$39 Cheap flight deals from Port Charlotte (RSW) to Winter Garden (ORL)

Earn rewards on top of your airline miles with Orbitz Rewards

Many airlines offer flexible change policies

Sign up to receive text alerts about your trip

This Weekend's Flight Deals from Port Charlotte to Winter Garden

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Fri, Oct 10 - Fri, Oct 10
RSW
Southwest Florida Intl.
MCO
Orlando Intl.
$342 Roundtrip, found 6 hours ago
$342
Roundtrip
found 6 hours ago
Select Southwest Airlines flight, departing Fri, Oct 10 from Southwest Florida Intl. to Orlando Intl., returning Fri, Oct 10, priced at $342 found 6 hours ago

Airfares from $39 One Way, $77 Round Trip from Port Charlotte to Winter Garden

Prices starting at $77 for return flights and $39 for one-way flights to Winter Garden were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Thu, Oct 23 - Thu, Oct 30
RSW
Fort Myers
MCO
Orlando
$77 Roundtrip, found 5 days ago
$77
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Thu, Oct 23 from Fort Myers to Orlando, returning Thu, Oct 30, priced at $77 found 5 days ago
Thu, Oct 23 - Thu, Oct 30
RSW
Fort Myers
MCO
Orlando
$87 Roundtrip, found 5 days ago
$87
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Thu, Oct 23 from Fort Myers to Orlando, returning Thu, Oct 30, priced at $87 found 5 days ago
Fri, Oct 31 - Tue, Nov 4
RSW
Fort Myers
MCO
Orlando
$121 Roundtrip, found 5 days ago
$121
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Fri, Oct 31 from Fort Myers to Orlando, returning Tue, Nov 4, priced at $121 found 5 days ago
Fri, Oct 31 - Tue, Nov 4
RSW
Fort Myers
MCO
Orlando
$131 Roundtrip, found 5 days ago
$131
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Fri, Oct 31 from Fort Myers to Orlando, returning Tue, Nov 4, priced at $131 found 5 days ago
Sun, Jan 11 - Wed, Jan 14
RSW
Fort Myers
MCO
Orlando
$137 Roundtrip, found 6 days ago
$137
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Sun, Jan 11 from Fort Myers to Orlando, returning Wed, Jan 14, priced at $137 found 6 days ago

Winter Garden economy flight packages

Price found within the past 48 hours. Click for updated prices.
Westgate Vacation Villas Resort
4.0-star property

Westgate Vacation Villas Resort

8/10 Very Good! (1,684 reviews)

Nov 7 - Nov 9

2 night stay

Sarasota (SRQ) to Orlando (MCO)

Southwest Airlines • Roundtrip • Coach
Price was $421, price is now $280 per person
$280
per person
found 23 hours ago
Always a good time at Westgate Resort

Reviewed on May 3, 2025

Westgate Town Center Resort
4.0-star property

Westgate Town Center Resort

8/10 Very Good! (1,360 reviews)

Nov 7 - Nov 9

2 night stay

Sarasota (SRQ) to Orlando (MCO)

Southwest Airlines • Roundtrip • Coach
Price was $439, price is now $292 per person
$292
per person
found 23 hours ago
We took our 3 year old nephew here and he had a BLAST! There is so much to do, we didn’t leave for 2 of the 3 days that we stayed. He’s about 42 inches which got him on most of the slides but not all. Keep size in mind when booking for little ones because if they’re under 40in they’re limited to the slides. He was a little bummed that he couldn’t do the pirates plunge (biggest slide) but there were enough distractions that it didn’t matter. Also, the lazy river is great! Just be careful with the big kids, they tend to knock the little ones over or into the wall because they’re just running through it. The water park is an extra fee FYI There’s “ice” skating, swan paddle boats, water park, mini golf, a train trolly, restaurants, arcade, jungle gym, multiple pools. Definitely a good spot if you don’t want to do the parks every day that you’re there! Highly recommend.

Reviewed on Apr 6, 2025

Parkway International Resort
3.0-star property

Parkway International Resort

9.4/10 Exceptional! (1,995 reviews)

Nov 7 - Nov 9

2 night stay

Sarasota (SRQ) to Orlando (MCO)

Southwest Airlines • Roundtrip • Coach
Price was $426, price is now $303 per person
$303
per person
found 23 hours ago
Very accommodating, convenient location, overall pleasant stay.

Reviewed on Sep 21, 2025

Don't see what you're looking for?
See all available trips from Port Charlotte to Winter Garden
View all trips

More About Flying To Winter Garden from Port Charlotte

Route Information for Flights from Port Charlotte to Winter Garden

Origin Airport IATA Code
RSW
Destination Airport IATA Code
ORL
Distance
134 mi
Direct Flight Airlines
Southwest Airlines
Earliest Flight Arrival
12:05PM UTC
Latest Flight Arrival
10:50PM UTC

Port Charlotte to Winter Garden

Orbitz can provide you with the greatest deals on a wide range of Port Charlotte to Winter Garden flights. Orbitz offers guaranteed low prices and offers you the convenience of cutting-edge mobile tools thus providing you with your best travel experience ever.

Mobile Apps for Port Charlotte to Winter Garden Flights

You can use our mobile app to find the cheapest prices for flights from Port Charlotte to Winter Garden. With this cutting-edge technology, you can check up on your flight’s status, gate number and luggage claim handling, and reserve exclusive deals on top hotels at short notice.

Loyalty Rewarded

For travelers who regularly book Port Charlotte to Winter Garden flights, our frequent flyer program offers even more low-cost air tickets. You will be able to store your miles in your personal Orbitz account and add them with ease to your future reservations.

Trouble-Free Traveling With Flight Alerts

Orbitz will not only provide you with the assistance that you require when purchasing flights from Port Charlotte to Winter Garden but will ensure that you remain fully updated on any flight delays, changes or disruptions by providing free alerts. Your Port Charlotte to Winter Garden flights alerts can be sent directly to your phone or email. You can also opt for these alerts to be sent to your family and friends so that everyone is kept informed of your travel plans.

 Budget Flying Made Simple

Finding cheap flights from Port Charlotte to Winter Garden is easy with Orbitz. You can pick and choose airlines for your international flights to create inexpensive yet convenient travel arrangements.

More Destinations

More Destinations

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.