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$60+ 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 1/15. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — CHI
Dec 23 — Dec 301
Mon 12/23
Mon 12/30
1 adult, Economy
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Cheap flight deals from Florida Keys to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Florida Keys (zzEOA) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated December 18, 2024.

Round-trip from

$116
(Cheapflightsfares)

One-way from

$60
(Mytrip)
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 December 18, 2024.

This Frontier deal was found by Cheapflights users on 12/18. 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.
Tue 12/3112:43 pmMIA - MDW
Nonstop3h 30mFrontier
Thu 1/97:30 amMDW - MIA
Nonstop3h 13mFrontier
Deal found 12/18$154
This eDestinos deal was found by Cheapflights users on 12/17. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/314:40 pmMIA - ORD
1 stop8h 19mFrontier
Thu 1/97:25 amORD - MIA
1 stop17h 27mFrontier
Deal found 12/17$180
This eDestinos deal was found by Cheapflights users on 12/18. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/311:42 pmMIA - ORD
Nonstop3h 30mSpirit Airlines
Thu 1/92:02 pmORD - MIA
Nonstop3h 14mSpirit Airlines
Deal found 12/18$190
This eDestinos deal was found by Cheapflights users on 12/17. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/314:40 pmMIA - ORD
1 stop8h 19mMultiple Airlines
Thu 1/92:02 pmORD - MIA
Nonstop3h 14mMultiple Airlines
Deal found 12/17$210
This eDestinos deal was found by Cheapflights users on 12/18. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/3111:06 amMIA - MDW
2 stops37h 14mMultiple Airlines
Mon 1/68:20 amMDW - MIA
1 stop13h 47mMultiple Airlines
Deal found 12/18$227
This American Airlines deal was found by Cheapflights users on 12/17. 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.
Tue 12/241:07 pmEYW - ORD
Nonstop3h 31mAmerican Airlines
Sat 1/1110:28 amORD - EYW
1 stop7h 39mAmerican Airlines
Deal found 12/17$254
This United Airlines deal was found by Cheapflights users on 12/17. 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.
Tue 12/2412:26 pmEYW - ORD
Nonstop3h 29mUnited Airlines
Tue 12/3111:02 amORD - EYW
Nonstop3h 11mUnited Airlines
Deal found 12/17$279
This Sun Country Air deal was found by Cheapflights users on 12/18. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/2411:59 amMIA - ORD
1 stop22h 04mSun Country Air
Tue 12/316:35 pmORD - MIA
1 stop15h 31mSun Country Air
Deal found 12/18$335
This Southwest deal was found by Cheapflights users on 12/17. 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 12/247:15 amMIA - MDW
2 stops7h 55mSouthwest
Tue 12/317:20 amMDW - MIA
1 stop6h 40mSouthwest
Deal found 12/17$377
This Delta deal was found by Cheapflights users on 12/17. 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 12/182:19 pmEYW - ORD
1 stop7h 46mDelta
Wed 1/15:45 amORD - EYW
1 stop5h 22mDelta
Deal found 12/17$628
This Delta deal was found by Cheapflights users on 12/17. 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 12/243:50 pmEYW - MDW
1 stop7h 16mDelta
Mon 12/306:00 amMDW - EYW
1 stop5h 07mDelta
Deal found 12/17$647

Find flights from Florida Keys to Chicago within your budget

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 December 18, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

MiamiChicago

MIA - ORD

MIAORD

Miami

Sun 1/26

10:00 am-12:29 pm

Nonstop3h 29m

Chicago O'Hare Intl

Wed 1/29

2:02 pm-6:16 pm

Nonstop3h 14m

$116

MiamiChicago

MIA - MDW

MIAMDW

Miami

Fri 2/14

3:52 pm-6:20 pm

Nonstop3h 28m

Chicago Midway

Sun 2/16

4:19 pm-8:30 pm

Nonstop3h 11m

$116

MiamiChicago

MIA - ORD

MIAORD

Miami

Thu 1/9

1:35 pm-10:42 pm

1 stop10h 07m

Chicago O'Hare Intl

Mon 1/13

7:50 am-1:52 am

1 stop17h 02m

$121

MiamiChicago

MIA - ORD

MIAORD

Miami

Wed 1/8

1:42 pm-4:12 pm

Nonstop3h 30m

Chicago O'Hare Intl

Sun 1/12

10:19 am-10:55 pm

1 stop11h 36m

$122

MiamiChicago

MIA - MDW

MIAMDW

Miami

Sat 1/18

8:10 am-10:20 am

Nonstop3h 10m

Chicago Midway

Sun 1/19

6:00 pm-10:00 pm

Nonstop3h 00m

$178

MiamiChicago

MIA - ORD

MIAORD

Miami

Thu 1/16

8:00 am-4:26 pm

1 stop9h 26m

Chicago O'Hare Intl

Sat 1/18

6:00 pm-10:21 pm

Nonstop3h 21m

$187

MiamiChicago

MIA - ORD

MIAORD

Miami

Thu 1/16

6:32 am-3:44 pm

1 stop10h 12m

Chicago O'Hare Intl

Sun 1/19

11:00 am-7:35 pm

1 stop7h 35m

$196

MiamiChicago

MIA - ORD

MIAORD

Miami

Fri 2/14

6:35 am-9:02 am

Nonstop3h 27m

Chicago O'Hare Intl

Mon 2/17

8:15 am-12:26 pm

Nonstop3h 11m

$197

MiamiChicago

MIA - ORD

MIAORD

Miami

Sat 1/18

8:00 am-1:28 pm

1 stop6h 28m

Chicago O'Hare Intl

Tue 1/21

7:05 am-1:46 pm

1 stop5h 41m

$216

MiamiChicago

MIA - MDW

MIAMDW

Miami

Fri 1/17

8:00 am-1:08 pm

1 stop6h 08m

Chicago Midway

Tue 1/21

9:34 am-5:00 pm

1 stop6h 26m

$216

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/17

Showing 1-10 of 36 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.

Travel insights for flights from Florida Keys to Chicago

Get recent, data-driven insights about flights from Florida Keys to Chicago including ideal travel times, pricing trends, and more.

What is the cheapest month to book a flight from Florida Keys to Chicago?

Currently, September is the cheapest month in which you can book a flight from Florida Keys to Chicago (average of $232). Flying from Florida Keys to Chicago in June is currently the most expensive (average of $308). 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 December 18, 2024.

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 December 18, 2024.
Peruse reviews from past customers who have flown with Spirit Airlines, American Airlines and United Airlines 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.
Southwest
8.1
Very good
4,848 reviews

Crew

8.7

Overall

8.1

Comfort

8.1

Food

7.2

Boarding

8.2

Entertainment

7.7

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

Southwest
8.1
Very good
4,848 reviews
Southwest
8.1
Very good
4,848 reviews

Crew

8.7

Overall

8.1

Comfort

8.1

Food

7.2

Boarding

8.2

Entertainment

7.7

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

Alaska Airlines
8.0
Very good
9,554 reviews
Southwest
8.1
Very good
4,848 reviews

Crew

8.7

Overall

8.1

Comfort

8.1

Food

7.2

Boarding

8.2

Entertainment

7.7

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

Delta
8.0
Very good
8,604 reviews
Southwest
8.1
Very good
4,848 reviews

Crew

8.7

Overall

8.1

Comfort

8.1

Food

7.2

Boarding

8.2

Entertainment

7.7

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

JetBlue
7.4
Good
3,279 reviews
Southwest
8.1
Very good
4,848 reviews

Crew

8.7

Overall

8.1

Comfort

8.1

Food

7.2

Boarding

8.2

Entertainment

7.7

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

United Airlines
7.4
Good
9,055 reviews
Southwest
8.1
Very good
4,848 reviews

Crew

8.7

Overall

8.1

Comfort

8.1

Food

7.2

Boarding

8.2

Entertainment

7.7

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

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 Frontier, which is currently one of the cheapest options available, starting at $60. Spirit Airlines flights start at $67 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: Republic Airways (100%), American Airlines (93%), Qatar Airways( 87%).

  • 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 $336, our data indicates the cheapest price to be $134. The most popular route (Miami - Chicago O'Hare Intl), is priced around $86.

  • 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, September is the cheapest month in which you can book a flight from Florida Keys to Chicago (average of $232). Flying from Florida Keys to Chicago in June is currently the most expensive (average of $308). 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

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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 December 18, 2024.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$211Average$419FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$224Average$394FlexibilityNo cancel feeOn-time69%
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