Chicago

$52+ Cheap flights from Florida 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 12/15. Fares are subject to change and may not be available on all flights or dates of travel.
MIA — CHI
Nov 29 — Dec 61
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Find flight deals from Florida to Chicago

Cheapest flights from Florida to Chicago
Explore the most affordable flight options available from Florida to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 30, 2025.

This CheapOair deal was found by Cheapflights users on 10/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/227:46 pmMCO - ORD
Nonstop3h 11mFrontier
Mon 11/246:15 pmORD - MCO
Nonstop3h 04mFrontier
Deal found 10/28$80
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Thu 11/139:00 pmMCO - ORD
Nonstop3h 06mMultiple Airlines
Sun 11/165:25 amORD - MCO
Nonstop2h 42mMultiple Airlines
Deal found 10/29$81
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Fri 11/78:24 pmMCO - MDW
Nonstop2h 56mFrontier
Sun 11/910:12 amMDW - MCO
Nonstop2h 38mFrontier
Deal found 10/29$81
This Cheapflightsfares deal was found by Cheapflights users on 10/29. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/710:17 amMCO - ORD
Nonstop3h 09mFrontier
Sun 11/95:25 amORD - MCO
Nonstop2h 42mFrontier
Deal found 10/29$82
This Frontier deal was found by Cheapflights users on 10/28. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/1510:30 amMCO - ORD
1 stop7h 43mFrontier
Mon 11/175:15 amORD - MCO
Nonstop2h 42mFrontier
Deal found 10/28$83
This Orbitz deal was found by Cheapflights users on 10/27. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/57:15 pmMCO - ORD
Nonstop3h 04mSpirit Airlines
Sun 12/712:09 pmORD - MCO
Nonstop2h 52mSpirit Airlines
Deal found 10/27$84
This Priceline deal was found by Cheapflights users on 10/30. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/148:14 pmMCO - MDW
Nonstop2h 56mFrontier
Sat 11/156:30 amMDW - MCO
1 stop6h 24mFrontier
Deal found 10/30$84
This Frontier deal was found by Cheapflights users on 10/28. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/710:17 amMCO - ORD
Nonstop3h 09mFrontier
Mon 11/105:15 amORD - MCO
Nonstop2h 42mFrontier
Deal found 10/28$85
This CheapOair deal was found by Cheapflights users on 10/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/67:15 amMCO - MDW
Nonstop2h 57mFrontier
Mon 11/108:00 amMDW - MCO
Nonstop2h 41mFrontier
Deal found 10/29$85
This Priceline deal was found by Cheapflights users on 10/30. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/199:00 pmMCO - ORD
Nonstop3h 06mMultiple Airlines
Thu 11/206:23 pmORD - MCO
Nonstop3h 04mMultiple Airlines
Deal found 10/30$86
This Cheapflightsfares deal was found by Cheapflights users on 10/28. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/139:00 pmMCO - ORD
Nonstop3h 06mSpirit Airlines
Mon 11/176:48 amORD - MCO
Nonstop2h 42mSpirit Airlines
Deal found 10/28$87
This Frontier deal was found by Cheapflights users on 10/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/176:35 amMCO - MDW
Nonstop2h 57mFrontier
Fri 11/284:46 pmMDW - MCO
Nonstop2h 48mFrontier
Deal found 10/30$87

Cheap flight deals from Florida to Chicago

Keep the following information in mind while searching for Florida to Chicago flight deals. Data was last updated October 30, 2025.

Most accurate provider

Justfly.com
3 stars

Most trusted provider

Justfly.com
3 stars

Round-trip from

$81
(Kiwi.com)

One-way from

$52
(Cheapflightsfares)

Popular in

June

Cheapest in

September

Average price

$179

Good round-trip deal

$82 or less

Good one-way deal

$61 or less
Provider with most accurate pricing for Orlando (ORL)-Chicago (CHI) flight deals.
Provider most trusted by Cheapflights users for Orlando (ORL)-Chicago (CHI) flights.
From Florida to Chicago (CHI)
One-way flight from Florida to Chicago (CHI)
Highest demand for flights based on searches. 7% potential increase in price ($14 potential increase over avg. RT price).
Cheapest flight prices on average. 2% potential price decrease ($4 potential savings vs. average RT price).
Average for round-trip flights in October 2025
Price to beat on a round-trip flight from Florida to Chicago (CHI).
Price to beat on a one-way flight from Florida to Chicago (CHI).

Cheapflights Fare Finder

 
Customize your flight search to find flights from Florida 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 October 30, 2025.
Use the filters below to find and compare flights from Florida to Chicago that are best for you.

Fly from

Florida

Fly to

Chicago

Route

Depart

Return

Price

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Wed 12/31

7:58 pm-9:58 pm

Nonstop3h 00m

Chicago Midway

Sat 1/3

2:16 pm-6:01 pm

Nonstop2h 45m

$97

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Mon 12/22

7:58 pm-9:58 pm

Nonstop3h 00m

Chicago Midway

Wed 12/31

3:10 pm-6:58 pm

Nonstop2h 48m

$97

MiamiChicago

MIA - ORD

MIAORD

Miami

Thu 11/27

8:10 am-10:35 am

Nonstop3h 25m

Chicago O'Hare Intl

Tue 12/2

11:40 am-3:47 pm

Nonstop3h 07m

$100

Fort LauderdaleChicago

FLL - ORD

FLLORD

Fort Lauderdale

Thu 11/27

6:05 pm-8:27 pm

Nonstop3h 22m

Chicago O'Hare Intl

Tue 12/2

5:00 am-9:04 am

Nonstop3h 04m

$100

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Tue 12/9

5:27 pm-10:11 pm

1 stop5h 44m

Chicago O'Hare Intl

Sat 12/13

7:20 am-11:12 am

Nonstop2h 52m

$109

TampaChicago

TPA - ORD

TPAORD

Tampa

Mon 11/17

6:15 am-5:15 pm

1 stop12h 00m

Chicago O'Hare Intl

Wed 11/19

6:05 pm-6:30 am

1 stop11h 25m

$110

Fort LauderdaleChicago

FLL - ORD

FLLORD

Fort Lauderdale

Fri 12/5

8:50 am-11:08 am

Nonstop3h 18m

Chicago O'Hare Intl

Sat 12/6

4:49 pm-11:57 pm

1 stop6h 08m

$110

Fort LauderdaleChicago

FLL - ORD

FLLORD

Fort Lauderdale

Thu 2/19

6:35 pm-9:00 pm

Nonstop3h 25m

Chicago O'Hare Intl

Tue 2/24

5:59 pm-10:08 pm

Nonstop3h 09m

$112

Fort LauderdaleChicago

FLL - ORD

FLLORD

Fort Lauderdale

Fri 11/14

10:07 pm-12:27 am

Nonstop3h 20m

Chicago O'Hare Intl

Mon 11/17

5:10 am-9:14 am

Nonstop3h 04m

$116

Fort LauderdaleChicago

FLL - ORD

FLLORD

Fort Lauderdale

Sun 2/1

7:00 am-9:23 am

Nonstop3h 23m

Chicago O'Hare Intl

Sat 2/7

8:41 am-12:45 pm

Nonstop3h 04m

$116

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

Showing 1-10 of 60 results
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Best time to book a flight from Florida to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Florida 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 to Chicago

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

Currently, January is the cheapest month in which you can book a flight from Florida to Chicago (average of $31). Flying from Florida to Chicago in June is currently the most expensive (average of $107). 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 FL to CHI?

Find hourly flight availability from Florida 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 October 30, 2025.

A simple way to save on the total cost of your ticket is to fly from Florida to Chicago in the evening. If you’re flexible enough to do this you can expect to save up to 27% on your trip compared to booking a flight at noon.

What is the cheapest day to fly from Florida to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Florida to Chicago. Price data was last updated on October 26, 2025.

Travelers seeking maximum savings on their Florida to Chicago flight should consider departing on Sunday evenings when fares are most often at their lowest. Saturday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

Florida to Chicago Travel Guide

If you fly into Chicago O’Hare International Airport you’ll be about 14 miles from the central Loop business district in the city. This airport took over as the primary one for the city some time ago. It used to be Midway. The airport serves more than 83 million travelers in a year, making it the sixth busiest one in the world.

The other place you might fly into is Midway International Airport. This one is closer to the Loop district at only eight miles away. The airport handles over 22 million passengers per year and is the second busiest airport in Illinois. The majority of flights going into Midway are operated by Southwest Airlines.

Southwest flies into Midway with stopovers in Baltimore, Atlanta, Birmingham, and Kansas City. You might also stop in Dallas, St. Louis, or Manchester in New Hampshire. None of the stopovers are much more than an hour and many of them are under that.

Related info for your journey

Find useful and relevant information for your journey from Florida to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
  • How can I reduce my carbon footprint when flying from Florida to Chicago?

    When traveling from Florida to Chicago, you can reduce your environmental impact by selecting the right flight. You can select a modern aircraft with the most up-to-date technology, which reduces emissions. Direct flights can also be beneficial as they require less fuel. You can fly during off-peak times when the flight is less populated and requires less fuel burn. Pick airlines that use alternative fuel sources such as biofuels, which can significantly decrease the carbon footprint. You can, as well, fly in economy class to ensure the lowest emissions per passenger.

  • What information should travelers be looking for when trying to determine if an airport or airline is sustainable when traveling from Florida to Chicago?

    When traveling from Florida to Chicago, passengers should look for airports and airlines that are certified by the FAA's "Green" program, the Carbon Disclosure Project (CDP), or the International Air Transport Association (IATA). Travelers should search for airlines and airports committed to using renewable energy sources, limiting waste, and controlling air and noise pollution. Travelers should also find out which airports and airlines are taking part in sustainability initiatives, such as offering eco-friendly transportation options or striving to reduce emissions and other environmental impacts.

  • What airlines operating from Florida to Chicago have sustainability practices in place and what are they?

    Alaska Airlines, American Airlines, Delta Airlines, JetBlue, and United Airlines have sustainability practices for flights from Florida to Chicago. These practices include fuel conservation initiatives, increased use of renewable energy sources, and recycled materials for their cabins and terminals. Other initiatives include the use of more efficient aircraft and the reduction of water and waste.

  • What airports serve Florida to Chicago flights?

    Flying from Florida to Chicago could involve a number of different airports. However, if you fly from the busiest airport in Florida, Orlando, you’ll find a lot of options going into Chicago O’Hare, as well as some that fly into Chicago Midway. You can find direct flights and some with short stopovers along the way.

  • Which airlines fly directly from Florida to Chicago?

    For direct flights into Chicago, you can book on Frontier Airlines, Spirit Airlines, or United. American Airlines also offers several direct flights into O’Hare. If you book on Southwest Airlines you’ll fly non-stop into Chicago Midway. The flights last about 2h 45m. Some of the low-cost carriers have fares offered between cities in Florida and Chicago.

  • What are the stopover options between Florida to Chicago?

    You’ll find stopovers on Spirit Airlines in Denver, Myrtle Beach, and Fort Lauderdale. The range from 40m-7h 31m. JetBlue has flights serving this route that go through Boston. United offers stopovers in Fort Lauderdale and Houston. American Airlines will stop in Charlotte. Delta has many flights that stop in Atlanta for under an hour.

  • Do I need a passport or a visa to fly from Florida to Chicago?

    You will not need your passport or a visa for this flight. This is domestic only.

  • How long is the flight from Florida to Chicago?

    There are many flights that can get you from Florida to Chicago in 3h. Fly via Frontier, Spirit Airlines, or Southwest to get the fastest option. The distance from Florida to Chicago is about 990 mi. All flights are typically nonstop.

  • What are the cheapest airlines to fly from Florida to Chicago one-way?

    The cheapest airline one-way is Spirit Airlines, with whom users have recently found tickets for as low as $65. However, be on the lookout for offers from Southwest and United Airlines, as they are both options that can get you from Florida to Chicago for a low price.

  • What are the most popular routes from Florida to Chicago?

  • What are the most reliable airlines from Florida to Chicago?

    The top 3 most reliable airlines when flying from Florida to Chicago are Cathay Pacific (94%), Austrian Airlines (92%) and Spirit Airlines (91%).

  • What are the cheapest flights from Florida to Chicago?

    Looking at all options, your cheapest flight can be booked for $59. While the most popular route (Fort Lauderdale - Chicago O'Hare Intl) can be booked for $69 on average, our data indicates $950 when flying from Florida to Chicago.

  • Can I find deals for flights from Florida to Chicago that include hotel bookings?

    Yes. In addition to deals on Florida to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Florida to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Florida to Chicago.

  • Can I find deals for business class flights from Florida to Chicago?

    Yes. Cheapflights offers flight deals from Florida 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 to Chicago?

    Currently, January is the cheapest month in which you can book a flight from Florida to Chicago (average of $31). Flying from Florida to Chicago in June is currently the most expensive (average of $107). 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 Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Porter
Benton Harbor

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Alternative routes for Florida to Chicago

See prices for flight routes from nearby airports that may be better suited for you.

Top 7 airlines flying from Florida to Chicago

Discover the top 7 airlines that operate flights from Florida 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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$46Average$181FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$69Average$168FlexibilityNo cancel feeOn-time65%
Allegiant AirCheapest$82Average$163FlexibilityNo cancel feeOn-time88%
DeltaCheapest$98Average$356FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$143Average$327FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$144Average$342FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$158Average$300FlexibilityNo cancel feeOn-time71%

Helpful tips for your next trip to Chicago

Get useful tips and recommendations to enhance your travel experience on your next trip to Chicago. Learn about must-visit attractions, local customs, transportation options, weather conditions, and other valuable tips to make your trip more enjoyable and hassle-free.
  • To find out if a particular airport is sustainable, passengers traveling from Florida to Chicago can check the Airport Carbon Accreditation list to see if the airport is certified.
  • At Miami International Airport (MIA), efforts have been made to reduce energy and water consumption and advance waste management. Chicago O'Hare International Airport (ORD) has also implemented green building practices and a carbon offset program as part of its sustainability initiatives.
  • Flying on this route, Southwest Airlines has adopted alternative fuels like biofuels, as well as various operational changes, like utilizing more efficient flight paths and cutting down on aircraft taxi time.

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