Florida

$67+ Cheap flights from Chicago (CHI) to Florida

CHI — MIA
Sep 30 — Oct 71
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Cheap flight deals from Chicago to Florida

Cheapest flights from Chicago to Florida

Wed 9/307:11 am -
Nonstop3h 12m
Thu 10/112:18 pm -
Nonstop3h 27m
Deal found 8/27$99
Sat 9/267:11 am -
Nonstop3h 12m
Sat 10/312:53 pm -
Nonstop3h 27m
Deal found 8/26$100
Tue 10/138:04 am -
Nonstop3h 08m
Tue 10/201:07 pm -
Nonstop3h 29m
Deal found 8/26$102
Wed 9/167:11 am -
Nonstop3h 12m
Fri 9/1812:18 pm -
Nonstop3h 27m
Deal found 8/26$104
Sat 10/248:04 am -
Nonstop3h 08m
Sat 10/311:05 pm -
Nonstop3h 32m
Deal found 8/29$105
Sat 10/37:11 am -
Nonstop3h 12m
Tue 10/612:53 pm -
Nonstop3h 27m
Deal found 8/28$107
Fri 9/257:11 am -
Nonstop3h 12m
Fri 10/212:18 pm -
Nonstop3h 27m
Deal found 8/26$108
Thu 10/17:11 am -
Nonstop3h 12m
Tue 10/612:53 pm -
Nonstop3h 27m
Deal found 8/28$109
Tue 9/157:11 am -
Nonstop3h 12m
Mon 9/2112:18 pm -
Nonstop3h 27m
Deal found 8/26$110
Thu 9/247:11 am -
Nonstop3h 12m
Thu 10/112:18 pm -
Nonstop3h 27m
Deal found 8/27$111
Sat 9/267:11 am -
Nonstop3h 12m
Tue 9/2912:53 pm -
Nonstop3h 27m
Deal found 8/26$112
Mon 9/147:11 am -
Nonstop3h 12m
Wed 9/1612:53 pm -
Nonstop3h 27m
Deal found 8/26$113

Find flight deals from Chicago to Florida

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$99
(CheapOair)

One-way from

$67
(CheapOair)

Popular in

June

Cheapest in

January

Average price

$274

Good round-trip deal

$112 or less

Good one-way deal

$44 or less
Provider with most accurate pricing for Chicago (CHI)-Orlando (ORL) flight deals.
Provider most trusted by Cheapflights users for Chicago (CHI)-Orlando (ORL) flights.
From Chicago (CHI) to Florida
One-way flight from Chicago (CHI) to Florida
Highest demand for flights based on searches. 14% potential increase in price ($46 potential increase over avg. RT price).
Cheapest flight prices on average. 3% potential price decrease ($10 potential savings vs. average RT price).
Average for round-trip flights in August 2026
Price to beat on a round-trip flight from Chicago (CHI) to Florida.
Price to beat on a one-way flight from Chicago (CHI) to Florida.

Cheapflights Fare Finder

 
Use the filters below to find and compare flights from Chicago to Florida that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoFort Lauderdale

ORD Chicago O'Hare Intl - FLL Fort Lauderdale

ORDFLL

Chicago O'Hare Intl

Thu 10/15

7:00 am-11:10 am

Nonstop3h 10m

Fort Lauderdale

Mon 10/19

9:15 pm-11:30 pm

Nonstop3h 15m

$171

ChicagoFort Lauderdale

MDW Chicago Midway - FLL Fort Lauderdale

MDWFLL

Chicago Midway

Wed 10/21

9:30 am-2:50 pm

1 stop4h 20m

Fort Lauderdale

Tue 10/27

5:45 pm-7:50 pm

Nonstop3h 05m

$181

ChicagoMiami

ORD Chicago O'Hare Intl - MIA Miami

ORDMIA

Chicago O'Hare Intl

Tue 10/20

1:55 pm-11:39 pm

1 stop8h 44m

Miami

Tue 10/27

9:00 am-11:29 am

Nonstop3h 29m

$191

ChicagoMiami

ORD Chicago O'Hare Intl - MIA Miami

ORDMIA

Chicago O'Hare Intl

Sat 10/3

9:00 am-6:52 pm

1 stop8h 52m

Miami

Tue 10/6

4:01 pm-6:32 pm

Nonstop3h 31m

$191

ChicagoMiami

ORD Chicago O'Hare Intl - MIA Miami

ORDMIA

Chicago O'Hare Intl

Wed 10/14

7:30 am-11:55 am

Nonstop3h 25m

Miami

Sat 10/17

8:54 am-4:34 pm

1 stop8h 40m

$191

ChicagoFort Lauderdale

MDW Chicago Midway - FLL Fort Lauderdale

MDWFLL

Chicago Midway

Wed 9/23

12:50 pm-8:05 pm

2 stops6h 15m

Fort Lauderdale

Wed 9/30

6:15 pm-9:55 pm

1 stop4h 40m

$196

ChicagoMiami

MDW Chicago Midway - MIA Miami

MDWMIA

Chicago Midway

Tue 10/27

7:55 am-5:30 pm

2 stops8h 35m

Miami

Sat 10/31

6:45 am-12:50 pm

2 stops7h 05m

$201

ChicagoMiami

MDW Chicago Midway - MIA Miami

MDWMIA

Chicago Midway

Sat 10/3

8:10 am-8:30 pm

2 stops11h 20m

Miami

Tue 10/6

7:00 am-12:25 pm

2 stops6h 25m

$207

ChicagoMiami

MDW Chicago Midway - MIA Miami

MDWMIA

Chicago Midway

Sat 10/3

8:10 am-8:30 pm

2 stops11h 20m

Miami

Mon 10/5

6:10 pm-11:15 pm

2 stops6h 05m

$207

ChicagoFort Lauderdale

MDW Chicago Midway - FLL Fort Lauderdale

MDWFLL

Chicago Midway

Wed 9/30

6:10 pm-10:10 pm

Nonstop3h 00m

Fort Lauderdale

Sat 10/3

7:15 am-9:20 am

Nonstop3h 05m

$217

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/27

Showing 1-10 of 60 resultsSorted by cheapest first
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Best time to book a flight from Chicago to Florida

Have a flexible travel schedule? Discover the best time to fly to Florida from Chicago with our price prediction graph.
Estimated round-trip price

Cheapflights Insights

Everything you need to know about your flight from Chicago to Florida

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

Currently, January is the cheapest month in which you can book a flight from Chicago to Florida (average of $227). Flying from Chicago to Florida in June is currently the most expensive (average of $353). 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 CHI to FL?

When flying from Chicago to Florida, the time of day you fly usually plays a role in the price. Save by searching for a flight in the morning, which can drop the price by up to 11% versus a flight in the evening.

Weekly flight availability from Chicago to Florida

The most flights from CHI to USFL are scheduled on a Saturday (51 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (41 on average).

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

Airfare is below average for this route at the moment.
Chicago to Florida flights typically cost between $190 and $350 in September.
The cheapest round-trip price found within the last 5 days was $171 on American Airlines (Sep 19-Sep 21).

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

The price you pay for your flight from Chicago to Florida may vary depending on when you book. For the best chance of a lower fare, look to book 29 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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

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

Reviews of airlines servicing Florida

Get a feel of what it's like to fly with Southwest,Delta, andUnited Airlines from Chicago to Florida by reading reviews from past customers. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Reviews

1 / 20
6.0
Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Reviews

1 / 20
6.0
Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Reviews

1 / 20
6.0
Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Reviews

1 / 20
6.0
Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Reviews

1 / 20
6.0
Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Reviews

1 / 20
6.0
Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.

Chicago to Florida Travel Guide

Florida often provides a refuge for residents in Chicago looking to get away from bitterly cold winters. The state is home to some of the most popular beaches and tourist destinations in the country, making it a great option for singles, couples and families looking for a getaway. Between Disney World, Miami Beach and the Florida Keys, there's no shortage of fun to be had in Florida.

Both Florida and Chicago are home to fun, hardworking locals who know how to enjoy the best that their hometowns have to offer. However, the climates couldn't be more different. Summers in Florida are hot and humid, much more so than Chicago summers, and winters in Florida tend to be mild and enjoyable. Native Chicagoans visiting Florida will feel right at home in the bustling metropolis that is Miami, and they can get the world-famous theme park experiences in Orlando/Kissimmee. The white sandy beaches of Florida's coastline provides plenty of space for visitors to relax, and Chicagoans will feel right at home, as they have plenty of access to beautiful beaches in their fair city too.

Put our convenient smart engine to use, and find cheap flights from Chicago to any of Florida's most popular destination cities for your next vacation getaway.

Related info for your journey

  • How long is the flight from Chicago to Florida?

    The flight from Chicago to Florida will vary depending on which city you plan to travel to, but all of the direct flights are relatively short, so you can arrive at your destination quickly. Flights to Orlando from Chicago last approximately two hours and 10 minutes, while a flight to Miami takes about an hour longer.

  • Which airlines operate flights from Chicago to Florida?

    Many major airlines offer flights from either of Chicago's main airports to multiple destinations in Florida. These carriers include United, Delta, American, Frontier, Spirit and jetBlue.

  • How frequent are flights between Chicago and Florida?

    Depending on the day of the week and the time of day, flights from Chicago to Florida take off almost every hour, and sometimes even more frequently than that. Some destinations may have more flights than others, so keep this in mind as you prepare your itinerary.

  • Which airports serve Chicago to Florida?

    Chicago is served by O'Hare international Airport and Chicago Midway International Airport. Florida is home to Miami International Airport, Pensacola International Airport, Daytona International Airport and Orlando International Airport, just to name a few.

  • Which direct flight route between Chicago and Florida is cheapest?

    The cheapest direct flight route between Chicago and Florida is the nonstop route from Chicago to Orlando. You can also find low fares for direct flights to Miami and Fort Lauderdale.

  • How busy are the airports in Chicago and Florida?

    There are a large number of flight options that can take travellers from the midwestern city of Chicago, the capital of Illinois, to Florida, affectionately known as the Sunshine State. All flights making the trip from Chicago to Florida will depart from a single airport—the behemoth major transportation hub of Chicago’s O’Hare International Airport (ORD). While there are a range of very popular destinations throughout the state of Florida, some of the most frequented locations are the southeastern city of Miami, serviced by Miami International Airport (MIA); the central Floridian city of Orlando, serviced by Orlando International Airport (MCO); and the western coastal city of Tampa, serviced by Tampa International Airport (TPA).

  • Which airlines fly directly from Chicago to Florida?

    A number of American-based airlines provide service from Chicago to various popular cities in Florida, and many of them offer options for non-stop flights. Three primary carriers provide a large portion of these service options. Specifically, these include the well-known companies American Airlines, United Airlines, and Delta Air Lines. The duration of non-stop flights from Chicago to Florida will vary based on the carrier and the destination city, so non-stop routes will run anywhere from about 2h and 39min to 3h 12min.

  • What are the layover options between Chicago and Florida?

    While there are many flights that operate directly from Chicago to various popular destination cities in Florida, there are also a great number of options that include at least a single layover. There are a broad number of potential layover cities on the route, but there are a handful of airports that see the most frequent layovers for flights that are Florida-bound. For instance, a great number of options will land at North Carolina’s Charlotte Douglas International Airport (CLT) before completing the final leg of the trip. Alternatively, there are several flights that will land at Texas’s Dallas/Fort Worth International Airport (DFW). Passengers will find that flights from Chicago to Florida that have layovers can range anywhere from 4h 31min to as long as about 13h 13min. These flights with layovers are usually not cheaper than those that fly directly to Florida.

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

    Travellers taking domestic flights from Chicago to Florida are not required to have a passport to make the trip. However, passengers will need to show a valid government-issued form of ID. That ID must include the traveller’s full name and date of birth. It should also have a photograph of the ID holder. A visa is also not required for the trip from Chicago to Florida.

  • How long is the flight from Chicago to Florida?

    There are many flights that can get you from Chicago to Florida in 3h 10m. Fly via JetBlue, Southwest, or United Airlines to get the fastest option. The distance between Chicago and Florida is about 1183 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    The cheapest airline one-way is Allegiant Air, with whom users have recently found tickets for as low as $28. However, be on the lookout for offers from Frontier and JetBlue, as they are both options that can get you from Chicago to Florida for a low price.

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

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

    Before booking your flight to Florida from Chicago, check out the most reliable airlines to get you to your destination on time: Avianca (75%), Copa Airlines (72%), United Airlines( 72%).

  • What are the cheapest flights from Chicago to Florida?

    Looking at all options, your cheapest flight can be booked for $88. While the most popular route (Chicago O'Hare Intl - Orlando) can be booked for $99 on average, our data indicates $916 when flying from Chicago to Florida.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Chicago to Florida 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 Chicago to Florida?

    Currently, January is the cheapest month in which you can book a flight from Chicago to Florida (average of $227). Flying from Chicago to Florida in June is currently the most expensive (average of $353). 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 are the most eco-friendly airlines from Chicago to Florida?

    United Airlines is considered the most eco-friendly airline from Chicago to Florida. The airline is an esteemed leader in environmental sustainability endeavors across the globe. United continues to be at the forefront of finding innovative ways to protect the environment and the skies for a more sustainable future by demonstrating key actions in its various flights. United purchases a blend of 30% low-carbon aviation biofuel and the regular 70% jet fuel from World energy. Sustainable aviation biofuel reduces greenhouse gas emissions by up to 60% on a lifecycle basis. In the Economy class flights, the airline is substituting traditional food options with a fully recyclable plated service. In the premium class, United Airlines uses green service ware. The plastic lids initially used have been swapped for beeswax snack wrappers, while the traditional stirring sticks have been replaced with an eco-friendly version, made of 100% bamboo.

  • How can I fly more sustainably from Chicago to Florida?

    While the air travel footprint on the global greenhouse gas emissions is at a lowly 2%, the number keeps growing. Nonetheless, there are certain measures that you can take to engage in more sustainable travel from Chicago to Florida. Choose to fly non-stop when viable to conserve fuel. While more expensive, flying non-stop from Chicago to Florida can reduce your carbon imprint on the environment. The plane discharges more emissions during departure and landing than while cruising. Given that the weight of the aircraft affects how much fuel it consumes, travelers are advised to pack light to reduce their impact on the plane's freight load. Also, try to avoid using plastic water bottles while flying.

See more FAQs

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Alternative routes for Chicago to Florida

Top 7 airlines flying from Chicago to Florida

AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$57Average$217FlexibilityNo cancel feeOn-time62%
DeltaCheapest$83Average$327FlexibilityNo cancel feeOn-timeN/A
Allegiant AirCheapest$84Average$208FlexibilityNo cancel feeOn-time88%
JetBlueCheapest$89Average$293FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$156Average$358FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$160Average$357FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$166Average$375FlexibilityNo cancel feeOn-time63%

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