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$62+ 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 5/1. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — CHI
May 10 — May 171
Sun 5/10
Sun 5/17
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 April 10, 2026.

This Frontier deal was found by Cheapflights users on 4/6. 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 4/912:04 pm
MIA
-
ORD
Nonstop3h 38m
Frontier
Sun 4/127:25 am
ORD
-
MIA
Nonstop3h 19m
Frontier
Deal found 4/6$88
This Frontier deal was found by Cheapflights users on 4/5. 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 4/912:04 pm
MIA
-
ORD
Nonstop3h 38m
Frontier
Mon 4/1311:59 am
ORD
-
MIA
Nonstop3h 19m
Frontier
Deal found 4/5$89
This Expedia deal was found by Cheapflights users on 4/6. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/16:30 am
MIA
-
ORD
1 stop11h 41m
Multiple Airlines
Sun 5/33:52 pm
ORD
-
MIA
Nonstop3h 19m
Multiple Airlines
Deal found 4/6$90
This CheapOair deal was found by Cheapflights users on 4/6. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/306:30 am
MIA
-
ORD
1 stop11h 41m
Multiple Airlines
Sat 5/23:52 pm
ORD
-
MIA
Nonstop3h 19m
Multiple Airlines
Deal found 4/6$91
This Expedia deal was found by Cheapflights users on 4/5. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/239:21 pm
MIA
-
ORD
Nonstop3h 38m
Multiple Airlines
Mon 4/2711:28 am
ORD
-
MIA
1 stop10h 03m
Multiple Airlines
Deal found 4/5$92
This Cheapflightsfares deal was found by Cheapflights users on 4/6. 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 4/306:30 am
MIA
-
ORD
1 stop11h 41m
Spirit Airlines
Sun 5/37:50 am
ORD
-
MIA
Nonstop3h 08m
Spirit Airlines
Deal found 4/6$93
This Mytrip deal was found by Cheapflights users on 4/8. 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 4/239:21 pm
MIA
-
ORD
Nonstop3h 38m
Multiple Airlines
Wed 4/294:03 pm
ORD
-
MIA
1 stop6h 48m
Multiple Airlines
Deal found 4/8$94
This CheapOair deal was found by Cheapflights users on 4/7. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/2410:41 am
MIA
-
ORD
Nonstop3h 24m
Spirit Airlines
Mon 4/277:50 am
ORD
-
MIA
Nonstop3h 08m
Spirit Airlines
Deal found 4/7$95
This CheapOair deal was found by Cheapflights users on 4/6. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/259:21 pm
MIA
-
ORD
Nonstop3h 38m
Multiple Airlines
Sat 5/29:16 am
ORD
-
MIA
1 stop5h 48m
Multiple Airlines
Deal found 4/6$97
This CheapOair deal was found by Cheapflights users on 4/6. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/16:30 am
MIA
-
ORD
1 stop11h 41m
Spirit Airlines
Sun 5/37:50 am
ORD
-
MIA
Nonstop3h 08m
Spirit Airlines
Deal found 4/6$98
This CheapOair deal was found by Cheapflights users on 4/8. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/159:30 pm
MIA
-
ORD
Nonstop3h 26m
Spirit Airlines
Mon 5/189:20 am
ORD
-
MIA
Nonstop3h 08m
Spirit Airlines
Deal found 4/8$100
This Frontier deal was found by Cheapflights users on 4/5. 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.
Fri 4/1011:35 am
MIA
-
MDW
Nonstop3h 26m
Frontier
Sat 4/116:30 am
MDW
-
MIA
Nonstop3h 10m
Frontier
Deal found 4/5$104

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 April 10, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$88
(CheapOair)

One-way from

$62
(CheapOair)
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 April 10, 2026.
Use the filters below to find and compare flights from Florida Keys to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

MiamiChicago

MIA - MDW

MIAMDW

Miami

Sat 5/30

7:00 am-9:15 am

Nonstop3h 15m

Chicago Midway

Mon 6/1

6:50 pm-10:50 pm

Nonstop3h 00m

$167

MiamiChicago

MIA - MDW

MIAMDW

Miami

Tue 5/5

6:15 am-11:40 am

1 stop6h 25m

Chicago Midway

Tue 5/12

12:55 pm-9:55 pm

2 stops8h 00m

$182

MiamiChicago

MIA - MDW

MIAMDW

Miami

Wed 5/20

3:00 pm-9:50 pm

1 stop7h 50m

Chicago Midway

Wed 5/27

12:55 pm-9:55 pm

2 stops8h 00m

$182

MiamiChicago

MIA - ORD

MIAORD

Miami

Sat 5/23

5:24 pm-8:08 pm

Nonstop3h 44m

Chicago O'Hare Intl

Mon 5/25

6:05 pm-10:27 pm

Nonstop3h 22m

$187

MiamiChicago

MIA - MDW

MIAMDW

Miami

Thu 5/14

5:45 pm-12:15 am

1 stop7h 30m

Chicago Midway

Tue 5/19

12:50 pm-9:10 pm

2 stops7h 20m

$192

MiamiChicago

MIA - ORD

MIAORD

Miami

Thu 5/21

6:20 am-2:20 pm

1 stop9h 00m

Chicago O'Hare Intl

Mon 5/25

3:05 pm-10:00 pm

1 stop5h 55m

$202

MiamiChicago

MIA - ORD

MIAORD

Miami

Fri 5/1

6:20 am-3:30 pm

2 stops10h 10m

Chicago O'Hare Intl

Fri 5/8

2:40 pm-10:00 pm

2 stops6h 20m

$207
Quickest round-trip

MiamiChicago

MIA - MDW

MIAMDW

Miami

Tue 5/12

6:40 am-8:50 am

Nonstop3h 10m

Chicago Midway

Thu 5/14

6:50 pm-10:50 pm

Nonstop3h 00m

$207

MiamiChicago

MIA - MDW

MIAMDW

Miami

Thu 5/7

6:05 am-8:20 am

Nonstop3h 15m

Chicago Midway

Sun 5/10

7:40 am-11:40 am

Nonstop3h 00m

$217

MiamiChicago

MIA - MDW

MIAMDW

Miami

Thu 5/14

6:05 am-8:20 am

Nonstop3h 15m

Chicago Midway

Sun 5/17

6:45 pm-10:45 pm

Nonstop3h 00m

$217

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/5

Showing 1-10 of 60 resultsSorted by cheapest first
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6

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 April 10, 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.

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 10, 2026.

The most flights from zzEOA to CHI are scheduled on a Wednesday (6 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (4 on average).

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 10, 2026.
Get a feel of what it's like to fly with Southwest,United Airlines, andAmerican 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
4,334 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,334 reviews
Southwest
8.0
Very good
4,334 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
United Airlines
7.4
Good
9,561 reviews
Southwest
8.0
Very good
4,334 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
American Airlines
7.1
Good
11,564 reviews
Southwest
8.0
Very good
4,334 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Spirit Airlines
6.3
Okay
8,606 reviews
Southwest
8.0
Very good
4,334 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Frontier
5.7
Fair
2,997 reviews
Southwest
8.0
Very good
4,334 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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, United Airlines, and Southwest can get you from Florida Keys to Chicago in just under 3h 44m. Your travel time can differ by up to 7h 55m. The distance between Florida Keys and Chicago is about 1198 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 Spirit Airlines, which is currently one of the cheapest options available, starting at $43. Frontier flights start at $44 while deals on JetBlue start at $71 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: Republic Airways (85%), United Airlines (72%), Qatar Airways( 71%).

  • 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 $449, our data indicates the cheapest price to be $188. The most popular route (Miami - Chicago O'Hare Intl), is priced around $61.

  • 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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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 April 10, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$249Average$315FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$344Average$457FlexibilityNo cancel feeOn-time71%

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