Visiting Maine has been on my radar for a while and this year, I finally pulled the trigger. The inspiration to actually make it happen came a few months ago while watching TV. An episode of Bizarre Foods — Delicious Destinations with Andrew Zimmern came on and he was visiting Portland, Maine. During the episode he ate mouthwatering foods like fresh Maine lobster, lobster rolls, and whoopie pies. While it was clear that Portland has a great food scene, the city itself, also piqued my interest.

During our travels, Annie, and I have discovered our love for smaller, walkable cities. Places like Charleston and Denver rank high on our list of favorite cities we’ve spent time in. After a little research, I’m confident we’ll love Portland too. It looks like a perfect mix between large town and small city, with a relaxing culture, fresh seafood and a thriving collection of breweries. We’re definitely excited to eat and drink our way through Portland!

Since we only need two or three days in Portland, I looked for another Maine location to add to the trip. So after three nights in Portland, we’re going to drive up the coast about 150 miles and stay three nights in Bar Harbor. Bar Harbor is a stone’s throw from Acadia National Park, one of America’s most popular national parks. Bar Harbor is also home to Cadillac Mountain, the highest point on the eastern seaboard, where you can often see the country’s first sunrise.

Needless to say we’re really excited about this trip!

Airfare

For the outbound flight, we’re flying into Portland International Jetport. On the way back, we’re flying out of Bangor International Airport, so we don’t have to drive all the way back to Portland. The Bangor airport is only about an hour from Bar Harbor.

Luckily, Chicago O’Hare has non-stop flights to and from both Portland and Bangor. Round-trip flights were pretty expensive at $578 per person. I always search flights as round-trip and as two one-way segments, because sometimes you can find better deals that way. Additionally, I like searching in one-way segments because it gives me more flexibility. If I choose to, I can redeem miles one direction and pay cash for the other.

Chicago to Portland

For the first leg of the trip, I decided to redeem American Airlines miles rather than pay cash.

Booking

The cash price for two tickets was $500, but I redeemed 26,000 miles instead. That comes out to a value of 1.92 cents per mile, which is well above the average of 1.4 cents per mile. Whenever you redeem miles on a domestic flight, the airlines still charge nominal fees. So in total, the cash cost for the flight from Chicago to Portland was $11.

Pro Tip: American Airlines allows you to change or cancel your trip for free. So I make a habit of checking every so often to see if there’s a better deal to be had. For this specific flight, the number of miles kept dropping, so I cancelled and rebooked the tickets four times.

I originally booked the flight for 37,000 miles, then 35,000, then 31,000, then 29,000 and finally 26,000 miles.

Bangor to Chicago

When I first started searching, the cash price for the flight home from Bangor was expensive, but so were the number of miles American Airlines wanted. Even though I could get a free flight, I didn’t want to redeem over 70,000 miles to do so.

So I spent a few weeks tracking the price and while there was a little fluctuation, it wasn’t changing enough to wait any longer. I finally booked the flights for $329 per person or $658 total.

Fortunately, I didn’t have to pay that entire amount of out pocket. That’s because I had $450 in American Airlines gift cards that I had acquired from my Hilton Honors American Express Aspire® Card and MyPoints.com.

Hilton Honors Aspire Card

In years past, the Hilton Honors Aspire card offers $250 in annual airline credits. These credits were intended to be used for incidental fees like baggage, seat assignment or change fees. However, up until 2021, there was a loophole whereby the credit would trigger when buying gift cards. So I would buy $250 in American Airlines gift cards each year and American Express would reimburse those purchases making the gift cards completely free.

American Express refreshed the Hilton Honors Aspire card in October of 2023 and changed the annual airline credit. The card now offers $200 in annual airline credits, available in $50 quarterly increments. That’s $50 less in total, but now it can be used for any eligible flight purchase, including gift cards.

MyPoints

The other source of American Airlines gift cards was MyPoints.com. MyPoints is similar to other shopping portals which give you points or miles if you start your purchase from their website. However, it’s unique in that they have even more ways to earn points, like doing surveys or watching videos. After earning enough points, you can redeem them for gift cards to lots of different merchants, including American Airlines.

Booking

As mentioned above, the price for the flight from Bangor to Chicago cost $658 for two tickets. I used $450 in American Airlines gift cards, dropping the total cost to $208.

To cover the rest of the price, I paid for the tickets with my Chase Sapphire Reserve® Card. I used this card because of the many travel-related benefits, like trip cancellation insurance, trip delay reimbursement and lost baggage reimbursement. But the main reason was for the annual travel credits.

Cardholders receive $300 in travel credits each cardmember year and I hadn’t used any up until this point. Chase automatically credited the $219 ($11 leftover on the outbound flight and $208 leftover on the inbound flight) back to me within a few days.

Pro Tip: Just like with the outbound flight, the inbound flight’s price kept dropping. I’ve now cancelled and rebooked this flight twice. The original cost was $658, then $618 and finally $473. The amount saved is available as a travel credit that I can use for a future flight.

So to wrap up the airfare, I redeemed 29,000 miles and paid $473 for the flights. But after using gift cards and the Chase Sapphire Reserve annual travel credits, I spent nothing, saving a total of $823! 

Hotel

Canopy by Hilton Portland Waterfront

When it came to hotel options, I wanted to use my free night award from Hilton, which expires in August. This is another benefit I receive from owning the Hilton Honors American Express Aspire® Card. Every card-opening anniversary, I receive a free night award certificate, valid at virtually any Hilton property worldwide. Plus, I also had tons of Hilton Honors points I could redeem for the other two nights.

A quick search of Hilton properties in downtown Portland, uncovered three options. A Hampton Inn, a Hilton Garden Inn and the Canopy by Hilton Portland Waterfront. To me, the decision to choose the latter was easy. The Canopy by Hilton was less than three years old and the most expensive hotel of the three.

I love newer and recently renovated hotels because they’re more likely to be clean and modern. When using my free night certificate, I also look for high-priced hotels so I can get the highest value possible.

When I made the booking, a standard room was going for $2,164 for three nights. A few weeks later, those same dates would now cost almost $2,600. From a points perspective, Hilton was asking for 80,000 points per night.

To use a free night award certificate with Hilton, you have to call them to book it. I gave the agent my award certificate number, the dates I wanted to stay and also that I wanted to use points for the other two nights.

Note: When you use a free night award certificate, it’ll appear on the reservation like you used points for that night. For whatever reason, Hilton’s system doesn’t show that correctly. So in the screen shot above, it says I redeemed 240,000 points, but I actually only redeemed 160,000. If you’re nervous about this, you can always review your Hilton account activity to confirm the correct amount of points were deducted.

In total, I booked our 3-night stay using my free night award certificate and 160,000 Hilton points. That saved me $2,164 and we get to stay at what is essentially a brand-new hotel in the heart of downtown Portland!

Bar Harbor Inn

For our 3-night stay in Bar Harbor, I booked a room at the Bar Harbor Inn. I found this hotel from a Conde Nast Traveler article about road-tripping up the Maine coast. The article mentioned the Bar Harbor Inn for its location and the Balance Rock Inn for its quaint intimacy.

However, as soon as I went to the Bar Harbor Inn’s website, I knew this was the place for us. It seems like a perfect combination of location, luxury and history.

The location is right in the heart of downtown and stands on eight acres along the coast of Frenchman Bay.

From a luxury standpoint, I was struck by the property’s photo gallery and the fact that they a luxury spa and two restaurants featuring waterfront dining. Additionally, there’s a slogan on their website that says “When People Think Coastal Maine Inn, This Is What They Picture.” I was sold!

Finally, it’s historic. It was originally built in 1887 as a men’s club, but has been operated as an inn since 1950. The current owners have made several updates and improvements over the years, including adding a new infinity-edge swimming pool and a continental breakfast building in 2019.

Booking

The Bar Harbor Inn isn’t affiliated with any major hotel brands. That rendered my Hilton and Marriott points useless. It also wasn’t available to book through third-party sites, like the Chase Travel Portal. So unfortunately that also meant that I couldn’t use my stash of Chase Ultimate Rewards points too book either.

So the only option was to book directly with the hotel and pay cash. I reserved a king room with a “grounds” view for a total cost, including taxes, of $1,533.

Rental Car

Rental cars are pretty expensive these days. I searched at Costco Travel, Budget, Avis, and a few others, but I found the most reasonable price at Budget. As always, after booking I input my reservation details in AutoSlash. They will monitor and email me if they find a better deal.

Maine 2024 Redemption Table

	Retail Cost	Our Cost	Miles and Points Used	Points Source
2 one-way tickets from Chicago (ORD) to Portland (PWM)	$250 per person ($500 total)	$0	26,000 AA miles	- Citi AAdvantage credit cards - E-rewards surveys - Miles for Opinions surveys - CSR annual travel credit
2 one-way tickets from Bangor (BGR) to Chicago (ORD)	$237 per person ($473 total)	$0	$450 American Airlines gift cards	- Hilton Honors Aspire Card - Mypoints.com - CSR annual travel credit
3 nights at the Canopy by Hilton Portland Waterfront	$652 per night + taxes ($2,164 total)	$0	1 free night certificate and 160,000 Hilton points	- Hilton Honors Aspire Card - Hilton Honors Card - E-rewards surveys - Guest Opinion Rewards surveys - Hilton hotel stays
3 nights at the Bar Harbor Inn	$469 per night + taxes ($1,533 total)	$1,533	N/A	N/A
6 day car rental	$466	$466	N/A	N/A
Total	$5,136	$1,999	- $450 AA gift cards - 26,000 AA miles - 1 free night certificate - 160,000 Hilton points	- $3,137 in total savings - 61% off retail cost

Bottom Line

All in all, I saved around 60% off the retail cost of this trip by using miles and credit card perks. Annie and I are both particularly excited about this trip. We can’t to experience what each of these small cities have to offer, from the spectacular scenery to the delicious food scene!

Trip Report Index

1. Using Points and Miles to get to Maine
2. Flight from Chicago to Portland
3. Canopy by Hilton Portland Waterfront
4. Bar Harbor Inn