Chicago

$56+ 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 5/28. Fares are subject to change and may not be available on all flights or dates of travel.
MIA — CHI
Jun 2 — Jun 91
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Florida to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 May 3, 2026.

This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/59:53 am
FLL
-
ORD
Nonstop3h 44m
Frontier
Tue 6/97:52 am
ORD
-
FLL
Nonstop3h 17m
Frontier
Deal found 4/28$91
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/39:53 am
FLL
-
ORD
Nonstop3h 44m
Frontier
Wed 6/107:52 am
ORD
-
FLL
Nonstop3h 17m
Frontier
Deal found 4/28$92
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/289:53 am
FLL
-
ORD
Nonstop3h 44m
Frontier
Sat 5/308:05 am
ORD
-
FLL
Nonstop3h 15m
Frontier
Deal found 4/30$93
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.
Wed 7/19:53 am
FLL
-
ORD
Nonstop3h 50m
Frontier
Sat 7/188:05 am
ORD
-
FLL
Nonstop3h 17m
Frontier
Deal found 4/29$95
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/299:53 am
FLL
-
ORD
Nonstop3h 32m
Multiple Airlines
Tue 8/45:26 pm
ORD
-
FLL
Nonstop3h 11m
Multiple Airlines
Deal found 4/28$97
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/269:53 am
FLL
-
ORD
Nonstop3h 32m
Frontier
Sat 8/297:55 am
ORD
-
FLL
Nonstop3h 17m
Frontier
Deal found 4/30$98
This Super.com deal was found by Cheapflights users on 5/2. 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.
Wed 5/279:53 am
FLL
-
ORD
Nonstop3h 44m
Frontier
Sun 5/318:05 am
ORD
-
FLL
Nonstop3h 15m
Frontier
Deal found 5/2$99
This 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/19:53 am
FLL
-
ORD
Nonstop3h 31m
Frontier
Thu 7/168:05 am
ORD
-
FLL
Nonstop3h 17m
Frontier
Deal found 4/30$100
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.
Wed 5/279:53 am
FLL
-
ORD
Nonstop3h 44m
Multiple Airlines
Sun 5/315:05 am
ORD
-
FLL
Nonstop3h 05m
Multiple Airlines
Deal found 4/29$101
This Super.com deal was found by Cheapflights users on 5/2. 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.
Fri 5/299:53 am
FLL
-
ORD
Nonstop3h 44m
Frontier
Wed 6/37:29 am
ORD
-
FLL
Nonstop3h 15m
Frontier
Deal found 5/2$102
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/49:53 am
FLL
-
ORD
Nonstop3h 31m
Frontier
Wed 7/88:05 am
ORD
-
FLL
Nonstop3h 17m
Frontier
Deal found 4/30$103
This Super.com 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/289:53 am
FLL
-
ORD
Nonstop3h 44m
Frontier
Sun 5/318:05 am
ORD
-
FLL
Nonstop3h 15m
Frontier
Deal found 4/30$105

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 May 3, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$91
(Kiwi.com)

One-way from

$56
(Spirit)

Popular in

March

Cheapest in

September

Average price

$161

Good round-trip deal

$93 or less

Good one-way deal

$42 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. 13% potential increase in price ($25 potential increase over avg. RT price).
Cheapest flight prices on average. 3% potential price decrease ($7 potential savings vs. average RT price).
Average for round-trip flights in May 2026
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 May 3, 2026.
Use the filters below to find and compare flights from Florida to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Wed 5/27

6:50 am-11:35 am

1 stop5h 45m

Chicago Midway

Tue 6/16

8:10 pm-11:45 pm

Nonstop2h 35m

$179

Fort LauderdaleChicago

FLL - ORD

FLLORD

Fort Lauderdale

Fri 5/15

8:55 pm-11:15 pm

Nonstop3h 20m

Chicago O'Hare Intl

Tue 5/19

10:49 am-7:50 pm

1 stop8h 01m

$182

Fort LauderdaleChicago

FLL - ORD

FLLORD

Fort Lauderdale

Tue 6/23

9:46 pm-11:59 pm

Nonstop3h 13m

Chicago O'Hare Intl

Tue 8/18

10:27 am-7:32 pm

1 stop8h 05m

$182

Fort LauderdaleChicago

FLL - ORD

FLLORD

Fort Lauderdale

Wed 7/15

1:00 pm-3:27 pm

Nonstop3h 27m

Chicago O'Hare Intl

Fri 7/17

12:58 pm-11:29 pm

1 stop9h 31m

$182

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Thu 6/4

7:13 am-9:22 am

Nonstop3h 09m

Chicago O'Hare Intl

Wed 6/10

6:02 am-9:45 am

Nonstop2h 43m

$184

Fort LauderdaleChicago

FLL - ORD

FLLORD

Fort Lauderdale

Sat 5/23

7:00 am-9:28 am

Nonstop3h 28m

Chicago O'Hare Intl

Tue 5/26

6:19 pm-10:35 pm

Nonstop3h 16m

$184

TampaChicago

TPA - ORD

TPAORD

Tampa

Mon 6/1

7:27 pm-9:38 pm

Nonstop3h 11m

Chicago O'Hare Intl

Wed 6/3

8:40 am-3:15 pm

1 stop5h 35m

$190

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Tue 6/2

2:25 pm-4:43 pm

Nonstop3h 18m

Chicago O'Hare Intl

Thu 6/4

9:05 am-2:43 pm

1 stop4h 38m

$194

TampaChicago

TPA - ORD

TPAORD

Tampa

Tue 6/2

1:45 pm-8:26 pm

1 stop7h 41m

Chicago O'Hare Intl

Tue 6/16

7:01 am-12:53 pm

1 stop4h 52m

$197

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Tue 6/9

6:15 am-12:00 pm

1 stop6h 45m

Chicago Midway

Tue 6/16

5:11 pm-10:51 pm

1 stop4h 40m

$197

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/1

Showing 1-10 of 60 resultsSorted by cheapest first
1
2
3
...
6

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

How far ahead should I book a flight from Florida to Chicago?

Booking 23 days in advance of your planned departure date is, on average, the best time to get cheap flights from Florida to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

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 $183). Flying from Florida to Chicago in March is currently the most expensive (average of $307). 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 May 3, 2026.

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 19% on your trip compared to booking a flight in the afternoon.

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 May 2, 2026.

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

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 May 3, 2026.

The most flights from USFL to CHI are scheduled on a Monday (52 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (37 on average).

How much does it cost to fly round-trip from Florida to Chicago?

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 09m. Fly via Southwest, Spirit Airlines, or United Airlines to get the fastest option. The distance from Florida to Chicago is about 1006 mi. This flight may include one or multiple stops.

  • 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 Emirates (92%), Cathay Pacific (90%) and United Airlines (82%).

  • 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 $138 on average, our data indicates $740 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 $183). Flying from Florida to Chicago in March is currently the most expensive (average of $307). 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
Benton Harbor
Lansing
Merrillville
Hammond
Porter

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Florida to Chicago

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

Top 8 airlines flying from Florida to Chicago

Discover the top 8 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 May 3, 2026.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$41Average$154FlexibilityNo cancel feeOn-time88%
FrontierCheapest$43Average$164FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$58Average$166FlexibilityNo cancel feeOn-time65%
DeltaCheapest$98Average$345FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$128Average$326FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$146Average$326FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$149Average$326FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$155Average$304FlexibilityNo 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.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.