Chicago

$45+ 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 2/1. Fares are subject to change and may not be available on all flights or dates of travel.
MIA — CHI
Jan 16 — Jan 231
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Cheap 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 December 17, 2025.

This Frontier deal was found by Cheapflights users on 12/16. 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.
Thu 12/257:46 amMCO - ORD
Nonstop3h 32mFrontier
Tue 1/65:29 pmORD - MCO
Nonstop2h 56mFrontier
Deal found 12/16$72
This Kiwi.com deal was found by Cheapflights users on 12/16. 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 12/2512:17 pmMCO - ORD
Nonstop3h 04mMultiple Airlines
Wed 1/75:29 pmORD - MCO
Nonstop2h 56mMultiple Airlines
Deal found 12/16$78
This Frontier deal was found by Cheapflights users on 12/16. 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.
Wed 12/247:46 amMCO - ORD
Nonstop3h 32mFrontier
Tue 1/65:29 pmORD - MCO
Nonstop2h 56mFrontier
Deal found 12/16$88
This Priceline deal was found by Cheapflights users on 12/14. 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.
Thu 12/2512:31 pmFLL - ORD
Nonstop3h 31mFrontier
Tue 1/272:53 pmORD - FLL
1 stop8h 27mFrontier
Deal found 12/14$88
This Frontier deal was found by Cheapflights users on 12/16. 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.
Wed 12/247:46 amMCO - ORD
Nonstop3h 32mFrontier
Wed 1/75:29 pmORD - MCO
Nonstop2h 56mFrontier
Deal found 12/16$94
This Kiwi.com deal was found by Cheapflights users on 12/16. 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.
Wed 12/244:56 pmMCO - ORD
Nonstop3h 06mMultiple Airlines
Tue 1/65:29 pmORD - MCO
Nonstop2h 56mMultiple Airlines
Deal found 12/16$95
This Super.com deal was found by Cheapflights users on 12/16. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/257:46 amMCO - ORD
Nonstop3h 32mFrontier
Thu 1/111:28 amORD - MCO
Nonstop2h 55mFrontier
Deal found 12/16$97
This Super.com deal was found by Cheapflights users on 12/16. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/257:58 pmMCO - MDW
Nonstop3h 00mFrontier
Thu 1/13:10 pmMDW - MCO
Nonstop2h 48mFrontier
Deal found 12/16$98
This Frontier deal was found by Cheapflights users on 12/15. 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.
Thu 12/2512:31 pmFLL - ORD
Nonstop3h 31mFrontier
Thu 1/17:20 amORD - FLL
Nonstop3h 16mFrontier
Deal found 12/15$98
This CheapOair deal was found by Cheapflights users on 12/15. 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.
Wed 12/317:58 pmMCO - MDW
Nonstop3h 00mFrontier
Mon 1/53:10 pmMDW - MCO
Nonstop2h 48mFrontier
Deal found 12/15$99
This Super.com deal was found by Cheapflights users on 12/16. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/231:11 pmFLL - ORD
Nonstop3h 31mFrontier
Thu 1/17:20 amORD - FLL
Nonstop3h 16mFrontier
Deal found 12/16$99
This Kiwi.com deal was found by Cheapflights users on 12/16. 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.
Wed 12/247:46 amMCO - ORD
Nonstop3h 32mMultiple Airlines
Wed 1/77:20 amORD - MCO
Nonstop2h 52mMultiple Airlines
Deal found 12/16$100

Find flight deals from Florida to Chicago

Keep the following information in mind while searching for Florida to Chicago flight deals. Data was last updated December 17, 2025.

Most accurate provider

Justfly.com
3 stars

Most trusted provider

Justfly.com
3 stars

Round-trip from

$71
(Priceline)

One-way from

$45
(CheapOair)

Popular in

March

Cheapest in

September

Average price

$198

Good round-trip deal

$78 or less

Good one-way deal

$52 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. 11% potential increase in price ($22 potential increase over avg. RT price).
Cheapest flight prices on average. 2% potential price decrease ($5 potential savings vs. average RT price).
Average for round-trip flights in December 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 December 17, 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

Thu 1/15

12:39 pm-10:19 pm

1 stop10h 40m

Chicago Midway

Sun 1/18

6:01 pm-9:49 pm

Nonstop2h 48m

$78

TampaChicago

TPA - ORD

TPAORD

Tampa

Thu 1/15

2:57 pm-4:58 pm

Nonstop3h 01m

Chicago O'Hare Intl

Sun 1/18

7:58 pm-11:59 pm

Nonstop3h 01m

$92

Fort LauderdaleChicago

FLL - ORD

FLLORD

Fort Lauderdale

Thu 1/15

9:25 pm-11:46 pm

Nonstop3h 21m

Chicago O'Hare Intl

Sun 1/18

12:44 pm-8:10 pm

1 stop6h 26m

$98

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Thu 1/29

4:02 pm-9:42 pm

1 stop6h 40m

Chicago O'Hare Intl

Thu 2/5

4:19 pm-11:57 pm

1 stop6h 38m

$98

Fort LauderdaleChicago

FLL - ORD

FLLORD

Fort Lauderdale

Thu 1/8

12:54 pm-7:41 pm

1 stop7h 47m

Chicago O'Hare Intl

Fri 1/9

5:32 pm-9:40 pm

Nonstop3h 08m

$98

Fort LauderdaleChicago

FLL - ORD

FLLORD

Fort Lauderdale

Thu 1/15

9:25 pm-11:46 pm

Nonstop3h 21m

Chicago O'Hare Intl

Mon 1/19

12:44 pm-8:10 pm

1 stop6h 26m

$98

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Wed 1/7

12:17 pm-2:21 pm

Nonstop3h 04m

Chicago O'Hare Intl

Fri 1/9

8:43 pm-7:43 am

1 stop10h 00m

$103

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Thu 1/15

8:30 am-10:32 am

Nonstop3h 02m

Chicago Midway

Thu 1/22

5:01 pm-12:31 am

1 stop6h 30m

$110

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Thu 2/5

5:49 pm-7:52 pm

Nonstop3h 03m

Chicago Midway

Mon 2/9

5:01 pm-12:31 am

1 stop6h 30m

$115

MiamiChicago

MIA - ORD

MIAORD

Miami

Wed 1/7

2:35 pm-5:00 pm

Nonstop3h 25m

Chicago O'Hare Intl

Sat 1/17

9:23 am-1:41 pm

Nonstop3h 18m

$115

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/15

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 $30). 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 December 17, 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 31% 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 December 13, 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. Monday mornings 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 2h 50m. Fly via Frontier, Spirit Airlines, or Southwest to get the fastest option. The distance from Florida to Chicago is about 998 mi. This flight may include one or multiple stops.

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

    The cheapest airline one-way is Emirates, with whom users have recently found tickets for as low as $460. However, be on the lookout for offers from Qatar Airways and Turkish 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 ANA (89%), Cathay Pacific (87%) and GOL (86%).

  • What are the cheapest flights from Florida to Chicago?

    Looking at all options, your cheapest flight can be booked for $70. While the most popular route (Tampa - Chicago O'Hare Intl) can be booked for $60 on average, our data indicates $747 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 $30). 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
Lansing
Merrillville
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 December 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$44Average$177FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$61Average$171FlexibilityNo cancel feeOn-time65%
Allegiant AirCheapest$72Average$150FlexibilityNo cancel feeOn-time88%
DeltaCheapest$98Average$358FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$131Average$334FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$148Average$328FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$157Average$301FlexibilityNo 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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