Sponsored: Inside the Ultimate Guys Weekend, II

Check out the first part of our ultimate guy’s weekend in Chicago here.

The next morning of our SPG weekend away, we met up with some Chicago friends who had agreed to show us around, and we visited Logan Square, which is apparently one of the city’s hipster enclaves. We then headed to brunch at Longman & Eagle, a Michelin-starred eatery with an evolving menu, 150 whiskies, and a knowledgeable bartender. Brunch turned into lunch, with duck egg hash and tete de cuchon being cleared away for cavatelli and a ploughman’s platter, and our cocktails turned to whisky flights.

Next up, back downtown for Mag Mile, which is Chicago’s main drag featuring anything and everything you could dream of seeing as a tourist in the city. We stopped at a couple of men’s stores (Vince and Tod’s), but it’s also where you’d go to see the Blackhawks and the Cubs. For all the Cubs fans out there, you may want to know that Starwood Preferred Guest is the official hotel and resort partner of the Chicago Cubs! What does this mean? That if you’re looking for access to all things Cubs, this is the Card for you. Though the time of year wasn’t ideal for catching a game, we spent the weekend checking out the Navy Pier, the History Museum, the House of Blues, and Second City. We also hit one of Chicago’s many liquor stores, seeing as you’re allowed to bring back up to 1.14 litres.

Now, the highlight of the trip: steak. Remember how there are forty-two world-class steakhouses near the Aloft? Well, we went to the best on the list: David Burke’s Primehouse. They have a pretty extensive menu and a lot to offer, but every single one of us went for the 55-day aged rib eye. The only thing better was touring the aging room afterwards.

The next day we checked out and I settled the incidentals on the bill using my SPG Amex Card’s Instant Awards, which I’d previously used to score a free breakfast at the hotel’s restaurant. These Instant Awards allow Cardmembers to redeem their Starpoints for a variety of in-hotel indulgences such as upgrading your room.

We finished our vacation at the Publican, a restaurant that deals mainly in pork and shellfish. Over oysters and beers (the Publican has about fifty, along with a beer sommelier on staff to help you sort through it all), we toasted our ultimate guy’s weekend. Now that feels like being rewarded! If you’re looking to plan the ultimate guy’s weekend away like ours, try consolidating all your spending on a single credit card like the Starwood Preferred Guest Credit Card from American Express. We’re already saving our Starpoints for our next getaway.

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