Sponsored: Inside the Ultimate Guys Weekend, I

So, last month I wrote about planning a trip using my Starwood Preferred Guest Credit Card from American Express, and this month a buddy and I hit Toronto’s favourite rival, traveling and booking accommodation using only Starpoints.

I booked flights on American Airlines, which is one of 150 airlines you can redeem Starpoints on; I also could’ve booked with United or Air Canada. Fun fact: you have the option to upgrade your seat with Starpoints. Second fun fact: if you’re flying with someone who wants to use their own points, you can transfer your Starpoints to thirty other frequent flyer programs. Talk about flexibility!

We arrived in downtown Chicago early in the evening. I booked us at the Aloft Chicago City Centre, mainly for one important reason: it’s located in the River North neighbourhood, which has forty-two world-class steakhouses nearby. We’ll revisit that fact next time.

The other nice thing about this Starwood property is that it’s pretty hip and plugged in: Wi-Fi is free, there’s a good business centre in the lobby, it’s the kind of place with a copy of Wired in the bathroom, and—this sounds boring but it’s important—desks have a few outlets on top of the desk, rather than tucked away somewhere, so you can keep all your iDevices powered up. The décor is nice too: it’s all clean lines, open space, brushed steel, and spectrograph patterns.

It was a bit late, so we asked our concierge at the SPG property to give us a recommendation for a restaurant nearby, something that would be a great first night out for our guys weekend. They recommended Au Cheval. Aside from a great beer and cocktail list (which would become a recurring theme), Au Cheval is known for well-executed, high-end versions of diner staples, like chopped chicken liver, chilli con carne, and foie gras terrine. What you want, though, is the burger. Burgers are ubiquitous when you travel south of the border, but skip all those airport burgers and wait for this one. The single is really a double, it’s greasy enough to be delicious without falling apart, and instead of thin-sliced and smoked bacon they use thick cut braised pork belly. Truly, those burgers were a great way to end the first day of an awesome trip.

Check in next week for the rest of our ultimate guys weekend. 

Photo courtesy of Edward Stodjakovic

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