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$47+ 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 12/12. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — CHI
Nov 18 — Nov 251
1 adult
Mon 11/18
Mon 11/25
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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 November 13, 2024.

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 November 13, 2024.

This Cheapflightsfares deal was found by Cheapflights users on 11/12. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/612:42 pmMIA - MDW
Nonstop3h 30mFrontier
Mon 12/98:15 amMDW - MIA
1 stop6h 13mFrontier
Deal found 11/12$111
This FlightHub deal was found by Cheapflights users on 11/12. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/144:38 pmMIA - ORD
Nonstop3h 29mMultiple Airlines
Tue 12/175:38 pmORD - MIA
1 stop5h 21mMultiple Airlines
Deal found 11/12$113
This Cheapflightsfares deal was found by Cheapflights users on 11/13. 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.
Sat 12/144:38 pmMIA - ORD
Nonstop3h 29mSpirit Airlines
Tue 12/178:02 pmORD - MIA
Nonstop3h 18mSpirit Airlines
Deal found 11/13$116
This eDestinos deal was found by Cheapflights users on 11/13. 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.
Sat 11/235:36 amMIA - ORD
1 stop30h 57mFrontier
Tue 11/266:00 amORD - MIA
1 stop17h 16mFrontier
Deal found 11/13$120
This eDestinos deal was found by Cheapflights users on 11/11. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/185:21 pmMIA - MDW
Nonstop3h 15mMultiple Airlines
Thu 11/2112:05 pmMDW - MIA
2 stops12h 50mMultiple Airlines
Deal found 11/11$159
This Southwest deal was found by Cheapflights users on 11/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/53:40 pmMIA - MDW
Nonstop3h 10mSouthwest
Tue 12/109:40 amMDW - MIA
Nonstop3h 05mSouthwest
Deal found 11/12$220
This Delta deal was found by Cheapflights users on 11/12. 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.
Sat 12/76:00 amMIA - MDW
1 stop6h 58mDelta
Sat 12/75:50 pmMDW - MIA
1 stop5h 03mDelta
Deal found 11/12$226
This United Airlines deal was found by Cheapflights users on 11/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/64:05 pmEYW - ORD
Nonstop3h 21mUnited Airlines
Sun 12/810:55 amORD - EYW
Nonstop3h 06mUnited Airlines
Deal found 11/11$249
This Delta deal was found by Cheapflights users on 11/11. 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.
Fri 12/66:20 pmEYW - ORD
1 stop6h 38mDelta
Sun 12/85:40 amORD - EYW
1 stop6h 44mDelta
Deal found 11/11$298
This American Airlines deal was found by Cheapflights users on 11/12. 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.
Tue 12/248:01 amEYW - ORD
1 stop5h 11mAmerican Airlines
Sat 1/115:00 amORD - EYW
1 stop7h 08mAmerican Airlines
Deal found 11/12$318
This Mytrip deal was found by Cheapflights users on 11/11. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/610:23 amEYW - ORD
2 stops15h 11mMultiple Airlines
Sun 12/89:58 amORD - EYW
3 stops29h 55mMultiple Airlines
Deal found 11/11$404
This Mytrip deal was found by Cheapflights users on 11/12. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/275:43 pmEYW - RFD
1 stop15h 12mAllegiant Air
Thu 1/210:07 amRFD - EYW
2 stops24h 02mAllegiant Air
Deal found 11/12$506

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 2,744,491 searches. Data last updated November 13, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

MiamiChicago

MIA - MDW

MIAMDW

Miami

Fri 12/6

12:42 pm-3:12 pm

Nonstop3h 30m

Chicago Midway

Mon 12/9

8:15 am-3:28 pm

1 stop6h 13m

$111

MiamiChicago

MIA - ORD

MIAORD

Miami

Sat 12/14

4:38 pm-7:07 pm

Nonstop3h 29m

Chicago O'Hare Intl

Tue 12/17

5:38 pm-11:59 pm

1 stop5h 21m

$113

MiamiChicago

MIA - ORD

MIAORD

Miami

Sat 12/14

4:38 pm-7:07 pm

Nonstop3h 29m

Chicago O'Hare Intl

Tue 12/17

8:02 pm-12:20 am

Nonstop3h 18m

$116

MiamiChicago

MIA - ORD

MIAORD

Miami

Sat 11/23

5:36 am-11:33 am

1 stop30h 57m

Chicago O'Hare Intl

Tue 11/26

6:00 am-12:16 am

1 stop17h 16m

$120

MiamiChicago

MIA - MDW

MIAMDW

Miami

Thu 12/5

8:06 am-6:12 pm

1 stop11h 06m

Chicago Midway

Sat 12/7

7:15 am-2:18 pm

2 stops30h 03m

$169

MiamiChicago

MIA - MDW

MIAMDW

Miami

Sat 12/14

6:30 am-8:40 am

Nonstop3h 10m

Chicago Midway

Mon 12/16

9:40 am-1:45 pm

Nonstop3h 05m

$209

MiamiChicago

MIA - MDW

MIAMDW

Miami

Sat 12/7

6:00 am-11:58 am

1 stop6h 58m

Chicago Midway

Sat 12/7

5:50 pm-11:53 pm

1 stop5h 03m

$226

Key WestChicago

EYW - ORD

EYWORD

Key West

Fri 12/6

4:05 pm-6:26 pm

Nonstop3h 21m

Chicago O'Hare Intl

Sun 12/8

10:55 am-3:01 pm

Nonstop3h 06m

$249

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 1/9

9:03 am-5:20 pm

1 stop9h 17m

Chicago O'Hare Intl

Fri 1/17

3:22 pm-9:12 am

2 stops16h 50m

$262

Key WestChicago

EYW - ORD

EYWORD

Key West

Fri 12/6

6:20 pm-11:58 pm

1 stop6h 38m

Chicago O'Hare Intl

Sun 12/8

5:40 am-1:24 pm

1 stop6h 44m

$298

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/12

Showing 1-10 of 31 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 November 13, 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.

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 November 13, 2024.

The most flights from zzEOA to CHI are scheduled on a Monday (4 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (1 on average).

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 November 13, 2024.
Peruse reviews from past customers who have flown with Frontier, Spirit Airlines 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.
Southwest
8.1
Very good
5,048 reviews

Boarding

8.3

Entertainment

7.7

Food

7.2

Overall

8.1

Comfort

8.1

Crew

8.7

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

Southwest
8.1
Very good
5,048 reviews
Southwest
8.1
Very good
5,048 reviews

Boarding

8.3

Entertainment

7.7

Food

7.2

Overall

8.1

Comfort

8.1

Crew

8.7

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

Alaska Airlines
8.0
Very good
9,434 reviews
Southwest
8.1
Very good
5,048 reviews

Boarding

8.3

Entertainment

7.7

Food

7.2

Overall

8.1

Comfort

8.1

Crew

8.7

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

Delta
8.0
Very good
8,789 reviews
Southwest
8.1
Very good
5,048 reviews

Boarding

8.3

Entertainment

7.7

Food

7.2

Overall

8.1

Comfort

8.1

Crew

8.7

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

United Airlines
7.4
Good
9,189 reviews
Southwest
8.1
Very good
5,048 reviews

Boarding

8.3

Entertainment

7.7

Food

7.2

Overall

8.1

Comfort

8.1

Crew

8.7

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

Allegiant Air
7.4
Good
856 reviews
Southwest
8.1
Very good
5,048 reviews

Boarding

8.3

Entertainment

7.7

Food

7.2

Overall

8.1

Comfort

8.1

Crew

8.7

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 $47. Spirit Airlines flights start at $51 while deals on United 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 cheapest flights from Florida Keys to Chicago?

    Looking for the cheapest flight from Florida Keys to Chicago? While on average our users pay $364, our data indicates the cheapest price to be $213. The most popular route (Miami - Chicago O'Hare Intl), is priced around $115.

  • 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 2,744,491 searches. Data last updated November 13, 2024.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$211Average$464FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$313Average$394FlexibilityNo cancel feeOn-time69%
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