36 Hours in Chicago

What does 36 hours in Chicago look like? A $50 holiday drink the size of my head pushed by a marketing genius, the Christkindlmarket, Beercade, lots of laughs at Second City, yummy bloody marys, Millennium Park, Cloud Gate and The Art Institute. Jam packed.

I traveled with my friend Naomi who was looking for a get-away as well, but was understanding when I had to return early due to a bit of a crisis at home. Full disclosure: The reason I took this trip was to qualify for Delta's Medallion program. I'm a point chaser and I'm chasing them harder now that I'm traveling more.

That $50 drink I mentioned (and I'm not kidding...$50 for a delicious Moscow mule!) was at Rudolph's bar. They call it a "pop-up" bar where they decorate like mad for a few weeks before the season and charge you a ridiculous amount for drinks and food. Brilliant.





Across the street from Rudoph's is a Christkindlmarket, which is next door to Wrigley Field. Although I do not celebrate I love this holiday - the lights and music are wonderful.



Naomi is a pinball player so we spent some time at Beercade where I played pinball for the first time in probably....35 years! She said I wasn't all that bad.



My favorite saying of all times!

We went to a show at Second City, which was fun. And that was all the first day.

I flew to Chicago early Friday morning landing at O'Hare at 8:30am. I spent the full day working from the airport before taking the train into the city. I love the flexibility of my new job. Not to mention FREE airport lounge access using my Chase Reserve credit card (where I earn three points for every travel and food dollar spent!)...I told you I was a point chaser.


Saturday we had a lovely breakfast, walked to Millennium Park to see the iconic Cloud Gate and I dropped Naomi off at The Art Institute before flying out that afternoon. Chicago is beautiful this time of year and a great way to spend the last $134 to make my Delta medallion upgrade! Woohoo!!





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