$147 Cheap flight deals from Jacksonville (JAX) to Freeport (AUG)

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 Jacksonville to Freeport

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.

Sat, Oct 10 - Fri, Oct 16
JAX
Jacksonville Intl.
PWM
Portland Intl. Jetport
$826 Roundtrip, found 3 days ago
$826
Roundtrip
found 3 days ago
Select American Airlines flight, departing Sat, Oct 10 from Jacksonville Intl. to Portland Intl. Jetport, returning Fri, Oct 16, priced at $826 found 3 days ago

Airfares from $147 One Way, $429 Round Trip from Jacksonville to Freeport

Prices starting at $429 for return flights and $147 for one-way flights to Freeport were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Mon, Nov 23 - Fri, Nov 27
JAX
Jacksonville
PWM
Portland
$429 Roundtrip, found 3 days ago
$429
Roundtrip
found 3 days ago
Select United flight, departing Mon, Nov 23 from Jacksonville to Portland, returning Fri, Nov 27, priced at $429 found 3 days ago
Mon, Nov 23 - Fri, Nov 27
JAX
Jacksonville
PWM
Portland
$434 Roundtrip, found 3 days ago
$434
Roundtrip
found 3 days ago
Select United flight, departing Mon, Nov 23 from Jacksonville to Portland, returning Fri, Nov 27, priced at $434 found 3 days ago
Mon, Nov 23 - Fri, Nov 27
JAX
Jacksonville
PWM
Portland
$444 Roundtrip, found 3 days ago
$444
Roundtrip
found 3 days ago
Select American Airlines flight, departing Mon, Nov 23 from Jacksonville to Portland, returning Fri, Nov 27, priced at $444 found 3 days ago
Mon, Nov 23 - Fri, Nov 27
JAX
Jacksonville
PWM
Portland
$444 Roundtrip, found 3 days ago
$444
Roundtrip
found 3 days ago
Select United flight, departing Mon, Nov 23 from Jacksonville to Portland, returning Fri, Nov 27, priced at $444 found 3 days ago
Wed, Oct 14 - Wed, Oct 21
JAX
Jacksonville
PWM
Portland
$456 Roundtrip, found 6 days ago
$456
Roundtrip
found 6 days ago
Select United flight, departing Wed, Oct 14 from Jacksonville to Portland, returning Wed, Oct 21, priced at $456 found 6 days ago

Freeport economy flight packages

Price found within the past 48 hours. Click for updated prices.
The Docent's Collection at 121 Middle Street
3.5-star property

The Docent's Collection at 121 Middle Street

9.6/10 Exceptional! (400 reviews)

Nov 25 - Nov 29

4 night stay

Jacksonville (JAX) to Portland (PWM)

Delta • Non-stop • Coach

Portland (PWM) to Jacksonville (JAX)

Southwest Airlines • Non-stop • Coach
Price was $1,606, price is now $1,379 per person
$1,379
per person
found 1 day ago

Evalina Hotel
2.5-star property

Evalina Hotel

10/10 Exceptional! (13 reviews)

Nov 25 - Nov 29

4 night stay

Jacksonville (JAX) to Portland (PWM)

Delta • Non-stop • Coach

Portland (PWM) to Jacksonville (JAX)

Southwest Airlines • Non-stop • Coach
Price was $1,855, price is now $1,471 per person
$1,471
per person
found 1 day ago
Centrally located in the Old Port, with views of the harbor, this was a last minute — therefore pricey — excellent find for a fall weekend getaway. Stylish, elegant rehab of 19th century granite industrial building. Whimsical decor notes referring to 19th century owner Evalina Fox. Nicely appointed kitchenette — though if you came to Portland for the foodie scene, you might end up just using it for breakfast, as we did. Only sour note was the disco music (coming in via the ventilation system?) from a nearby establishment audible during business hours. Well, if you pick a hotel in the middle of things, you get the noise and bustle that comes from being in the middle of things. That said, we’d come again, but shoot for a penthouse/upper floor unit farther from the street-level mania.

Reviewed on Oct 5, 2026

The Docent's Collection at 178 Middle Street
3.5-star property

The Docent's Collection at 178 Middle Street

9.6/10 Exceptional! (70 reviews)

Nov 25 - Nov 29

4 night stay

Jacksonville (JAX) to Portland (PWM)

Delta • Non-stop • Coach

Portland (PWM) to Jacksonville (JAX)

Southwest Airlines • Non-stop • Coach
Price was $1,689, price is now $1,443 per person
$1,443
per person
found 1 day ago
This place is gorgeous! I highly recommend it. Beautiful modern design with everything you might need. Great central location. A bit hard to find. Parking was A lot! But made life easier. Will stay here again.

Reviewed on Oct 6, 2026

Don't see what you're looking for?
See all available trips from Jacksonville to Freeport
View all trips

More About Flying To Freeport from Jacksonville

Route Information for Flights from Jacksonville to Freeport

Origin Airport IATA Code
JAX
Destination Airport IATA Code
AUG
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Jacksonville to Freeport

Rack up your savings with low-cost flights from Jacksonville to Freeport with Orbitz On-the-Go. Orbitz On-the-Go offers mobile-only deals and cutting edge mobile tools to help you find bargain flights from Jacksonville to Freeport.

Mobile-Only Deals on Jacksonville to Freeport flights

Find guaranteed low prices on Jacksonville to Freeport flights using Orbitz On-the-Go. You can book discount domestic flights from Jacksonville to Freeport, and international tickets on Jacksonville to Freeport flights using our mobile site and apps.

Free Alerts Are No Surprise

Not only will you find cheap tickets on flights from Jacksonville to Freeport, but Orbitz free alerts will keep you up to speed on flight status, plus gate and baggage claim details. Receive instant updates via your choice of email, voice or text. Orbitz keeps you easily on task and on budget.

Share Itineraries on Flights from Jacksonville to Freeport

Are you traveling for business, pleasure or a combination of both? Keep family, friends and business contacts posted on flight and gate info. Just use MyTrips for iPhone, Android and web phones like Blackberry and Windows.

Add Smiles to Your Miles with Sales and Deals on Jacksonville to Freeport Flights

Travel planning is easy when you store your frequent flyer and loyalty program information on your Orbitz account. Then snag a low-fare air ticket on Jacksonville to Freeport flights, and you’re done. No muss, no fuss. Your miles will fly by with Orbitz On-the-Go cutting edge mobile tools and guaranteed low prices.

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.