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$80+ 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 6/11. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — CHI
may. 6 — may. 131
mar. 5/6
mar. 5/13
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 mayo 1, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$135
(Cheapflightsfares)

One-way from

$80
(Cheapflightsfares)

Popular in

March

Cheapest in

June

Average price

$406
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. 17% potential increase in price ($81 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 May 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 mayo 1, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 4/30. 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.
vie. 5/163:15 pmMIA - ORD
Nonstop3h 26mSpirit Airlines
lun. 5/199:55 amORD - MIA
Nonstop3h 15mSpirit Airlines
Deal found 4/30$135
This Kiwi.com deal was found by Cheapflights users on 4/29. 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. 5/3010:59 pmMIA - ORD
1 stop9h 05mMultiple Airlines
dom. 6/18:17 amORD - MIA
Nonstop3h 13mMultiple Airlines
Deal found 4/29$155
This Southwest deal was found by Cheapflights users on 4/30. 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. 6/37:00 amMIA - MDW
Nonstop3h 10mSouthwest
mié. 6/45:10 pmMDW - MIA
Nonstop2h 55mSouthwest
Deal found 4/30$197
This American Airlines deal was found by Cheapflights users on 4/30. 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.
vie. 5/309:27 pmMIA - ORD
Nonstop3h 29mAmerican Airlines
dom. 6/14:50 pmORD - MIA
Nonstop3h 08mAmerican Airlines
Deal found 4/30$198
This eDestinos deal was found by Cheapflights users on 4/30. 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.
jue. 5/297:24 pmMIA - MDW
1 stop25h 19mFrontier
lun. 6/27:05 amMDW - MIA
1 stop24h 00mFrontier
Deal found 4/30$205
This Cheapflightsfares deal was found by Cheapflights users on 4/30. 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.
sáb. 5/317:35 pmMIA - ORD
1 stop22h 40mFrontier
dom. 6/19:56 pmORD - MIA
1 stop30h 48mFrontier
Deal found 4/30$208
This Delta deal was found by Cheapflights users on 4/29. 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. 6/145:30 amMIA - ORD
1 stop8h 00mDelta
sáb. 6/216:15 pmORD - MIA
1 stop5h 42mDelta
Deal found 4/29$217
This Delta deal was found by Cheapflights users on 4/30. 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. 6/48:10 amMIA - MDW
1 stop4h 43mDelta
mar. 6/1712:44 pmMDW - MIA
1 stop7h 32mDelta
Deal found 4/30$217
This Mytrip deal was found by Cheapflights users on 4/28. 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. 5/155:35 pmEYW - RFD
1 stop24h 16mAllegiant Air
mié. 5/218:33 amRFD - EYW
1 stop6h 23mAllegiant Air
Deal found 4/28$251
This United Airlines deal was found by Cheapflights users on 4/30. 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.
sáb. 5/2412:22 pmMIA - ORD
Nonstop3h 33mUnited Airlines
lun. 5/2610:54 amORD - MIA
Nonstop3h 20mUnited Airlines
Deal found 4/30$280
This Southwest deal was found by Cheapflights users on 4/30. 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. 5/176:50 amMIA - ORD
2 stops10h 55mSouthwest
mié. 5/211:50 pmORD - MIA
1 stop7h 05mSouthwest
Deal found 4/30$289
This Delta deal was found by Cheapflights users on 4/30. 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.
lun. 6/26:25 pmEYW - ORD
1 stop6h 33mDelta
mar. 6/1711:20 amORD - EYW
1 stop7h 19mDelta
Deal found 4/30$314

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 mayo 1, 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

vie. 5/16

3:15 pm-5:41 pm

Nonstop3h 26m

Chicago O'Hare Intl

lun. 5/19

9:55 am-2:10 pm

Nonstop3h 15m

$135

MiamiChicago

MIA - ORD

MIAORD

Miami

vie. 5/30

10:59 pm-7:04 am

1 stop9h 05m

Chicago O'Hare Intl

dom. 6/1

8:17 am-12:30 pm

Nonstop3h 13m

$155

MiamiChicago

MIA - MDW

MIAMDW

Miami

mié. 7/2

6:30 am-8:40 am

Nonstop3h 10m

Chicago Midway

sáb. 7/5

7:10 pm-11:10 pm

Nonstop3h 00m

$179

MiamiChicago

MIA - ORD

MIAORD

Miami

vie. 5/30

9:27 pm-11:56 pm

Nonstop3h 29m

Chicago O'Hare Intl

dom. 6/1

4:50 pm-8:58 pm

Nonstop3h 08m

$198

MiamiChicago

MIA - MDW

MIAMDW

Miami

jue. 5/29

7:24 pm-7:43 pm

1 stop25h 19m

Chicago Midway

lun. 6/2

7:05 am-8:05 am

1 stop24h 00m

$205

MiamiChicago

MIA - ORD

MIAORD

Miami

sáb. 5/31

7:35 pm-5:15 pm

1 stop22h 40m

Chicago O'Hare Intl

dom. 6/1

9:56 pm-5:44 am

1 stop30h 48m

$208

MiamiChicago

MIA - ORD

MIAORD

Miami

sáb. 6/14

5:30 am-12:30 pm

1 stop8h 00m

Chicago O'Hare Intl

sáb. 6/21

6:15 pm-12:57 am

1 stop5h 42m

$217

MiamiChicago

MIA - MDW

MIAMDW

Miami

sáb. 6/14

5:30 am-9:41 am

1 stop5h 11m

Chicago Midway

mar. 6/17

12:44 pm-9:16 pm

1 stop7h 32m

$217

Key WestChicago

EYW - RFD

EYWRFD

Key West

jue. 5/15

5:35 pm-4:51 pm

1 stop24h 16m

Chicago Greater Rockford

mié. 5/21

8:33 am-3:56 pm

1 stop6h 23m

$251

MiamiChicago

MIA - ORD

MIAORD

Miami

sáb. 5/24

12:22 pm-2:55 pm

Nonstop3h 33m

Chicago O'Hare Intl

lun. 5/26

10:54 am-3:14 pm

Nonstop3h 20m

$280

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

Showing 1-10 of 33 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 mayo 1, 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 mayo 1, 2025.

The most flights from zzEOA to CHI are scheduled on a Monday (4 on average). You will have fewer flight options on Thursday, 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 mayo 1, 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
9,972 reviews

Overall

8.0

Entertainment

7.1

Comfort

7.9

Boarding

8.1

Crew

8.5

Food

7.1

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
9,972 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Overall

8.0

Entertainment

7.1

Comfort

7.9

Boarding

8.1

Crew

8.5

Food

7.1

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
4,294 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Overall

8.0

Entertainment

7.1

Comfort

7.9

Boarding

8.1

Crew

8.5

Food

7.1

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
7,934 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Overall

8.0

Entertainment

7.1

Comfort

7.9

Boarding

8.1

Crew

8.5

Food

7.1

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
8,696 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Overall

8.0

Entertainment

7.1

Comfort

7.9

Boarding

8.1

Crew

8.5

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Allegiant Air
7.3
Good
734 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Overall

8.0

Entertainment

7.1

Comfort

7.9

Boarding

8.1

Crew

8.5

Food

7.1

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 $80. Southwest flights start at $90 while deals on Frontier start at $98 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 (94%), United Airlines (81%), Air New Zealand( 78%).

  • 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 $436, our data indicates the cheapest price to be $198. The most popular route (Miami - Chicago O'Hare Intl), is priced around $75.

  • 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
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 mayo 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$224Average$394FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$259Average$388FlexibilityNo cancel feeOn-time71%

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