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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 11/20. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — CHI
dic. 10 — dic. 171
mié. 12/10
mié. 12/17
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 noviembre 10, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$96
(Spirit)

One-way from

$68
(Super.com)
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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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 noviembre 10, 2025.

This Spirit deal was found by Cheapflights users on 11/8. 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 Spirit is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/38:10 amMIA - ORD
Nonstop3h 25mSpirit Airlines
sáb. 12/67:41 pmORD - MIA
Nonstop3h 16mSpirit Airlines
Deal found 11/8$96
This Flightnetwork deal was found by Cheapflights users on 11/8. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/38:10 amMIA - ORD
Nonstop3h 25mSpirit Airlines
jue. 12/47:41 pmORD - MIA
Nonstop3h 16mSpirit Airlines
Deal found 11/8$97
This Priceline deal was found by Cheapflights users on 11/9. 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.
vie. 12/54:08 pmMIA - ORD
Nonstop3h 28mMultiple Airlines
lun. 12/811:01 amORD - MIA
1 stop11h 17mMultiple Airlines
Deal found 11/9$98
This Kiwi.com deal was found by Cheapflights users on 11/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 12/54:08 pmMIA - ORD
Nonstop3h 28mSpirit Airlines
jue. 12/111:52 pmORD - MIA
1 stop6h 02mSpirit Airlines
Deal found 11/8$99
This Kiwi.com deal was found by Cheapflights users on 11/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/87:09 pmMIA - MDW
1 stop14h 37mFrontier
sáb. 12/132:59 pmMDW - MIA
Nonstop3h 10mFrontier
Deal found 11/8$100
This Priceline deal was found by Cheapflights users on 11/9. 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.
mar. 12/94:08 pmMIA - ORD
Nonstop3h 28mSpirit Airlines
jue. 12/117:41 pmORD - MIA
Nonstop3h 16mSpirit Airlines
Deal found 11/9$101
This CheapOair deal was found by Cheapflights users on 11/7. 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.
vie. 11/212:05 pmMIA - MDW
1 stop28h 10mFrontier
dom. 12/72:59 pmMDW - MIA
Nonstop3h 10mFrontier
Deal found 11/7$101
This Kiwi.com deal was found by Cheapflights users on 11/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/94:08 pmMIA - ORD
Nonstop3h 28mSpirit Airlines
dom. 12/147:41 pmORD - MIA
Nonstop3h 16mSpirit Airlines
Deal found 11/8$102
This Frontier deal was found by Cheapflights users on 11/8. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 12/68:09 pmMIA - MDW
Nonstop3h 21mFrontier
vie. 12/128:42 pmMDW - MIA
1 stop10h 51mFrontier
Deal found 11/8$102
This WAYA deal was found by Cheapflights users on 11/9. 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 WAYA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 12/46:05 amMIA - ORD
1 stop12h 22mMultiple Airlines
dom. 12/77:41 pmORD - MIA
Nonstop3h 16mMultiple Airlines
Deal found 11/9$103
This Kiwi.com deal was found by Cheapflights users on 11/10. 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.
jue. 12/46:05 amMIA - MDW
1 stop13h 03mMultiple Airlines
dom. 12/72:59 pmMDW - MIA
Nonstop3h 10mMultiple Airlines
Deal found 11/10$103
This Kiwi.com deal was found by Cheapflights users on 11/9. 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.
jue. 11/2712:28 pmMIA - ORD
1 stop12h 40mMultiple Airlines
mar. 12/211:40 amORD - MIA
Nonstop3h 07mMultiple Airlines
Deal found 11/9$104

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 noviembre 10, 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

mié. 12/3

8:10 am-10:35 am

Nonstop3h 25m

Chicago O'Hare Intl

sáb. 12/6

7:41 pm-11:57 pm

Nonstop3h 16m

$96

MiamiChicago

MIA - ORD

MIAORD

Miami

vie. 1/30

5:30 am-7:54 am

Nonstop3h 24m

Chicago O'Hare Intl

dom. 2/1

8:59 am-1:17 pm

Nonstop3h 18m

$108

MiamiChicago

MIA - ORD

MIAORD

Miami

vie. 12/12

2:19 pm-10:11 pm

1 stop8h 52m

Chicago O'Hare Intl

vie. 1/16

6:57 pm-11:14 pm

Nonstop3h 17m

$147

MiamiChicago

MIA - MDW

MIAMDW

Miami

mar. 12/9

1:05 pm-3:20 pm

Nonstop3h 15m

Chicago Midway

mar. 12/16

9:00 am-1:05 pm

Nonstop3h 05m

$157

MiamiChicago

MIA - MDW

MIAMDW

Miami

vie. 2/6

4:40 pm-6:55 pm

Nonstop3h 15m

Chicago Midway

lun. 2/9

9:40 am-1:45 pm

Nonstop3h 05m

$157

MiamiChicago

MIA - ORD

MIAORD

Miami

mar. 12/16

4:08 pm-6:36 pm

Nonstop3h 28m

Chicago O'Hare Intl

lun. 12/22

6:05 pm-10:21 pm

Nonstop3h 16m

$171

MiamiChicago

MIA - MDW

MIAMDW

Miami

vie. 1/9

7:15 am-1:55 pm

2 stops7h 40m

Chicago Midway

lun. 1/12

5:30 pm-9:30 pm

Nonstop3h 00m

$172

MiamiChicago

MIA - MDW

MIAMDW

Miami

jue. 2/19

12:25 pm-7:35 pm

2 stops8h 10m

Chicago Midway

mar. 2/24

5:00 am-12:05 pm

1 stop6h 05m

$182

MiamiChicago

MIA - MDW

MIAMDW

Miami

vie. 1/23

7:15 am-1:55 pm

2 stops7h 40m

Chicago Midway

mar. 1/27

3:15 pm-10:00 pm

1 stop5h 45m

$182

MiamiChicago

MIA - MDW

MIAMDW

Miami

vie. 12/12

6:20 am-8:35 am

Nonstop3h 15m

Chicago Midway

dom. 12/14

9:10 am-4:30 pm

1 stop6h 20m

$187

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/8

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 noviembre 10, 2025.

When flying from Florida Keys to Chicago, the time of day you fly usually plays a role in the price. Save by searching for a flight at noon, which can drop the price by up to 34% versus a flight in the evening.

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 noviembre 10, 2025.

The most flights from zzEOA to CHI are scheduled on a Monday (4 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (2 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 noviembre 10, 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
4,236 reviews

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Boarding

8.1

Crew

8.6

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
4,236 reviews
Southwest
8.0
Very good
4,236 reviews

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Boarding

8.1

Crew

8.6

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
9,012 reviews
Southwest
8.0
Very good
4,236 reviews

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Boarding

8.1

Crew

8.6

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
11,045 reviews
Southwest
8.0
Very good
4,236 reviews

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Boarding

8.1

Crew

8.6

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
8,135 reviews
Southwest
8.0
Very good
4,236 reviews

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Boarding

8.1

Crew

8.6

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
3,113 reviews
Southwest
8.0
Very good
4,236 reviews

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Boarding

8.1

Crew

8.6

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?

    Spirit Airlines, Southwest, and Delta can get you from Florida Keys to Chicago in just under 3h 15m. Your travel time can differ by up to 2h 03m. 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 United Airlines, which is currently one of the cheapest options available, starting at $79. Southwest flights start at $79 while deals on Spirit Airlines start at $84 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 (83%), Air New Zealand (83%), Republic Airways( 83%).

  • 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 $589, our data indicates the cheapest price to be $201. The most popular route (Miami - Chicago O'Hare Intl), is priced around $68.

  • 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
Hammond
Porter
Benton Harbor
Merrillville

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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 noviembre 10, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$224Average$537FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$289Average$398FlexibilityNo cancel feeOn-time71%

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