I think it’s time to cross the Atlantic Ocean and recap a trip I took that was closer to home. For my birthday last year, Mr. Chuckles and I went on a short break to the Windy City, Chicago.
Day 1: Navy Pier, big buildings, and big food
We arrived in the city around noon. Coming from Toronto, Chicago is just a short 2 hour flight or 8.5 hour drive away. We flew Porter Airlines and stayed at the Hilton on Magnificent Mile; we were able to find a room on sale via Expedia.
We started our self-guided tour of Chicago with a walk at Navy Pier, a 3300 foot long pier along the shore of Lake Michigan. As per its namesake, the site served as a training centre for the US Navy during World War II. Nowadays, it encompasses 50 acres of parks, shops, restaurants, gardens, and exhibition facilities.



After our stroll, we headed down along the Chicago River and caught the classic shots of downtown Chicago. Everything just looks big out here.


The food is big too. For dinner, we went to the Purple Pig which is advertised as a small plates or tapas style restaurant. These were absolutely not small plates as we know them. The server suggested 4-6 items for the two of us, and we ended up with effectively 6 entrees, enough to feed a small family. Or maybe a big family. This meal was reflective of the remaining food experiences we would have in Chicago, just huge portion sizes all around. When you order a small cappuccino here, expect something closer to a bowl of soup.
Day 2: The Bean, architecture, and molecular gastronomy
We made the requisite stop in Millennium Park to see Cloud Gate, also known as ‘The Bean’. Definitely looks like a bean!

For lunch, we went out in search of deep dish pizza and found it at Lou Malnati’s.

In the afternoon, we went on the well-hyped Chicago Architecture Foundation river cruise. This is apparently a ‘top ten’ tour in Chicago and according to many TripAdvisor reviews, is a must-do for Chicago visitors. Well, we did it! It was actually quite an interesting 1.5 hour boat ride along the Chicago River with a guide telling us about the city’s various architectural landmarks. It would have been a better experience on a warm spring day, but unfortunately we arrived during the midst of a polar vortex that extended well into April, so it was pretty breezy on the boat deck.



Our evening was the highlight of our entire trip. Mr. Chuckles took me out to the incredible Alinea, the only three Michelin star restaurant in Chicago. It was featured in an episode of Chef’s Table on Netflix, which you must watch if you haven’t already. The story of chef Grant Achatz is fascinating and learning about it makes you truly appreciate what he’s done with this restaurant.








Day 3: Pancakes, Chicago dogs, ribs and Second City
No photos from this day. We had a mega portion of breakfast at a pancake place near our hotel and then lunch at Portillo’s for the classic Chicago hot dog. In the evening we enjoyed the most delicious ribs at Twin Anchors, before catching a show at Second City MainStage. The Second City show was highly recommended, but I didn’t find it particularly memorable or entertaining. I think I much prefer stand-up to sketch comedy and would opt for a night at Comedy Cellar in New York City instead.
Day 4: Baseball and cool cocktails
We happened to time our trip during the week of the Cubs home opener, so grabbed tickets for this. The game was actually postponed by a day because of the aforementioned polar vortex; it was snowing in mid-April! We sat in the cheap seats but had a lot of fun. We even caught a glimpse of owner Thomas Ricketts, who came up to mingle with us common folk.


On our final evening, we met up with some old friends from home who also happened to be in Chicago. We went to Roister, which is the casual sister restaurant of Alinea, and had a huge plate of duck plus more.
This was followed by drinks at Aviary next door, where they serve quite the menu of innovative cocktails.
Cheers to a great trip and another year of food and travel!

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