Chicago Made Easy 2


Travel shows like Drinking Made Easy, The Layover and No Reservations are a great inspiration for places to visit that may not be on the typical tourist’s agenda. This is my attempt at making a one day itinerary in Chicago without all of the gross shit that Bourdain eats.

Drinking on Chicago Boat Tour

Maria and Karissa taking in the sights.

I try to hide it but I am a tourist and sometimes touristy stuff can be really fun. Karissa, Scott, Maria and I started our day with an architectural boat tour of the city and we made very sure to pick the tour company that has a bar onboard, Windella Bour Tours. While the other passengers rushed to the top of the boat for the best view we settled in on the lower deck in the shade near the bar with a great view of all of the buildings. As you can expect the beers were not the cheapest but it was worth it on a nice summer day to have a beer while taking in the sights. The tour goes around the river and out towards Navy Pier for little over an hour. If you manage to sneak your opaque beer cup off of the boat it’s a great vessel for public drinking on the way to your next stop as you can see in the top image.

I was not very interested in our next stop until we arrived and I saw how grand it is in person. The Millenium Cloud Gate or The Chicago Bean was packed full of tourists but it was still a cool sight and I was thoroughly impressed with how large it is while at the same time grossed out at the thousands of dirty handprints on it. The Tavern at The Park sits just below the bean and it has some top of the line people watching available from the giant patio along with giant beers.

After having drinks all afternoon we were thirsty for a drink so we stopped by the rooftop bar at The Wit for a beer with a view. It has some good views but word is that the view from one of the other rooftop bars whose name I can’t remember is better, you can cut this one out of the tour and not miss much. The next bar on our tour was my selection, The Green Door Tavern. This bar was featured on Drinking Made Easy and I insisted that we stop there for a drink. The Green Door Tavern is one of the first structures that was built after the great Chicago fire and it features a distinctive lean much like Heinolds from my time in Oakland. The Green Door drink menu is filled with prohibition era cocktails, I would recommend the French 75 for a refreshing gin drink.

Chicago Pizza and Oven Grinder Chicago Pizza Pot Pie

I would take a trip back just to get the pizza pot pie at Chicago Pizza and Oven Grinder Co.

Now the entire day was not just drinking, we actually started the day with a late brunch and we got appetizers throughout the day but now it was time for dinner and shit got serious. Karissa took us to Chicago Pizza & Oven Grinder Company the home of the famous pizza pot pie that I never heard of. Everything here was delicious… everything!  Our meal here was one of my favorite dining experiences ever. The house salad feeds four and the sour cream garlic and sweet & sour poppy-seed dressings were delectable especially when you mix them. Also with the salad we got an order of the mediterranean bread  which comes out as a blanket of goodness. The pizza pot pie is exactly what it sounds like, dough filled with thick sauce, mushrooms and cheese, I give it my highest rating ever of 9 thumbs up. After our amazing meal we were done for, it was back home to relax and prepare for another day of eating and drinking in the fine city of Chicago. [aside title=”Pro Tip”]When you give your name to the host at Chicago Pizza & Oven Grinder Co. and he just keeps going on with his business don’t worry he has the list in his head and he will not forget you.[/aside]

There are a couple of other places that we could not fit into our day but I would highly recommend that you make time to visit them. Go to Cafe Iberico for tapas, it’s relatively inexpensive and they have great service and even better food. The Old Town Tavern, is a true bar, no food except for potato chips, cash only, jukebox and the owner paints portraits of political figures in sexually compromising situations. If you’re looking for a suit or some clothes there are some great shops in Chicago that only have a couple of locations in the country like SuitSupply, Topman and Zara. I just went in and looked at all of the cool clothes that I can’t afford right now, damn budget travel.

Chicago was awesome and you should all go there. If you already live there then just go out and act like a tourist for the day it’s fun.

Flip Out


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2 thoughts on “Chicago Made Easy

  • Rudy Chavez

    good post, try hotdogs if your still in town, let’t put Eucador on your travel plans, and let’s make it happen, dieing to go down there and explore retirement possabilities. Some days I get the urge bad.

    Keep in touch, enjoy the journey and be well. love Pa