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I recently wrote about how my latest trip to the USA didn’t really get off to the most luxurious of starts and promised to redeem my ‘travel hacking credentials’ with some details about how I booked the rest of the trip.

The idea here isn’t to show you how to copy every element (some of the exact deals no longer exist), but instead to share, in more general terms, the practical process I go through when booking flights and hotels. I think there are two key aspects really:

• Think flexibly – use the full range of travel hacking tools and knowledge at your disposal.
• Always collect free Miles / Points (if doing so is quick and easy), even if you don’t have an obvious and immediate use in mind.

As a bit of fun, I’ve decided to give each element of the trip a ‘Travel Hacking Score’ (please feel free to take issue with my scores in the comments – otherwise I am essentially just marking my own homework here!). For me, InsideFlyer is all about sharing how to travel better for less (‘better’ can mean convenience, comfort, fun, etc) so that’s the yardstick I’m using.

Stage 1: Manchester to Madrid

I booked a Ryanair flight for £25.00.

Glamorous? No.

Practical? Yes.

The time of the flight suited my schedule perfectly and I can get a train straight to Manchester Airport for ~£10.

When you’ve got Points/Miles in lots of different programmes the range of options open to you can be huge, but sometimes simple is best. I didn’t love being squashed in a middle-seat on a completely packed flight, but it’s only a couple of hours and the convenience and value more than made up for that.

It may not be a universally popular opinion among IF readers, but I think the low cost carriers are great (at least for those of us outside London). I am still relatively young and not hugely tall or wide though, so I can certainly understand why others may take a different view.

Travel Hacking Score: 4/10 – That may seem high for Ryanair, but it was by far the most convenient (and cheapest) way for me to get to Madrid, so deserves some points. Getting stuck in a middle seat, with my carry-on wedged where my feet were supposed to go, means I don’t think anything higher than 4 can be justified.

Madrid

I stayed at the Holiday Inn Piramides  – nothing remarkable, but absolutely fine. Good value (~ £55 per night) and a very good location (walkable to much of the city, and a metro station literally next door with a direct service to the Airport).

The real benefit of staying here over similar options though, was to help hit some of my IHG Rewards Club ‘Accelerate targets‘. Averaging everything out, my 2 night stay earned me ~20,000 IHG Points in total, which I value at about £80. Given the reasonable price paid, that represents a superb rebate (+8% cashback from Quidco too!).

If you aren’t using Points/Miles for a stay, you should (usually) be earning Points/Miles from it. Taking full advantage of the best promotions each quarter means that rebates of 50%+ are regularly achievable, once you factor bonus Points / cashback etc.

Travel Hacking Score: 8/10 – Getting well over 50% in value back (mostly as Points), while enjoying a perfectly good stay at a solid hotel in a great city deserves a good score. Particularly as it involved working out the most efficient way to complete my ‘Accelerate’ targets too – which isn’t always as easy as it sounds!

Madrid to Chicago

I flew Iberia Business Class for just 34,000 Avios + ~£100 in taxes/fees.

For off-peak dates, Iberia to/from North/Central America remains one of the best Avios ‘sweetspots’. Madrid to Chicago, for example, is a 10+ hour flight!

I hadn’t flown Iberia long-haul for a few years and was impressed by the new cabin (Youtube video here). The staggered 1 -2 -1 layout they use is one of my favourites, because the middle seats right next to each other (‘E’ + ‘G’) are fantastic when travelling with someone, or you can have total privacy instead by opting for a ‘true’ window seat (‘A’ and ‘L’ – the ones properly next to the windows). Reserving your seat in Business Class in advance is free and easy to do online with Iberia.

The service was good, the food was almost excellent (everything apart from one of the main dishes, which was a bit lacking), and the entertainment system had some new films I hadn’t seen. The seat/bed was comfortable and the booze flowed extremely liberally (I encountered the strongest G&T of my life – and that’s saying something!), so all in all, an extremely enjoyable way to spend the day.

Travel Hacking Score: 9/10 – To the best of my knowledge, Madrid-Chicago is the furthest you can fly in Business Class for 34,000 + £100 these days. Transferring Avios to book from Iberia Plus and travelling off-peak both boost the score, but I would need to have booked during one of Iberia’s regular discounts for this to get a 10.

Chicago

I wanted to try out a couple of different places and maximise the generous Hilton promotions available at the time.

For the first night I booked the Embassy Suites Downtown Magnificent Mile, which turned out to be a fantastic choice!

It’s the first time I’ve stayed at an Embassy Suites and I loved it (I also really like IHG’s Staybridge Suites brand). The room was a large ‘full’ suite (separate living area) with wonderful views, on the top floor. The member of staff at check in was the perfect combination of friendly yet efficient (which is highly appreciated after a long flight) and service generally was on point.

Embassy Suites include free drinks and food in the evening (as well as breakfast) for all guests, so are a really good option if you don’t have elite status but still like a few free perks when travelling.

You might think that because it’s complimentary the quality wouldn’t be good, but it was. I missed the hot food in the evening, but the drinks go on for 2 hours, you can have up to 4, and there was plenty of choice including local craft beer and simple cocktails. It was busy and there was some queuing involved, but that was to be expected and I’ve waited for longer at plenty of busy bars.

Breakfast was (surprisingly) superb –  one of the best hotel breakfast I can remember having for a long time: steaming hot (not overcooked!) scrambled eggs, crispy bacon, tasty sausages, fresh pancakes, ripe fruit, good juice and coffee etc. I didn’t even get round to trying the ‘made to order’ stuff that was also included.

I booked using the MVP rate (you can check out our full list of Hilton discount codes here), which knocked a good chunk (~20%) off the lowest standard rate, resulting in a rate of about £85.

Booking using the MVP rate is a very good way to save a few quid when booking Hilton hotels in the Americas (you can fast track to Gold status in just 4 stays too!). Technically, you are supposed to be a member of an affiliated sports organisation, but I’ve never been asked to produce any documentation (or heard of anyone ever being asked). You can join the US Golf Association for $10, if you’d rather be safe than sorry.

Combining the various Hilton bonuses I earned 8,488 Honors Points, worth about £34 to me.

Add up the 8 free drinks (4 per person), the free food in the evening and breakfast, and you’re looking at tremendous value!

Travel Hacking Score: 8/10 – If you include the discount for using the MVP rate and the Points earned, I saved/got back over 50% in value. For a great hotel in a top location, with so many extras included too, that’s a very fair score.

The second night in Chicago was at the Hilton Palmer House. The hotel lobby/bar area is a fantastic historic space and the room was certainly spacious, if dated.

The Club Lounge (free access due to my status matched Diamond status) was solid for the USA – decent breakfast and ok food in the evening, with soft drinks and a few snacks during the day.

As with most US hotel lounges, you had to pay if you wanted alcoholic drinks – and to be honest, if you’re paying, I’d strongly recommend a cocktail at the bar instead.

Overall, I liked Palmer House, but felt that if they just spent a bit of money updating things and improving the service a little, it could be a genuinely stunning place.

Again, I booked using the MVP rate, paying ~£80 in total. For that I earned 9,264 Hilton Points (worth about £37).

You get a 1,000 Points bonus for having Diamond status at Hiltons, but not at Embassy Suites, which is why the Points total is higher here despite the room being slightly cheaper.

Travel Hacking Score: 7/10 – In some ways maybe the travel hacking score should be higher here (MVP rate, lots of Points, Diamond benefits from status match etc), but I just didn’t like it quite as much as the Embassy Suites.

Remember: it is a holiday, so staying where you actually want to stay is obviously a very important consideration – Miles and Points are there to help you travel ‘better’, not dictate it. I liked the Hilton Palmer House and am glad I tried it, but know that if I was back in Chicago anytime soon, I’d happily pay a bit more/earn fewer Points to stay at the Embassy Suites.

Bottom line

The aim of this post was to share some tips and explain a little more about the process of how I go about ‘travel hacking’ in practice. I hope it is a bit more useful than a traditional review piece.

To get the very best deals, flexibility is the key. By mixing Ryanair with a long-haul Business Class Avios bargain and switching between hotel chains to take advantage of the best prices and best bonus offers (+ using discount codes, cashback websites, etc),  I think I managed to ‘travel better for less’ pretty well on this trip.

In the rest of the series, I’ll be looking at where I stayed (+ how and why!) in Washington DC, Boston and New York, as well as how I got home.

Do you think my ‘Travel Hacking Scores’ are fair?