Planning the Ultimate Guy’s Weekend

Having recently picked up a Starwood Preferred Guest Credit Card from American Express, I started racking up points with the help of 10,000 bonus points for spending $1,000 within the three months. I’m now planning a trip with some buddies for the ultimate guy’s weekend away to Chicago. We had a few itineraries in mind though, which one would you choose?


Baseball season is over, but there’s plenty to do in Toronto’s favourite rival. There’s awesome restaurants like the Publican and Au Cheval, fun times at the iconic Second City, and the fantastic Goose Island Brewery, which I love. You can get a few flights for between 25,000 and 50,000 Starpoints, depending on when you leave, and the W Chicago has rooms starting at 13,000 Starpoints for the weekend. Alternatively, you can stay near the Mag Mile in Aloft Chicago City Center, starting at 10,000 Starpoints.


It seems like there are a million attractions in Boston, but if you’re heading to the City of Champions, you should check out a Patriots game, visit the South End and shuck some oysters, and figure out a way to go yachting; that seems like the thing to do in New England. Also, if you and your buddies feel like learning something, you could do the liberty trail. You can get a non-stop flight for 25,000 Starpoints, and get rooms at the Liberty, a Luxury Collection hotel for 12,000 Starpoints, or any of the sixteen other SPG hotel properties for a bit less.

New York

Tough to narrow down all the awesome things going on in New York, but with an SPG Amex Card, you can bid on a few different Moments experiences. I love the sound of an experience that gives you the chance to watch the New York Rangers in style in the SPG Luxury Suite, which is full of complimentary food and beverages, not too shabby! You can also pick up a room at the Weston in Times Square for about 25,000 points, with a bunch of upgrades available, or Le Parker Meridien, steps away from Fifth Avenue for a comparable amount. Actually, there are about thirty-three Starwood hotels in the area, so you’re not hurting for choice.

Fun fact: At the front desk of any hotel, you can ask the concierge what the Instant Awards are for that particular hotel and exchange Starpoints for everything from room service to massages. See what I mean about feeling rewarded?

We’re looking forward to heading to Chicago but are wondering which location you’d choose. Let us know what your dream weekend away looks like by voting on our Facebook page.

Photo courtesy of Wilhelm Joys Andersen

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