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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 7/19. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — CHI
jun. 17 — jun. 241
mar. 6/17
mar. 6/24
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 junio 12, 2025.

Round-trip from

$141
(Mytrip)

One-way from

$68
(Booking.com)

Popular in

March

Cheapest in

June

Average price

$268
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. 17% potential increase in price ($78 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 June 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 junio 12, 2025.

This Mytrip deal was found by Cheapflights users on 6/10. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 7/17:00 amMIA - ORD
1 stop24h 37mSpirit Airlines
mar. 7/81:43 pmORD - MIA
Nonstop3h 17mSpirit Airlines
Deal found 6/10$141
This American Airlines deal was found by Cheapflights users on 6/11. 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.
jue. 8/146:39 amMIA - ORD
Nonstop3h 25mAmerican Airlines
lun. 8/188:05 amORD - MIA
Nonstop3h 07mAmerican Airlines
Deal found 6/11$159
This Cheapflightsfares deal was found by Cheapflights users on 6/10. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/96:53 pmMIA - MDW
Nonstop3h 15mFrontier
lun. 10/1310:03 pmMDW - MIA
Nonstop3h 00mFrontier
Deal found 6/10$160
This Southwest deal was found by Cheapflights users on 6/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 7/125:45 amMIA - MDW
Nonstop3h 05mSouthwest
dom. 7/138:45 pmMDW - MIA
Nonstop3h 05mSouthwest
Deal found 6/10$177
This FlightHub deal was found by Cheapflights users on 6/10. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 8/216:00 amMIA - ORD
1 stop5h 39mMultiple Airlines
dom. 8/246:45 amORD - MIA
Nonstop3h 13mMultiple Airlines
Deal found 6/10$179
This United Airlines deal was found by Cheapflights users on 6/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 7/84:16 pmMIA - ORD
Nonstop3h 34mUnited Airlines
mar. 7/157:01 amORD - MIA
Nonstop3h 17mUnited Airlines
Deal found 6/10$197
This Delta deal was found by Cheapflights users on 6/11. 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.
jue. 8/78:11 amMIA - ORD
1 stop5h 39mDelta
dom. 8/109:00 amORD - MIA
1 stop7h 10mDelta
Deal found 6/11$217
This Delta deal was found by Cheapflights users on 6/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 7/128:11 amMIA - MDW
1 stop5h 18mDelta
mar. 7/156:00 amMDW - MIA
1 stop6h 07mDelta
Deal found 6/10$217
This Southwest deal was found by Cheapflights users on 6/9. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 8/297:35 amMIA - ORD
1 stop9h 50mSouthwest
mar. 9/26:00 amORD - MIA
1 stop5h 05mSouthwest
Deal found 6/9$252
This Frontier deal was found by Cheapflights users on 6/12. 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.
vie. 8/297:50 amMIA - ORD
1 stop11h 38mFrontier
lun. 9/15:10 amORD - MIA
1 stop5h 10mFrontier
Deal found 6/12$255
This Delta deal was found by Cheapflights users on 6/12. 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.
mié. 10/16:00 pmEYW - ORD
1 stop6h 53mDelta
mié. 10/86:00 amORD - EYW
1 stop6h 08mDelta
Deal found 6/12$289
This American Airlines deal was found by Cheapflights users on 6/12. 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.
mié. 10/17:31 pmEYW - ORD
1 stop5h 17mAmerican Airlines
mié. 10/85:15 amORD - EYW
2 stops6h 45mAmerican Airlines
Deal found 6/12$328

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 junio 12, 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

mar. 7/1

7:00 am-6:37 am

1 stop24h 37m

Chicago O'Hare Intl

mar. 7/8

1:43 pm-6:00 pm

Nonstop3h 17m

$141

MiamiChicago

MIA - ORD

MIAORD

Miami

jue. 8/14

6:39 am-9:04 am

Nonstop3h 25m

Chicago O'Hare Intl

lun. 8/18

6:00 am-10:08 am

Nonstop3h 08m

$158

MiamiChicago

MIA - MDW

MIAMDW

Miami

jue. 10/9

6:53 pm-9:08 pm

Nonstop3h 15m

Chicago Midway

lun. 10/13

10:03 pm-2:03 am

Nonstop3h 00m

$160

MiamiChicago

MIA - MDW

MIAMDW

Miami

sáb. 7/12

5:45 am-7:50 am

Nonstop3h 05m

Chicago Midway

dom. 7/13

8:45 pm-12:50 am

Nonstop3h 05m

$177

MiamiChicago

MIA - ORD

MIAORD

Miami

mar. 7/8

4:16 pm-6:50 pm

Nonstop3h 34m

Chicago O'Hare Intl

mar. 7/15

7:01 am-11:18 am

Nonstop3h 17m

$197

MiamiChicago

MIA - ORD

MIAORD

Miami

jue. 8/7

8:11 am-12:50 pm

1 stop5h 39m

Chicago O'Hare Intl

dom. 8/10

9:00 am-5:10 pm

1 stop7h 10m

$217

MiamiChicago

MIA - MDW

MIAMDW

Miami

sáb. 7/12

8:11 am-12:29 pm

1 stop5h 18m

Chicago Midway

mar. 7/15

6:00 am-1:07 pm

1 stop6h 07m

$217

MiamiChicago

MIA - ORD

MIAORD

Miami

lun. 6/16

12:20 pm-4:58 pm

1 stop5h 38m

Chicago O'Hare Intl

mar. 6/24

1:43 pm-6:00 pm

Nonstop3h 17m

$244

MiamiChicago

MIA - ORD

MIAORD

Miami

vie. 8/29

7:35 am-4:25 pm

1 stop9h 50m

Chicago O'Hare Intl

mar. 9/2

6:00 am-12:05 pm

1 stop5h 05m

$252

MiamiChicago

MIA - ORD

MIAORD

Miami

vie. 8/29

7:50 am-6:28 pm

1 stop11h 38m

Chicago O'Hare Intl

lun. 9/1

5:10 am-11:20 am

1 stop5h 10m

$255

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

Showing 1-10 of 32 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 junio 12, 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.

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 junio 12, 2025.
Peruse reviews from past customers who have flown with Alaska Airlines, Southwest and Delta from Florida Keys to Chicago to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Entertainment

7.1

Comfort

7.8

Food

7.1

Boarding

8.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Entertainment

7.1

Comfort

7.8

Food

7.1

Boarding

8.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,287 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Entertainment

7.1

Comfort

7.8

Food

7.1

Boarding

8.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,946 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Entertainment

7.1

Comfort

7.8

Food

7.1

Boarding

8.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,790 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Entertainment

7.1

Comfort

7.8

Food

7.1

Boarding

8.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Entertainment

7.1

Comfort

7.8

Food

7.1

Boarding

8.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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. Frontier flights start at $71 while deals on United Airlines 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: United Airlines (69%), Air New Zealand (69%), American Airlines( 59%).

  • 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 $513, our data indicates the cheapest price to be $141. The most popular route (Miami - Chicago O'Hare Intl), is priced around $106.

  • 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 Florida Keys?

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

Browse thousands of different options on Cheapflights for your next trip

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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 junio 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$224Average$394FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$289Average$423FlexibilityNo cancel feeOn-time71%

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