So you’re in Chicago for three days and don’t know where to start?
Here are a few things that you should definitely check out.
The John Hancock CenterThis building is often overlooked by tourists who instead choose to go to the Sears tower. The Sears tower is the second tallest free standing building in the Americas so there’s definitely some attraction to going there I suppose. But, if you want to avoid the crowds and pricey observation deck fees I would recommend the John Hancock Center. This is the fourth tallest (at the time that this blog entry was written) building in Chicago. Getting up to the 96th floor is free and you can enjoy the view while sipping a lovely cocktail, beer or eating some appetizers. The drinks are a little expensive but for the amazing views they’re definitely worth the price (and they aren’t bad either!)

The Art Institute of ChicagoThis is probably one of the largest collections of art I have ever seen. Spending an afternoon here will only start to skim the surface of the collection. Also, it is easy to get lost in the buildings so grab a map. The Art Institute has some amazing pieces including some pretty notable ones: Van Gogh’s Self Portrait, Seurat’s Sunday Afternoon on the Island of La Grande Jatte, Hopper’s Nighthawks to name but a few… Luckily if you happen to be there before the end of February admission is free so you can go back a few times if you just can’t fit it all in one day.
Museum of Contemporary PhotographyI would recommend that if you’re into photography you check the current exhibit online before going. The gallery is very small and I think may only have an exhibit at a time. I was a little disappointed given the collection they have available for viewing online and unfortunately I didn’t check the current exhibit before going. The current exhibit seemed more interested in the medium than anything else (it felt like the accompanying literature was really trying to convince me why the images should be on the wall… I wasn’t quite convinced.)
The NeighbourhoodsChicago is a city of neighbourhoods. I would highly recommend that visiting the neighbourhoods be part of any traveler’s trip – really without it you will not have seen any of Chicago!! There’s Chinatown – maybe go for some Dim Sum? There are numerous really good restaurants in the Chinatown Square. Pilsen: this is a Mexican area – wow. I cannot stop dreaming of my antojito plate from Nuevo Leon! Wicker Park – this area has amazing restaurants, bars and nightlife.
Music – from Jazz to Techno - I was lucky enough to experience a bit of both!
SmartbarLocated under the more reknown Metro hall, Smartbar is a small dark basement club in Wrigleyville. This place plays various types of electronic music. The night we went we saw a DJ from Detroit called Moodyman, the night before they had hosted A-Trak a more electro DJ. Moodyman’s set was really good and quickly left us wanting more. There was one very memorable track that included some jazz trumpet – it really worked - I had never heard anything like it before. The crowd seemed really into the music – a lot of people dancing and really looking like they were there to enjoy the music. I would definitely go back.
Green Mill Cocktail LoungeLocated near Smartbar, this is definitely not an electronic music club. Sit down if you can find an empty table, have a drink and listen to some jazz in an almost smokey atmosphered room. (Thankfully, no smoking allowed.) In the words of the bouncer “it’s a quiet room” (which for those who have never been to a jazz bar means – please don’t talk while the musicians are playing.) And I can really understand why. I was pretty amazed at the performance we saw on Sunday night here. The resident Sunday night band (singer Kimberly Gordon, Chris Foreman on Hammond B-3 organ and Andy Brown on guitar) was pretty good and kept me entertained for a full two sets before I decided I was too tired to keep my eyes open. Seeing these people perform really made me want to check out the local jazz scene back at home. The venue itself was amazing – it felt like I had stepped back some 50 years in time and really set the mood for the performance.
Architecture and Art on the StreetReally, going to Chicago for me was a lot about being surrounded by some amazing architecture. Walking throughout the downtown area it seems like almost every building is interesting in some way. Even down to the sleek Trump Tower.


Marina City

Cloud Gate
A few little side notes:The CTA (the public transportation system) offers 3-day (72 hour) and 7-day passes to visitors. They’re completely worth it and will get you on any CTA vehicle at any time within your 72 hour time limit. It’s really quite nice to be able to jump on and off buses and on and off the trains.

The Navy PierThis is a pier extending on Lake Michigan that pretty much seems to exclusively cater to tourists. This isn’t exactly my type of place but if you want to go on a Ferris wheel or have kids I could see how this could be fun – especially in the summer. In the winter it’s fairly quiet – especially on a Monday morning.


This is just a taste of my trip to Chicago. I ate a lot of really amazing food. And of course, more pictures can be found on flickr. Three days didn't seem like enough time. We packed a lot into our little trip and I came home feeling like I have a better understanding of the city. The highlights of my trip were definitely the John Hancock, the Art Institute, Green Mill Cocktail Lounge, and Nuevo Leon in Pilsen.