Top 3 Things To Do in Chicago

08/08/2016 2 Comments
Top Things to Do in Chicago

Ah the Chicago, the Windy City!


I have spent many years flying in and out of Chicago while traveling from east coast to west coast. However, in 2011, I was lucky enough to make a ground visit right before The Oprah Show taped it’s last episode. It was a beautiful spring weekend to explore the city with my Aunt and we truly loved our time in Chi-town (thanks Kanye ;-))

Here are 3 things I thought were must dos:

Architecture Tour


My hands down favorite thing was the Architecture Tour along the Chicago river. The first morning we arrived we struck up a conversation with an older man who was working at our hotel. He said he always told hotel guests it is the number one thing to do in Chicago and he always received great feedback. Well I agree it’s a must! I’m not necessarily into architecture but you get to hear the history behind this great city and why the buildings are all so important. Not to mention seeing the city by boat is always more fun in my eyes. Click the link above for more information has to prices and amenities on the boats, but in my opinion it was the best 1.5 hours I spent in Chicago.

Visiting Millennium Park/Grant Park



Visiting Millennium Park and seeing The Bean is one of those touristy things to do however, I think it’s always fun to get pictures in front of a well known land mark. You may have to fight the crowd to get just the right picture but afterwards take a relaxing stroll or bike ride through the gardens of Grant Park. The parks run parallel to Lake Michigan which makes another great route to walk or ride your bike rental along. There are a lot of art exhibits and children play areas through out the parks as well. If you have a beautiful afternoon during your visit then this area is a must!

The Magnificent Mile

imageIf you are a foodie or love to shop, then I suggest perusing down the Magnificent Mile. I wish we had had more time to check out the eateries and shops along this beautiful stretch of the city, hello I’m a foodie! This part of Michigan Avenue hosts events through out the year, they even have a half and 5k marathon event every year.


Extra tip: If your budget permits, it’s a nice splurge to enjoy the view of the river from Chicago Cut Steakhouse, while eating a fabulous steak dinner. I wish I had taken a picture of our meal and our view, but I was thoroughly in the moment back then 😉 (It’s rated the #1 steakhouse in the city, 2015)

Unfortunately one of the top things to do is no longer an option (Oprah=Chicago=California), however I’m thankful I got to see one of her last shows taped live in her Chicago studio. I’m also thankful it brought me to this beautiful city 🙂

Harpo Studios // Cupcake N Dreams

I felt like Chicago had a different vibe from New York City, which I enjoyed. I loved it’s history and place in American culture and it’s a must on any USA destination list!

Cupcake N Dreams

New Yorker blogging about travel and lifestyle things that make me happy!


  1. Reply

    Annie Malone


    I’m so jealous of your trip to Chicago. I’m dying to get up there for a visit. I’d love to do some shopping on the magnificent mile too 🙂

    • Reply

      Cupcake N Dreams


      It’s a great one to put on your list! Thanks for stopping by Annie 🙂