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Using Points and Miles to Get to Boston October 2024

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Our daughter Brynn is a freshman volleyball player at Northeastern University in Boston. Once her team’s schedule was released over the summer, we wanted find a weekend to see her play in her home arena. We had a few dates to choose from and decided to visit the last weekend of October. That weekend was also parents weekend, so Annie, Rory and I traveled to Boston to visit her.

I began researching flights and hotels while we were still deciding which weekend to visit. In general, I found prices to be pretty high across the board. After watching airfare for several months, I noticed that as soon as the calendar flipped to August, prices went up and never came back down.

These days, most flights are full flights, so there’s no incentive for airlines to reduce prices as the departure date nears. For future air travel, I’m going to book tickets at least three months in advance. In this case, I had a stash of airline miles, travel credits and points, and used all three to book this “free” trip!

In This Post

Airfare

Brynn had games Friday and Saturday afternoon. So we chose to fly to Boston on a 7a.m. flight Friday morning. For the trip home, we knew we were going to leave on Sunday but were very flexible on the departure time. I compared costs on multiple airlines, both using miles and paying cash. After an extensive amount of research, the best options for us were a United Airlines flight out to Boston and an American Airlines flight coming home.

Chicago to Boston

Initially, we planned to visit Brynn in November and I had booked one-way tickets on United. The cash price was $475.41, but I used $400 in United TravelBank cash to bring the cost down to just $75.41. I received those TravelBank credits from my Hilton Honors American Express Aspire Card. Until late 2023, the card had a $250 annual airline reimbursement perk, meant to offset incidental airline fees. However, adding money to TravelBank was a loophole that would qualify for reimbursement. So at the start of every calendar year, I would add $250 to my TravelBank to use at some future date. Within a few days, that money would be credited back to me as statement credit.

Note: The Hilton Honors Aspire Card airline credit perk now offers up to $50 in statement credits each quarter, for a total of up to $200 back each year on eligible flight purchases.

When we changed the weekend of our visit, I cancelled the original United flight and received $475.11 as a travel credit. The new flight cost only $355.41, so I applied my travel credit, which covered the entire amount. Plus, I still have $120 in travel credits to use on my next United flight.

Boston to Chicago

Flights back to Chicago on Sunday were expensive. It didn’t matter what airline or the time of day. So I decided to use some of my American Airlines AAdvantage miles to book our tickets home. I didn’t get amazing value from this redemption, but it still reduced my cash cost to almost nothing.

The cash cost for three tickets on the 10:23am flight was $835. Instead of paying cash, I used 79,500 miles and paid $16.80 in taxes and fees.

Hotel

Hyatt Centric Faneuil Hall Boston

Northeastern University is located in Boston’s Back Bay neighborhood. It’s a nice neighborhood but doesn’t have as many restaurants or activities as downtown Boston. Since the school is only a handful of subway stops from downtown, I decided to book a hotel downtown instead.

I had free night awards available from both Marriott and IHG, so I started my search with them. The issue I ran into is that those free night awards are capped at 35,000 points (Marriott) and 40,000 points (IHG). While it’s possible to top those off with some points, I still couldn’t find any hotels in the area with point prices low enough for me to utilize my award certificates.

So I turned my search over to Hyatt. I had Hyatt points that I intended to use for a trip to Hawaii in 2020 that never happened. Those points were basically a sunk cost at this point, so I decided it was time to put them to use.

I was deciding between the Hyatt Regency Boston and the Hyatt Centric Faneuil Fall Boston. The Hyatt Regency didn’t have any two bedroom rooms available, so the choice was made for the Hyatt Centric. The Hyatt Centric brand is described as full-service lifestyle hotels located in prime destinations. That was certainly true for the Hyatt Centric in Boston. It’s located next door to the Old Statehouse, which is a stop along the Freedom Trail. Plus, as the hotel’s name suggests, it’s also very close to Faneuil Hall and Quincy Market, other vary popular tourist attractions.

Hyatt Centric Faneuil Fall Boston (Photo Courtesy of Hyatt).

Cash prices were sky high, coming in at $1,337 the day I finally booked the hotel.

Luckily they had rooms with two beds available for 29,000 points per night. I already had 43,000 points in my Hyatt account, so I transferred another 15,000 points from Chase to Hyatt. I’ve been rapidly building my Chase Ultimate Rewards points balance recently, so I didn’t mind parting with some points to top of my Hyatt balance. Chase Ultimate Rewards is my favorite transferable points program because it’s relatively easy to earn points and you can transfer those points to airlines and hotel partners.

So two nights in Boston cost me 58,000 Hyatt points, saving me $1,337.

Boston 2024 Redemption Table

Retail CostOur CostMiles and Points UsedPoints Source
3 one-way tickets from Chicago (ORD) to Boston (BOS)$118 per person ($355 total)$0$355 United TravelBank credits- Amex Hilton Aspire card
3 one-way tickets from Boston (BOS) to Chicago (ORD)$278 per person
($835 total)		$1779,500 AA miles- Amex Hilton Aspire card
2 nights at Hyatt Centric Faneuil Hall Boston$549 per night + taxes ($1337 total)$058,000 Hyatt points- Chase Ultimate Rewards
Total$2,527$17- 79,500 UA miles
- 58,000 Hyatt points
- $355 travel credits		- $2,510 in total savings
- 99% off retail cost

Bottom Line

All in all, we saved 99% off the retail cost of this trip by using points and miles. Better yet, we spent some quality time with Brynn and got to see a Northeastern volleyball victory!

Trip Report Index

  1. Using Points and Miles to get to Boston

Using Points and Miles to get to Portland and Bar Harbor

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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!

Using Points and Miles to get to Portland and Bar Harbor

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!

In This Post

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.

The total cash price round-trip for two people was $1,156.

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 one-way tickets from Chicago to Portland was $500.

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.

In the end, I redeemed 26,000 miles for the Chicago to Portland flight.

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.

The original cash price for two one-way tickets was $658.

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.

Original booking
Booking #2
Current booking
The final cash price for two one-way tickets is $185 cheaper than my original booking.

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

Photo Courtesy of Hilton Hotels.

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.

The cash price for three nights.
The points needed for the same three nights.
I’m saving $2,164 by using my free night award and 160,000 points!

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.

Photo Courtesy of Bar Harbor Inn.

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 CostOur CostMiles and Points UsedPoints Source
2 one-way tickets from Chicago (ORD) to Portland (PWM)$250 per person ($500 total)$026,000 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)$01 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)$1,533N/AN/A
6 day car rental$466$466N/AN/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

Hilton Chicago Oak Brook Hills Resort

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Hilton Chicago Oak Brook Hills Entrance
The Hilton Chicago Oak Brook Hills Resort

One of the perks of owning the Hilton Honors American Express Aspire Card is receiving up to $400 in annual statement credits for eligible purchases made at participating Hilton resorts. The difficulty in using this benefit, is that it only applies to those specific properties Hilton classifies as “resorts”. In the United States, the vast majority of these are located in warm-weather climates like Florida, California or Arizona.

Note: Prior to 2024, the resort credit was $250 per year, however it now comes in two $200 semi-annual credits (one credit to use January to June and the other to use July through December).

As someone who lives just outside Chicago, I’m pretty much in a Hilton resort wasteland. In order to use this benefit, I have to plan a whole vacation like in 2022 when I stayed at the Hotel del Coronado.

Fortunately, Illinois has one property that does classify as a resort, the Hilton Chicago Oak Brook Hills Resort. Since the resort credit is “use it or lose it”, I’ve gotten into the habit of booking a room here when I don’t have plans to use the credit elsewhere. I’ve stayed at this resort twice in the last six years — once in 2018 and again in late 2023. Both times the sole reason was to use up the resort credit before it expired.

In This Post

History and Location

The hotel was built in the 1980s, so I assumed it would be a little dated. When I stayed there in 2018, however, I was pleasantly surprised as it had recently completed a dual-phased renovation. When Hilton took control of the property in 2014, their stated renovation goals were:

  1. Stress the “resort culture” and its most stunning feature, the views
  2. Enhance the overall look and functionality of meeting rooms and guestrooms
  3. Improve use and flow of the lobby, restaurants, and public spaces

Even in 2023, the renovation still looks great even though it’s been seven years already. The resort is conveniently located just 17 miles from O’Hare Airport and 20 miles from downtown Chicago.

Lobby

The result of the relatively recent overhaul is a modern and elegant lobby. It still looks brand new and that clean, modern feeling reverberates throughout the entire hotel.

Hotel Rooms

During my 2023 stay, the goal was to earn the most Hilton points I could without spending more than $250. So I booked a suite that had a bedroom plus living room. In addition, I booked the more expensive “double points” rate to earn twice as many base points.

King Bedroom Suite with Living Room

The suite itself was really nice! Everything from the carpet to the furniture looked brand new. Assuming the room had been renovated several years ago, it has aged very well.

When I opened the door to the suite, I found myself in a large living room. There was easily room for three to four people to fit comfortably amongst the couch, chair and desk.

Across from the couch was a wall-mounted flat screen TV, making this room a perfect hang out area.

The bedroom was located through the living room doorway. What’s really nice about the suite is you can shut the door and close off the bedroom from the living room. That’s a nice privacy option if you’re staying with family or friends and want to have some separation.

The bedroom was big, fitting a king bed, a dresser and two night stands. There were a lot of gold accents, and I particularly liked the headboard, all of which made the room feel elevated.

The Bathroom

Compared to the room itself, the bathroom was just average. One thing I noticed is that the tile work between the toilet and shower showed signs of wear. That area of a hotel bathroom must wear quickly because I’ve noticed this in many hotel rooms over the years.

Bottom Line

The “double points” room rate, including taxes, was $218. I also charged a beer and some hot wings to the room, so the total bill came to $249.42. Within a few business days, that entire amount was reimbursed by the resort credit. What’s great about the whole thing is I still earned Hilton points for my stay. In total, I earned 12,025 Hilton points for a stay I paid absolutely $0 for!

Standard Two Queen Beds Room

My original stay in 2018 was during the summer and I had my two daughters with me. The goal of that stay was to have a resort-like, one day, stay-cation on the cheap. The room rate on that stay was higher, so I booked a standard room with two queen beds.

The view from our room of the outdoor pool and Willow Crest Golf Club.

Our room was clean and being on one of the upper floors, it had a beautiful view. On a clear day you can even see the Chicago skyline to the east. The room was on the back side of the resort, so we had views of the beautifully manicured golf course and the outdoor pool. We even had a birds eye view of an outdoor wedding that occurred that afternoon.

Using Elite Status Benefits

Executive Lounge

Another benefit I receive as a Hilton Honors American Express Aspire cardholder, is Hilton Diamond Status, which provides access to the Executive Lounge.

I visited the Executive Lounge the morning after my stay to check out the free breakfast. There were only three hot food options available that morning — scrambled eggs, sausage and breakfast potatoes. They also had fruit, a variety of bread to eat as is or toast and yogurt. To drink they had bottled water, soda and a Starbucks coffee machine.

Hotel Amenities

Pools

The outdoor pool area can’t complete with sprawling resorts you might find in warmer climates, but it’s pretty nice for what it is. Even though we didn’t arrive until after lunch, there were several lounge chairs still available. Keeping with the “resort culture” theme, the hotel had staff walking around taking drink and food orders. They also have a snack shop called Noonan’s right next to the pool where those relaxing pool side can pick up a quick snack or beverage.

There was no reason for us to use the indoor pool on such a nice summer day, but it’s a nice option for off-season or rainy days. They also have a few ping pong tables by the indoor pool that we enjoyed.

Dining

Things have certainly changed from 2018 to 2023 in terms dining benefits for those with elite status.

Back in 2018, I received vouchers for the Sunday breakfast buffet worth $18 per person. The breakfast buffet was top notch and had everything you might want. From eggs to oatmeal, waffles to pancakes, even lox and bagels, the buffet had all the breakfast basics covered. There was also a chef making omelets and waffles to order!

Post-pandemic, the resort offers access to complimentary breakfast in the Executive Lounge for up to two guests for qualifying Hilton Honors members in lieu of the $15 daily food and beverage credit.

Room Service

Room service is one thing that hasn’t changed. Back in 2018, my daughters were young and thought it’d be fun to order room service for dinner. The menu had some nice options and everything we ordered was very good. I had the charcuterie pizza which is exactly what it sounds like. Cheese pizza with several different types of Italian meat toppings and it was very tasty! My kids liked their burgers and fries and really just enjoyed the whole room service experience.

B. Restaurant / B. Lounge / B. Cafe

Next to the lobby is the restaurant space. The resort calls it three different things but everything is really in one large space. The restaurant serves breakfast, lunch and dinner while the lounge is a good spot to have a happy hour cocktail. The cafe focuses on quick items like Starbucks coffee, pastries and grab-n-go options.

Golf

The Willow Crest Golf Club looks like a nice track and is a Certified Audubon Cooperative Sanctuary, which preserves wildlife habitat while protecting the property’s natural resources.

The hotel has many other amenities that I haven’t taken advantage of, including a fitness center and meeting/conference rooms.

Miscellaneous

During the summer weekends, there’s a lot of action happening across the resort. It was very lively! During the day, the hotel had a kids station setup poolside. Kids could be entertained with arts and crafts while their parents enjoyed the pool. At night, they set out chairs so guests could watch a movie al fresco.

Preparing for the outdoor showing of Guardians of the Galaxy 2

Bottom Line

I’ve enjoyed both stays at the Hilton Chicago Oak Brook Hills resort. It’s recently renovated and has many of those “resort culture” amenities that you’d expect from a Hilton resort property. 

Using Points and Miles to get to Charleston

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Visiting Charleston, South Carolina has always been on our bucket list. For going on 9 years, it’s also been the backdrop to one of our favorite Bravo reality shows, Southern Charm. This reality TV show follows the professional and personal lives of a group of Charleston singles. While some people might be ashamed to watch a show like this, we have two friends who also enjoy it as much as we do. It’s our collective guilty pleasure!

While the show has it’s share of ridiculousness, it also highlights southern culture and modern day aristocracy, which is quite interesting. So earlier this summer, the four of us decided to plan a long weekend together in October to visit Charleston.

Using Points and Miles to get to Charleston
Charleston’s famous Rainbow Row.

We’re eager to doing some of the typical touristy stuff on this trip. But we’re also looking forward to learning about the history of the “Holy City” and especially to tasting some quintessential Lowcountry cuisine. Additionally, we’re going to be silly and visit some popular spots from Southern Charm, like Craig Conover’s pillow store and one of Leva Bonaparte’s restaurants.

In This Post

Airfare

The cost of my initial itinerary was $868.

Fall is my busy season, so I can only take one day off of work for this. So the plan was to fly into Charleston first thing on Saturday and fly home on Monday, so I can be back at work on Tuesday. That round-trip itinerary would’ve cost $868.

Instead of round-trip flights, though, I typically book two one-way flights to get more flexibility. That way, if I choose, I can use miles one direction and pay cash for the other.

United Airlines offers multiple nonstop flights per day between Chicago and Charleston, whereas American Airlines only offers one. While I prefer to fly American because of my Platinum Elite status, their daily flight to Charleston is right in the middle of the day. We want to get as close to a full day in Charleston that Saturday, so we went with United.

Chicago to Charleston

I booked us on the first United Airlines flight of the day on Saturday. It gets us into Charleston around 10:30am, so we’ll have essentially the entire day to enjoy. The cash price for two one-way tickets was just under $214, which is pretty cheap. However, I have a bunch of United MileagePlus miles, so I decided to save the cash and use miles. United charged 17,200 miles for the two tickets. The value of that miles redemption is 1.2 cents per mile. Most people value UA miles at 1.1 cents per mile, so the redemption is just a little over average. However, it really just came down to saving the money.

The flight from Chicago to Charleston would’ve cost either $214 or 17,200 miles + $11.

Whenever you redeem miles on a domestic flight, the airlines still charge nominal fees. In total, I paid $11 for the two one-way tickets and saved $203 on this leg of the trip.

Charleston to Chicago

United was charging $586 or 51,800 miles to fly home on the mid-day Monday flight. Neither option was a good deal, so I looked at flights leaving Tuesday instead. There’s a flight at 6:15 a.m., which gets to Chicago before 8:00 a.m. That means I could still get in a full day’s work on Tuesday. Besides giving us all-day Monday to enjoy Charleston, the cost of the flight is also way less than the Monday flight.

The price for two one-way tickets on the Tuesday morning flight was $218, and I decided to use some of my United TravelBank credits to cover the cost. One of the perks of the Hilton Honors American Express Aspire Card is that it annually reimburses up to $250 in airline incidental fees charged to the card. Adding money to TravelBank qualifies for reimbursement, so at the start of every calendar year, I add $250 to my TravelBank to use at some future time. Wtihin a few days, that money is credited back to me as statement credit. So I used $200 in my TravelBank towards the purchase, taking my out of pocket costs down to just $18.

The bottom line is that flights which would’ve cost $868 in cash, were paid for instead by changing the date of our return leg, redeeming 17,200 United MileagePlus miles and spending a total of $29.

Hotel

The Lindy Renaissance Charleston

Photo Courtesy of Marriott Hotels.

When it came to hotel options, I wanted to use my free night award with Marriott before it expired in December. As a cardholder of the Marriott Bonvoy Business™ American Express® Card, I receive a free night award certificate every year. The award, valid at hotels costing up to 35,000 points per night, is given annually on your card-opening anniversary. Even better, you can add up to 15,000 extra points from your account to redeem your free night award at hotels above the 35,000 point redemption limit. The certificate must be used within a year of receipt, so the time to use it was now.

There are four Marriott properties right in the center of Charleston. There’s the Grand Bohemian Hotel, the Hotel Bella Grace, the Courtyard Charleston Historic District and The Lindy Renaissance Charleston. The Lindy Renaissance was the cheapest at around $427/night and charged around 45,000 points/night. Since I can add up to 15,000 points to my 35,000 point free night award, this was the only one of the four properties that worked.

I’m saving $979 by using my free night award and 55,000 points!

When I booked our 2-night stay, the total cash rate was $979. So I’m getting great value by using my free night certificate and 55,000 Marriott points. The $125 annual fee on my Marriott Bonvoy Amex card is well worth it when I can use the free night award to erase a $300+ hotel night cost.

All in all, I saved $979 on our 2-night stay in the heart of downtown Charleston!

Courtyard Charleston-North Charleston

Once I booked the 6:15a.m. flight on Tuesday, I decided it would be better to stay near the airport Monday night. It means getting to sleep in a few extra minutes and save us money as well. Spending Monday night at The Lindy Renaissance would’ve cost $373, including taxes and fees.

Photo Courtesy of Marriott Hotels.

Instead, I booked us at the Courtyard Charleston-North Charleston, which is about 10 minutes from the airport. I reserved it through my wife’s Chase Sapphire Preferred account to take advantage of the annual $50 statement credit for hotel stays purchased through the Chase Travel Portal. The portal is just like any 3rd party booking site (i.e. Expedia or Orbitz), and the cost is often higher than booking directly with the hotel. You also don’t get any status benefits when booking through 3rd party sites. However, I wasn’t concerned with status benefits at this kind of hotel and getting $50 back made it well worth it.

Booking directly with Marriott would’ve cost $133, including taxes and fees, or 13,600 Marriott points. Instead, going through the Chase Travel Portal, our one night stay at the Courtyard Charleston-North Charleston will cost $135 – $50, for a total of only $85.

Charleston 2023 Redemption Table

Retail CostOur CostMiles and Points UsedPoints Source
2 one-way tickets from Chicago (ORD) to Charleston (CHS)$107 per person ($214 total)$5.60 taxes and fees ($11 total)17,200 UA miles- United Explorer Card
- Miles from flying, dining and shopping portals
- Opinion Miles Club surveys
2 one-way tickets from Charleston (CHS) to Chicago (ORD)$109 per person
($218 total)		$18$200 United TravelBank credits- Amex Hilton Aspire card
2 nights at The Lindy Renaissance Charleston Hotel$428 per night + taxes ($979 total)$01 free night certificate and 55,000 Marriott points- Marriott Bonvoy Business American Express Card
1 night at the Courtyard by Marriott North Charleston$119 + taxes per night ($135 total)$85$50 statement credit- Chase Sapphire Preferred
Total$1,546$114- 17,200 UA miles
- 1 free night certificate
- 55,000 Marriott points
- $250 travel credits		- $1,432 in total savings
- 93% off retail cost

Bottom Line

All in all, we’re going to save around 93% off the retail cost of this trip by using points and miles. Annie and I have only heard great things about Charleston, and we’re really looking forward to spending time there. We can’t wait to immerse ourselves in this old world southern charm and eat some classic southern comfort food. And maybe, if we’re lucky, we’ll run into some of the stars of Southern Charm!

Trip Report Index

  1. Using Points and Miles to get to Charleston
  2. The Lindy Renaissance Charleston Hotel
  3. Where to Eat in Charleston