One (Very Cold) Day in Chicago

We only had one day in Chicago on our cross-country road trip, so we did our best to get a taste of the many great things the city has to offer during the winter months.While the timing wasn’t ideal in terms of weather, we still managed to enjoy ourselves.

Here’s the complete round up:

1. Dinner at Big Star Chicago
We arrived on a Tuesday night, and after the long drive from Toronto we just wanted to check into our hotel and find some good eats. Upon a friend’s recommendation we hit up Big Star Chicago for cheap tacos and bourbon. For my Toronotonian readers, this is reminiscent of Grand Electric, but it’s much bigger, tastier and with a far less pretentious staff. Oh, and it’s cash only. The wait list was over an hour long when we arrived at around 8:30pm, but we headed to the bar and two stools opened up almost instantly – we REALLY lucked out. I tried the pollo (chicken), panza (pork belly) and a pescado (fish) taco. The pollo was my fav, followed by the pescado.  The old fashioneds I ordered to wash it all down were smooth and not too sweet. Each taco was only a few dollars each, and drinks ranged from $1 beers to $25+ shots of bourbon.




2. Breakfast at Yolk
It was the mention of red velvet french toast that sold me on Yolk. Basically a swiss roll of red velvet cake filled with cream cheese icing dipped in egg and grilled, this was the most decadent thing I have eaten before noon to the best of my recollection. I ordered regular breakfast and one slice of the red velvet goodness to share with my road trip companion, Megan. There are a few locations around the city and there happened to be one right next door to our hotel – too convenient!


I wrote an entire post about my much anticipated visit to this beautiful wedding boutique. To sum it up though, it’s a bride’s whimsical dream come true.


4. Memorial Park
All I could think about while at Memorial Park is how nice it would be in the summer. There is skating at the park in the winter though, and if we had more time we might have done this. The bean is a magnificent thing to see in real life. I’m curious how they keep it so shiny in the winter months. Even more interesting is the Jay Pritzker Pavilion which is near the bean and is unlike an outdoor theater I have ever seen. Leave it to Frank Gehry to design something so curvy and compelling. I’m curious to know what the acoustics are like!


5. Art Institute of Chicago
This part of our day wasn’t planned so well. We arrived at the Art Institute at 4pm – exactly one hour before close. This meant admission was only $10 compared to the $23 regular admission, but it also meant a super duper abridged version of a vast collection. We powered through the modern art wing and managed to take in some impressionism pieces, but we really could have spent days here and I loved every minute of it.



6. Giardano’s
Chicago is known for its deep dish pizza, so this was at the top of my ‘to eat’ list. We were given recommendations for different places, but Giardano’s kept coming up. We were in a food coma after a couple of slices of the deluxe veggie for dinner (breakfast didn’t help), but absolutely no regrets on this one. Why hasn’t this been picked up in Toronto yet? My waistline thinks it’s probably for the best. This place also offers super cheap lunch specials and there are locations all across the city. So good!!!



7. Blue Chicago
We were told blues was the thing to do for a night on the town in Chicago. A couple of things pointed us to Blue Chicago and we weren’t disappointed. The bar tender was a bit standoffish, we overheard him say in a somewhat negative tone, “we get our regulars in here, but we also get our irregulars.” Somewhat surprising given the number of bills from all around the world pasted above the bar with scribbles of memories from their donors. The live band was highly entertaining and knew how to work the crowd with classic numbers – worth the $8 cover. We showed up around 8:40pm and the music went on at 9pm. The place didn’t really fill up until closer to 10pm, so we scored prime bar seats with a great view. We also managed to score several shout outs to Canada from the lead singer.



Next time I go to Chicago, I would extend my stay and plan for a visit during the summer when being outside is a pleasure and not a pain. Seriously this Canadian could not handle the cold!

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