Chicago

$80+ Cheap flights from Florida to Chicago (CHI)

MIA — CHI
Dec 5 — Dec 121
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Cheap flight deals from Florida to Chicago

Cheapest flights from Florida to Chicago

Fri 12/2511:00 am -
Nonstop3h 30m
Thu 12/318:59 am -
Nonstop3h 22m
Deal found 11/3$140
Sat 11/71:05 pm -
Nonstop3h 32m
Mon 11/234:00 pm -
Nonstop3h 07m
Deal found 11/4$141
Fri 11/131:05 pm -
Nonstop3h 32m
Mon 11/167:55 am -
Nonstop3h 07m
Deal found 11/3$142
Fri 11/209:02 pm -
Nonstop3h 32m
Mon 11/234:00 pm -
Nonstop3h 07m
Deal found 11/1$143
Sat 11/71:05 pm -
Nonstop3h 32m
Sat 11/147:55 am -
Nonstop3h 07m
Deal found 11/2$144
Fri 12/411:28 am -
Nonstop3h 32m
Wed 12/92:59 pm -
Nonstop3h 11m
Deal found 11/2$145
Thu 12/1011:25 am -
Nonstop3h 35m
Thu 12/175:58 am -
1 stop10h 14m
Deal found 11/2$146
Wed 11/259:02 pm -
Nonstop3h 32m
Fri 11/274:00 pm -
Nonstop3h 07m
Deal found 11/1$147
Fri 11/209:02 pm -
Nonstop3h 32m
Tue 11/242:52 pm -
1 stop21h 44m
Deal found 11/1$148
Thu 12/311:28 am -
Nonstop3h 32m
Sun 12/610:29 pm -
1 stop9h 49m
Deal found 11/2$149
Fri 12/1111:25 am -
Nonstop3h 35m
Mon 12/147:00 am -
Nonstop3h 10m
Deal found 11/4$150
Tue 12/88:00 am -
1 stop9h 42m
Tue 12/152:59 pm -
Nonstop3h 11m
Deal found 11/4$151

Find flight deals from Florida to Chicago

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$140
(CheapOair)

One-way from

$80
(Super.com)

Popular in

June

Cheapest in

February

Average price

$202

Good round-trip deal

$63 or less

Good one-way deal

$68 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. 15% potential increase in price ($45 potential increase over avg. RT price).
Cheapest flight prices on average. 3% potential price decrease ($8 potential savings vs. average RT price).
Average for round-trip flights in November 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

 
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

Fort LauderdaleChicago

FLL Fort Lauderdale - ORD Chicago O'Hare Intl

FLLORD

Fort Lauderdale

Mon 11/16

7:03 pm-12:45 am

1 stop6h 42m

Chicago O'Hare Intl

Wed 12/31

12:00 am-1:00 am

Nonstop0h 00m

$109

Fort LauderdaleChicago

FLL Fort Lauderdale - ORD Chicago O'Hare Intl

FLLORD

Fort Lauderdale

Tue 3/9

4:35 pm-10:20 pm

1 stop6h 45m

Chicago O'Hare Intl

Wed 12/31

12:00 am-1:00 am

Nonstop0h 00m

$109

Fort LauderdaleChicago

FLL Fort Lauderdale - ORD Chicago O'Hare Intl

FLLORD

Fort Lauderdale

Tue 12/29

7:35 pm-12:02 am

1 stop5h 27m

Chicago O'Hare Intl

Wed 12/31

12:00 am-1:00 am

Nonstop0h 00m

$114

MiamiChicago

MIA Miami - ORD Chicago O'Hare Intl

MIAORD

Miami

Tue 11/17

8:45 am-2:51 pm

1 stop7h 06m

Chicago O'Hare Intl

Wed 12/31

12:00 am-1:00 am

Nonstop0h 00m

$119

Fort LauderdaleChicago

FLL Fort Lauderdale - ORD Chicago O'Hare Intl

FLLORD

Fort Lauderdale

Thu 11/12

7:35 am-12:20 pm

1 stop5h 45m

Chicago O'Hare Intl

Wed 12/31

12:00 am-1:00 am

Nonstop0h 00m

$129

Fort LauderdaleChicago

FLL Fort Lauderdale - ORD Chicago O'Hare Intl

FLLORD

Fort Lauderdale

Fri 11/13

11:21 am-5:17 pm

1 stop6h 56m

Chicago O'Hare Intl

Wed 12/31

12:00 am-1:00 am

Nonstop0h 00m

$129

Fort LauderdaleChicago

FLL Fort Lauderdale - ORD Chicago O'Hare Intl

FLLORD

Fort Lauderdale

Tue 11/17

2:27 pm-8:14 pm

1 stop6h 47m

Chicago O'Hare Intl

Wed 12/31

12:00 am-1:00 am

Nonstop0h 00m

$129

Fort LauderdaleChicago

FLL Fort Lauderdale - ORD Chicago O'Hare Intl

FLLORD

Fort Lauderdale

Wed 11/11

8:55 am-2:38 pm

1 stop6h 43m

Chicago O'Hare Intl

Wed 12/31

12:00 am-1:00 am

Nonstop0h 00m

$129

Fort LauderdaleChicago

FLL Fort Lauderdale - ORD Chicago O'Hare Intl

FLLORD

Fort Lauderdale

Wed 11/11

6:35 am-12:20 pm

1 stop6h 45m

Chicago O'Hare Intl

Wed 12/31

12:00 am-1:00 am

Nonstop0h 00m

$134

MiamiChicago

MIA Miami - ORD Chicago O'Hare Intl

MIAORD

Miami

Mon 12/7

9:00 am-11:36 am

Nonstop3h 36m

Chicago O'Hare Intl

Wed 12/31

12:00 am-1:00 am

Nonstop0h 00m

$136

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/1

Showing 1-10 of 60 resultsSorted by cheapest first
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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

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, February is the cheapest month in which you can book a flight from Florida to Chicago (average of $199). Flying from Florida to Chicago in June is currently the most expensive (average of $361). 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?

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 25% on your trip compared to booking a flight at noon.

Weekly flight availability from Florida to Chicago

The most flights from USFL to CHI are scheduled on a Monday (59 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (31 on average).

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

Airfare is below average for this route at the moment.
Florida to Chicago flights typically cost between $221 and $410 in December.
The cheapest round-trip price found within the last 5 days was $198 on Frontier (Dec 16-Dec 21).

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

Booking 43 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 day to fly from Florida to Chicago?

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.

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

  • 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.

  • How long is the flight from Florida to Chicago?

    There are many flights that can get you from Florida to Chicago in 2h 40m. Fly via Delta, United 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 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 (100%), Cathay Pacific (89%) and Japan Airlines (87%).

  • What are the cheapest flights from Florida to Chicago?

    Looking at all options, your cheapest flight can be booked for $168. While the most popular route (Tampa - Chicago O'Hare Intl) can be booked for $160 on average, our data indicates $705 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, February is the cheapest month in which you can book a flight from Florida to Chicago (average of $199). Flying from Florida to Chicago in June is currently the most expensive (average of $361). 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
Merrillville
Lansing
Valparaiso
Hammond
Saint Joseph
Porter

Browse thousands of different options on Cheapflights for your next trip

Alternative routes for Florida to Chicago

Top 7 airlines flying from Florida to Chicago

AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$47Average$234FlexibilityNo cancel feeOn-time62%
Allegiant AirCheapest$57Average$164FlexibilityNo cancel feeOn-time88%
DeltaCheapest$98Average$308FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$129Average$290FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$157Average$364FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$160Average$380FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$164Average$355FlexibilityNo cancel feeOn-time71%

Helpful tips for your next trip to Chicago

  • 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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