Hi,

I have a dilemma you experts might assist me with.

I'm looking into buying tickets for 2 adults from SJC to DEN.

I have 79K miles in UA, and tons for points with Chase Sapphire.

I have 3 options I've found:
1) UA r/t. 50K each ticket. Basically transfer 21K miles from Chase, and get 2 reward tickets (plus pay 25$ per luggage of course...)

2) One way UA, One way Southwest (transferring from Chase). Transfer 18K points to SW, and buy 2 award tickets (using 50K UA miles).

3) SW (transfer 50K points from Chase). Keep my UA miles for future flights.

Which is better? I mean if I use my UA miles it seems I save in at a very low ratio (less than 1 cent per mile)

How much is it to buy a ticket?

Apparently for the specific flights you want, UA has no saver space available. Instead, you are finding redemption at 2x the saver level. It's basically last seat availability. That's a very dear redemption. I only redeem at the saver level. It depends on how cash rich you are, and whether you have other opportunities for the miles. This will help you determine whether to spend cash or miles.

If I read you correctly, and I might not, you can spend:

50K - 2 Southwest tickets
100K - 2 UA tickets

I would choose the Southwest redemption UNLESS travel time on UA is several hours shorter.

Flights aren't cheap (July...). So SW r/t is 800$ for 2 tickets, UA is ~1050$.

Cash flow is not an issue, and I will fly with the family a few times in the coming years, so I'm mostly looking to get the best value for the miles/cash/chase points.

It seems to me Chase might be the way to go (500 points for 800$ is 1.6X, which is a good ratio for UR). Whereas UA miles might be better used for saver awards in the future, or routes that don't have cheap direct alternatives.

Am I right? Am I missing anything?

Regarding the flights - both are same length (nonstop) and on the same hours.

UA is 100K (79K miles I have there + 21K transferred from Chase)
SW is 50K (all transferred from Chase)

The following are my 2 cents. In short, you have plenty of issues need to work on.

1. DEN is a UA hub. So it is always better to fly SFO-DEN in hope for better award inventory.

2. You can also fly WN with SFO/OAK-DEN.

3. Except emergency, it is pretty much a waste to spend 50K in for a domestic economy award ticket.

4. Detail about your proposed travel is needed.

I will be flying with my wife (and 7 months old infant) for a few days in the Rocky mountains.

The closest airport is SJC. SFO is also good (40 minutes). OAK is not relevant.

I'm looking to fly on 7.26 and return on 7.31. There isn't much flexibility on the dates, just a little if really saves money (same length, just move it by a day or two)

Since we are flying with a baby, we are only considering non-stop flights, and we don't want fly very early or late in the day. Flights leaving between 9-13 am are relevant.

I think this are mainly the only details/constraints I can think of.

An award flight six weeks out may cost you tons in miles. Limiting your flight window to the hours you've stated increases the degree of difficulty. Although I'm not from the area, I've probably been in the Bay Area at least 30 times and find your "OAK is not relevant" comment strangely limiting when your alternative is to spend $800-1050.

I'm going to assume your trip is absolutely necessary because otherwise, I'd recommend planning more in advance and going at another time when you might find saver award rates or cheaper cash fares. I'm also going to assume that OAK is not relevant because there aren't nonstop trips. If cash flow isn't an issue, fly WN and earn some RR points (and others, using a card that has a travel category bonus), especially since the base fare is cheaper than UA and you shouldn't need to worry about baggage fees.

If you want to cut the cost, you can book one way on WN (or UA) with cash and the other way with points--domestic one ways are now generally priced the same whether as part of a RT or a standalone one way, which means that you could see if any of the routes might offer a one-way saver rate that you could pair with a more modest cash fare.

The only saver options are either with a stop (increasing a 2 hours flight to be over 6) or early in the morning (6 am flight)/late at night (10pm).

Since I'm flying with an infant, heading to the airport in the middle of the night, or having a 6 hours flights instead of 2 are just not worth saving a couple hundred of bucks.

But what I'm taking from the thread (and correct me if I'm wrong) that UA miles are worth more (assuming you find saver tickets). So it is wise to keep them in the account for future use (flights I'll know of many months in advance and not 6 weeks before the travel data).
Is that right?

Saver awards are available. The issue is the above criteria is what strike everything down.

Which saver awards are available? At what times? I didn't find any for those dates?

I am seeing saver award availability for.....

7/26: SFO-DEN (all with 2x seats available)

8:30p - 11:57p
7:00p - 10:30p
5:00a - 8:30a
5:20p - 8:21p
6:50a - 10:24a
4:15p - 7:54p


7/30: DEN-SFO (2x seats)

2:15p - 4:00p


7/31: DEN-SFO (2x seats)

6:00a - 7:33a
6:55a - 8:30a


If you can change your travel to 7/26 - 7/30, then you could book early evening / afternoon flights for both you and your wife for 50k miles and about $12.00

If you want to stay until the 31st, then I would book the outbound with miles (25k + $12 for two people) and pay cash for the return (approx $183-237 pp on United)

at the high end, you would be using 25,000 miles to save $576.00 or approx 2.3cpm which is not a bad redemption for domestic.

Yes, that is indeed a good option (Sadly can't return on the 30th).

Though, if the cost is 25K + ~200$ pp, isn't it wiser to fly Southwest using transferring points from my Chase card? I mean, that would be something like 25K points for a return ticket. At a "bad" assumption that Chase point wroth 1c, that is 250$ per ticket. So I costs me almost the same, and I keep my UA miles for future flights.

Am I missing anything?

Try booking through Chase Ultimate Rewards, on the Chase site......

7/26 SFO-DEN Frontier F9664 11:50AM nonstop
7/31 Den-SFO Frontier F9657 06:45AM nonstop
16,576 Ultimate Reward points each, Roundtrip
Total UR Points for two roundtrip: 33,152
Other airlines (Virgin, United, Delta), and later departure times, also available, but at higher points.

Never flew with them, but don't they like charge a lot extra for luggage and carry-on? Since we are 2 adults plus a small baby, we will be traveling with luggage (or 2) and a carry-on bag.

When I was searching for my best rate for flight using Chase UR points, my best option was transferring to Southwest. The 2 free checked bags per person was an added bonus. I saved about 7K points per ticket over using Chase portal. May be an option for you.

ALSO available through Chase Ultimate Rewards, on the Chase site......

7/26 SFO-DEN UNITED UA223 10:55AM nonstop
7/31 DEN-SFO UNITED UA268 09:55AM nonstop
31,136 Ultimate Reward points each, Roundtrip
Total UR Points for two roundtrip: 62,272
Lots of earlier and later departure times also available, at higher and lower points.
Take a look.