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Where to Eat in Charleston

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Charleston, South Carolina is a full-fledged foodie town. The city’s restaurants expertly use the sea and surrounding areas to create quintessential Southern menus. The city sits below the original coastline of the Carolinas and is therefore often referred to as the Lowcountry. Regional favorites, such as she-crab soup, shrimp and grits and fried green tomatoes are staples of Lowcountry cuisine.

This past fall, I spent a long weekend with Annie and two of our friends, eating and drinking our way through Charleston. While there’s no shortage of fabulous dining options, below are my favorites.

In This Post

The Top 4

Poogan’s Porch

My favorite meal of the trip was lunch at Poogan’s Porch. The restaurant opened in 1976 and is located in the heart of downtown on Queen Street. Originally a spacious home built in the late 1800s, it still exhibits much of that old-world charm.

Even on a Monday in October, we had to wait around 20 minutes without a reservation. That’s usually a good sign! Luckily they have a decent-size bar, so we enjoyed cocktails while we waited. Once seated, we browsed the menu of typical Lowcountry staples. This was our last full day in Charleston and I had already checked off most of the “must-have” dishes on my list. So for this meal, I focused on regional favorites I’d yet to sample.

Where to Eat in Charleston
You have to order the Fried Green Tomatoes!

The four of us began our meal by splitting the fried green tomatoes appetizer. The tomatoes themselves are outstanding but the delectable pimento cheese and bacon jam sauce takes it to a new level. The dish combines the crispy texture of the tomatoes and hits you with a mix of sweet and savory flavors. It was a definite highlight!

Annie and I decided to split an entree, so I also ordered a cup of she-crab soup for myself. It’s a traditional Charleston soup that incorporates blue crab meat, heavy stock, sherry and crab roe. It was very similar to a lobster bisque, with a beautiful rich taste.

Leon’s Oyster Shop

My favorite dinner of the trip was the one we had at Leon’s Oyster Shop. Even though the casual and relaxed restaurant is located on “famous” King Street, it’s not actually downtown. However, it’s not far, taking only 10 minutes by car from our downtown hotel.

Leon’s opened in 2014 in an old autobody shop. They preserved much of its old life, with functioning garage doors and concrete floors. It gives off a “roadside joint” kind of vibe and is known for its oysters, Southern-style seafood & fried chicken. In 2020 they intensified that vibe by whitewashing the front facade and adding a large “filling station-style” covered patio.

The old industrial history is still alive in the huge inside dining room.

My order was the fried chicken and I didn’t even need the menu. A few months before the trip, Leon’s fried chicken was featured on an episode of Bravo’s Southern Charm. In the episode, cast members Shep Rose and Whitney Sudler-Smith ordered in Leon’s fried chicken for a boys night in. It looked so good on television, I knew I’d order if given the opportunity.

The fried chicken entree comes in either a 2-piece or half chicken size, and you get to choose a couple sides as well. It came out hot and crispy and had a great flavor.

While the food is certainly the draw, I think Leon’s is so popular because of the atmosphere. It’s a fun and lively place where people can enjoy everything from cheap beer to fine champagne.

167 Raw Oyster Bar

Our first lunch of the trip was at 167 Raw Oyster Bar, located on King Street. The restaurant’s interior has a Cape Cod feeling to it and they also have a cozy courtyard. Luckily we didn’t have to wait for a table because that doesn’t seem to be the norm.

Food-wise, we decided to split a bunch of dishes including raw oysters, ceviche, a lobster roll and an oyster po’ boy sandwich.

With “raw bar” literally in the restaurant’s name, of course we had to try the raw oysters. The oyster varieties change daily based on what the fishermen bring in. We didn’t know the differences between the various oyster varieties, but our waiter went over everything for us. The ones we chose were quite good.

The Lobster Roll is solid!

The ceviche was fine but I’d skip it next time. However, the lobster roll was terrific and so was the oyster po’ boy. They also offer shrimp po’ boys and scallop po’ boys and I’m sure they’re delicious as well.

Blind Tiger Pub

The Blind Tiger Pub was another food destinations that came to our attention from Bravo’s Southern Charm. Shep Rose mentioned it as a favorite spot of his and that was good enough for us. Located on Broad Street, the restaurant’s entrance is unassuming, giving it speakeasy vibes.

From the street, you couldn’t even tell if anybody was inside the place. However, upon entering, it was full of people enjoying weekend brunch. While the inside reminded me of your standard college bar, it’s their enormous back patio and elevated pub fare that makes it a destination.

We had to wait for a table on a Sunday at lunchtime. To pass the time we enjoyed cocktails at the bar and waited patiently for a table to open up outside. The award winning outdoor patio is really cool. There’s nice brick work all over the patio and it seems to go on forever. It also has a full bar right out on the patio.

The Shrimp and Grits are amazing!

For this meal, I zeroed in on the shrimp and grits. It was another Lowcountry staple I wasn’t going to miss! The dish had pan-seared shrimp, andouille sausage, peppers and caramelized onions, in a sherry cream sauce and served over grits. My arteries might’ve been angry with me, but the flavor was so rich and fabulous! I wanted to slurp up that sherry cream sauce with a straw!

Other Restaurants

Home Team BBQ

Barbecue was the last regional food we’d yet to try on our trip. There’s no shortage of available options in Charleston, so we searched online reviews to narrow down the choices. We settled on the downtown location of Home Team BBQ for our final dinner of the trip. The place itself is looks very cool and is decorated just how you’d imagine a barbecue joint should be. They have plenty of seating and a large bar inside. They also have a big open air patio, plus a screened-in patio that can host private events.

The food itself was good, but not remarkable. We have good barbecue in Chicago and this was on par with that. However, it didn’t compare with the outstanding barbecue we had in Austin, Texas. I don’t know whether to chalk that up to Texas barbecue being better or if we would’ve been more impressed somewhere else.

While the food was solid, the main disappointment was the service. It was a Monday evening, so the place wasn’t packed. However, it took a really long time to get the waitress to take our order. Once the food arrived, we pretty much never saw her again. I even had to flag her down to ask for the check. It could’ve been an off night, but it definitely left a bitter taste in my mouth.

Mesu

Another Southern Charm inspired meal was dinner at Mesu, located right in the heart of the action on King Street. It’s owned by Leva Bonaparte, who’s been a cast member on the show for a few years. The food is a fusion of Mexican and Sushi, which sounded really interesting.

As we’d done a few times in Charleston, we split a bunch of items so we could try more dishes than we could on our own. We started with chips and salsa, which were just as you’d expect. For our entrees, we split a variety of tacos and sushi rolls. I found the food to be quite good, but I wouldn’t really call it fusion. The menu just has both Mexican food and sushi.

The atmosphere, however, was not what I expected. Leva owns several restaurants and bars around Charleston, and the vibe that comes through on the show is very upscale. That being said, I don’t think I’ve ever seen Mesu on the show, so I shouldn’t have assumed it would be similar. As it turns out, it’s not an upscale place at all. It’s way more casual than I expected and felt more like a neighborhood sports bar than anything else. The decorations are vibrant, but the restaurant was loud and hot. Plus the seating wasn’t too comfortable which made me not want to hang out long after we were finished.

Bottom Line

Almost our entire Charleston trip was focused around food. Dining out was the entertainment and there’s no shortage of incredible establishments to choose from. Charleston’s history, dating back to the 1600s, and its proximity to the Atlantic Ocean have inspired a hyper-local food known as Lowcountry cuisine. Experiencing the different culinary specialties Charleston has to offer is a great way to experience the city and absorb the culture.

Trip Report Index

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

An Upgrade, a Tornado and a Redeye: A Review of American Airlines’ Embraer 175 First Class from Chicago to Portland

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Normally what you’d find here is a review of my recent flight from Chicago to Portland. After all, I was excited to write about my first ever complimentary upgrade to domestic first class. However, Mother Nature had other ideas! So I’m not reviewing the cabin and seats, the amenities or the food service (hint: there was none). Instead I’m going to share the craziness that began with a complimentary upgrade, was interrupted by a tornado and ended with a redeye flight to Portland. 

The Upgrade

Once American Airlines gamified their rewards program in 2022, earning elite status became more about spending than flying. That change made elite status attainable and I set out on quest to attain status to see if it was worth having. In June 2022 I attained Gold elite status. In January 2023 I attained Platinum elite status and did again in February of 2024. I’ll continue to have Platinum elite status through March 2025. Before this trip, I’d only used my elite status for priority check-ins and boarding and picking Main Cabin Extra Seats at booking.

So as I always do, I booked Main Cabin Extra seats for the flight to Portland. As the trip got closer, I started monitoring the first class cabin for open seats. As of the night before the flight, there were five open seats in first class! So I was cautiously optimistic that both Annie and I might get upgraded.

The morning of the flight, I received an email from American Airlines confirming upgrades for Annie and me. I was really excited about this, but not because getting domestic first class on a two hour flight is so amazing. It was just fun to finally have my Platinum elite status secure an upgrade. 

Receiving this email on departure day was exciting!

Cue the Delays

The trouble starting during the course of the day as I got several notifications from American Airlines about flight delays. Sometime earlier in the day, the plane we were scheduled to be on had been delayed on one of its legs. That delayed each subsequent flight, so every few hours my flight was delayed by 20 minutes or so. By the time we headed to the airport, our flight had been delayed an hour in total. But it could be worse…and soon will be!

The Tornado

An Upgrade, a Tornado and a Redeye: A Review of American Airlines’ Embraer 175 First Class from Chicago to Portland
Waiting out a tornado warning on the tarmac is a vulnerable feeling!

The flight got delayed again as soon as we sat down at our gate. The weather service had been forecasting the possibility of severe weather that evening, but I was hoping we could still make it out beforehand. Our final “official” departure time was set for 8:45pm.

Annie and I were the first to board the plan and we took our seats in 4D and 4F. As per usual, the plane sat at the gate for quite a while after boarding had been completed. I was still hopeful we’d beat the weather but was getting more anxious with every passing minute.

Finally, the pilot gave the “flight attendants, prepare for takeoff” call and we taxied out to the tarmac to get in line with the other aircrafts. We sat out on the tarmac for another 20 minutes or so and didn’t move an inch. Eventually the pilot got on the intercom and informed us that we had to return to the gate due to severe weather approaching. But we didn’t go anywhere, the plane just stayed on right where it was.

It wasn’t even raining yet, but an ominous feeling spread over everyone knowing a bad storm was coming. Then I was startled when everyone’s phone made that jarring emergency alert sound. Our phones urged us to take shelter now! The incoming storm prompted the evacuation of the FAA control tower at O’Hare and passengers in the airport took shelter. That led to a ground stop, causing all planes to stop moving on the tarmac.

So instead of going back to the gate, we had to wait out the storm inside the plane. Within a few minutes it started raining hard. Then the wind kicked up and the plane started to rock forcefully back and forth. The wind gusts were so strong it actually felt like we were flying and going through strong turbulence.

I started feeling more vulnerable when my daughter texted me to say that the local news channel was talking about tornadoes on the ground at O’Hare. According to some reports, there were a total of 27 tornados in the Chicagoland area that night. It was also confirmed that an EF-0 twister is what blew through O’Hare, reaching peak wind gusts of 80 miles per hour.

I’m really not sure how long the storm lasted. But once the tornado warning expired, the air traffic controllers returned to the tower. At that point they had us return to the gate and deboard the plane. Once back in the airport , we were hoping there’d be an agent around to tell us what would happen next. It was probably around 10:45pm at that point, so the only people around were the cleaning crew. There was nobody to ask questions to, nobody to help us.

The Redeye

As we waited at the gate to see what was going to happen, my initial thought was a pessimistic one. I figured we’d wait at the gate like idiots before American finally cancelled the flight. So I called them to see what options we had. The agent on the phone could see that my flight hadn’t been cancelled yet and put me on hold. While on hold I realized that any new flight she would book us on would be the next day. So Annie and I agreed that we’d rather take a chance and see what happens with our original flight. 

It was radio silence for long time. We’d get excited when an employee would walk toward our gate and be deflated when he or she kept on walking. Finally around 1am, an agent finally informed us that they received approval to fly to Portland. They announced that we could board once they completed a quick cleaning. Everyone audibly moaned because there was nothing to clean! All we did that night was board and deboard the plane. A few minutes later the agent announced they wouldn’t clean the plane and we could reboard in a few minutes!

We eventually took off at 1:45am. At that point in our evening, Anne and I just wanted to get as much sleep as we could. So did everybody else. The crew didn’t bother to do food service in first class and didn’t serve drinks to anyone. I didn’t mind not getting the typical domestic first class experience since sleep was the first priority. It’s just kind of ironic that my first ever upgrade didn’t amount to much.

Bottom Line

The last piece to the story is that when we landed in Portland it was 4:45am. I’d rented a car I was supposed to pick up at 10:30pm the night before. The rental car companies didn’t open until 6am, so at that point we had to take a seat and wait for them to open. We finally got our car and headed to the hotel, sleepy but with a unique story to tell.

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

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

Hotel Indy, Indianapolis, a Tribute Portfolio Hotel

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Last month, a high profile college basketball game between Arizona and Purdue brought Annie and me to Indianapolis. We wanted to enjoy the game and evening with a few drinks, so we decided to stay overnight, instead of driving back to Chicago. Having manufactured a free night from of a recent Marriott promotion, I chose to use that free night certificate and 7,000 Marriott points to stay at the Hotel Indy, Indianapolis, a Tribute Portfolio Hotel.

In This Post

History

The hotel was originally constructed in 1969 as the State Life Insurance building. Back then it was a concrete cube, made up of large panes of glass, concrete and metal. During that midcentury-modern period, this type of architecture was known as Brutalist architecture. The building served as office space for 50 years.

Then in 2019, after the building’s sale, the new owners began developing it into a hotel. The original building was five-stories, but a sixth floor was added to accommodate more guest rooms and a rooftop lounge with skyline views. After a two years of construction, the hotel opened for business in October 2021.

Marriott calls their Tribute Portfolio brand a “family of independent boutique hotels”. That means every hotel in this brand is unique and in many cases pays homage to the local culture and history.

Location

I chose this hotel for its proximity to the Gainbridge Fieldhouse, where the game was being played. The property is located downtown, in the city’s Wholesale District. It’s just one block from the arena, but also a short walk to Lucas Oil Stadium and the Indiana Convention Center.

My only gripe about the location is that it’s across the street from the bus terminal and county corrections office. While I didn’t feel unsafe, some of the people walking around the area seemed a bit shady.

Parking

The hotel offers valet parking for $45 per night, but I decided to use Spot Hero to book a much cheaper spot only a block from the hotel.

Lobby

The lobby isn’t the biggest, but it’s new and styled with clean lines and colorful furniture. The lobby, as well as our room, had an exposed concrete ceiling, which was obviously something kept from the original architecture. The look reminded me of loft apartments that keep exposed walls.

Hotel Indy, a Tribute Portfolio Hotel

The Room

Our room was located on the 5th floor. In the elevator bank there was another cutout in the ceiling to expose the old concrete. I particularly liked the styling of the carpet, with the geometric shapes and pops of color.

The open space right as we walked in the room made it feel larger than it was. The hotel designers kept with the theme, but in this case the entire ceiling was old concrete. I wish they hadn’t kept the concrete ceiling theme in the room itself. To me, it made the room feel a little cold and unwelcoming.

However, the room had everything you’d need, including a king bed, a small chaise lounge, a small table, a smart TV and a coffee station with refrigerator. Plus, as you’d expect with a newer hotel, there were plenty of outlets and USB ports.

The Bathroom

The bathroom was clean and modern and I particularly liked the lighted circle mirror.

Hotel Amenities

Dining

There are multiple dining options within the hotel. Around the corner from the front desk is The Brandon coffee bar which is open until 2 p.m. The Hulman, a full service restaurant, is also located on the first floor near the lobby. The third option is The Cannon Ball Lounge on the 6th floor.

The Hulman

The Hulman offers Indy-inspired American fare. While the restaurant has a nice look to it, the reviews seem to be hit or miss.

The Cannonball Lounge

The Cannonball Lounge is located on the hotel’s 6th floor. It’s one of Indianapolis’ only rooftop lounges, where guests can enjoy craft cocktails, small bites, and local beers. The lounge has floor-to-ceiling windows to gaze at the cityscape while sipping on drinks. It also has an outdoor rooftop with terrific views of downtown Indianapolis.

Photo courtesy of Marriott Hotels.

Fitness Center

There is no spa or pool, but they do have a 24-hour fitness center equipped with cardio machines, free weights, yoga mats, and more.

Bottom Line

I always prefer newly renovated hotels. They’re clean, modern and usually there’s no “ick” factor. The Hotel Indy fits those adjectives but I think the style may not appeal to everyone. For me, I didn’t love the exposed concrete ceilings in the room itself. It was a nice touch in the lobby and common areas, but I prefer my room to be more traditional.

That being said it is really close for people attending nearby concerts or sporting events.

Trip Report Index

  1. Manufacturing a “Free” Hotel Night in Indianapolis
  2. Hotel Indy, Indianapolis, a Tribute Portfolio Hotel

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.