How many flights depart from Chicago to Florida on average per week?

1,064 flights are operational weekly from Chicago to Florida as of August 2025. The most popular departure day for this route is Fri, with 18% of flights per week taking off on this day.

What airlines fly to Florida?

American Airlines, Spirit Airlines and United Airlines are the top three most popular airlines that fly to Florida from Chicago according to our data. American Airlines is the first choice among our users, with 30% of people opting to fly with this airline when traveling to Florida. Keep in mind that there are 10 different airlines that fly to Florida on a routine basis, so you have a few additional options to choose from.

What is the cheapest airline that flies from Chicago to Florida?

Spirit Airlines and Frontier are the most popular carriers operating from Chicago to Florida

How many flights depart from Chicago to Florida on average per day?

As of August 2025, there are 152 flights per day flying from Chicago to Florida. The most common time of day flights depart is 6:00PM, with 53% of flights taking off at noon.

When did momondo last update prices for flights from Chicago to Florida?

Prices for flights from Chicago to Florida were last updated today.

How many operators does momondo search for flights from Chicago to Florida?

The number of operators available for flights from Chicago to Florida is 8 as of August 2025.

How old do you have to be to fly from Chicago to Florida?

The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago to Florida.

What documentation or ID do you need to fly to Florida?

The travel and health documents required for your trip to Florida can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Florida. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$29 Cheap Flights from Chicago to Florida in 2025

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Find the cheapest flights from Chicago to Florida

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

1:07 pm - 5:00 pmORD-RSW

2h 53mnonstop

7:00 am - 9:07 amRSW-ORD

3h 07mnonstop

$59Spirit Airlines

Find Deal

Tue, Aug 19 - Tue, Aug 26

1:07 pm - 5:00 pmORD-RSW

2h 53mnonstop

7:00 am - 9:07 amRSW-ORD

3h 07mnonstop

$63Spirit Airlines

Find Deal

Tue, Sep 2 - Wed, Sep 3

8:49 pm - 12:35 amORD-MCO

2h 46mnonstop

5:24 pm - 7:44 pmMCO-ORD

3h 20mnonstop

$75Frontier

Find Deal

Fri, Oct 3 - Sun, Oct 5

8:49 pm - 12:35 amORD-MCO

2h 46mnonstop

5:24 pm - 7:44 pmMCO-ORD

3h 20mnonstop

$78Frontier

Find Deal

Fri, Oct 3 - Mon, Oct 6

2:10 pm - 6:10 pmMDW-MIA

3h 00mnonstop

4:05 pm - 6:15 pmMIA-MDW

3h 10mnonstop

$137Southwest

Find Deal

Mon, Sep 8 - Sat, Sep 13

2:10 pm - 6:10 pmMDW-MIA

3h 00mnonstop

7:10 am - 11:45 amMIA-MDW

5h 35m1 stop

$147Southwest

Find Deal

Mon, Sep 8 - Wed, Sep 10

10:58 am - 3:08 pmORD-PBI

3h 10mnonstop

4:10 pm - 6:33 pmPBI-ORD

3h 23mnonstop

$229United Airlines

Find Deal

Thu, Oct 2 - Mon, Oct 6

1:39 pm - 5:38 pmORD-PBI

2h 59mnonstop

1:17 pm - 3:31 pmPBI-ORD

3h 14mnonstop

$231American Airlines

Find Deal

Sat, Oct 18 - Sat, Oct 25

9:50 am - 1:55 pmORD-PBI

3h 05mnonstop

5:41 pm - 7:50 pmPBI-ORD

3h 09mnonstop

$233American Airlines

Find Deal

Sat, Sep 6 - Mon, Sep 8

10:58 am - 3:08 pmORD-PBI

3h 10mnonstop

4:50 pm - 12:14 amPBI-ORD

8h 24m1 stop

$284United Airlines

Find Deal

Thu, Oct 2 - Sun, Oct 5

Southwest flights from Chicago to Florida

Our best Southwest deals on Chicago to Florida flight tickets

Southwest

Sep 8

MDW2:10 pmChicago Midway

3h 00m

MIA6:10 pmMiami

Sep 13

MIA4:05 pmMiami

3h 10m

MDW6:15 pmChicago Midway

$137

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Southwest

Sep 8

MDW2:10 pmChicago Midway

3h 00m

MIA6:10 pmMiami

Sep 10

MIA7:10 amMiami

5h 35m

1 stop

MDW11:45 amChicago Midway

$147

Find similar

Southwest

Sep 8

MDW2:10 pmChicago Midway

3h 00m

MIA6:10 pmMiami

Sep 10

MIA11:40 amMiami

8h 30m

2 stops

MDW7:10 pmChicago Midway

$152

Find similar

Spirit Airlines flights from Chicago to Florida

Our best Spirit Airlines deals on Chicago to Florida flight tickets

Spirit Airlines

Aug 19

ORD1:07 pmChicago O'Hare Intl

2h 53m

RSW5:00 pmFort Myers SW Florida Intl

Aug 26

RSW7:00 amFort Myers SW Florida Intl

3h 07m

ORD9:07 amChicago O'Hare Intl

$59

Find similar

Spirit Airlines

Sep 2

ORD1:07 pmChicago O'Hare Intl

2h 53m

RSW5:00 pmFort Myers SW Florida Intl

Sep 3

RSW7:00 amFort Myers SW Florida Intl

3h 07m

ORD9:07 amChicago O'Hare Intl

$63

Find similar

Spirit Airlines

Oct 3

ORD5:31 pmChicago O'Hare Intl

2h 53m

RSW9:24 pmFort Myers SW Florida Intl

Oct 5

RSW7:00 amFort Myers SW Florida Intl

3h 13m

ORD9:13 amChicago O'Hare Intl

$68

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Tue 8/19

1:07 pm-5:00 pm

Nonstop2h 53m

Fort Myers SW Florida Intl

Tue 8/26

7:00 am-9:07 am

Nonstop3h 07m

$59

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Tue 9/2

1:07 pm-5:00 pm

Nonstop2h 53m

Fort Myers SW Florida Intl

Wed 9/3

7:00 am-9:07 am

Nonstop3h 07m

$63

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Fri 10/3

8:49 pm-12:35 am

Nonstop2h 46m

Orlando

Sun 10/5

5:24 pm-7:44 pm

Nonstop3h 20m

$75

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Fri 10/3

8:49 pm-12:35 am

Nonstop2h 46m

Orlando

Mon 10/6

5:24 pm-7:44 pm

Nonstop3h 20m

$78

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Mon 9/8

2:10 pm-6:10 pm

Nonstop3h 00m

Miami

Sat 9/13

4:05 pm-6:15 pm

Nonstop3h 10m

$137

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Mon 9/8

2:10 pm-6:10 pm

Nonstop3h 00m

Miami

Wed 9/10

7:10 am-11:45 am

1 stop5h 35m

$147

ChicagoWest Palm Beach

ORD - PBI

ORDPBI

Chicago O'Hare Intl

Thu 10/2

10:58 am-3:08 pm

Nonstop3h 10m

Palm Beach Intl

Mon 10/6

4:10 pm-6:33 pm

Nonstop3h 23m

$229

ChicagoWest Palm Beach

ORD - PBI

ORDPBI

Chicago O'Hare Intl

Sat 10/18

1:39 pm-5:38 pm

Nonstop2h 59m

Palm Beach Intl

Sat 10/25

1:17 pm-3:31 pm

Nonstop3h 14m

$231

ChicagoWest Palm Beach

ORD - PBI

ORDPBI

Chicago O'Hare Intl

Sat 9/6

9:50 am-1:55 pm

Nonstop3h 05m

Palm Beach Intl

Mon 9/8

5:41 pm-7:50 pm

Nonstop3h 09m

$233

ChicagoWest Palm Beach

ORD - PBI

ORDPBI

Chicago O'Hare Intl

Thu 10/2

10:58 am-3:08 pm

Nonstop3h 10m

Palm Beach Intl

Sun 10/5

4:50 pm-12:14 am

1 stop8h 24m

$284

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How to get the cheapest flight ticket from Chicago to Florida

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Other information

What is the cheapest month to fly to Florida?

In general, September is the cheapest month to fly from Chicago to Florida. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $177. If you’re not able to fly to Florida in September, then August is your next best option. Flight prices from Chicago to Florida during August average around $204.

What is the cheapest day to depart on your flight to Florida?

On average, the least expensive day to fly to Florida from Chicago is on a Thursday. momondo users have found tickets for Thursday departures for as low as $432. However, this price may fluctuate depending on the airline, the season, and holidays. Be sure to avoid booking your departure on a Sunday as prices are generally higher than usual. According to our data, the average ticket price to Florida on Sunday is $453.

What is the cheapest time of day to depart on your flight to Florida?

Flying to Florida from Chicago in the evening is the least expensive time of day to depart. momondo users have found prices as low as $239 when looking at flights departing in the evening. Flights to Florida are more costly in the morning, with an average ticket price of $474. Departure times in the morning fall within the peak daily travel times, which is why tickets can be more expensive.

What is the cheapest Chicago to Florida flight route?

Fly from Chicago Greater Rockford to Orlando Sanford Intl for the best Chicago - Florida flight prices

How far in advance should I book a flight to Florida?

You are more likely to see cheaper flights to Florida from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Florida for around $270 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Florida from Chicago for as low as $221 on momondo.

What cabin class options are available on Chicago to Florida flights?

There are 4 cabin classes available to choose from on Chicago to Florida flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Chicago to Florida flights?

No. A direct flight is the cheapest option for a flight between Chicago to Florida.

When did momondo last update prices for flights from Chicago to Florida?
Prices for flights from Chicago to Florida were last updated today.
How many operators does momondo search for flights from Chicago to Florida?
The number of operators available for flights from Chicago to Florida is 8 as of August 2025.
How old do you have to be to fly from Chicago to Florida?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago to Florida.
What documentation or ID do you need to fly to Florida?
The travel and health documents required for your trip to Florida can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Florida. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from Chicago to Florida?
momondo data reveals that the most frequently booked plane model on the route from Chicago to Florida is Boeing 737-800, representing 20.11% of all bookings. The subsequent popular models are Airbus A321neo at 11.49%, Airbus A321-100/200 at 8.95%, and Boeing 737 MAX 8 at 8.79%.

Best airlines flying from Chicago to Florida

Compare and see reviews for airlines that fly from Chicago to Florida with momondo

Airline	Rating	Free Cancellation	Price
Frontier	PriceFrom $37	Free Cancellation	Rating 5.9 3,239 reviews	Search Frontier flights
Spirit Airlines	PriceFrom $64	Free Cancellation	Rating 6.3 8,048 reviews	Search Spirit Airlines flights
Sun Country Air	PriceFrom $69	Free Cancellation	Rating 6.9 334 reviews	Search Sun Country Air flights
Allegiant Air	PriceFrom $89	Free Cancellation	Rating 7.2 702 reviews	Search Allegiant Air flights
Southwest	PriceFrom $112	Free Cancellation	Rating 8.0 4,246 reviews	Search Southwest flights
United Airlines	PriceFrom $127	Free Cancellation	Rating 7.4 8,900 reviews	Search United Airlines flights
Delta	PriceFrom $131	Free Cancellation	Rating 8.0 7,981 reviews	Search Delta flights
American Airlines	PriceFrom $158	Free Cancellation	Rating 7.2 10,000 reviews	Search American Airlines flights
Alaska Airlines	PriceFrom $176	Free Cancellation	Rating 8.0 10,000 reviews	Search Alaska Airlines flights
JetBlue	PriceFrom $233	Free Cancellation	Rating 7.2 2,914 reviews	Search JetBlue flights

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Florida?

It is quick and easy to find Chicago to Florida flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Florida that suits you.

Can I find flights from Chicago to Florida with flexible booking policies on momondo?

Yes. All flights to Florida from Chicago on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Chicago to Florida?

Once all potential Chicago to Florida flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Chicago to Florida right now. Can momondo alert me if prices change?

Price alerts on flights to Florida from Chicago are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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Find better results for your trip to Florida

Popular cities in Florida

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Cheap flights from Chicago to Florida from $29

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Florida departing on 9/19. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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Big names and deals

Filter for what you want

Filter for what you want

Trusted and free

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Find the cheapest flights from Chicago to Florida

Cheap round-trip flights

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Cheap last minute flights

Cheap direct flights

Southwest flights from Chicago to Florida

Our best Southwest deals on Chicago to Florida flight tickets

Spirit Airlines flights from Chicago to Florida

Our best Spirit Airlines deals on Chicago to Florida flight tickets

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How to get the cheapest flight ticket from Chicago to Florida

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Florida?

What is the cheapest day to depart on your flight to Florida?

What is the cheapest time of day to depart on your flight to Florida?

What is the cheapest Chicago to Florida flight route?

Fly from Chicago Greater Rockford to Orlando Sanford Intl for the best Chicago - Florida flight prices

How far in advance should I book a flight to Florida?

What cabin class options are available on Chicago to Florida flights?

There are 4 cabin classes available to choose from on Chicago to Florida flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Chicago to Florida flights?

No. A direct flight is the cheapest option for a flight between Chicago to Florida.

What is the cheapest airline that flies from Chicago to Florida?

Spirit Airlines and Frontier are the most popular carriers operating from Chicago to Florida

What airlines fly to Florida?

How many flights depart from Chicago to Florida on average per day?

As of August 2025, there are 152 flights per day flying from Chicago to Florida. The most common time of day flights depart is 6:00PM, with 53% of flights taking off at noon.

How many flights depart from Chicago to Florida on average per week?

1,064 flights are operational weekly from Chicago to Florida as of August 2025. The most popular departure day for this route is Fri, with 18% of flights per week taking off on this day.

When did momondo last update prices for flights from Chicago to Florida?

How many operators does momondo search for flights from Chicago to Florida?

How old do you have to be to fly from Chicago to Florida?

What documentation or ID do you need to fly to Florida?

What is the most popular plane model from Chicago to Florida?

Best airlines flying from Chicago to Florida

Compare and see reviews for airlines that fly from Chicago to Florida with momondo

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Florida?

Can I find flights from Chicago to Florida with flexible booking policies on momondo?

How can momondo help me find flights from Chicago to Florida?

I’m not ready to book a flight from Chicago to Florida right now. Can momondo alert me if prices change?

An easier way to manage your Florida trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to Florida

Popular cities in Florida

Popular flights according to clicks in the last 7 days on momondo