In 2008, Stephen White and Bill Hamar crafted a tour to Chicago that soon became one of their all time favourites. Its combination of architectural walking and boat tours, entrances to galleries, dance performances, and even a cooking class combine to capture the heart and soul of this magnificent city. I was excited to join them for my first trip to Chicago this past May 1-7th.

Follow me on Day 1 + 2 of the tour after the break:

Day 1: Victoria

A 3:30am start to a long but thankfully uneventful day of travel. I won’t bore you with any pictures of the AKAL air porter, YYJ, the inside of an Alaska Airlines plane, etc. Upon landing at O’Hare, my husband Nathan and I quickly learned how to navigate the subway – a 40 min ride that would take us to downtown Chicago.

We had the privilege (?) of leaving 2 hours ahead of the rest of the 42 tour members.  Our job being to arrive, check in and prepare a welcome party for the weary travellers. A fruitful trip to Trader Joes (if you haven’t been, it’s a grocery mecca for Foodies) and we had $300 worth of cheese, crackers, meat, fruit, and 12 bottles of wine. Sorry folks – the same bottle that you’ll find here is a fraction of the price there. Needless to say, said weary travellers were welcomed with a feast of charcuterie and a glass of their favourite. I don’t know how we fit 42 people into one hotel room….but it was festive.

Day 2: Chicago

There it is – the city all in one view.
There it is – the city all in one view.

We started the day with a riverboat cruise through downtown Chicago which was led by an architectural docent. The tour was fascinating, showing us all of the famous buildings and the history behind them (Trump tower, Wrigley Building, Willis Tower, Chicago Tribune, Civic Opera Building….the list goes on). Also, who knew that in the late 1800s Chicago decided to completely reverse the flow of the river through civil engineering – a highly ambitious feat that thankfully was a success and completed in 1900. I loved this tour, because it set the tone for the rest of the tour. When I came across each of these buildings in the coming days, I was able to recognize them and appreciate their importance. Nathan and I don’t usually do things like boat tours, brushing them off as “tourist traps.” I’m sure some of them are, but this particular cruise, led by the Chicago Architecture Foundation, was truly fascinating.

But cold. Incredibly cold. After we hit dry land, it took 2 baths and a shower to regain a comfortable 98 body temperature. But then we were off again – just Nathan and I – to explore. After finding a “25 best eats in Chicago under $10” guide, we decided to try Toni Patisserie, which made delightful french inspired sandwiches, bakery items and fanciful cakes. My “Croque Fromage” was buttery, cheesy and incredibly comforting.  Nathan’s ham sandwich was a little bit jealous.

A short stroll later and we hit Millennium park. The art installations in this park are truly beautiful. They are of course striking, but they also fit within the lush greenery of the park. This might be one of Nathan and my favourite activities while on vacation – Sitting in a park.

That evening the group reconvened to travel to Second City, a renowned comedy club that was one home to famous alumni like Joan Rivers, John Belushi, Dan Aykroyd, Eugene Levy, Andy Dick, Jane Lynch, Mike Myers, Steve Carell, Stephen Colbert, Amy Poehler, and Tina Fey (just to name a few). The two act scripted show was so funny, but if you stuck around for the “3rd Act”, you were treated to side-splitting improv comedy that was current, a little bit political and so clever.

We got a full taste of the city and it was only Day 2 – Check back in for the remainder of the adventure!

We’re on a boat! This Architectural boat cruise was fascinating.
We’re on a boat! This Architectural boat cruise was fascinating.
Looks dark? That’s because it was incredibly cold and windy.
Looks dark? That’s because it was incredibly cold and windy.
This building has the most beautiful blue/green iridescent quality.
This building has the most beautiful blue/green iridescent quality.
The building that gum bought – The Wrigley Building.
The building that gum bought – The Wrigley Building.
This sandwich from Tony Patisserie was a mixture of mozzarella, gruyere and goat. Nathan’s ham sanny was jealous.
This sandwich from Tony Patisserie was a mixture of mozzarella, gruyere and goat. Nathan’s ham sanny was jealous.
The entrance to Millenium Park.
The entrance to Millenium Park.
I’ve seen bigger.
I’ve seen bigger.
Go stand under the bean, and you’ll see multiple reflections of yourself.
Go stand under the bean, and you’ll see multiple reflections of yourself.
Second City! We came for a laugh.
Second City! We came for a laugh.
This famous comedy club was home to dozens of SNL alumni. The show did not disappoint.
This famous comedy club was home to dozens of SNL alumni. The show did not disappoint.