Search Cheap Flights to
Portland from $253

Search 400 airlines and 321,000 hotels worldwide.

Stop Planning & Start Exploring

FREE 24 hour cancellation on most flights

Cheap round-trip flights to Portland

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Spirit Airlines
Spirit Airlines
JetBlue Airways
Delta
Spirit Airlines
Caribbean Airlines
Delta
American Airlines
Air Canada
Copa
American Airlines
Spirit Airlines
American Airlines
United
Cayman Airways
American Airlines

Flights to Portland starting at $253

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 $253 to $708.
  • 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 hotel in Long Bay. Enjoy free WiFi, breakfast (surcharge), and room service. Popular attractions Long Bay Beach and Reach Falls are located ...
8.2/10 Very Good! (164 reviews)
It was lovely there.

Reviewed on Nov 15, 2025

Opens in a new windowSea Cliff Resort
Geejam

Geejam

4.5 out of 5
San San, Port Antonio Port Antonio Portland
Book a stay at this 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! (74 reviews)
It’s a given that Geejam is a beautifully appointed hotel but the real gem is the staff. Spent the last few days at Geejam while they navigated no power and limited internet but they worked to ensure our comfort. Special acknowledgement to Nadine and Brian who went above and beyond!

Reviewed on Nov 17, 2025

Opens in a new windowGeejam
Jamaica Palace Hotel

Jamaica Palace Hotel

3.5 out of 5
Williamsfield Port Antonio Portland
Book a stay at this business-friendly hotel in Port Antonio. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the property ...
8.2/10 Very Good! (258 reviews)
The room was clean. Breakfast and lunch was great. Thr staff was very friendly and accommodating.

Reviewed on Nov 22, 2025

Opens in a new windowJamaica Palace Hotel
Save an average of 15% on thousands of hotels when you're signed in
Great Huts

Great Huts

3 out of 5
8-10 Boston Bay Port Antonio Portland
Book a stay at this beach resort in Port Antonio. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff in our reviews. Popular ...
9/10 Wonderful! (205 reviews)
elp not to offer services like the spa unless they’re actually available, or at least post when they are and how much notice is needed. The food was decent, but it would be nice to have a little more variety or different options each day. Some of the servers could also use a bit of basic training ...

Reviewed on Oct 26, 2025

Opens in a new windowGreat Huts
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.