NHL Winter Classic + New Year’s Trip to Chicago

By 10xT Reader Robert Wells

New Year’s weekend has become a weekend we look forward to every year, as we have a tradition of traveling to the annual NHL Winter Classic outdoor hockey game. We have traditionally stayed in a big city to celebrate New Year’s and then traveled to the game next day/year.

This year, with the game being only an hour and a half away at Notre Dame in South Bend, Indiana, it was easy to put this trip together. My brother was even able to join us – he took care of his own flights with Southwest Rapid Rewards points.

Flying from Dallas to Chicago

Our stash of Southwest miles we earned from attempting to get the companion pass came in handy yet again as we were able to get a one-way trip for two for next to nothing. Good thing, too! This would have been an expensive trip over New Year’s weekend.

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We flew back to Dallas on American Airlines and were upgraded to first-class — I have elites status from work travel — so it made for a nice 2.5-hour flight home.

To get to the game, we rented a car when we landed in Chicago.

Dallas (DAL) to Midway (MDW) on Southwest

• Points Used: 7,300 Southwest Rapid Rewards points
• Source of Points: Chase Southwest Rapid Rewards® Premier Credit Card
• Cost Out of Pocket: $11.20 (Taxes)
• Cost Without Points: $787.96

Chicago (ORD) to Dallas (DFW) on American Airlines

• Points Used: 25,000 AA Miles + Complimentary upgrade
• Source of Points: Barclays Aviator Red Mastercard
• Cost Out of Pocket: $11.20 (Taxes)
• Cost Without Points: $1,088.60

Two Nights at the Gwen, Luxury Collection, Chicago

Chicago has a lot of great places to choose from to stay. We booked the Gwen in the Loop area of Chicago. It’s is a former Starwood property that is now part of Marriott. Personally, I feel like I get a little better treatment at the former Starwood properties than heritage Marriotts. It also has great access to the majority of the city and was very walkable as we were only a block away from Michigan Avenue and the Magnificent Mile.

Since I travel quite a bit for work, I have elite status with Marriott. One of the perks offered to those who stay 50 nights in a year is a choice of a gift. I chose 5 Suite Night Awards which allows you to upgrade cash or award nights. You can also select to receive another 5 Suite Night Awards when you hit 75 nights in a year. There are other perks you can choose at 50 and 75 nights, respectively, but I always choose Suite Night Awards.

I used my Suite Night upgrades and was able to get the second largest suite the property had to offer. The suite was especially helpful since we were traveling with my brother so the privacy of having our own room and him getting his own bed was a win for all parties!

We chose to use a combination of cash and points because the rate the day before New Year’s was so inexpensive.

There was no lounge for Platinum Elite members (and higher), but we received a $14 per person credit at the restaurant for breakfast. The front desk was nice enough to include my brother – even though the benefit is supposed to be for two people. On average, we spent $10 per day as a group.

We booked the other night with 35,000 Marriott points bringing the total cost of the stay to 35,000 points + $131. Not bad for New Year’s weekend in Chicago at a 5-star hotel!

• Points Used: 35,000 Marriott + 2 Suite Night Awards
• Source of Points: Marriott Premier Business Card
• Cost Out of Pocket: $100 (One night on cash we split with my brother)
• Cost Without Points: $1,300.00

New Year’s Eve in Chicago & NHL Winter Classic

We spent New Year’s Eve in downtown Chicago and attended a great party at Navy Pier, where we also were able to see a firework show over the downtown skyline.

On New Year’s Day, we attended the NHL Winter Classic, an annual outdoor NHL hockey game played at a major venue such as a baseball or football stadium. This year the game was played at the University of Notre Dame — it was a great venue for the event. We even had the chance to tour the campus before the game started. Fortunately, it wasn’t the coldest game we have attended — that was at Soldier Field in Chicago.

This was an amazing trip and we can’t wait to see where our miles and points will take us next!