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$48+ 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 4/3. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — CHI
feb. 25 — mar. 41
mar. 2/25
mar. 3/4
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 febrero 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$89
(Mytrip)

One-way from

$48
(Cheapflightsfares)

Popular in

February

Cheapest in

August

Average price

$536
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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Highest demand for flights based on searches. 12% potential increase in price ($55 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($14 potential savings vs. average RT price).
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Average for round-trip flights in February 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 febrero 20, 2025.

This Mytrip deal was found by Cheapflights users on 2/19. 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.
jue. 4/35:52 amMIA - ORD
Nonstop3h 37mSpirit Airlines
mar. 4/84:32 pmORD - MIA
Nonstop3h 13mSpirit Airlines
Deal found 2/19$89
This FlightHub deal was found by Cheapflights users on 2/19. 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.
mié. 3/510:45 amMIA - ORD
1 stop6h 46mMultiple Airlines
mar. 3/112:34 pmORD - MIA
Nonstop3h 13mMultiple Airlines
Deal found 2/19$91
This Trip.com deal was found by Cheapflights users on 2/19. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 3/512:42 pmMIA - MDW
Nonstop3h 31mFrontier
dom. 3/97:25 amMDW - MIA
Nonstop3h 12mFrontier
Deal found 2/19$92
This Frontier deal was found by Cheapflights users on 2/20. 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.
jue. 3/69:45 amMIA - ORD
1 stop8h 41mFrontier
sáb. 3/82:25 pmORD - MIA
1 stop9h 00mFrontier
Deal found 2/20$112
This Delta deal was found by Cheapflights users on 2/20. 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. 3/198:05 amMIA - ORD
1 stop5h 36mDelta
mar. 3/252:55 pmORD - MIA
1 stop5h 44mDelta
Deal found 2/20$218
This Delta deal was found by Cheapflights users on 2/20. 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. 3/196:10 pmMIA - MDW
1 stop5h 13mDelta
mar. 3/252:55 pmMDW - MIA
1 stop5h 26mDelta
Deal found 2/20$218
This American Airlines deal was found by Cheapflights users on 2/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 4/268:16 pmMIA - ORD
Nonstop3h 31mAmerican Airlines
jue. 5/12:50 pmORD - MIA
Nonstop3h 09mAmerican Airlines
Deal found 2/18$220
This Southwest deal was found by Cheapflights users on 2/20. 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.
mar. 4/17:25 amMIA - MDW
1 stop7h 15mSouthwest
mar. 4/15:35 pmMDW - MIA
Nonstop3h 00mSouthwest
Deal found 2/20$229
This American Airlines deal was found by Cheapflights users on 2/20. 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. 4/2412:56 pmEYW - ORD
Nonstop3h 37mAmerican Airlines
lun. 4/288:05 amORD - EYW
Nonstop3h 17mAmerican Airlines
Deal found 2/20$309
This Delta deal was found by Cheapflights users on 2/20. 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. 4/243:00 pmEYW - ORD
1 stop6h 50mDelta
lun. 4/281:15 pmORD - EYW
1 stop6h 15mDelta
Deal found 2/20$329
This Delta deal was found by Cheapflights users on 2/20. 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. 4/246:13 pmEYW - MDW
1 stop5h 13mDelta
lun. 4/286:04 amMDW - EYW
1 stop7h 01mDelta
Deal found 2/20$329
This United Airlines deal was found by Cheapflights users on 2/19. 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.
vie. 3/73:59 pmEYW - ORD
Nonstop3h 41mUnited Airlines
mar. 3/1110:51 amORD - EYW
Nonstop3h 12mUnited Airlines
Deal found 2/19$350

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 febrero 20, 2025.

Fly from

Florida Keys

Fly to

Chicago

Route

Depart

Return

Price

MiamiChicago

MIA - ORD

MIAORD

Miami

jue. 4/3

5:52 am-8:29 am

Nonstop3h 37m

Chicago O'Hare Intl

mar. 4/8

4:32 pm-8:45 pm

Nonstop3h 13m

$89

MiamiChicago

MIA - ORD

MIAORD

Miami

mié. 3/5

10:45 am-4:31 pm

1 stop6h 46m

Chicago O'Hare Intl

mar. 3/11

2:34 pm-6:47 pm

Nonstop3h 13m

$91

MiamiChicago

MIA - MDW

MIAMDW

Miami

mié. 3/5

12:42 pm-3:13 pm

Nonstop3h 31m

Chicago Midway

dom. 3/9

7:25 am-11:37 am

Nonstop3h 12m

$92

MiamiChicago

MIA - ORD

MIAORD

Miami

jue. 3/6

6:00 am-10:50 am

1 stop5h 50m

Chicago O'Hare Intl

sáb. 3/8

2:25 pm-12:25 am

1 stop9h 00m

$112

MiamiChicago

MIA - ORD

MIAORD

Miami

mié. 3/19

8:05 am-12:41 pm

1 stop5h 36m

Chicago O'Hare Intl

mar. 3/25

2:55 pm-9:39 pm

1 stop5h 44m

$218

MiamiChicago

MIA - MDW

MIAMDW

Miami

mié. 3/19

6:10 pm-10:23 pm

1 stop5h 13m

Chicago Midway

mar. 3/25

2:55 pm-9:21 pm

1 stop5h 26m

$218

MiamiChicago

MIA - ORD

MIAORD

Miami

sáb. 4/26

8:16 pm-10:47 pm

Nonstop3h 31m

Chicago O'Hare Intl

jue. 5/1

2:50 pm-6:59 pm

Nonstop3h 09m

$220

MiamiChicago

MIA - MDW

MIAMDW

Miami

mar. 4/1

7:25 am-1:40 pm

1 stop7h 15m

Chicago Midway

mar. 4/1

5:35 pm-9:35 pm

Nonstop3h 00m

$229

Key WestChicago

EYW - ORD

EYWORD

Key West

jue. 4/24

12:56 pm-3:33 pm

Nonstop3h 37m

Chicago O'Hare Intl

lun. 4/28

8:05 am-12:22 pm

Nonstop3h 17m

$309

Key WestChicago

EYW - ORD

EYWORD

Key West

jue. 4/24

3:00 pm-8:50 pm

1 stop6h 50m

Chicago O'Hare Intl

lun. 4/28

1:15 pm-8:30 pm

1 stop6h 15m

$329

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

Showing 1-10 of 34 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, 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 febrero 20, 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.

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 febrero 20, 2025.

The most flights from zzEOA to CHI are scheduled on a Monday (4 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (4 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 febrero 20, 2025.
Peruse reviews from past customers who have flown with Southwest, Alaska 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
4,411 reviews

Entertainment

7.6

Overall

8.1

Food

7.1

Crew

8.7

Boarding

8.2

Comfort

8.1

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
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Overall

8.1

Food

7.1

Crew

8.7

Boarding

8.2

Comfort

8.1

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.

Alaska Airlines
8.0
Very good
9,692 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Overall

8.1

Food

7.1

Crew

8.7

Boarding

8.2

Comfort

8.1

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.

Delta
8.0
Very good
8,220 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Overall

8.1

Food

7.1

Crew

8.7

Boarding

8.2

Comfort

8.1

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.

JetBlue
7.4
Good
3,070 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Overall

8.1

Food

7.1

Crew

8.7

Boarding

8.2

Comfort

8.1

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
8,766 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Overall

8.1

Food

7.1

Crew

8.7

Boarding

8.2

Comfort

8.1

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.

  • 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 $48. Frontier flights start at $48 while deals on Southwest start at $90 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 (79%), Qatar Airways (77%), Air New Zealand( 77%).

  • 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 $434, our data indicates the cheapest price to be $104. The most popular route (Miami - Chicago O'Hare Intl), is priced around $76.

  • 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
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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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 febrero 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$211Average$381FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$224Average$379FlexibilityNo cancel feeOn-time69%
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