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

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

What airlines fly to Orlando?

Southwest, Frontier and Delta are the top three most popular airlines that fly to Orlando 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. Keep in mind that there are 5 different airlines that fly to Orlando on a routine basis, so you have a few additional options to choose from.

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

As of July 2025, there are 53 flights per week flying from Chicago Midway Airport to Orlando. The most common day of the week flights depart is Thu, with 23% of flights taking off on this day.

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

As of July 2025, there are 7 flights per day flying from Chicago Midway Airport to Orlando. The most common time of day flights depart is 9:00AM, with 51% of flights taking off at noon.

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

Prices for flights from Chicago Midway Airport to Orlando are refreshed on a daily basis.

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

As of July 2025, there are 5 operators available to choose from for flights from Chicago Midway Airport to Orlando.

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

The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago Midway Airport to Orlando.

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

The necessary travel and health documents for your Orlando 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.

$44 Cheap Flights from Chicago Midway Airport to Orlando in 2025

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Find the cheapest flights from Chicago Midway Airport to Orlando

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

8:35 am - 12:20 pmMDW-MCO

2h 45mnonstop

6:23 pm - 8:22 pmMCO-MDW

2h 59mnonstop

$103Frontier

Find Deal

Mon, Jul 28 - Thu, Jul 31

8:35 am - 12:20 pmMDW-MCO

2h 45mnonstop

6:23 pm - 8:22 pmMCO-MDW

2h 59mnonstop

$106Frontier

Find Deal

Mon, Aug 11 - Sat, Aug 16

9:17 am - 1:03 pmMDW-MCO

2h 46mnonstop

1:33 pm - 3:29 pmMCO-MDW

2h 56mnonstop

$107Frontier

Find Deal

Fri, Aug 22 - Mon, Aug 25

6:45 pm - 10:20 pmMDW-MCO

2h 35mnonstop

7:10 am - 8:55 amMCO-MDW

2h 45mnonstop

$131Southwest

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Thu, Aug 14 - Tue, Aug 19

11:40 am - 7:20 pmMDW-MCO

6h 40m1 stop

5:40 pm - 7:25 pmMCO-MDW

2h 45mnonstop

$141Southwest

Find Deal

Sat, Aug 30 - Thu, Sep 4

5:50 pm - 9:25 pmMDW-MCO

2h 35mnonstop

7:30 am - 9:20 amMCO-MDW

2h 50mnonstop

$144Southwest

Find Deal

Sat, Nov 8 - Tue, Nov 11

7:00 am - 2:15 pmMDW-MCO

6h 15m2 stops

8:40 pm - 10:25 pmMCO-MDW

2h 45mnonstop

$146Southwest

Find Deal

Sat, Sep 20 - Thu, Sep 25

9:32 am - 8:44 pmMDW-SFB

10h 12m1 stop

10:55 am - 3:02 pmSFB-MDW

5h 07m1 stop

$195Allegiant Air

Find Deal

Fri, Aug 22 - Mon, Aug 25

9:32 am - 8:44 pmMDW-SFB

10h 12m1 stop

6:55 pm - 8:42 amSFB-MDW

14h 47m1 stop

$196Allegiant Air

Find Deal

Fri, Aug 22 - Sun, Aug 24

7:07 pm - 9:47 amMDW-SFB

13h 40m1 stop

8:10 am - 2:04 pmSFB-MDW

6h 54m1 stop

$204Allegiant Air

Find Deal

Fri, Aug 15 - Mon, Aug 18

Frontier flights from Chicago Midway Airport to Orlando

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

Frontier

Jul 18

MDW8:35 amChicago Midway

2h 45m

MCO12:20 pmOrlando

Jul 25

MCO1:10 pmOrlando

2h 56m

MDW3:06 pmChicago Midway

$98

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Frontier

Jul 28

MDW8:35 amChicago Midway

2h 45m

MCO12:20 pmOrlando

Jul 31

MCO6:23 pmOrlando

2h 59m

MDW8:22 pmChicago Midway

$103

Find similar

Frontier

Aug 11

MDW8:35 amChicago Midway

2h 45m

MCO12:20 pmOrlando

Aug 16

MCO6:23 pmOrlando

2h 59m

MDW8:22 pmChicago Midway

$106

Find similar

Southwest flights from Chicago Midway Airport to Orlando

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

Southwest

Aug 14

MDW6:45 pmChicago Midway

2h 35m

MCO10:20 pmOrlando

Aug 19

MCO7:10 amOrlando

2h 45m

MDW8:55 amChicago Midway

$131

Find similar

Southwest

Aug 30

MDW11:40 amChicago Midway

6h 40m

1 stop

MCO7:20 pmOrlando

Sep 4

MCO5:40 pmOrlando

2h 45m

MDW7:25 pmChicago Midway

$141

Find similar

Southwest

Nov 8

MDW5:50 pmChicago Midway

2h 35m

MCO9:25 pmOrlando

Nov 11

MCO7:30 amOrlando

2h 50m

MDW9:20 amChicago Midway

$144

Find similar

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

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 Orlando?

The month of September is, on average, the cheapest month to fly to Orlando from Chicago Midway Airport, with most prices found around $173. If you’re not able to fly to Orlando in September, then August is your next best option. Flight prices from Chicago Midway Airport to Orlando during August average around $182.

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

Our data shows that Tuesday is the least expensive day to fly to Orlando. Tickets to fly out on this day can be as low as $266. On the other hand, Monday is the most expensive day to depart from Chicago Midway Airport because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $316.

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

The cheapest time of day to fly to Orlando is in the afternoon when flights can be purchased for as low as $249. In contrast, the most expensive time of day to depart to Orlando is at noon when prices are around $304.

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?

You are more likely to see cheaper flights to Orlando from Chicago Midway Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Orlando for around $308 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Orlando from Chicago Midway Airport for as low as $229 on momondo.

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

There are 1 cabin classes 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 flights?

You could potentially save up to 15% on your flight if you consider stops on a Chicago Midway Airport to Orlando flight.

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

As of July 2025, prices for Chicago Midway Airport to Orlando flights are approximately 30% cheaper when compared to flights at the same time last year.

When to book flights from Chicago Midway Airport to Orlando

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to Orlando 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 (MDW to ORL) flight deals and tips

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

Best Price Found	$44
Fastest flight time	2h 30m
Direct flights	Every day
Airports in Orlando	2 airports

The best one-way flight to Orlando from Chicago Midway Airport in the past 72 hours is $44. The best round-trip flight deal from Chicago Midway Airport to Orlando found on momondo in the last 72 hours is $103.

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

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

There are 2 airports near Orlando: Orlando (MCO), Orlando Sanford Intl (SFB)

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How far is Chicago Midway to Orlando by plane?
Orlando is 982.0 mi away from Chicago Midway. Flights usually cover this in 2h 30m, depending on flying conditions and air traffic around both airports.
When did momondo last update prices for flights from Chicago Midway Airport to Orlando?
Prices for flights from Chicago Midway Airport to Orlando are refreshed on a daily basis.
How many operators does momondo search for flights from Chicago Midway Airport to Orlando?
As of July 2025, there are 5 operators available to choose from for flights from Chicago Midway Airport to Orlando.
How old do you have to be to fly from Chicago Midway Airport to Orlando?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago Midway Airport to Orlando.
What documentation or ID do you need to fly to Orlando?
The necessary travel and health documents for your Orlando 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?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Chicago Midway Airport to Orlando is Airbus A321neo (14.56% of total bookings). The next most popular plane models are Airbus A320neo (13.61%), Boeing 737 MAX 8 (13.23%), and Boeing 737-800 Passenger/BBJ2 (winglets) (10.51%).
What is the most popular airline from Chicago Midway Airport to Orlando?
momondo data reveals that the most frequently booked airline on the route from Chicago Midway Airport to Orlando is Frontier, representing 56% of all bookings. The subsequent popular airlines are Southwest at 43% and Spirit Airlines at 2%.

Best airlines flying from Chicago Midway Airport to Orlando

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

Airline	Rating	Free Cancellation	Price
Spirit Airlines	PriceFrom $63	Free Cancellation	Rating 6.3 8,055 reviews	Search Spirit Airlines flights
Frontier	PriceFrom $103	Free Cancellation	Rating 5.9 3,271 reviews	Search Frontier flights
Delta	PriceFrom $196	Free Cancellation	Rating 8.0 7,951 reviews	Search Delta flights
Southwest	PriceFrom $224	Free Cancellation	Rating 8.0 4,249 reviews	Search Southwest flights
United Airlines	PriceFrom $248	Free Cancellation	Rating 7.4 8,846 reviews	Search United Airlines flights

Southwest Flights From Chicago Midway Airport to Orlando
Across 51 Southwest flights from Chicago Midway Airport to Orlando this week, the average price was $396, with the best Southwest deals starting from $224 round-trip. 4,249 users have rated Southwest on momondo, with an average score of 8.0/10.
Frontier Flights From Chicago Midway Airport to Orlando
Frontier (5.9/10 from 3,271 reviews) operates around 2 flights from Chicago Midway Airport to Orlando in any given week. The average Frontier airfare for this route is around $215, with deals from around $103 rare but found on momondo. Referenced prices are for round-trip Chicago Midway Airport to Orlando flight searches in the last 72 hours.

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

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Chicago to Orlando for you.

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 provides multiple filters to help you find the best flight to Orlando from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

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

If you are simply researching potential flights to Orlando, momondo offers a useful price alert feature which will track prices for flights to Orlando from Chicago and alert you when they change.

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Cheap flights from Chicago Midway Airport to Orlando from $44

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Find the cheapest flights from Chicago Midway Airport to Orlando

Cheap round-trip flights

Cheap one-way flights

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Frontier flights from Chicago Midway Airport to Orlando

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

Southwest flights from Chicago Midway Airport to Orlando

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

See travel insights to Orlando from

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

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 Orlando?

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

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

The cheapest time of day to fly to Orlando is in the afternoon when flights can be purchased for as low as $249. In contrast, the most expensive time of day to depart to Orlando is at noon when prices are around $304.

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?

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

There are 1 cabin classes 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 flights?

You could potentially save up to 15% on your flight if you consider stops on a Chicago Midway Airport to Orlando flight.

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

As of July 2025, prices for Chicago Midway Airport to Orlando flights are approximately 30% cheaper when compared to flights at the same time last year.

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

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

What airlines fly to Orlando?

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

As of July 2025, there are 7 flights per day flying from Chicago Midway Airport to Orlando. The most common time of day flights depart is 9:00AM, with 51% of flights taking off at noon.

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

As of July 2025, there are 53 flights per week flying from Chicago Midway Airport to Orlando. The most common day of the week flights depart is Thu, with 23% of flights taking off on this day.

When to book flights from Chicago Midway Airport to Orlando

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

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

Best Price Found

Fastest flight time

Direct flights

Airports in Orlando

How far is Chicago Midway to Orlando by plane?

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

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

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

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

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

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

Best airlines flying from Chicago Midway Airport to Orlando

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

Southwest Flights From Chicago Midway Airport to Orlando

Frontier Flights From Chicago Midway Airport to Orlando

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 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 the United States

Fly into one of these airports located in Orlando

Airports listed have a maximum distance of 18.3 mi from Orlando