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$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 10/19. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — CHI
Aug 9 — Aug 161
Sat 8/9
Sat 8/16
1 adult, Economy
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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 August 4, 2025.

Round-trip from

$131
(Kiwi.com)

One-way from

$68
(Cheapflightsfares)

Popular in

March

Cheapest in

June

Average price

$328
From Florida Keys to Chicago (CHI)
Search Deals
One-way flight from Florida Keys to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 17% potential increase in price ($79 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Find flight deals from Florida Keys to Chicago

Cheapest flights from Florida Keys to Chicago
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 August 4, 2025.

This Kiwi.com deal was found by Cheapflights users on 8/2. 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.
Sun 9/77:00 amMIA - ORD
Nonstop3h 18mSpirit Airlines
Thu 9/1110:27 amORD - MIA
Nonstop3h 12mSpirit Airlines
Deal found 8/2$131
This Southwest deal was found by Cheapflights users on 8/3. 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.
Thu 9/1812:35 pmMIA - MDW
Nonstop3h 10mSouthwest
Mon 9/222:10 pmMDW - MIA
Nonstop3h 00mSouthwest
Deal found 8/3$132
This American Airlines deal was found by Cheapflights users on 8/2. 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.
Fri 9/56:20 amMIA - ORD
Nonstop3h 20mAmerican Airlines
Mon 9/86:09 amORD - MIA
Nonstop3h 05mAmerican Airlines
Deal found 8/2$137
This Southwest deal was found by Cheapflights users on 8/4. 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 10/217:35 amMIA - ORD
1 stop6h 10mSouthwest
Tue 11/46:05 amORD - MIA
1 stop5h 00mSouthwest
Deal found 8/4$146
This Kiwi.com deal was found by Cheapflights users on 8/2. 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 9/612:18 pmMIA - ORD
1 stop5h 27mMultiple Airlines
Tue 9/910:27 amORD - MIA
Nonstop3h 12mMultiple Airlines
Deal found 8/2$155
This Frontier deal was found by Cheapflights users on 8/2. 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.
Mon 10/206:53 pmMIA - MDW
Nonstop3h 15mFrontier
Mon 10/2710:03 pmMDW - MIA
Nonstop3h 00mFrontier
Deal found 8/2$155
This eDestinos deal was found by Cheapflights users on 8/1. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/126:00 amMIA - ORD
1 stop19h 32mFrontier
Sat 8/167:00 amORD - MIA
1 stop22h 30mFrontier
Deal found 8/1$179
This Delta deal was found by Cheapflights users on 8/2. 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 9/38:10 amMIA - MDW
1 stop5h 18mDelta
Tue 9/910:35 amMDW - MIA
1 stop6h 50mDelta
Deal found 8/2$217
This United Airlines deal was found by Cheapflights users on 8/2. 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.
Thu 11/64:00 pmEYW - ORD
Nonstop3h 46mUnited Airlines
Sat 11/86:02 amORD - EYW
1 stop7h 07mUnited Airlines
Deal found 8/2$274
This Priceline deal was found by Cheapflights users on 8/2. 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.
Thu 11/62:25 pmEYW - ORD
1 stop4h 58mSpirit Airlines
Fri 11/75:05 amORD - EYW
1 stop7h 25mSpirit Airlines
Deal found 8/2$305
This Delta deal was found by Cheapflights users on 8/3. 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 8/711:48 amEYW - ORD
1 stop6h 08mDelta
Tue 9/99:47 amORD - EYW
1 stop6h 38mDelta
Deal found 8/3$363
This Delta deal was found by Cheapflights users on 8/3. 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 8/72:03 pmEYW - MDW
1 stop4h 44mDelta
Tue 9/96:00 amMDW - EYW
1 stop6h 05mDelta
Deal found 8/3$363

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 August 4, 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

Sun 9/7

7:00 am-9:18 am

Nonstop3h 18m

Chicago O'Hare Intl

Thu 9/11

10:27 am-2:39 pm

Nonstop3h 12m

$131

MiamiChicago

MIA - MDW

MIAMDW

Miami

Thu 9/18

12:35 pm-2:45 pm

Nonstop3h 10m

Chicago Midway

Mon 9/22

2:10 pm-6:10 pm

Nonstop3h 00m

$132

MiamiChicago

MIA - ORD

MIAORD

Miami

Fri 9/5

7:59 pm-10:26 pm

Nonstop3h 27m

Chicago O'Hare Intl

Sun 9/7

6:09 am-10:14 am

Nonstop3h 05m

$137

MiamiChicago

MIA - ORD

MIAORD

Miami

Tue 10/21

7:35 am-12:45 pm

1 stop6h 10m

Chicago O'Hare Intl

Tue 11/4

6:05 am-12:05 pm

1 stop5h 00m

$146

MiamiChicago

MIA - ORD

MIAORD

Miami

Sat 9/6

12:18 pm-4:45 pm

1 stop5h 27m

Chicago O'Hare Intl

Tue 9/9

10:27 am-2:39 pm

Nonstop3h 12m

$155

MiamiChicago

MIA - MDW

MIAMDW

Miami

Mon 10/20

6:53 pm-9:08 pm

Nonstop3h 15m

Chicago Midway

Mon 10/27

10:03 pm-2:03 am

Nonstop3h 00m

$155

MiamiChicago

MIA - ORD

MIAORD

Miami

Tue 8/12

6:00 am-12:32 am

1 stop19h 32m

Chicago O'Hare Intl

Sat 8/16

7:00 am-6:30 am

1 stop22h 30m

$179

MiamiChicago

MIA - MDW

MIAMDW

Miami

Wed 9/3

6:00 am-9:36 am

1 stop4h 36m

Chicago Midway

Wed 9/3

4:25 pm-12:24 am

1 stop6h 59m

$217

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 11/6

4:00 pm-6:46 pm

Nonstop3h 46m

Chicago O'Hare Intl

Sat 11/8

6:02 am-2:09 pm

1 stop7h 07m

$274

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 11/6

2:25 pm-6:23 pm

1 stop4h 58m

Chicago O'Hare Intl

Fri 11/7

5:05 am-1:30 pm

1 stop7h 25m

$305

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/3

Showing 1-10 of 31 results
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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 $321). 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 August 4, 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.

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 August 4, 2025.
Get a feel of what it's like to fly with Alaska Airlines, Southwest, and Delta from Florida Keys to Chicago by reading reviews from past customers. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Comfort

7.8

Food

7.1

Boarding

8.1

Entertainment

7.1

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Aug 2025

BOI - LAX

flying in first class, my husband froze the entire flight and was miserable. first class does not offer blankets or any entertainment. (TV etc)
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Comfort

7.8

Food

7.1

Boarding

8.1

Entertainment

7.1

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Aug 2025

BOI - LAX

flying in first class, my husband froze the entire flight and was miserable. first class does not offer blankets or any entertainment. (TV etc)
Southwest
8.0
Very good
4,246 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Comfort

7.8

Food

7.1

Boarding

8.1

Entertainment

7.1

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Aug 2025

BOI - LAX

flying in first class, my husband froze the entire flight and was miserable. first class does not offer blankets or any entertainment. (TV etc)
Delta
8.0
Very good
7,987 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Comfort

7.8

Food

7.1

Boarding

8.1

Entertainment

7.1

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Aug 2025

BOI - LAX

flying in first class, my husband froze the entire flight and was miserable. first class does not offer blankets or any entertainment. (TV etc)
United Airlines
7.4
Good
8,912 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Comfort

7.8

Food

7.1

Boarding

8.1

Entertainment

7.1

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Aug 2025

BOI - LAX

flying in first class, my husband froze the entire flight and was miserable. first class does not offer blankets or any entertainment. (TV etc)
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Comfort

7.8

Food

7.1

Boarding

8.1

Entertainment

7.1

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Aug 2025

BOI - LAX

flying in first class, my husband froze the entire flight and was miserable. first class does not offer blankets or any entertainment. (TV etc)

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.

  • What are the cheapest airlines to fly from Florida Keys to Chicago one-way?

    To fly one-way, consider booking your trip with Spirit Airlines, which is currently one of the cheapest options available, starting at $68. American Airlines flights start at $69 while deals on Southwest start at $69 one-way.

  • What are the most popular routes from Florida Keys to Chicago?

    When deciding which route to take from Florida Keys to Chicago consider Miami - Chicago O'Hare Intl, Miami - Chicago Midway or Key West - Chicago O'Hare Intl as they are the most popular.

  • What are the most reliable airlines from Florida Keys to Chicago?

    Before booking your flight to Chicago from Florida Keys, check out the most reliable airlines to get you to your destination on time: Qatar Airways (52%), American Airlines (31%), Envoy Air( 31%).

  • What are the cheapest flights from Florida Keys to Chicago?

    Looking for the cheapest flight from Florida Keys to Chicago? While on average our users pay $359, our data indicates the cheapest price to be $199. The most popular route (Miami - Chicago O'Hare Intl), is priced around $85.

  • Can I find deals for flights from Florida Keys to Chicago that include hotel bookings?

    Yes. In addition to deals on Florida Keys to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Florida Keys to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Florida Keys to Chicago.

  • Can I find deals for business class flights from Florida Keys to Chicago?

    Yes. Cheapflights offers flight deals from Florida Keys to Chicago 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 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 $321). 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

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Valparaiso
Chesterton

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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.
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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 August 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$224Average$394FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$259Average$378FlexibilityNo cancel feeOn-time71%

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