
I’ve been meaning to put something up about my trips to chicago for a while— Yes, trips. Plural. I have had the opportunity (or obligation?) to visit the Windy City on two separate occasions. The first was for my SapientStart training, which lasted a week in January, and the second was for a wedding; Meagan’s cousin Mark called us out, last minute style, for his wedding at the end of February. I was going to write two separate entries, on each respective return, but I found it would have been easier and more efficient to treat both visits as one long visit, since I was seeing different parts of the city on each trip. The first trip, mostly dominated by seminars in the Loop, allowed for my coworkers and I to explore the downtown core.


At night, it’s empty, and at rush hour it’s bustling. This isn’t really my cup of tea, but it was still an interesting cultural experience. We did most of the tourist traps, like the Art Institute, and deep dish pizza. I tried to get as much localite culture as you can within the Loop, but it’s not very accommodating. It’s like trying to find a good watering hole, or good cheap eats on King and Yonge. Luckily, a few chicago residence who were also in our training seminar showed us a few good spots that were easily accessible from our office.

Heaven on Seven is an authentic cajun restaurant, hidden away on the seventh floor of an office tower in the Loop. No signage, and no instructions, it seems like this place caters to financial staffers who know what’s up. We got drinks and watched a game at Blue Frog, near State and Hubbard, where we were applauded by the serving staff for playing quarters. Blue Frog is apparently Chicago’s oldest karaoke shit-hole, but they weren’t even doing any karaoke on the night that we arrived, so we just played drinking games until we had to roll back to our hotel rooms.

We went to the original Billy Goat Tavern, on lower Michigan below the Wrigley Building. Remember that SNL piece where Bill Murray and Dan Aykroyd yell “Cheezborger! Cheezborger! No fries, cheeps! No Pepsi, Coke!” ? Well that was all based on this place. This place is also responsible for the Cubs Curse, so the localites we brought here actually had to bite their tongues since most Cubs fans hate this place. Burgers are 2.65, beers are 3.50. Can’t really go wrong there.
A few other local corner bars and restaurants were visited, and after the whole thing was over, I was exhausted. Working from 9 until 5, and then exploring the city from 5:00 pm until 1:00 am for five days was tolling. Leaving after only exploring the loop, albeit a lot of it, was pretty disappointing and uninspiring, though. I’m not the kind of guy that drives to work in a sedan and shops for briefcases at bargain basement department stores – I really wanted to explore the outer rim of Chicago, like Wicker Park, Logan Square and Wrigleyville, but I didn’t get the chance. Luckily I got invited to this wedding, and this gave me the perfect opportunity to explore these areas.
On the second visit, we had delicious tapas at Cafe Iberico. We had delicious tacos at Big Star; which I highly suggest for anyone in the market for a five page whisky, tequila and bourbon menu. Across the street from that is the super-stealthy Violet Hour; where they have one of the best cocktail menus I’ve ever seen. It’s modelled like a speak-easy, and again there’s no signage or branding on any of the walls outside; you walk in through what appears to be plywood scaffolding, and you pull the curtains back to reveal an experience straight out of the 1920′s. They have pretentious rules too, like no cell phones, no cameras, no swearing … Moving on, we had an amazingly rich breakfast at Longman and Eagle; where Meagan became satiated on Chicken and Waffles, and Alex had Biscuits and Sausage Gravy. In terms of Food and Drink, these areas are far superior to the places I went on my last visit, as was the shopping!




Some notes regarding Swag searching in Chicago:
- JCrew on Michigan ave. is not any different from the JCrew in Buffalo. Exact same stock, barely any collaborations, but helpful staff that are willing to order things from other stores for you.
- Both Levis stores, in Wicker Park and downtown, have amazing selections. They carry most of the collaborations, and each stores caters to different markets so they keep different stocks and different items. The pendleton and filson stuff was mostly sold out in my size, but was super cheap compared to the prices you find online. I tried to grab that PendletonXLevis workshirt, but they didn’t have it in my size… bummer. The Filson stuff was insanely good, too.
- Overall, the vintage shopping in Wicker Park is about on par with Toronto. I heard it was better in Wrigleyville, but we didn’t get a chance to checkout any stores over there.
- Stuff I got cheap: A Jcrew henley on sale, a RRL shirt on sale for 40 bucks, and a levis work shirt.
- We tried to find FAO Schwartz, to buy a Catan expansion, but we found out it had been gone for 6 years. Some infodesk lady at the Water Tower Place laughed in our faces for asking… Tourists.

This visit, we got a chance to visit the Field Museum and the Museum of Contemporary Art. Both, I thought were a bit of a let down. The Field Museum not only felt like a day care, where the didactic nature of everything felt like it was speaking to children who can’t hold their attention on anything for longer than 20 seconds, but it also felt like they are seriously hurting for budget. The shows were cheap and they oversold a number of exhibits that were just rehashed permanent collection. It made me love our ROM a little more, through each room I traversed. The Museum of Contemporary Art was alright, there were a couple of good shows, but also a few really poor ones. I felt like the Art Institute, which we briefly visited on my first trip in January, was mostly permanent collection, but it was modern american classics; that we don’t get to see much of in Canada. The couple of exhibit shows that they did have were really good new media shows, and I wanted to go back to see more, but we couldn’t squeeze it in.
Couple more treats from the duty free, that you can’t get here.


As always, I’m on tumblr pretty much everyday, while I only use this blog for larger publishings.
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