$68+ Cheap flights from Florida Keys to Chicago (CHI)
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 4/15. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — CHI
Apr 6 — Apr 131
1 adult, Economy
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Find cheap flights from Florida Keys to Chicago 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.Cheap flight deals from Florida Keys to Chicago
Keep the following information in mind while searching for Florida Keys to Chicago flight deals. Data was last updated April 1, 2025.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $125 (Cheapflightsfares) |
One-way from | $68 (Cheapflightsfares) |
Popular in | July |
Cheapest in | August |
Average price | $386 |
Find flight deals from Florida Keys to Chicago
Cheapest flights from Florida Keys to ChicagoExplore the most affordable flight options available from Florida Keys to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 1, 2025.
Explore the most affordable flight options available from Florida Keys to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 1, 2025.
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.
Fri 5/93:15 pmMIA - ORD
Nonstop3h 26mSpirit Airlines
Tue 5/139:55 amORD - MIA
Nonstop3h 15mSpirit Airlines
Deal found 4/1![Spirit Airlines logo]()
$125
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/101:03 pmMIA - MDW
Nonstop3h 26mFrontier
Tue 4/156:00 amMDW - MIA
Nonstop3h 08mFrontier
Deal found 3/31![Frontier logo]()
$128
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/73:15 pmMIA - ORD
Nonstop3h 26mMultiple Airlines
Thu 5/86:00 amORD - MIA
1 stop8h 00mMultiple Airlines
Deal found 4/1![Multiple Airlines logo]()
$150
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/105:05 amMIA - MDW
Nonstop3h 10mSouthwest
Sun 5/118:40 pmMDW - MIA
Nonstop3h 00mSouthwest
Deal found 4/1![Southwest logo]()
$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 5/108:35 amMIA - ORD
Nonstop3h 34mAmerican Airlines
Sun 5/117:16 pmORD - MIA
Nonstop3h 16mAmerican Airlines
Deal found 4/1![American Airlines logo]()
$179
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/249:04 amMIA - ORD
1 stop6h 00mFrontier
Thu 5/16:00 amORD - MIA
1 stop8h 00mFrontier
Deal found 4/1![Frontier logo]()
$198
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/306:00 amMIA - ORD
1 stop7h 13mJetBlue
Wed 5/74:03 pmORD - MIA
1 stop7h 10mJetBlue
Deal found 3/31![JetBlue logo]()
$217
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2912:57 pmMIA - ORD
1 stop6h 40mDelta
Tue 6/31:30 pmORD - MIA
1 stop5h 02mDelta
Deal found 3/31![Delta logo]()
$227
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/187:00 amMIA - MDW
1 stop5h 56mDelta
Wed 6/2510:39 amMDW - MIA
1 stop7h 42mDelta
Deal found 3/31![Delta logo]()
$237
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/249:03 amEYW - ORD
1 stop15h 13mMultiple Airlines
Fri 4/2511:53 amORD - EYW
1 stop26h 03mMultiple Airlines
Deal found 3/31![Multiple Airlines logo]()
$272
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.
Tue 4/157:15 amMIA - ORD
1 stop5h 35mSouthwest
Tue 4/151:30 pmORD - MIA
1 stop6h 25mSouthwest
Deal found 3/31![Southwest logo]()
$273
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/1812:20 pmMIA - ORD
Nonstop3h 35mUnited Airlines
Tue 6/247:00 amORD - MIA
Nonstop3h 17mUnited Airlines
Deal found 3/31![United Airlines logo]()
$277
Cheapflights Fare Finder
Customize your flight search to find flights from Florida Keys to Chicago 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 1, 2025.
Use the filters below to find and compare flights from Florida Keys to Chicago that are best for you.
Fly from
Florida Keys
Fly to
Chicago
Route
Depart
Return
Price
MiamiChicago
MIA - ORD
MIAORD
Miami
Fri 5/9
3:15 pm-5:41 pm
Nonstop3h 26m
Chicago O'Hare Intl
Tue 5/13
9:55 am-2:10 pm
Nonstop3h 15m
$125
MiamiChicago
MIA - MDW
MIAMDW
Miami
Tue 4/15
11:03 am-1:31 pm
Nonstop3h 28m
Chicago Midway
Sat 4/19
7:25 am-11:30 am
Nonstop3h 05m
$140
MiamiChicago
MIA - ORD
MIAORD
Miami
Wed 5/7
3:15 pm-5:41 pm
Nonstop3h 26m
Chicago O'Hare Intl
Thu 5/8
6:00 am-3:00 pm
1 stop8h 00m
$150
MiamiChicago
MIA - MDW
MIAMDW
Miami
Sat 5/10
5:05 am-7:15 am
Nonstop3h 10m
Chicago Midway
Sun 5/11
8:40 pm-12:40 am
Nonstop3h 00m
$177
MiamiChicago
MIA - ORD
MIAORD
Miami
Sat 5/10
8:35 am-11:09 am
Nonstop3h 34m
Chicago O'Hare Intl
Sun 5/11
10:00 am-2:13 pm
Nonstop3h 13m
$179
MiamiChicago
MIA - ORD
MIAORD
Miami
Thu 4/24
9:04 am-2:04 pm
1 stop6h 00m
Chicago O'Hare Intl
Thu 5/1
6:00 am-3:00 pm
1 stop8h 00m
$198
MiamiChicago
MIA - ORD
MIAORD
Miami
Wed 4/30
6:00 am-12:13 pm
1 stop7h 13m
Chicago O'Hare Intl
Sat 5/3
1:13 pm-10:37 pm
1 stop8h 24m
$217
MiamiChicago
MIA - ORD
MIAORD
Miami
Thu 5/29
12:57 pm-6:37 pm
1 stop6h 40m
Chicago O'Hare Intl
Wed 6/4
1:30 pm-7:32 pm
1 stop5h 02m
$227
MiamiChicago
MIA - MDW
MIAMDW
Miami
Wed 6/18
5:35 pm-9:38 pm
1 stop5h 03m
Chicago Midway
Mon 6/30
12:41 pm-7:21 pm
1 stop5h 40m
$237
Key WestChicago
EYW - ORD
EYWORD
Key West
Thu 4/24
9:03 am-11:16 pm
1 stop15h 13m
Chicago O'Hare Intl
Fri 4/25
11:53 am-2:56 pm
1 stop26h 03m
$272
Showing 1-10 of 37 results
Best time to book a flight from Florida Keys to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Florida Keys 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 Florida Keys to Chicago
What is the cheapest month to book a flight from Florida Keys to Chicago?
Currently, August is the cheapest month in which you can book a flight from Florida Keys to Chicago (average of $245). Flying from Florida Keys to Chicago in March is currently the most expensive (average of $323). 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 EOA to CHI?
Find hourly flight availability from Florida Keys to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 1, 2025.
When flying from Florida Keys to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
Weekly flight availability from Florida Keys to Chicago
Explore weekly flight availability from Florida Keys to Chicago. 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 1, 2025.
The most flights from zzEOA to CHI are scheduled on a Monday (4 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (2 on average).
Rainfall in Chicago by month
Plan your trip to Chicago by taking into account the average rainfall totals by month.
In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.
Temperature in Chicago by month
Plan your trip to Chicago by taking into account the average temperature totals by month.
If weather is an important factor for your trip to Chicago, 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 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated April 1, 2025.
Peruse reviews from past customers who have flown with Alaska Airlines, Southwest and Delta from Florida Keys to Chicago 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.
Crew
8.5
Comfort
7.9
Boarding
8.2
Overall
8.0
Food
7.1
Entertainment
7.1
Reviews
1 / 20
10.0
ExcellentCheri,Jan 2025
FAT - SEA
Crew
8.5
Comfort
7.9
Boarding
8.2
Overall
8.0
Food
7.1
Entertainment
7.1
Reviews
1 / 20
10.0
ExcellentCheri,Jan 2025
FAT - SEA
Crew
8.5
Comfort
7.9
Boarding
8.2
Overall
8.0
Food
7.1
Entertainment
7.1
Reviews
1 / 20
10.0
ExcellentCheri,Jan 2025
FAT - SEA
Crew
8.5
Comfort
7.9
Boarding
8.2
Overall
8.0
Food
7.1
Entertainment
7.1
Reviews
1 / 20
10.0
ExcellentCheri,Jan 2025
FAT - SEA
Crew
8.5
Comfort
7.9
Boarding
8.2
Overall
8.0
Food
7.1
Entertainment
7.1
Reviews
1 / 20
10.0
ExcellentCheri,Jan 2025
FAT - SEA
Crew
8.5
Comfort
7.9
Boarding
8.2
Overall
8.0
Food
7.1
Entertainment
7.1
Reviews
1 / 20
10.0
ExcellentCheri,Jan 2025
FAT - SEA
Related info for your journey
Find useful and relevant information for your journey from Florida Keys to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Florida Keys?
Book flights to Florida Keys if you plan to visit one of these locationsMerrillville
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton
Browse thousands of different options on Cheapflights for your next trip
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Alternative routes for Florida Keys to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Top 2 airlines flying from Florida Keys to Chicago
Discover the top 2 airlines that operate flights from Florida Keys to Chicago. 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 1, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$224 | Average$379 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$239 | Average$388 | FlexibilityNo cancel fee | On-time71% |