The first goal I set on my points journey was to take my wife, Annie, on a 5th anniversary vacation to Maui. I wanted to accumulate enough points to get free airfare, hotel and car rental, not including taxes and fees. Applying for new credit and making purchases on the right cards are how I’m going to make this a reality.

Airfare

Annie and I have been American AAdvantage® members for a while and have some miles saved up that we could redeem. Although flying American to Hawaii is an option, there are no direct flights from Chicago to Maui. Also round trip airfare awards in coach can cost around 72,500 miles. If you pay cash for flights, they can be quite expensive – a test search in August shows American at over $1,200 and United at over $1,300 round trip from Chicago to Maui.

A little research shows that we can fly other airlines for far fewer miles. However, to be able to redeem an award ticket on a different airline, we need transferable points.

I decided on the Chase Sapphire Preferred Card to begin earning transferable points. Read “How Did I Choose My First Credit Card?” to see why this card was the right decision for me. I applied for the card on 4/5/18 and due to some large expected expenses, I met the minimum spending requirement very easily. I also added Annie as an authorized user for 5,000 extra bonus points. And finally, I referred her for a Chase Sapphire Preferred Card as well. The referral got me 10,000 bonus points and once she hits her minimum spending requirement, she’ll bank another 50,000 bonus points. In total, we’ll have at least 123,000 Chase Ultimate Rewards® points after all the bonuses and points earned through spending.

On top of that, I decided to pair the Sapphire Preferred with the Chase Freedom Card. The Freedom card’s welcome bonus is 15,000 points after meeting the minimum spending requirement. It also earns 5% cash back in rotating quarterly categories. Those points can be transferred to my Chase Sapphire Ultimate Rewards points to provide even more value.

In October of 2018, I also decided to apply for the United Explorer Card and earned the 50,000 point welcome bonus. Now I have more than the 90,000 miles required to fly Annie and I to Hawaii in coach.

The plan is to use either Chase Ultimate Rewards points or United miles to pay for our airfare to Hawaii. Below are some options:

• United Airlines – round trip flights are 45,000 miles in economy; 190,000 miles in business
• Singapore Air – round trip flights via United are 40,000 miles in economy; 60,000 miles in business
• Korean Air – round trip flights via Delta are 25,000 miles in economy; 45,000 miles in business (unfortunately as of 8/25/18, Korean Air is no longer an Chase UR partner)

All of these options far surpass the redemption reward options on American Airlines. At this point, my sights are set on Singapore Air business class flights for 60,000 miles. Compare that with flying coach on American for 72,500! With Chase UR points, I can transfer them to Singapore Air and then redeem those miles on United, which is one of their Star Alliance partners.

Hotel

We know we want to stay at the Grand Wailea, A Waldorf Astoria Resort, which is part of the Hilton family of hotels. Rates can run from $500 a night for a terrace view room, to $1,000+ for suites. Point redemptions for a standard room at the hotel are 95,000 points per night. If we want to stay for a week, we’re going to need 665,000 points! However, there are two easy ways to reduce the total number of points needed.

1. Elite Status: with Silver or higher status, you get 1 free night when you redeem 4 nights
2. Hilton Honors Aspire Credit Card: a perk of this card is 1 free weekend night each year

With elite status and the Aspire card, we can stay for 7 nights while only redeeming 5 nights worth of points. To achieve this goal, I need a Hilton branded credit card to accumulate the necessary points. Hilton has an exclusive partnership with American Express and offers several card options.

You can read my review of these cards here, but I went with the Hilton Honors Aspire Card. While this is the top-level card and carries a $450 annual fee, the perks more than pay for the fee. The perks that we’ll use at the Grand Wailea are:

1. The annual free night (value around $500)
2. The possibility of an upgrade; we’ll book the lowest level room but can get space-available room upgrades including suites (value unknown)
3. $250 Hilton resort credit, which we’ll use for food, spa, activities, etc. (value $250)
4. $100 property credit at Waldorf Astoria (value $100)

This card has other perks not related to our stay at the Grand Wailea, which I intend to use, like the $250 airline fee credit. With all of these perks, it’s easy to see why the Aspire card is so valuable.

Car Rental

Initially, I was so focused on airfare and hotel that I completely forgot that we’d need a rental car on Maui. Having a car on Maui is a must and the costs can really add up. A full size car for a week can cost between $250 and $450 and a fun convertible could go for between $900 and $1,200 per week! This is where taking surveys comes into play. Hertz is a rewards partner in the E-rewards program, and I can take enough surveys to get a free convertible. A weekly specialty car rental at Hertz costs 4,400 points at the standard reward rate and 8,800 at the AnyDay rate (not subject to blackout periods).

Progress (updated monthly)

*As of January 2020, with the trip now booked, I’m going to stop tracking my progress on a monthly basis.

Goal	Airfare (120,000 Chase Ultimate Rewards points)	Hotel (500,000 Hilton Honors points)	Car Rental (7,500 Hertz Gold Plus points)
Jan 2020	176,171 points	238,945 points	293 points
Dec 2019	203,846 points	610,719 points	7,793 points
Nov 2019	200,431 points	598,848 points	7,793 points
Oct 2019	190,155 points	560,327 points	6,693 points
Sept 2019	186,654 points	556,983 points	5,593 points
Aug 2019	183,563 points	535,323 points	5,593 points
July 2019	181,776 points	514,194 points	4,493 points
June 2019	177,630 points	498,681 points	3,393 points
May 2019	171,288 points	488,829 points	3,393 points
Apr 2019	199,556 points	461,036 points	3,393 points
Mar 2019	182,591 points	455,515 points	1,193 points
Feb 2019	175,397 points	437,555 points	1,193 points
Jan 2019	170,551 points	428,572 points	1,193 points
Dec 2018	167,128 points	396,689 points	6 points
Nov 2018	166,750 points	320,146 points	6 points
Oct 2018	166,210 points	313,382 points	5 points
Sept 2018	162,073 points	282,339 points	5 points
Aug 2018	134,646 points	268,772 points	5 points
July 2018	131,553 points	156,487 points	5 points
June 2018	73,619 points	24,310 points	5 points
May 2018	71,348 points	10,310 points	0 points
Apr 2018	0 points	9,000 points	0 points

January 2020 Details:

• Chase Ultimate Rewards points gained: -27,775 = 11,225 everyday spending – 4,000 transfer to United – 35,000 transfer to Hyatt
• Hilton Honors points gained: -371,774 = 381 everyday spending + 7,000 from E-rewards redemption for Scott + 845 from Guest Opinion Rewards – 380,000 hotel redemption
• Hertz Gold Plus points gained: -7,500 = -7,500 car rental redemption

December 2019 Details:

• Chase Ultimate Rewards points gained: 3,415 = 3,415 everyday spending
• Hilton Honors points gained: 11,871 = 8,084 everyday spending + 2,956 Amex spending bonus + 760 from Guest Opinion Rewards + 71 Lyft rides
• Hertz Gold Plus points gained: 0 = 0

November 2019 Details:

• Chase Ultimate Rewards points gained: 10,276 = 10,227 everyday spending + 49 from Chase shopping portal
• Hilton Honors points gained: 38,521 = 8,641 everyday spending + 2,044 Amex spending bonus + 26,580 from hotel stays (4 nights) + 976 from Guest Opinion Rewards + 280 Lyft rides
• Hertz Gold Plus points gained: 1,100 = 1,100 from E-rewards redemption for Annie

October 2019 Details:

• Chase Ultimate Rewards points gained: 3,491 = 3,491 everyday spending
• Hilton Honors points gained: 3,344 = 2,484 everyday spending + 860 from Guest Opinion Rewards
• Hertz Gold Plus points gained: 1,100 = 1,100 from E-rewards redemption for Scott

September 2019 Details:

• Chase Ultimate Rewards points gained: 3,091 = 3,091 everyday spending
• Hilton Honors points gained: 21,660 = 6,785 everyday spending + 7,000 from E-rewards redemption for Scott + 7,000 from E-rewards redemption for Annie + 875 from Guest Opinion Rewards
• Hertz Gold Plus points gained: 0 = 0

August 2019 Details:

• Chase Ultimate Rewards points gained: 1,787 = 1,787 everyday spending
• Hilton Honors points gained: 21,129 = 705 everyday spending + 19,724 from hotel stays (4 nights) + 700 from Guest Opinion Rewards
• Hertz Gold Plus points gained: 1,100 = 1,100 from E-rewards redemption for Annie

July 2019 Details:

• Chase Ultimate Rewards points gained: 4,146 = 4,109 everyday spending + 37 from Chase shopping portal
• Hilton Honors points gained: 15,513 = 523 everyday spending + 7,000 from E-rewards redemption for Scott + 7,000 from E-rewards redemption for Annie + 990 from Guest Opinion Rewards
• Hertz Gold Plus points gained: 1,100 = 1,100 from E-rewards redemption for Scott

June 2019 Details:

• Chase Ultimate Rewards points gained: 6,342 = 6,342 everyday spending
• Hilton Honors points gained: 9,852 = 2,484 everyday spending + 2,000 from 2019 unlimited bonus + 5,190 from Guest Opinion Rewards + 178 Lyft rides
• Hertz Gold Plus points gained: 0 = 0

May 2019 Details:

• Chase Ultimate Rewards points gained: -28,268 = 4,733 everyday spending – 1 Amazon purchase – 33,000 points redeemed
• Hilton Honors points gained: 27,793 = 8,329 everyday spending + 2,634 from hotel stay (1 night) + 7,000 from E-rewards redemption for Scott + 7,000 from E-rewards redemption for Annie + 2,830 from Guest Opinion Rewards
• Hertz Gold Plus points gained: 0 = 0

April 2019 Details:

• Chase Ultimate Rewards points gained: 18,918 = 15,000 Chase Freedom Unlimited sign-up bonus + 4,425 everyday spending
• Hilton Honors points gained: 5,521 = 4,046 everyday spending + 1,475 from Guest Opinion Rewards
• Hertz Gold Plus points gained: 2,200 = 1,100 from E-rewards redemption for Scott + 1,100 from E-rewards redemption for Annie

March 2019 Details:

• Chase Ultimate Rewards points gained: 4,554 = 4,554 everyday spending
• Hilton Honors points gained: 17,960 = 2,740 everyday spending + 7,000 from E-rewards redemption for Scott + 7,000 from E-rewards redemption for Annie + 1,220 from Guest Opinion Rewards
• Hertz Gold Plus points gained: 0 = 0

February 2019 Details:

• Chase Ultimate Rewards points gained: 4,846 = 4,686 everyday spending + 160 from Chase shopping portal
• Hilton Honors points gained: 8,983 = 7,728 everyday spending + 1,255 from Guest Opinion Rewards
• Hertz Gold Plus points gained: 0 = 0

January 2019 Details:

• Chase Ultimate Rewards points gained: 3,423 = 3,423 everyday spending
• Hilton Honors points gained: 31,883 = 8,497 everyday spending + 6,826 from hotel stay (1 night) + 7,000 from E-rewards redemption for Scott + 7,000 from E-rewards redemption for Annie + 2,620 from Guest Opinion Rewards
• Hertz Gold Plus points gained: 1,187 = 1,100 from E-rewards redemption for Scott + 87 from car rental

December 2018 Details:

• Chase Ultimate Rewards points gained: 378 = 378 everyday spending
• Hilton Honors points gained: 76,543 = 14,783 everyday spending + 40,000 Amex spending bonus + 10,000 points purchase + 10,000 points purchase bonus promotion + 1,760 from Guest Opinion Rewards
• Hertz Gold Plus points gained: 0

November 2018 Details:

• Chase Ultimate Rewards points gained: 510 = 510 everyday spending
• Hilton Honors points gained: 6,764 = 6,409 everyday spending + 355 from Guest Opinion Rewards
• Hertz Gold Plus points gained: 1 = 1 from registration bonus

October 2018 Details:

• Chase Ultimate Rewards points gained: 4,137 = 4,137 everyday spending
• Hilton Honors points gained: 31,043 = 13,827 everyday spending + 7,000 from E-rewards redemption for Scott + 7,000 from E-rewards redemption for Annie + 3,015 from Guest Opinion Rewards +  201 from dining rewards network
• Hertz Gold Plus points gained: 0

September 2018 Details:

• Chase Ultimate Rewards points gained: 27,427 = 15,000 Chase Freedom sign-up bonus + 12,427 everyday spending
• Hilton Honors points gained: 13,567 = 10,052 everyday spending + 3,515 from Guest Opinion Rewards
• Hertz Gold Plus points gained: 0

August 2018 Details:

• Chase Ultimate Rewards points gained: 3,093 = 3,093 everyday spending
• Hilton Honors points gained: 112,285 = 75,000 Hilton Card sign-up bonus + 13,947 everyday spending + 6,903 from hotel stay (1 night) + 7,000 from E-rewards redemption for Scott + 7,000 from E-rewards redemption for Annie + 2,435 from Guest Opinion Rewards
• Hertz Gold Plus points gained: 0

July 2018 Details:

• Chase Ultimate Rewards points gained: 57,934 = 55,748 transfer from Annie + 2,186 everyday spending
• Hilton Honors points gained: 132,177 = 100,000 Aspire Card sign-up bonus + 19,059 everyday spending + 12,792 from hotel stay (1 night) + 213 from dining rewards network + 113 from Hilton shopping portal
• Hertz Gold Plus points gained: 0

June 2018 Details:

• Chase Ultimate Rewards points gained: 2,271 = 2,271 everyday spending
• Hilton Honors points gained: 14,000 = 7,000 from E-rewards redemption for Scott + 7,000 from E-rewards redemption for Annie
• Hertz Gold Plus points gained: 5 = 5 from registration bonus

May 2018 Details:

• Chase Ultimate Rewards points gained: 71,348 = 50,000 CSP sign-up bonus + 5,000 authorized user bonus + 10,000 referral bonus + 6,348 everyday spending
• Hilton Honors points gained: 1,310 = 310 from dining rewards network + 1,000 dining rewards network bonus for first dine
• Hertz Gold Plus points gained: 0

Trip Report Index

1. Introduction and Planning
2. Using Points and Miles to get to Hawaii
3. How a Flight Change Put 45,000 Miles Back in My United Account
4. Postponing Hawaii Due to a Pandemic
5. Flight from Chicago to Maui
6. Grand Wailea Maui, A Waldorf Astoria Resort
7. Activities in Maui
8. Flight from Kahului to Honolulu
9. Hyatt Regency Waikiki Beach Resort And Spa
10. Activities in Honolulu
11. Flight from Honolulu to Chicago