A few months ago, over a few cocktails, a group of my friends and I thought we should take a long weekend trip to Chicago to scout out a city none of us had visited before. Usually these brilliant ideas never take flight past the 2:00 am hour after the bar closes for the night, but we kicked ourselves into gear and booked the flights and we would soon be on our way to Chi-town.
I didn’t go into the trip knowing too much about the city, but I was pleasantly surprised. It’s much larger than I ever thought, with skyscrapers aplenty. The downtown area seemed to go on and on with great shops and restaurants. I would describe it as a cleaner, less crowded version of NYC.
A trip to Chicago wouldn’t be worth it unless you savor the delight that is deep dish pizza. We hit up Gino’s East and it was worth every single calorie. The girls could only do one slice, that’s how thick and heavy the pizza is.
A couple of years ago when my fellow Wicked Domestic went to Chicago, she and Matt highly suggested we check out the architecture tours that take place on the Chicago River. The tour was so interesting, even for people not particularly interested in architecture and to learn about all the different styles of architecture that Chicago has to offer. All of the buildings are relatively new because of the Great Chicago Fire of 1871, when all the citys’ buildings were burned to the ground.
The Chicago River was my favorite areas of the downtown area. They have a great river walk, where you can stroll along the river and pop in and out of different restaurants and bars. Here are me and Chris at Flatwater.
The city has a bunch of awesome roof top bars as well. And surprise…we hit up a few of them! With all the super tall buildings, it was the ultimate urban scene.
The Whit roof top bar
C-View roof top
We made our way over to Wrigleyville (which is basically like Fenway, but way bigger) and did and little sneaking into Wrigley Field.
The bars around Wrigley were just like Fenway, just more plentiful. Here’s a group pic of us at our favorite spot, Casey Morans.
When you’re in a major city, you’ve got to check out an observatory on a tall building. So, we took the elevator 96 stories up the Hancock Tower for a cocktail overlooking Lake Michigan and the city. It was really breathtaking.
Haley, myself and Joan enjoying ourselves in the windy city
And the boys…Kevin, Chris and Matt
We also hit up the Chicago Institute of Art, Millenium Park, Oak Street Beach on Lake Michigan, Wicker Park for brunch and more. Chicago has so much to offer, yet it wasn’t overwhelming at all. The food was great, the drinks divine and the company superb.
And clearly, when you go to Chicago, you’ve got to jump on the Harry Carey cow with clown glasses…that’s just a given.
I do have one regret: I really wanted to sing and dance on a float to “Shake it a-baby” like Ferris Bueller, but I guess you can’t have it all.