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$58+ 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 10/10. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — CHI
Oct 24 — Oct 311
Fri 10/24
Fri 10/31
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 September 24, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$106
(Cheapflightsfares)

One-way from

$58
(Kiwi.com)

Popular in

March

Cheapest in

June

Average price

$288
Provider with most accurate pricing for Key West-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Key West-Chicago (CHI) flights.
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From Florida Keys to Chicago (CHI)
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One-way flight from Florida Keys to Chicago (CHI)
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Highest demand for flights based on searches. 20% potential increase in price ($91 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 24, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 9/24. 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 10/109:10 amMIA - MDW
Nonstop3h 17mFrontier
Mon 10/134:24 pmMDW - MIA
Nonstop3h 02mFrontier
Deal found 9/24$106
This Cheapflightsfares deal was found by Cheapflights users on 9/23. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/177:00 amMIA - ORD
Nonstop3h 22mSpirit Airlines
Sun 10/1910:27 amORD - MIA
Nonstop3h 02mSpirit Airlines
Deal found 9/23$107
This Kiwi.com deal was found by Cheapflights users on 9/24. 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.
Thu 10/167:00 amMIA - ORD
Nonstop3h 22mSpirit Airlines
Sun 10/1910:27 amORD - MIA
Nonstop3h 02mSpirit Airlines
Deal found 9/24$108
This Kiwi.com deal was found by Cheapflights users on 9/23. 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.
Sat 10/186:00 amMIA - ORD
Nonstop3h 18mSpirit Airlines
Sun 10/1910:27 amORD - MIA
Nonstop3h 02mSpirit Airlines
Deal found 9/23$109
This Priceline deal was found by Cheapflights users on 9/23. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/166:43 pmMIA - ORD
1 stop7h 41mMultiple Airlines
Mon 10/2010:27 amORD - MIA
Nonstop3h 02mMultiple Airlines
Deal found 9/23$110
This Cheapflightsfares deal was found by Cheapflights users on 9/24. 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.
Thu 10/97:00 amMIA - ORD
Nonstop3h 22mSpirit Airlines
Mon 10/1310:27 amORD - MIA
Nonstop3h 02mSpirit Airlines
Deal found 9/24$111
This Cheapflightsfares deal was found by Cheapflights users on 9/23. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/116:00 amMIA - ORD
Nonstop3h 18mSpirit Airlines
Sun 10/2610:27 amORD - MIA
Nonstop3h 02mSpirit Airlines
Deal found 9/23$112
This Priceline deal was found by Cheapflights users on 9/23. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/186:00 amMIA - ORD
Nonstop3h 18mSpirit Airlines
Sat 11/19:27 amORD - MIA
Nonstop3h 03mSpirit Airlines
Deal found 9/23$113
This Kiwi.com deal was found by Cheapflights users on 9/23. 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.
Fri 10/177:00 amMIA - ORD
Nonstop3h 22mSpirit Airlines
Mon 10/2710:27 amORD - MIA
Nonstop3h 02mSpirit Airlines
Deal found 9/23$114
This Priceline deal was found by Cheapflights users on 9/23. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/167:00 amMIA - ORD
Nonstop3h 22mMultiple Airlines
Tue 10/2111:00 amORD - MIA
1 stop6h 45mMultiple Airlines
Deal found 9/23$115
This Mytrip deal was found by Cheapflights users on 9/23. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/186:00 amMIA - ORD
Nonstop3h 18mMultiple Airlines
Fri 10/2411:51 amORD - MIA
1 stop7h 08mMultiple Airlines
Deal found 9/23$116
This Frontier deal was found by Cheapflights users on 9/24. 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.
Sat 11/17:05 pmMIA - MDW
Nonstop3h 17mFrontier
Tue 12/98:00 amMDW - MIA
Nonstop3h 15mFrontier
Deal found 9/24$116

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 September 24, 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

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 10/16

3:30 pm-7:34 am

1 stop17h 04m

Chicago O'Hare Intl

Sat 10/18

7:43 pm-2:40 pm

1 stop17h 57m

$187

MiamiChicago

MIA - MDW

MIAMDW

Miami

Thu 10/16

11:50 am-1:55 pm

Nonstop3h 05m

Chicago Midway

Mon 10/20

8:10 am-12:10 pm

Nonstop3h 00m

$207

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 10/16

3:30 pm-7:34 am

1 stop17h 04m

Chicago O'Hare Intl

Sun 10/19

5:50 am-4:04 pm

1 stop9h 14m

$214

MiamiChicago

MIA - ORD

MIAORD

Miami

Wed 10/15

6:15 pm-11:58 pm

1 stop6h 43m

Chicago O'Hare Intl

Mon 10/20

1:25 pm-9:27 pm

1 stop7h 02m

$217

MiamiChicago

MIA - ORD

MIAORD

Miami

Tue 10/21

12:20 pm-4:11 pm

1 stop4h 51m

Chicago O'Hare Intl

Wed 10/22

5:20 am-11:04 am

1 stop4h 44m

$217

MiamiChicago

MIA - MDW

MIAMDW

Miami

Fri 12/12

7:25 pm-11:30 pm

1 stop5h 05m

Chicago Midway

Mon 12/15

6:20 am-12:25 pm

1 stop5h 05m

$217

MiamiChicago

MIA - MDW

MIAMDW

Miami

Fri 11/7

8:30 am-12:28 pm

1 stop4h 58m

Chicago Midway

Mon 11/10

6:00 am-2:35 pm

1 stop7h 35m

$217

MiamiChicago

MIA - MDW

MIAMDW

Miami

Sat 11/1

8:30 am-12:31 pm

1 stop5h 01m

Chicago Midway

Tue 11/4

6:00 am-1:11 pm

1 stop6h 11m

$217

Key WestChicago

EYW - ORD

EYWORD

Key West

Wed 10/15

10:02 am-1:15 pm

1 stop28h 13m

Chicago O'Hare Intl

Sun 10/19

5:50 am-4:04 pm

1 stop9h 14m

$227

Key WestChicago

EYW - ORD

EYWORD

Key West

Sat 10/11

10:47 am-3:45 pm

1 stop5h 58m

Chicago O'Hare Intl

Thu 10/16

5:50 am-4:04 pm

1 stop9h 14m

$240

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/24

Showing 1-10 of 60 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 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 September 24, 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 September 24, 2025.
Get a feel of what it's like to fly with Southwest, United Airlines, and American Airlines 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.
Southwest
8.0
Very good
4,244 reviews

Comfort

8.0

Overall

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Southwest
8.0
Very good
4,244 reviews
Southwest
8.0
Very good
4,244 reviews

Comfort

8.0

Overall

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
United Airlines
7.4
Good
8,928 reviews
Southwest
8.0
Very good
4,244 reviews

Comfort

8.0

Overall

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,244 reviews

Comfort

8.0

Overall

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Spirit Airlines
6.3
Okay
8,042 reviews
Southwest
8.0
Very good
4,244 reviews

Comfort

8.0

Overall

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Frontier
5.8
Fair
3,163 reviews
Southwest
8.0
Very good
4,244 reviews

Comfort

8.0

Overall

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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.

  • How long is the flight from Florida Keys to Chicago?

    Southwest, Delta, and United Airlines can get you from Florida Keys to Chicago in just under 3h 05m. Your travel time can differ by up to 3h 38m. The distance between Florida Keys and Chicago is about 1183 mi. This flight may include one or multiple stops.

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

    To fly one-way, consider booking your trip with Frontier, which is currently one of the cheapest options available, starting at $72. United Airlines flights start at $79 while deals on Southwest start at $79 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: American Airlines (33%), Qatar Airways (33%), Envoy Air( 33%).

  • 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 $367, our data indicates the cheapest price to be $178. The most popular route (Miami - Chicago O'Hare Intl), is priced around $81.

  • 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
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 September 24, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$224Average$499FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$259Average$378FlexibilityNo cancel feeOn-time71%

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