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Portland from $249

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Cheap round-trip flights to Portland

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Flights to Portland starting at $249

Have you been telling yourself, “2025 is the year I travel more and sit less”? Well, here we are and there you are. So, where are you going? Looks like a flight to Portland is calling. Good thing we can help you bag that flight out of town for cheap, so you can get your resolutions resolved.

Travel like you mean it

When you land it’s not straight to the tourist traps for you. You have things to do and see in Portland that aren’t on a map or in the “Best of. . .” guides. You know this region is filled with hidden haunts, locals-only know favorites, and the off-beat-so-weird-it’s-amazing places. And you plan to find every last one of them. Good thing you’ll save a grip of cash on your flight so you can daytrip far and wide.

You won’t have to wing it

So how do you score that killer deal on a flight to Portland? Easy, go through us. These aren’t pie in the sky deals, but ones you can actually score. Filter flights to Portland by:

  • Hotwire Hot Rate: Do you have a flexible schedule? Hit up the Hotwire Hot Rate and land a super cheap flight to Portland. We’ll reveal the airline and exact time after you book.
  • Price: How low can we go? Find out. We have prices from $249 to $891.
  • Duration: Want to get to Portland as fast as you can? Or maybe you don’t mind taking your time to save a few bucks here and there.
  • Departure or Arrival: Like to arrive in the a.m. to get your day going? Or are you a night owl that knows the best fun happens late night? The choice is yours.

So are you going to live up to those travel plans or kick the can to next year? Book your flight to Portland today and get going.

Last Minute Hotel Deals in Portland

Sea Cliff Resort

Sea Cliff Resort

3 out of 5
Ross Craig, Long Bay, Portland
Stay at this 3-star hotel in Long Bay. Enjoy free WiFi, breakfast (surcharge), and room service. Popular attractions Long Bay Beach and Reach Falls are located ...
8/10 Very Good! (154 reviews)
"The views at the property are exceptional. It’s gives a cabin vibe. It’s a great choice if you want to unplug and relax. I went alone and I felt very peaceful. It’s a small property and the only thing to do onsite is really eat, relax and take in the views. I definitely also recommend that you only ..."

Reviewed on Aug 20, 2025

Sea Cliff Resort
Jamaica Palace Hotel

Jamaica Palace Hotel

3.5 out of 5
Williamsfield, Port Antonio, Portland
Stay at this 3.5-star business-friendly hotel in Port Antonio. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the ...
8.2/10 Very Good! (244 reviews)
"Always wanted to stay there. Property and pool was amazing. Rooms are ok, could use a little work. Breakfast was decent. Would return for a short stay"

Reviewed on Aug 7, 2025

Jamaica Palace Hotel
Geejam

Geejam

4.5 out of 5
San San, Port Antonio, Port Antonio, Portland
Stay at this 4.5-star luxury hotel in Port Antonio. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. ...
9.6/10 Exceptional! (71 reviews)
"Beautiful hotel"

Reviewed on Aug 20, 2025

Geejam
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LF Jungle Retreat

LF Jungle Retreat

3 out of 5
Lots 32-40, Willamsfield, Port Antonio
Stay at this 3-star hotel in Port Antonio. Enjoy free WiFi, free parking, and a rooftop terrace. Popular attractions Trident Castle and Frenchman's Cove Beach ...
8.4/10 Very Good! (40 reviews)

Reviewed on Aug 25, 2025

LF Jungle Retreat
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.