Last weekend, Will and I traveled to Chicago and then to Wisconsin to pick up our new puppy, Oliver-Sebastian. We left Toronto at 2 a.m. on Friday morning and after a (surprisingly) fun drive, made it into the city for 9:30 a.m. It was perfect timing because we could enjoy the whole day in Chicago, starting with breakfast at Sunny Side Up & Coffee Shop.
Will and I loved walking around and enjoying the city. After breakfast, we walked along the Magnificent Mile and went in a couple retail stores, before realizing that we really didn’t want to spend the whole day inside going from shop to shop.
We ended up walking the whole strip, ending up at the Bean. We had so much fun walking through the gardens and enjoying the beautiful day.
My favourite of all was the Navy Pier! We enjoyed ice cream, great sights and even got a caricature drawn! We did end up doing a little shopping, and I changed my outfit to get some sun on my legs.
Will had the Go Pro attached to him the entire time and got some great footage. I’m excited to pull together the video with him and share it with you soon.
We were so blessed with the best weather for our day! We decided to head out of the city around 4 p.m. and the rain started to fall right when we got in the car. We stayed at the Westin Chicago North Shore, since it was budget-friendly and an hour outside the city (aka an hour closer to Wisconsin to pick up our puppy the next day).
We had the best time together and couldn’t have asked for a better day together. Chicago is a beautiful city, and easy to enjoy on a budget!
When you’re traveling in a new city, go into hotels and ask the concierge for recommendations on where to eat. They always know the best places in the city and can point you in the right direction.