Which airline has the best punctuality record on Chicago to Orlando flights?

According to our data, Frontier have had the least number of delays on this route over the last 12 months; with about 11% of their flights experiencing any sort of delay.

What airlines fly to Orlando Airport?

Southwest, Frontier and Spirit Airlines are the top three most popular airlines that fly to Orlando Airport from Chicago Midway Airport according to our data. Southwest is the first choice among our users, with 49% of people opting to fly with this airline when traveling to Orlando Airport. Keep in mind that there are 4 different airlines that fly to Orlando Airport on a routine basis, so you have a few additional options to choose from.

What is the most punctual flight time for Chicago to Orlando flights?

Generally, flights departing at night tend to experience fewer delays. Flights in the evening have, in the past, seen delays more frequently in comparison.

What is the cheapest airline that flies from Chicago Midway to Orlando?

Frontier and Southwest are the most popular carriers operating from Chicago Midway to Orlando

What day of the week experiences the fewest flight delays on this route?

Tuesday is statistically the day of the week which experiences the fewest number of delays on this flight route. Sunday has historically seen more delays on average compared to the rest of the week.

How often are flights from Chicago to Orlando delayed?

Historically, on average around 13% of flights between Chicago and Orlando have experienced a delay on any given week. The average delay length over the past 12 months has been 137 minutes.

How many operators does momondo search for flights from Chicago Midway Airport to Orlando Airport?

As of December 2025, there are 4 operators available to choose from for flights from Chicago Midway Airport to Orlando Airport.

How old do you have to be to fly from Chicago Midway Airport to Orlando Airport?

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago Midway Airport to Orlando Airport.

What documentation or ID do you need to fly to Orlando Airport?

The necessary travel and health documents for your Orlando Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

$49 Cheap Flights from Chicago Midway Airport to Orlando Airport in 2025/26

Q: How many flights depart from Chicago Midway Airport to Orlando Airport on average per day?

The number of flights available between Chicago Midway Airport and Orlando Airport is 5 per day as of December 2025. The most frequent departure time is 1:00PM, with 44% of daily flights leaving in the afternoon.

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6:10 am - 5:27 pm

MDW

MCO

10h 17m1 stop

3:01 pm - 5:05 pm

MCO

MDW

3h 04mnonstop

$93Frontier

Thu, Jan 8 - Sun, Jan 18

3:00 pm - 5:31 am

MDW

MCO

13h 31m1 stop

5:49 pm - 7:52 pm

MCO

MDW

3h 03mnonstop

$94Frontier

Mon, Jan 12 - Fri, Jan 23

8:00 am - 11:49 am

MDW

MCO

2h 49mnonstop

12:20 pm - 2:26 pm

MCO

MDW

3h 06mnonstop

$95Frontier

Sat, Feb 21 - Thu, Feb 26

4:31 pm - 8:18 pm

MDW

MCO

2h 47mnonstop

3:01 pm - 5:05 pm

MCO

MDW

3h 04mnonstop

$96Frontier

Fri, Jan 9 - Sun, Jan 18

11:39 am - 5:39 pm

MDW

MCO

5h 00m1 stop

3:01 pm - 5:05 pm

MCO

MDW

3h 04mnonstop

$98Frontier

Wed, Jan 14 - Sun, Jan 18

5:01 pm - 12:31 am

MDW

MCO

6h 30m1 stop

12:46 pm - 10:19 pm

MCO

MDW

10h 33m1 stop

$99Frontier

Thu, Jan 22 - Thu, Jan 29

1:20 pm - 12:01 am

MDW

MCO

9h 41m1 stop

5:49 pm - 7:52 pm

MCO

MDW

3h 03mnonstop

$100Frontier

Tue, Jan 27 - Sun, Feb 1

4:31 pm - 8:18 pm

MDW

MCO

2h 47mnonstop

6:10 am - 10:31 am

MCO

MDW

5h 21m1 stop

$101Frontier

Fri, Jan 9 - Wed, Jan 14

11:05 am - 11:58 pm

MDW

MCO

11h 53m1 stop

7:05 am - 9:09 am

MCO

MDW

3h 04mnonstop

$103Frontier

Thu, Jan 15 - Fri, Jan 16

4:31 pm - 8:18 pm

MDW

MCO

2h 47mnonstop

7:05 am - 9:09 am

MCO

MDW

3h 04mnonstop

$104Frontier

Mon, Jan 12 - Fri, Jan 16

Frontier flights from Chicago Midway Airport to Orlando Airport

Our best Frontier deals on Chicago Midway Airport to Orlando Airport flight tickets

Frontier

Jan 8

MDW6:10 amChicago Midway

10h 17m

1 stop

MCO5:27 pmOrlando

Jan 18

MCO3:01 pmOrlando

3h 04m

MDW5:05 pmChicago Midway

$93

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Frontier

Jan 12

MDW9:15 amChicago Midway

12h 42m

1 stop

MCO10:57 pmOrlando

Jan 23

MCO5:49 pmOrlando

3h 03m

MDW7:52 pmChicago Midway

$94

Find similar

Frontier

Feb 21

MDW8:00 amChicago Midway

2h 49m

MCO11:49 amOrlando

Feb 26

MCO12:20 pmOrlando

3h 06m

MDW2:26 pmChicago Midway

$95

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

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Route

Depart

Return

Price

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Thu 1/8

6:10 am-5:27 pm

1 stop10h 17m

Orlando

Sun 1/18

3:01 pm-5:05 pm

Nonstop3h 04m

$93

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Mon 1/12

3:00 pm-5:31 am

1 stop13h 31m

Orlando

Fri 1/23

5:49 pm-7:52 pm

Nonstop3h 03m

$94

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Sat 2/21

8:00 am-11:49 am

Nonstop2h 49m

Orlando

Thu 2/26

12:20 pm-2:26 pm

Nonstop3h 06m

$95

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Fri 1/9

4:31 pm-8:18 pm

Nonstop2h 47m

Orlando

Sun 1/18

3:01 pm-5:05 pm

Nonstop3h 04m

$96

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Wed 1/14

11:39 am-5:39 pm

1 stop5h 00m

Orlando

Sun 1/18

3:01 pm-5:05 pm

Nonstop3h 04m

$98

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Thu 1/22

5:01 pm-12:31 am

1 stop6h 30m

Orlando

Thu 1/29

12:46 pm-10:19 pm

1 stop10h 33m

$99

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Tue 1/27

1:20 pm-12:01 am

1 stop9h 41m

Orlando

Sun 2/1

5:49 pm-7:52 pm

Nonstop3h 03m

$100

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Fri 1/9

4:31 pm-8:18 pm

Nonstop2h 47m

Orlando

Wed 1/14

6:10 am-10:31 am

1 stop5h 21m

$101

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Thu 1/15

11:05 am-11:58 pm

1 stop11h 53m

Orlando

Fri 1/16

7:05 am-9:09 am

Nonstop3h 04m

$103

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Mon 1/12

4:31 pm-8:18 pm

Nonstop2h 47m

Orlando

Fri 1/16

7:05 am-9:09 am

Nonstop3h 04m

$104

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How to get the cheapest flight ticket from Chicago Midway Airport to Orlando Airport

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

Delays

Other information

What is the cheapest month to fly to Orlando Airport?

The cheapest month to fly to Orlando Airport from Chicago Midway Airport is in January. Flight prices, which tend to average around $198, are often lower during this time because this is during the off-season. If you aren’t able to travel during the month of January, then book flights to Orlando Airport from Chicago Midway Airport during September instead. Flights to Orlando Airport in September, while not as cheap as those in January, still average around $214.

What is the cheapest day to depart on your flight to Orlando Airport?

The cheapest day to depart from Chicago Midway Airport to Orlando Airport is on a Tuesday. Travelers who choose to depart for Orlando Airport on a Tuesday will often find tickets for as low as $257. The most expensive day to fly to Orlando Airport is Monday, with ticket prices averaging around $301.

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

In the afternoon is the cheapest time of day to fly from Chicago Midway Airport to Orlando Airport when you can find flight prices for as low as $244. Flying to Orlando Airport in the afternoon is an ideal time because this is during off-peak travel hours. Flights at noon are often more expensive with an average ticket price of $299.

What is the cheapest Chicago Midway to Orlando flight route?

Fly from Chicago Midway to Orlando for the best Chicago Midway - Orlando flight prices

How far in advance should I book a flight to Orlando Airport?

You are more likely to see cheaper flights to Orlando Airport from Chicago Midway Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Orlando Airport for around $285 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Orlando Airport from Chicago Midway Airport for as low as $241 on momondo.

What cabin class options are available on Chicago Midway to Orlando flights?

There is only 1 cabin class available to choose from on Chicago Midway to Orlando 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 Midway Airport to Orlando Airport flights?

No. A direct flight is the cheapest option for a flight between Chicago Midway Airport to Orlando Airport.

How have Chicago Midway Airport to Orlando Airport flight prices changed over time?

As of December 2025, prices for Chicago Midway Airport to Orlando Airport flights are approximately 44% more expensive when compared to flights at the same time last year.

When to book flights from Chicago Midway Airport to Orlando Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to Orlando Airport according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap Chicago Midway Airport to Orlando Airport (MDW to MCO) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Orlando Airport

Best Price Found	$96
Fastest flight time	2h 30m
Direct flights	Every day

The best one-way flight to Orlando Airport from Chicago Midway Airport in the past 72 hours is $96. The best round-trip flight deal from Chicago Midway Airport to Orlando Airport found on momondo in the last 72 hours is $149.

The fastest flight from Chicago Midway Airport to Orlando Airport takes 2h 30m

Direct flights go from Chicago Midway Airport to Orlando Airport every day.

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How far is Chicago Midway to Orlando by plane?
There are 990.5 mi between Chicago Midway and Orlando. In terms of flight time, this usually takes a little over 2h 30m.
When did momondo last update prices for flights from Chicago Midway Airport to Orlando Airport?
Prices for flights from Chicago Midway Airport to Orlando Airport are updated daily.
How many operators does momondo search for flights from Chicago Midway Airport to Orlando Airport?
As of December 2025, there are 4 operators available to choose from for flights from Chicago Midway Airport to Orlando Airport.
How old do you have to be to fly from Chicago Midway Airport to Orlando Airport?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago Midway Airport to Orlando Airport.
What documentation or ID do you need to fly to Orlando Airport?
The necessary travel and health documents for your Orlando Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Chicago Midway Airport to Orlando Airport?
momondo data reveals that the most frequently booked plane model on the route from Chicago Midway Airport to Orlando Airport is Airbus A321neo, representing 17.93% of all bookings. The subsequent popular models are Airbus A320neo at 13.64%, Boeing 737 MAX 8 at 12.42%, and Boeing 737-800 Passenger/BBJ2 (winglets) at 9.95%.
What is the most popular airline from Chicago Midway Airport to Orlando Airport?
momondo data reveals that the most frequently booked airline on the route from Chicago Midway Airport to Orlando Airport is Southwest, representing 49% of all bookings. The subsequent popular airlines are Frontier at 48%, Spirit Airlines at 1%, and Delta at 1%.

Best airlines flying from Chicago Midway Airport to Orlando Airport

Compare and see reviews for airlines that fly from Chicago Midway Airport to Orlando Airport with momondo

Airline	Rating	Free Cancellation	Price
Spirit Airlines	PriceFrom $63	Free Cancellation	Rating 6.3 8,175 reviews	Search Spirit Airlines flights
Frontier	PriceFrom $87	Free Cancellation	Rating 5.8 3,084 reviews	Search Frontier flights
Delta	PriceFrom $196	Free Cancellation	Rating 7.9 8,008 reviews	Search Delta flights
Southwest	PriceFrom $198	Free Cancellation	Rating 7.9 4,252 reviews	Search Southwest flights

Southwest Flights From Chicago Midway Airport to Orlando Airport
The lowest priced Southwest flight from Chicago Midway Airport to Orlando Airport from the last 72 hours was $198. Generally, Southwest has 35 flights on this route every week with an average price of $394. Southwest is rated 7.9/10 by our users.
Frontier Flights From Chicago Midway Airport to Orlando Airport
The best Frontier deal for Chicago Midway Airport to Orlando Airport flight tickets found on momondo in the last 72 hours was $87, round-trip. It should be noted that an average Frontier flight deal for this route in this time was higher, at $198 round-trip. Frontier operates 2 flights out of Chicago Midway Airport into Orlando Airport in an average week, so prices vary by time and availability. 3,084 Frontier reviews by users on momondo have scored the airline at 5.8/10.

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Sanford

Mount Dora

The Villages

Titusville

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Bay Lake

Sebring

Daytona Beach Shores

Cocoa

Palm Coast

Palm Bay

Flagler Beach

Why use momondo?

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

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Chicago to Orlando. Millions of users trust and use momondo every year so you are in good hands.

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

All flight searches from Chicago to Orlando on momondo can be filtered to show those which offer flexible booking policies.

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

momondo helps you find the best flight between Chicago and Orlando by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

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

Yes momondo offers price alerts on flights to Orlando from Chicago. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

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Cheap flights from Chicago Midway Airport to Orlando from $49

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 Midway Airport to Orlando departing on 1/14. 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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How to get the cheapest flight ticket from Chicago Midway Airport to Orlando Airport

What is the cheapest month to fly to Orlando Airport?

What is the cheapest day to depart on your flight to Orlando Airport?

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

What is the cheapest Chicago Midway to Orlando flight route?

Fly from Chicago Midway to Orlando for the best Chicago Midway - Orlando flight prices

How far in advance should I book a flight to Orlando Airport?

What cabin class options are available on Chicago Midway to Orlando flights?

There is only 1 cabin class available to choose from on Chicago Midway to Orlando 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 Midway Airport to Orlando Airport flights?

No. A direct flight is the cheapest option for a flight between Chicago Midway Airport to Orlando Airport.

How have Chicago Midway Airport to Orlando Airport flight prices changed over time?

As of December 2025, prices for Chicago Midway Airport to Orlando Airport flights are approximately 44% more expensive when compared to flights at the same time last year.

What is the cheapest airline that flies from Chicago Midway to Orlando?

Frontier and Southwest are the most popular carriers operating from Chicago Midway to Orlando

What airlines fly to Orlando Airport?

How often are flights from Chicago to Orlando delayed?

Historically, on average around 13% of flights between Chicago and Orlando have experienced a delay on any given week. The average delay length over the past 12 months has been 137 minutes.

What is the most punctual flight time for Chicago to Orlando flights?

Generally, flights departing at night tend to experience fewer delays. Flights in the evening have, in the past, seen delays more frequently in comparison.

What day of the week experiences the fewest flight delays on this route?

Tuesday is statistically the day of the week which experiences the fewest number of delays on this flight route. Sunday has historically seen more delays on average compared to the rest of the week.

Which airline has the best punctuality record on Chicago to Orlando flights?

According to our data, Frontier have had the least number of delays on this route over the last 12 months; with about 11% of their flights experiencing any sort of delay.

How many flights depart from Chicago Midway Airport to Orlando Airport on average per day?

The number of flights available between Chicago Midway Airport and Orlando Airport is 5 per day as of December 2025. The most frequent departure time is 1:00PM, with 44% of daily flights leaving in the afternoon.

How many flights depart from Chicago Midway Airport to Orlando Airport on average per week?

As of December 2025, there are 39 flights per week flying from Chicago Midway Airport to Orlando Airport. The most common day of the week flights depart is Thu, with 28% of flights taking off on this day.

When to book flights from Chicago Midway Airport to Orlando Airport

Cheap Chicago Midway Airport to Orlando Airport (MDW to MCO) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Orlando Airport

Best Price Found

Fastest flight time

Direct flights

How far is Chicago Midway to Orlando by plane?

When did momondo last update prices for flights from Chicago Midway Airport to Orlando Airport?

How many operators does momondo search for flights from Chicago Midway Airport to Orlando Airport?

How old do you have to be to fly from Chicago Midway Airport to Orlando Airport?

What documentation or ID do you need to fly to Orlando Airport?

What is the most popular plane model from Chicago Midway Airport to Orlando Airport?

What is the most popular airline from Chicago Midway Airport to Orlando Airport?

Best airlines flying from Chicago Midway Airport to Orlando Airport

Compare and see reviews for airlines that fly from Chicago Midway Airport to Orlando Airport with momondo

Southwest Flights From Chicago Midway Airport to Orlando Airport

Frontier Flights From Chicago Midway Airport to Orlando Airport

Traveling to a place near Orlando?

Why use momondo?

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

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

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

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

An easier way to manage your Orlando Airport 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 Orlando

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