Chicago

$55+ 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 8/14. Fares are subject to change and may not be available on all flights or dates of travel.
MIA — CHI
ago. 5 — ago. 121
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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 julio 31, 2025.

Round-trip from

$105
(Kiwi.com)

One-way from

$55
(Cheapflightsfares)

Popular in

June

Cheapest in

September

Average price

$184

Good round-trip deal

$70 or less

Good one-way deal

$52 or less
From Florida to Chicago (CHI)
One-way flight from Florida to Chicago (CHI)
Highest demand for flights based on searches. 4% potential increase in price ($8 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 July 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).

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 julio 31, 2025.

This Kiwi.com deal was found by Cheapflights users on 7/31. 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. 9/122:07 pmMCO - ORD
Nonstop3h 05mSpirit Airlines
mié. 9/246:30 amORD - MCO
Nonstop2h 43mSpirit Airlines
Deal found 7/31$105
This Cheapflightsfares deal was found by Cheapflights users on 7/29. 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.
vie. 8/226:30 amMCO - MDW
Nonstop2h 52mFrontier
lun. 8/254:24 pmMDW - MCO
Nonstop2h 50mFrontier
Deal found 7/29$106
This Cheapflightsfares deal was found by Cheapflights users on 7/29. 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.
mar. 8/58:00 amMCO - ORD
Nonstop3h 14mFrontier
mar. 8/1211:28 amORD - MCO
Nonstop2h 59mFrontier
Deal found 7/29$107
This Kiwi.com deal was found by Cheapflights users on 7/29. 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.
mié. 8/202:07 pmMCO - ORD
Nonstop3h 03mMultiple Airlines
jue. 8/287:46 pmORD - MCO
Nonstop3h 06mMultiple Airlines
Deal found 7/29$111
This Priceline deal was found by Cheapflights users on 7/30. 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.
vie. 9/1210:55 amTPA - MDW
Nonstop2h 49mFrontier
vie. 9/196:21 amMDW - TPA
Nonstop2h 36mFrontier
Deal found 7/30$117
This Kiwi.com deal was found by Cheapflights users on 7/29. 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.
mié. 9/108:15 amTPA - ORD
Nonstop3h 03mMultiple Airlines
dom. 9/218:05 amORD - TPA
Nonstop3h 00mMultiple Airlines
Deal found 7/29$117
This Cheapflightsfares deal was found by Cheapflights users on 7/31. 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.
jue. 8/288:28 amTPA - ORD
Nonstop2h 58mSpirit Airlines
mar. 9/211:21 amORD - TPA
Nonstop2h 35mSpirit Airlines
Deal found 7/31$118
This Cheapflightsfares deal was found by Cheapflights users on 7/29. 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.
jue. 9/115:01 amTPA - ORD
Nonstop3h 09mFrontier
dom. 9/148:05 amORD - TPA
Nonstop3h 00mFrontier
Deal found 7/29$127
This Kiwi.com deal was found by Cheapflights users on 7/31. 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.
sáb. 10/186:00 amMIA - ORD
Nonstop3h 15mSpirit Airlines
jue. 10/3010:27 amORD - MIA
Nonstop3h 12mSpirit Airlines
Deal found 7/31$131
This Cheapflightsfares deal was found by Cheapflights users on 7/31. 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.
mié. 9/178:25 pmFLL - ORD
Nonstop3h 23mSpirit Airlines
dom. 9/2111:57 amORD - FLL
Nonstop3h 05mSpirit Airlines
Deal found 7/31$132
This American Airlines deal was found by Cheapflights users on 7/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 9/66:20 amMIA - ORD
Nonstop3h 20mAmerican Airlines
lun. 9/87:25 pmORD - MIA
Nonstop3h 10mAmerican Airlines
Deal found 7/28$137
This Southwest deal was found by Cheapflights users on 7/30. 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.
vie. 9/1912:35 pmMIA - MDW
Nonstop3h 10mSouthwest
dom. 9/212:45 pmMDW - MIA
Nonstop3h 00mSouthwest
Deal found 7/30$137

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 julio 31, 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 - ORD

MCOORD

Orlando

vie. 9/12

2:07 pm-4:12 pm

Nonstop3h 05m

Chicago O'Hare Intl

mié. 9/24

6:30 am-10:13 am

Nonstop2h 43m

$105

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

vie. 8/22

6:30 am-8:22 am

Nonstop2h 52m

Chicago Midway

lun. 8/25

4:24 pm-8:14 pm

Nonstop2h 50m

$106

OrlandoChicago

MCO - ORD

MCOORD

Orlando

mar. 8/5

8:00 am-10:14 am

Nonstop3h 14m

Chicago O'Hare Intl

mar. 8/12

11:28 am-3:27 pm

Nonstop2h 59m

$107

OrlandoChicago

MCO - ORD

MCOORD

Orlando

mié. 8/20

2:07 pm-4:10 pm

Nonstop3h 03m

Chicago O'Hare Intl

jue. 8/28

7:46 pm-11:52 pm

Nonstop3h 06m

$111

TampaChicago

TPA - ORD

TPAORD

Tampa

mié. 9/10

8:15 am-10:18 am

Nonstop3h 03m

Chicago O'Hare Intl

dom. 9/21

8:05 am-12:05 pm

Nonstop3h 00m

$117

TampaChicago

TPA - MDW

TPAMDW

Tampa

vie. 9/12

10:55 am-12:44 pm

Nonstop2h 49m

Chicago Midway

vie. 9/19

6:21 am-9:57 am

Nonstop2h 36m

$117

TampaChicago

TPA - ORD

TPAORD

Tampa

jue. 8/28

8:28 am-10:26 am

Nonstop2h 58m

Chicago O'Hare Intl

mar. 9/2

11:21 am-2:56 pm

Nonstop2h 35m

$118

TampaChicago

TPA - ORD

TPAORD

Tampa

jue. 9/11

5:01 am-7:10 am

Nonstop3h 09m

Chicago O'Hare Intl

dom. 9/14

8:05 am-12:05 pm

Nonstop3h 00m

$127

MiamiChicago

MIA - ORD

MIAORD

Miami

sáb. 10/18

6:00 am-8:15 am

Nonstop3h 15m

Chicago O'Hare Intl

jue. 10/30

10:27 am-2:39 pm

Nonstop3h 12m

$131

Fort LauderdaleChicago

FLL - ORD

FLLORD

Fort Lauderdale

mié. 9/17

8:25 pm-10:48 pm

Nonstop3h 23m

Chicago O'Hare Intl

dom. 9/21

11:57 am-4:02 pm

Nonstop3h 05m

$132

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

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, August is the cheapest month in which you can book a flight from Florida to Chicago (average of $245). Flying from Florida 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 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 julio 31, 2025.

When flying from Florida 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 to Chicago

Explore weekly flight availability from Florida 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 julio 31, 2025.

The most flights from USFL to CHI are scheduled on a Thursday (44 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (26 on average).

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 julio 31, 2025.
Read reviews from past customers who have flown Southwest, Delta, and United Airlines from Florida to Chicago. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.

Overall

8.0

Boarding

8.1

Food

7.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

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.

Overall

8.0

Boarding

8.1

Food

7.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

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.
8.0
Very good

Overall

8.0

Boarding

8.1

Food

7.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

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.

Overall

8.0

Boarding

8.1

Food

7.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

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.

Overall

8.0

Boarding

8.1

Food

7.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

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.

Overall

8.0

Boarding

8.1

Food

7.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

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.

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

    The cheapest airline one-way is Frontier, with whom users have recently found tickets for as low as $55. However, be on the lookout for offers from Spirit Airlines and American 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 (92%), United Airlines (84%) and Austrian Airlines (83%).

  • What are the cheapest flights from Florida to Chicago?

    Looking at all options, your cheapest flight can be booked for $67. While the most popular route (Fort Lauderdale - Chicago O'Hare Intl) can be booked for $87 on average our data indicates $1,290 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, August is the cheapest month in which you can book a flight from Florida to Chicago (average of $245). Flying from Florida 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 Chicago?

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

Browse thousands of different options on Cheapflights for your next trip

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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 julio 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$46Average$188FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$67Average$184FlexibilityNo cancel feeOn-time65%
Allegiant AirCheapest$90Average$159FlexibilityNo cancel feeOn-time88%
DeltaCheapest$114Average$398FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$149Average$338FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$157Average$362FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$158Average$305FlexibilityNo 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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