Bean there, done that in Chicago

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!

9 responses to “Bean there, done that in Chicago”

  1. See, I think it looks like a cycling helmet…
    Isn’t Chicago-style pizza the BEST?! Of course, New York style is fantastic as well so…??? It’s an ongoing battle. Where I live, we can get authentic Chicago-style, (and authentic Neopolitan – like, literally certified by some board in Naples!), but not authentic New York style. What about in Toronto?


    1. I actually prefer the New York slice! There probably is Chicago style deep dish pizza in Toronto but I haven’t come across it myself. I did go to a place with Detroit style pizza once, which is also thicker crust and in a pan, so similar to Chicago deep dish. But I think some pizza aficionados might be angry with me for saying that!

      Liked by 1 person

      1. I’m not so sure, but we’ll keep it just between us, just in case. 😉


  2. […] made it over there after a trip to the area in search of Chicago-style hot dogs. The inauthentic Chicago dogs were disappointing but the street art was […]


  3. […] those of you looking for a top notch foodie destination stateside, I highly recommend Chicago, Illinois. Mr. Chuckles and I visited the Windy City a couple years ago and had some incredible eats there. […]


  4. […] a series of traditional meals in the Big Apple, we had the chance to head to the Midwest and visit Chicago to experience our first ‘theatrical’ dining experience, on my birthday. Alinea is one […]


  5. […] designed by architect David Childs, who also created Burj Khalifa in Dubai and the Willis Tower in Chicago. Construction began in 2006 and the tower’s steel structure was topped out in 2012, with the […]


  6. […] view of the nicest street in the Windy City was seen from the Riverwalk while we waited to board a Chicago Architecture Cruise. Magnificent […]


  7. […] around my 30-something birthday, so Mr. Chuckles and I decided to celebrate with our first visit to Chicago — heart of the Midwestern United States. Back in those pre-pandemic days, we lived just a […]


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