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$64+ 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 2/10. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — CHI
Jan 31 — Feb 71
Sat 1/31
Sat 2/7
1 adult, Economy
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Cheap 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 January 1, 2026.

This Kiwi.com deal was found by Cheapflights users on 12/30. 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.
Wed 12/312:35 pmMIA - ORD
Nonstop3h 25mSpirit Airlines
Sun 1/46:05 pmORD - MIA
Nonstop3h 16mSpirit Airlines
Deal found 12/30$193
This Cheapflightsfares deal was found by Cheapflights users on 12/30. 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.
Wed 12/3112:10 pmMIA - MDW
Nonstop3h 27mFrontier
Sat 1/32:24 pmMDW - MIA
Nonstop3h 10mFrontier
Deal found 12/30$228
This United Airlines deal was found by Cheapflights users on 12/30. 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 12/317:15 amMIA - ORD
Nonstop3h 34mUnited Airlines
Thu 1/15:50 pmORD - MIA
Nonstop3h 20mUnited Airlines
Deal found 12/30$249
This United Airlines deal was found by Cheapflights users on 12/30. 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 12/317:15 amMIA - ORD
Nonstop3h 34mUnited Airlines
Sat 1/32:15 pmORD - MIA
Nonstop3h 20mUnited Airlines
Deal found 12/30$278
This United Airlines deal was found by Cheapflights users on 12/30. 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 12/317:15 amMIA - ORD
Nonstop3h 34mUnited Airlines
Sun 1/412:50 pmORD - MIA
1 stop8h 50mUnited Airlines
Deal found 12/30$284
This Delta deal was found by Cheapflights users on 12/30. 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 12/312:01 pmMIA - ORD
1 stop6h 37mDelta
Thu 1/11:35 pmORD - MIA
1 stop8h 31mDelta
Deal found 12/30$289
This Southwest deal was found by Cheapflights users on 12/29. 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 12/306:30 amMIA - MDW
Nonstop3h 15mSouthwest
Sat 1/38:40 pmMDW - MIA
Nonstop3h 00mSouthwest
Deal found 12/29$321
This Southwest deal was found by Cheapflights users on 12/30. 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.
Wed 12/311:05 pmMIA - MDW
Nonstop3h 15mSouthwest
Sat 1/35:05 amMDW - MIA
1 stop6h 15mSouthwest
Deal found 12/30$351
This American Airlines deal was found by Cheapflights users on 12/30. 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.
Wed 12/311:15 pmEYW - ORD
Nonstop3h 35mAmerican Airlines
Mon 1/58:10 amORD - EYW
Nonstop3h 35mAmerican Airlines
Deal found 12/30$361
This Southwest deal was found by Cheapflights users on 12/30. 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.
Wed 12/311:05 pmMIA - MDW
Nonstop3h 15mSouthwest
Sun 1/48:10 amMDW - MIA
Nonstop3h 05mSouthwest
Deal found 12/30$362
This Southwest deal was found by Cheapflights users on 12/29. 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 12/306:30 amMIA - MDW
Nonstop3h 15mSouthwest
Sun 1/48:10 amMDW - MIA
Nonstop3h 05mSouthwest
Deal found 12/29$381
This Delta deal was found by Cheapflights users on 12/30. 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.
Tue 12/305:01 pmMIA - MDW
1 stop6h 21mDelta
Thu 1/19:50 amMDW - MIA
1 stop7h 34mDelta
Deal found 12/30$384

Find 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 January 1, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$77
(Kiwi.com)

One-way from

$64
(Frontier)
Provider with most accurate pricing for Key West-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Key West-Chicago (CHI) flights.
Search Deals
From Florida Keys to Chicago (CHI)
Search Deals
One-way flight from Florida Keys to Chicago (CHI)
Search Deals

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 January 1, 2026.
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 - MDW

MIAMDW

Miami

Fri 1/16

4:29 pm-6:54 pm

Nonstop3h 25m

Chicago Midway

Mon 1/19

7:20 pm-11:25 pm

Nonstop3h 05m

$84

MiamiChicago

MIA - ORD

MIAORD

Miami

Sat 2/21

8:00 am-10:38 am

Nonstop3h 38m

Chicago O'Hare Intl

Sun 2/22

8:59 am-8:51 pm

1 stop10h 52m

$91

MiamiChicago

MIA - MDW

MIAMDW

Miami

Wed 2/11

12:10 pm-7:07 pm

1 stop7h 57m

Chicago Midway

Sun 2/15

6:15 am-10:28 am

Nonstop3h 13m

$94

MiamiChicago

MIA - ORD

MIAORD

Miami

Tue 1/13

5:54 am-8:18 am

Nonstop3h 24m

Chicago O'Hare Intl

Fri 1/16

6:57 pm-11:14 pm

Nonstop3h 17m

$95

MiamiChicago

MIA - ORD

MIAORD

Miami

Wed 2/25

9:53 pm-7:54 am

1 stop11h 01m

Chicago O'Hare Intl

Fri 2/27

7:23 pm-11:39 pm

Nonstop3h 16m

$98

MiamiChicago

MIA - ORD

MIAORD

Miami

Wed 2/18

2:52 pm-12:40 am

1 stop10h 48m

Chicago O'Hare Intl

Sun 2/22

9:18 am-1:36 pm

Nonstop3h 18m

$99

MiamiChicago

MIA - MDW

MIAMDW

Miami

Fri 3/13

11:13 am-1:41 pm

Nonstop3h 28m

Chicago Midway

Sun 3/15

6:00 am-10:13 am

Nonstop3h 13m

$107

MiamiChicago

MIA - ORD

MIAORD

Miami

Tue 4/7

6:15 am-8:41 am

Nonstop3h 26m

Chicago O'Hare Intl

Sat 4/11

4:51 pm-8:58 pm

Nonstop3h 07m

$154

MiamiChicago

MIA - MDW

MIAMDW

Miami

Fri 2/6

4:40 pm-6:55 pm

Nonstop3h 15m

Chicago Midway

Tue 2/10

5:30 pm-9:30 pm

Nonstop3h 00m

$177

MiamiChicago

MIA - ORD

MIAORD

Miami

Fri 2/13

9:53 pm-7:54 am

1 stop11h 01m

Chicago O'Hare Intl

Sun 2/15

8:59 am-8:51 pm

1 stop10h 52m

$195

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/31

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 January 1, 2026.

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 January 1, 2026.
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
4,253 reviews

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

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
4,253 reviews
Southwest
8.0
Very good
4,253 reviews

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

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
9,128 reviews
Southwest
8.0
Very good
4,253 reviews

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

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
11,069 reviews
Southwest
8.0
Very good
4,253 reviews

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

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
8,253 reviews
Southwest
8.0
Very good
4,253 reviews

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

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
5.7
Fair
3,067 reviews
Southwest
8.0
Very good
4,253 reviews

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

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?

    Frontier, Spirit Airlines, and Southwest can get you from Florida Keys to Chicago in just under 3h 15m. Your travel time will be generally consistent. The distance between Florida Keys and Chicago is about 1183 mi. All flights are typically nonstop.

  • 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 $41. Spirit Airlines flights start at $47 while deals on Southwest start at $78 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: United Airlines (79%), Air New Zealand (79%), Republic Airways( 79%).

  • 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 $581, our data indicates the cheapest price to be $180. The most popular route (Miami - Chicago O'Hare Intl), is priced around $65.

  • 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.

See more FAQs

Traveling to a place near Chicago?

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

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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 January 1, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$249Average$431FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$289Average$427FlexibilityNo cancel feeOn-time71%

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