My Big Fat Hotwire XL Trip – Chicago

My first destination of eight! I don’t know about you, but when I think of Chicago, my mind immediately goes to pizza.

After checking in to my hotel, I went to Small Cheval for lunch (and one of the best cheeseburgers of my life)! They had Garlic Aioli and multiple types of ketchup on tap, so I was already impressed. Don’t forget to order a milkshake, they are good and bring more than boys to the yard.

I spent some time working with my team in office – we have a new Expedia space in Chicago and everything about it rocks. It’s stunning and reminds me of a Kimpton – hip but not too hip. Did I mention there was a nap room, library, and literally a guided meditation for employees was offered while I was there? #LifeAtExpedia

After work, I stood (and even sat) in the scary all-glass Skydeck. I only screamed a little, and everyone there laughed at me as the kind photographer kept telling me to step back so I was fully dangling my life 103 floors above Chicago’s concrete.

I grabbed frosé from the Taco Bell Cantina (anyone who has met me knows Taco Bell is sacred), and then got some real deep dish with the team from Lou Malnati’s. For the record, I’ve tried Giordano’s, and Lou Malnati’s has my heart. Next time I’ll try Pequod’s.

After dinner I had to check out The Bean. It’s one of Chicago’s most iconic spots, and even in stormy weather, you can get good pictures.

Because one milkshake is never enough, my teammate (also named Michelle) and I went to Dylan’s Candy Bar and each ordered THE BEST OF BOTH WORLDS milkshakes. I ordered the Carnival and she got the S’mores. We recommend both for taste and insta-worthiness. It was a sweet way to end my time in Chicago.