Miles and points have truly been a blessing in my life and in the life of my family. Since I started collecting miles and points back in early 2013, miles and points have taken us literally around the globe to places we might have never dreamed of being able to afford to see. From our very first family vacation on miles and points to Lake Tahoe in 2014, to Yellowstone, Disney World, Machu Picchu, Singapore, California, Seattle and places in between.
(SEE ALSO: The 9 amazing sights I saw this year)
But the trip we just got back from was probably the first trip we’ve taken that was what most people I know would classify as “ridiculous” in how short it was.
Christmas present to go to Chicago
My family are pretty big Harry Potter fans and when I was in Chicago last month for the Thanksgiving Day parade, I saw an ad for a show called Potted Potter at the Broadway Playhouse in Chicago, which bills itself as “all seven Harry Potter books in 70 hilarious minutes”. I knew if there was any way possible to pull this off, this would make for an awesome Christmas present.
Along with my wife and I, 2 of my kids are big Harry Potter fans, so we set about trying to plan a trip for 4. Logistics are tough with a family as large as mine, and for awhile it looked like we were not going to be able to find childcare and my wife was not going to be able to go.
Originally we were going to try for a day trip where we would fly to Chicago in the morning, see a matinee show and then fly back home in the evening. Not staying overnight makes the logistics a bit easier. But in the end, we couldn’t make that happen and thanks to my in-laws being off work between Christmas and New Year’s, we found tickets where we’d catch an afternoon flight out, see an evening show, and fly back home early the next morning
An expensive present / trip?
Now of course Southwest wanted to throw a wrinkle into all this by CANCELING our original flight 18 hours before departure for snow that doesn’t exist. Thankfully this didn’t disrupt our plans too much – just caused us to take an earlier flight meaning we had more time to spend in Chicago (not a BAD thing!)
But when I was talking about this Christmas present to a friend, she commented “Wow that’s an expensive Christmas present”
And I can understand how it might look like that to someone not in the miles and points world. But let’s take a look at our total expenses
- Flights – These are cheap $49 Southwest flights, so it was 24,000 Southwest points + $44.80 for the flights. We’ll also pay $10 for airport parking
- Hotel – I’m not sure how to count this. We could and would have used points, but cash rates were so cheap coupled with an Accelerate promotion made it more lucrative to pay cash. I guess count this as the $75 we spent
- Tickets – we used hottix.org to get “half price” tickets but the total for 4 of us was still $220
- Food and activities – we’ll probably end up paying $30-50 for lunch and dinner and random stuff
So call it $400 total for the 4 of us? On the expensive side for Christmas presents (at least for us) but not completely unreasonable.
As I’ve said before, you still have to pay your food and activity costs, but the beauty of miles and points is that when your flight and lodging costs are covered, EVERYWHERE is as cheap as ANYWHERE!
A “fake” trip
While we’ve done short trips before, this is my first “fake” trip where it feels like this would be so ridiculous if not for miles and points. And I’m certainly glad for it!
What about you? What has your most ridiculous / fake trip been, thanks to miles and points? Leave a note in the comments
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Dan Miller travels with his wife and 6 (SIX!) children. He loves to help families travel for free / cheap, especially larger families. If you are looking for help, drop him an email at 
I’ve done daytrips to Chicago four times now from MSY. It’s very easy with cheap flights and easy transportation on the “L” to the Loop. I enjoy not carrying any luggage or worrying about a hotel.
My wife and I just did the same thing last week to go see Hamilton in Chicago. Flights were $750 r/t from SMF, but thanks to points and the companion pass, our only out of pocket were the tickets to Hamilton. No way we would have spent $2600 on a one night trip without points/miles.
In September we flew from Pittsburgh to Denver just to see a Chris Tomlin concert at the Red Rocks Amphitheater. It was a great concert at an incredible venue. It was totally worth it – having a Southwest Companion Pass made the trip even sweeter!
First of all, thank you for supporting the arts!! I so appreciate your family going out of its way to see new work. You might want to book the Cursed Child in NYC this spring.
Just FYI, for non-theater people, as a theater professional, those apps and sites often are there because we’re just trying to put butts in seats. You might do well to contact the box office and see what kind of deal or added value you could get (house seats (those are centrally located seats), some kind of talk-back, a meet and greet, etc). Also, If I put my small theater tickets on TDF/TKTS for $9, you end up paying more than the 9 I get. So with a little work, often you can get the tickets for the discount, especially in smaller and non Broadway venues. You’re also totally correct about the “half-price”. It definitely is often inflated prior to sale.
am I missing something here — you paid cash for hotel, food, and tickets for the show. You found cheap southwest tickets but decided to pay with points instead.
This wasn’t made possible by points, it was made possible by you being willing and able to do a day trip which for many people is uncommon.
Nevertheless it sounds like a great deal you out together and lots of fun.
I think it was a grand and spontaneous trip! Even though you paid for the hotel the Accelerate offer gains probably paid it back.
How was the show? 70 hilarious minutes actually cover it all? I also know some Harry Potter fans so will need to be on the lookout for the show.
I would highly recommend it to anyone who has read / enjoyed the Harry Potter series. I thought they did a good job of covering it. There’s also a show called “Puffs” that tells the stories from the perspective of a bunch of Hufflepuffs that I’ve heard good things about
This is a bit like “mileage runs” but with a “real” reason to travel. I do like to combine both of these ideas if possible. Last May, I spent one night in Cleveland to visit the Rock and Roll Hall of Fame. This was part of a series of mileage runs to get me to United Million Miler status. I stayed at the Westin Cleveland using points. I used one of my SPG Platinum Suite certificates to get an upgraded room overlooking Lake Erie. I took a red eye from SFO so arrived very early on Saturday morning, but using the SPG Your24 benefits (with 75 nights stay), I was able to checkin when I arrived at 7am (even had a complementary breakfast in the Executive Lounge), and a late checkout the next day at 4pm. Also, signed up for annual membership in the Rock Hall so I could visit multiple days during my visit, and it’s 100% tax deductible. How’s that for win? Happy New Year to all readers!!
Nice! Due to our super early flight the Holiday Inn Express let us check in early too and we got a 2nd breakfast too! Love it when that happens!
I’ve never thought of my small trips as “fake,” but my wife and I have done many trips like this. We’ve used the SW Companion Pass to fly from FLL to Chicago to see the Cubs in the afternoon and Steve Winwood that evening, to Phoenix to see U2 and catch a Diamondbacks game, to Tampa to see the Dali Museum. We’ve also used the Pass to not only go to every baseball stadium, but to return to some cities just to get a stamp in my baseball passport(I wasn’t aware of the passport book when we first started going to the ballparks).
Good story. I’m not a Southwest flyer much but I think I would have just paid cash for the $49 tickets. You would have earned miles in addition to the cheap price. Alternatively I’m wondering if using flexible points would also have been better at that price point.
I’ve never done such a short leisure trip but did use Avios and Radisson nights to take my son to the Formula 1 race in Mexico City a few years ago. The event tickets cost a ton and none of the credit card concierge service could help but we wouldn’t have gone if not for free first class seats and hotel.
I just took my 10 y/o daughter to London (from Los Angeles) to see Hamilton. Tickets are a lot less there if you can find them. It was a quick trip but I don’t consider it fake – I’m aware that others think I’m ridiculous, of course. 🙂 We gave her the theater tickets for Christmas and then told her to hurry up and pack because our flight was at 5:30!
I was able to find award flights on short notice on AA outbound (using AS miles) and UA return. I found the hotel rates quite reasonable considering the time of year so I just paid cash (and earned more points!) for that. I’m the daughter of a (now retired) airline pilot – I aged out of my flight benefits decades ago but grew up taking day trips to other states for lunch or back-to-school shopping or whatever so these types of trips don’t seem unusual to me – I just have to pay for them now!