:15 am-11:31 pm
1 stop16h 16m
Miami
Thu 5/15
8:46 am-1:34 pm
1 stop5h 48m
ChicagoMiami
ORD - MIA
ORDMIA
Chicago O'Hare Intl
Wed 7/23
7:01 am-11:18 am
Nonstop3h 17m
Miami
Wed 7/23
4:16 pm-6:50 pm
Nonstop3h 34m
ChicagoMiami
ORD - MIA
ORDMIA
Chicago O'Hare Intl
Tue 5/6
7:00 pm-11:12 pm
Nonstop3h 12m
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.
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 April 18, 2025.
The best time to book flights from Chicago to Key Largo is 39 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 24, 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 24, 2025.
The most flights from CHI to KE9 are scheduled on a Wednesday (51 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (32 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 24, 2025.
Peruse reviews from past customers who have flown with Alaska Airlines, Southwest and Delta 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.
Comfort
Food
Boarding
Crew
Overall
Entertainment
Reviews
Anonymous,Apr 2025
LAS - STS
Comfort
Food
Boarding
Crew
Overall
Entertainment
Reviews
Anonymous,Apr 2025
LAS - STS
Comfort
Food
Boarding
Crew
Overall
Entertainment
Reviews
Anonymous,Apr 2025
LAS - STS
Comfort
Food
Boarding
Crew
Overall
Entertainment
Reviews
Anonymous,Apr 2025
LAS - STS
Comfort
Food
Boarding
Crew
Overall
Entertainment
Reviews
Anonymous,Apr 2025
LAS - STS
Comfort
Food
Boarding
Crew
Overall
Entertainment
Reviews
Anonymous,Apr 2025
LAS - STS
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.
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.
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 24, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$39 | Average$177 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$68 | Average$188 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$160 | Average$382 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$177 | Average$394 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$180 | Average$396 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$201 | Average$388 | FlexibilityNo cancel fee | On-time63% |