Is Southwest the cheapest airline to fly with from Chicago Midway Airport to Orlando Airport?

With an average price of $395 return, Southwest is not the cheapest airline to fly from Chicago Midway Airport to Orlando Airport with. Instead, for the lowest price, our data suggests flying with Spirit Airlines, where a return flight costs $193 on average.

Does Southwest fly direct to Orlando Airport from Chicago Midway Airport?

Yes, Southwest does offer direct flights for the route, with around 39 flights per week.

What’s the cheapest day of the week to fly from Chicago Midway Airport to Orlando Airport with Southwest?

On average, the cheapest day of the week to fly from Chicago Midway Airport to Orlando Airport with Southwest is Friday, when prices are around $88. The most expensive day is generally Tuesday, where the average price is around $153.

What’s the cheapest month to fly from Chicago Midway Airport to Orlando Airport with Southwest?

The cheapest month for Southwest flights to Orlando Airport from Chicago Midway Airport is generally August, where plane tickets cost $138 on average. If possible, try to avoid the most expensive months of January and September, where tickets cost $293 and $331 respectively.

$79 Cheap Southwest Flights from Chicago Midway Airport to Orlando Airport

MDW - MCO

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Flight Deals

Cheap Southwest Flight Deals from Chicago Midway Airport to Orlando Airport

Here are some of the best deals found on KAYAK recently from Southwest for round-trip flights from Chicago Midway Airport to Orlando Airport that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Discover the best prices for you by selecting your travel dates on KAYAK.

Round-trip

One-way

Last minute

Direct

Recent round-trip Southwest flight deals from Chicago Midway Airport to Orlando Airport

Sat, Feb 14 - Thu, Feb 19

6:50 pm - 10:30 pmMDW-MCO

2h 40mnonstop

6:50 am - 8:45 amMCO-MDW

2h 55mnonstop

$157Southwest

Find Deal

Sat, Feb 21 - Thu, Feb 26

6:50 pm - 10:30 pmMDW-MCO

2h 40mnonstop

6:50 am - 8:45 amMCO-MDW

2h 55mnonstop

$168Southwest

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Sat, Jan 17 - Sat, Jan 24

9:45 am - 2:50 pmMDW-MCO

4h 05m1 stop

8:20 pm - 10:10 pmMCO-MDW

2h 50mnonstop

$174Southwest

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Tue, Oct 28 - Fri, Oct 31

7:05 am - 10:35 amMDW-MCO

2h 30mnonstop

10:20 am - 2:25 pmMCO-MDW

5h 05m1 stop

$178Southwest

Find Deal

Sat, Oct 25 - Tue, Oct 28

2:50 pm - 6:25 pmMDW-MCO

2h 35mnonstop

9:50 am - 11:35 amMCO-MDW

2h 45mnonstop

$179Southwest

Find Deal

Thu, Jan 1 - Tue, Jan 6

5:05 am - 8:40 amMDW-MCO

2h 35mnonstop

9:15 am - 12:30 pmMCO-MDW

4h 15m1 stop

$184Southwest

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Tue, Oct 28 - Fri, Oct 31

1:15 pm - 8:00 pmMDW-MCO

5h 45m1 stop

10:20 am - 2:25 pmMCO-MDW

5h 05m1 stop

$192Southwest

Find Deal

Sat, Jan 17 - Sat, Jan 24

9:45 am - 2:50 pmMDW-MCO

4h 05m1 stop

6:40 am - 11:25 amMCO-MDW

5h 45m1 stop

$193Southwest

Find Deal

Wed, Jan 7 - Sat, Jan 17

5:30 pm - 9:05 pmMDW-MCO

2h 35mnonstop

3:30 pm - 6:45 pmMCO-MDW

4h 15m1 stop

$195Southwest

Find Deal

Tue, Nov 11 - Tue, Nov 11

5:05 am - 8:40 amMDW-MCO

2h 35mnonstop

5:40 pm - 7:30 pmMCO-MDW

2h 50mnonstop

$197Southwest

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Useful Info

Low season	May
High season	March
Cheapest flight	$79
Average price round-trip	$252

Best time to beat the crowds with an average 0% drop in price.

Most popular time to fly with an average 21% increase in price.

Flight from Chicago Midway Airport to Orlando Airport

(price for this month)

When to Book Flights with Southwest from Chicago Midway Airport to Orlando Airport

Average price per month

Flight prices as travel date approaches

Is Southwest the cheapest airline to fly with from Chicago Midway Airport to Orlando Airport?
With an average price of $395 return, Southwest is not the cheapest airline to fly from Chicago Midway Airport to Orlando Airport with. Instead, for the lowest price, our data suggests flying with Spirit Airlines, where a return flight costs $193 on average.
What is the cheapest Southwest flight from Chicago Midway Airport to Orlando Airport?
In the last 3 days, the lowest price for a flight with Southwest from Chicago Midway Airport to Orlando Airport was $77 for a return flight and $46 for a one-way flight.
Does Southwest fly direct to Orlando Airport from Chicago Midway Airport?
Yes, Southwest does offer direct flights for the route, with around 39 flights per week.
What’s the cheapest day of the week to fly from Chicago Midway Airport to Orlando Airport with Southwest?
On average, the cheapest day of the week to fly from Chicago Midway Airport to Orlando Airport with Southwest is Friday, when prices are around $88. The most expensive day is generally Tuesday, where the average price is around $153.
What’s the cheapest month to fly from Chicago Midway Airport to Orlando Airport with Southwest?
The cheapest month for Southwest flights to Orlando Airport from Chicago Midway Airport is generally August, where plane tickets cost $138 on average. If possible, try to avoid the most expensive months of January and September, where tickets cost $293 and $331 respectively.

8.0

Very good4,248 verified ratings

8.0Comfort

7.5Entertainment

8.6Crew

7.0Food

8.1Boarding

Pros +

Cons -

Show reviews that mention

10.0 Wonderful

Gabriel, Sep 2025

DEN-SMF

Connecting flight is on time and boarding was a breeze!

10.0 Wonderful

Gabriel, Sep 2025

LGA-DEN

Easy boarding process. No delays!

10.0 Wonderful

Melissa, Sep 2025

MDW-DTW

Excellent

10.0 Wonderful

Melissa, Sep 2025

MSY-MDW

Excellent. Would encourage Southwest to keep current boarding procedures with free style seating. Makes for a fantastic experience

10.0 Wonderful

Robert, Sep 2025

RNO-LAS

As always, the entire Southwest experience was perfect. Purchasing the tickets on the Southwest web site was effortless, departure and arrival gates were spotless and comfortable, plane was clean and comfortable, crew was excellent and flight was on time. Wheelchair service in Las Vegas at departure was somewhat chaotic and disjointed, but I am not sure if that was Southwest problem, airport problem or combination.

4.0 Mediocre

Ashish, Sep 2025

PHX-OGG

Southwest airlines boarding process is the worst. Period.

8.0 Very good

Verified traveler, Sep 2025

LAS-DTW

Good

10.0 Wonderful

Verified traveler, Sep 2025

CLT-BWI

Always liked SW

10.0 Wonderful

Lynda, Sep 2025

MDW-OKC

Clear communication

10.0 Wonderful

Lynda, Sep 2025

BNA-MDW

On time-smooth flights-clear communication

Everything you need to know for your flight from Chicago Midway Airport to Orlando Airport

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First Class flights from Chicago Midway Airport to Orlando Airport

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MDW - MCO

$79 Find Cheap Southwest Flights from Chicago Midway Airport to Orlando Airport

Search hundreds of travel sites at once for deals on Southwest flights from Chicago Midway Airport to Orlando Airport

Cheap Southwest Flight Deals from Chicago Midway Airport to Orlando Airport

Recent round-trip Southwest flight deals from Chicago Midway Airport to Orlando Airport

Recent one-way Southwest flight deals from Chicago Midway Airport to Orlando Airport

Recent last minute Southwest flight deals from Chicago Midway Airport to Orlando Airport

Recent direct Southwest flight deals from Chicago Midway Airport to Orlando Airport

Good to know

When to Book Flights with Southwest from Chicago Midway Airport to Orlando Airport

FAQs for flying to Orlando Airport with Southwest

Is Southwest the cheapest airline to fly with from Chicago Midway Airport to Orlando Airport?

What is the cheapest Southwest flight from Chicago Midway Airport to Orlando Airport?

Does Southwest fly direct to Orlando Airport from Chicago Midway Airport?

What’s the cheapest day of the week to fly from Chicago Midway Airport to Orlando Airport with Southwest?

What’s the cheapest month to fly from Chicago Midway Airport to Orlando Airport with Southwest?

Southwest Customer Reviews

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Everything you need to know for your flight from Chicago Midway Airport to Orlando Airport

Cabin class types available on flights to Orlando Airport

Cabin classes available on flights to Chicago Midway Airport. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

Complete your trip to Orlando Airport with a hotel stay or car rental

Flights to other popular destinations

The most popular flights on KAYAK according to clicks in the last 2 weeks. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

Find deals for your return flight

Top Southwest flights

The most popular destinations for flights with Southwest according to clicks from KAYAK users. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.