Is Southwest the cheapest airline to fly with from Chicago O'Hare Intl Airport to Orlando Airport?

With an average price of $320 return, Southwest is not the cheapest airline to fly from Chicago O'Hare Intl Airport to Orlando Airport with. Instead, for the lowest price, our data suggests flying with Spirit Airlines, where a return flight costs $175 on average.

Does Southwest fly direct to Orlando Airport from Chicago O'Hare Intl Airport?

Yes, Southwest does offer direct flights for the route, with around 14 flights per week.

What’s the cheapest day of the week to fly from Chicago O'Hare Intl Airport to Orlando Airport with Southwest?

On average, the cheapest day of the week to fly from Chicago O'Hare Intl Airport to Orlando Airport with Southwest is Tuesday, when prices are around $78. The most expensive day is generally Wednesday, where the average price is around $108.

What’s the cheapest month to fly from Chicago O'Hare Intl Airport to Orlando Airport with Southwest?

The cheapest month for Southwest flights to Orlando Airport from Chicago O'Hare Intl Airport is generally September, where plane tickets cost $112 on average. If possible, try to avoid the most expensive months of November and March, where tickets cost $219 and $334 respectively.

$79 Cheap Southwest Flights from Chicago O'Hare Intl Airport to Orlando Airport

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Flight Deals

Cheap Southwest Flight Deals from Chicago O'Hare Intl Airport to Orlando Airport

Here are some of the best deals found on KAYAK recently from Southwest for round-trip flights from Chicago O'Hare Intl 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 O'Hare Intl Airport to Orlando Airport

Wed, Dec 24 - Wed, Dec 31

1:45 pm - 8:25 pmORD-MCO

5h 40m1 stop

6:50 am - 12:15 pmMCO-ORD

6h 25m1 stop

$177Southwest

Find Deal

Sat, Feb 28 - Wed, Mar 4

3:45 pm - 10:55 pmORD-MCO

6h 10m1 stop

7:30 am - 12:15 pmMCO-ORD

5h 45m1 stop

$187Southwest

Find Deal

Wed, Dec 31 - Wed, Jan 7

1:45 pm - 9:45 pmORD-MCO

7h 00m1 stop

7:30 am - 12:15 pmMCO-ORD

5h 45m1 stop

$197Southwest

Find Deal

Mon, Jan 19 - Sat, Jan 24

1:45 pm - 7:35 pmORD-MCO

4h 50m1 stop

6:10 am - 1:00 pmMCO-ORD

7h 50m1 stop

$217Southwest

Find Deal

Tue, Oct 28 - Fri, Oct 31

1:30 pm - 9:40 pmORD-MCO

7h 10m2 stops

7:00 am - 12:45 pmMCO-ORD

6h 45m1 stop

$218Southwest

Find Deal

Wed, Nov 12 - Fri, Nov 14

3:45 pm - 7:25 pmORD-MCO

2h 40mnonstop

9:05 am - 11:10 amMCO-ORD

3h 05mnonstop

$221Southwest

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Sun, Feb 15 - Fri, Feb 20

2:15 pm - 9:10 pmORD-MCO

5h 55m1 stop

6:15 am - 1:00 pmMCO-ORD

7h 45m1 stop

$223Southwest

Find Deal

Mon, Nov 10 - Fri, Nov 14

6:05 am - 9:45 amORD-MCO

2h 40mnonstop

7:45 pm - 9:50 pmMCO-ORD

3h 05mnonstop

$231Southwest

Find Deal

Sat, Feb 21 - Thu, Feb 26

3:05 pm - 10:20 pmORD-MCO

6h 15m1 stop

9:25 pm - 12:15 pmMCO-ORD

15h 50m2 stops

$234Southwest

Find Deal

Sat, Feb 28 - Wed, Mar 4

3:45 pm - 10:55 pmORD-MCO

6h 10m1 stop

8:55 pm - 12:50 pmMCO-ORD

16h 55m2 stops

$239Southwest

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Useful Info

Low season	September
High season	March
Cheapest flight	$79
Average price round-trip	$259

Best time to beat the crowds with an average 23% drop in price.

Most popular time to fly with an average 33% increase in price.

Flight from Chicago O'Hare Airport to Orlando Airport

(price for this month)

When to Book Flights with Southwest from Chicago O'Hare Intl Airport to Orlando Airport

Average price per month

Flight prices as travel date approaches

Is Southwest the cheapest airline to fly with from Chicago O'Hare Intl Airport to Orlando Airport?
With an average price of $320 return, Southwest is not the cheapest airline to fly from Chicago O'Hare Intl Airport to Orlando Airport with. Instead, for the lowest price, our data suggests flying with Spirit Airlines, where a return flight costs $175 on average.
What is the cheapest Southwest flight from Chicago O'Hare Intl Airport to Orlando Airport?
In the last 3 days, the lowest price for a flight with Southwest from Chicago O'Hare Intl Airport to Orlando Airport was $89 for a return flight and $40 for a one-way flight.
Does Southwest fly direct to Orlando Airport from Chicago O'Hare Intl Airport?
Yes, Southwest does offer direct flights for the route, with around 14 flights per week.
What’s the cheapest day of the week to fly from Chicago O'Hare Intl Airport to Orlando Airport with Southwest?
On average, the cheapest day of the week to fly from Chicago O'Hare Intl Airport to Orlando Airport with Southwest is Tuesday, when prices are around $78. The most expensive day is generally Wednesday, where the average price is around $108.
What’s the cheapest month to fly from Chicago O'Hare Intl Airport to Orlando Airport with Southwest?
The cheapest month for Southwest flights to Orlando Airport from Chicago O'Hare Intl Airport is generally September, where plane tickets cost $112 on average. If possible, try to avoid the most expensive months of November and March, where tickets cost $219 and $334 respectively.

8.0

Very good4,238 verified ratings

8.0Comfort

8.1Boarding

7.0Food

8.6Crew

7.5Entertainment

Pros +

Cons -

Show reviews that mention

6.0 Okay

Thomas, Oct 2025

DAL-SAT

Late again.

6.0 Okay

Thomas, Oct 2025

CMH-DAL

Just the usual delays

2.0 Poor

TODD, Oct 2025

CMH-MDW

2.5 hours late but no one said why.

10.0 Wonderful

Aleksandar, Oct 2025

OAK-SAN

On time, and it was not full flight

4.0 Mediocre

Annette, Oct 2025

LGA-MCI

Flight was delayed due to plane not passing inspection And one of the crew had to time out and we had to wait for another one A 3 hour delay

10.0 Wonderful

Gerald, Oct 2025

SJC-PDX

Boarding quick & efficient. Crew was friendly. Arrived early

6.0 Okay

Hung, Oct 2025

PHX-ABQ

mandatory demand customer to check their carry on because not enough people check bags.

8.0 Very good

Annette, Oct 2025

MCI-LGA

Good non stop is always good

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!

Everything you need to know for your flight from Chicago O'Hare Intl Airport to Orlando Airport

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Cabin class types available on flights to Orlando Airport

First Class flights from Chicago O'Hare Intl Airport to Orlando Airport

Business Class flights from Chicago O'Hare Intl Airport to Orlando Airport

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$79 Find Cheap Southwest Flights from Chicago O'Hare Intl Airport to Orlando Airport

Search hundreds of travel sites at once for deals on Southwest flights from Chicago O'Hare Intl Airport to Orlando Airport

Cheap Southwest Flight Deals from Chicago O'Hare Intl Airport to Orlando Airport

Recent round-trip Southwest flight deals from Chicago O'Hare Intl Airport to Orlando Airport

Recent one-way Southwest flight deals from Chicago O'Hare Intl Airport to Orlando Airport

Recent last minute Southwest flight deals from Chicago O'Hare Intl Airport to Orlando Airport

Recent direct Southwest flight deals from Chicago O'Hare Intl Airport to Orlando Airport

Good to know

When to Book Flights with Southwest from Chicago O'Hare Intl Airport to Orlando Airport

FAQs for flying to Orlando Airport with Southwest

Is Southwest the cheapest airline to fly with from Chicago O'Hare Intl Airport to Orlando Airport?

What is the cheapest Southwest flight from Chicago O'Hare Intl Airport to Orlando Airport?

Does Southwest fly direct to Orlando Airport from Chicago O'Hare Intl Airport?

What’s the cheapest day of the week to fly from Chicago O'Hare Intl Airport to Orlando Airport with Southwest?

What’s the cheapest month to fly from Chicago O'Hare Intl Airport to Orlando Airport with Southwest?

Southwest Customer Reviews

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Everything you need to know for your flight from Chicago O'Hare Intl Airport to Orlando Airport

Cabin class types available on flights to Orlando Airport

Cabin classes available on flights to Chicago O'Hare Intl 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.

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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.