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How I leveraged credit card perks to save almost $800 on a trip to Chicago and Boston

April 28, 2021
11 min read
Chicago Aerial Cityscape at Sunrise
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Last month, I took a spontaneous trip to Chicago and Boston. I didn’t have a good reason — except it had been five months since my last trip and I felt I could do it safely. But most of all, I had more than $763 in travel and dining credits from my rewards cards burning a hole in my pocket. Instead of spending them at the In-N-Out drive-thru for a burger, I could be eating my way through the best restaurants in Chicago.

At that point, I didn’t know when I’d be traveling abroad again, so putting the up to $250 resort credit from my Hilton Honors American Express Aspire Card to use for a stay at LondonHouse Chicago sounded good to me. Plus, I needed one more night to qualify for Hyatt Globalist status and a free Category 4 award night for staying with five different Hyatt brands. A night at the fairly new Hyatt House Chicago West Loop would take care of that.

The information for the Hilton Aspire Amex card has been collected independently by The Points Guy. The card details on this page have not been reviewed or provided by the card issuer.

In total, I saved $763 on a weeklong trip, thanks to travel credits from my credit cards.

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Hilton Aspire -  $340 worth of dining and Hilton hotel savings

(Photo by Eric Helgas for The Points Guy)

The Hilton Aspire is one of my favorite cards and I easily offset the $450 annual fee (see rates and fees) every year thanks to all the perks it offers. On this particular trip, I saved $340 just on dining and hotel charges alone:

  • $250 off my bill at LondonHouse
  • $70 credit for checked bag fees
  • $20 off dining

The annual $250 resort credit was applied to my $300 hotel bill at LondonHouse, which was nice. Much to my chagrin, my sister likes to travel with a big bag that needs to be checked. I was happy not to be paying $70 in checked bag fees, thanks to my Hilton Aspire's airline fee credit. I also got a free checked bag on the Chicago-Boston segment thanks to my Citi® / AAdvantage® Platinum Select® World Elite Mastercard®, which was a nice bonus.

The Hilton Aspire comes with a monthly $20 dining credit through 2021 (up to $220) (eligibility limited and enrollment required). I managed to put that to good use on a visit to Portillo's in Chicago. Now do you get why I'm so obsessed with this card? I can't wait until international travel starts back up and I'll be able to maximize the card's benefits even further.

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Marriott Bonvoy Brilliant Amex - $20 savings on dinner

(Photo by Eden Batki/The Points Guy)

I reluctantly applied for the Marriott Bonvoy Brilliant® American Express® Card last year and already, this card is shaping up to be worthwhile. I used the Global Entry fee credit to pay for my sister's application, so I don't have to wait for her after using the TSA PreCheck line when we're traveling together. Her application is still processing, but this was a necessary expense and the card knocked $100 off. I've also gotten more than $154 in savings via Amex Offers this year.

But I won't factor in all of that since it does not apply to this trip. Like the Hilton Aspire, the Marriott Bonvoy Brilliant Amex card offers a monthly $20 dining credit at U.S. restaurants (up to $220 through Dec. 31, 2021; eligibility limited and enrollment required). On this trip, I used it to cover a late-night trip to the Sprinkles cupcake ATM. So. Worth. It.

Amex Blue Business Plus - $50 savings on Marriott

The Blue Business® Plus Credit Card from American Express is hands-down one of my favorite credit cards. Not only does it earn 2x Membership Rewards points on the first $50,000 spent each calendar year (then 1x), but it has no annual fee (see rates and fees) and gets me access to Amex Offers. This year alone, I’ve saved more than $90 thanks to Amex Offers on this card. A premium credit card that pays for itself is nice, but a card that pays you is even better.

I was targeted for a $50 Marriott credit valid on bookings of $250 or more, which I used to book a three-night stay at the Courtyard Boston Copley Square. The hotel had a great location in Back Bay and the credit knocked $50 off an already low rate, so needless to say, I was thrilled.

You may be wondering why I didn’t use the $300 Marriott hotel credit from my Amex Brilliant Card. That credit is valid on spending at the hotels participating in the Marriott Bonvoy program and unfortunately, prepaid hotel rates don’t qualify. I didn’t want to pay a higher rate just to use this credit, so I opted for the Amex Blue Business to save $50. Plus, I’ll have an opportunity to use the Brilliant credit during an upcoming stay at the JW Marriott Anaheim, so this worked out nicely.

Citi Prestige® Card - $228 savings on dining

(Photo by The Points Guy)

The Citi Prestige® Card comes with Priority Pass membership. The only Priority Pass "lounge" option in San Francisco's (SFO) Terminal 3 was Giants Clubhouse, where I received a $28 dining credit. Since our flight was early in the morning, we didn't have a chance to grab breakfast at home, so it was nice to have that covered by Priority Pass.

During the pandemic, the Citi Prestige expanded the $250 travel credit to cover restaurants and grocery spending. Last year I finally took up cooking, so using these credits at the grocery store was easy. This year, I still had my $200 credit by the time March rolled around, so I thought, why not treat myself? My sister and I had dinner at the Purple Pig and Girl & the Goat while in Chicago.


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We enjoyed both restaurants, which were not cheap. The combined bill came to more than $200. Now I'm not in the habit of eating at upscale places like this regularly, but this was a special trip for my sister, so we decided to splurge. Seeing a $200 credit at the end of our trip took the sting out of that big expense. There were no regrets — and it was such a fun way to put that credit to good use.

The information for the Citi Prestige Card has been collected independently by The Points Guy. The card details on this page have not been reviewed or provided by the card issuer.

Related: Why I’m downgrading my Citi Prestige despite getting $1,200 in value last year

Citi® / AAdvantage® Platinum Select® World Elite Mastercard® - $125 flight discount

Boston wasn't part of my original plan, but after a few days in Chicago, my sister and I thought, why not? It's a 2.5-hour flight and we weren't ready to go home. The most convenient flights I found the day-of came to just under $130 for two people. Luckily, I brought along the $125 flight discount* I earned with the Citi® / AAdvantage® Platinum Select® World Elite Mastercard®. It knocked $125 off the total, we got the flight we wanted and visited a new city for less than $5 out of pocket. Huge win.

*Earn a $125 flight discount after spending $20,000 or more in a cardmember year and renewing the card

15,000 AAdvantage miles for a rescheduled flight

This isn't quite money saved from a credit card, but I thought I'd share it anyway. The night of our departure, I went online to check in for our flights (don't judge me for waiting until five hours before) and noticed our flight had been canceled. We'd been rebooked for the next day, with a stopover that would have gotten us to Chicago way later than we would have preferred.

I ended up canceling our American flight and rebooking a direct one with United. It worked out well and American proactively credited me 15,000 AAdvantage miles for the inconvenience. Now I can use those miles for another domestic trip, which is always a win. Most likely, I'll let them stack with my existing AAdvantage balance for a fun trip to Asia once that becomes possible again. Based on TPG's valuation of AAdvantage miles, these miles are worth $210. Not bad for the inconvenience of a rescheduled flight.

Bottom line

By now, some of you are thinking, "But you didn't really save $763. You paid annual fees on those cards." That's true, but I'm very careful in selecting credit cards that offer value beyond just the sign-up bonus. When I keep a card in my wallet long term, it has to offer benefits worth significantly more than the annual fee. Often, this comes in the form of points as well as fixed-value benefits like travel credits and elite status benefits.

My intention here is to demonstrate how it's possible to get that value out of a single trip. When travel resumes, I'll get to use these benefits to their full potential (i.e., Hilton Diamond status from the Aspire Card, the free checked bags with the AAdvantage Platinum, etc.). In the meantime, I'm pretty happy to reduce my out-of-pocket expenses like this trip.

For rates and fees of the Hilton Aspire Card, click here.
For rates and fees of the Blue Business Plus card, click here.

Featured image by Getty Images
Editorial disclaimer: Opinions expressed here are the author’s alone, not those of any bank, credit card issuer, airline or hotel chain, and have not been reviewed, approved or otherwise endorsed by any of these entities.