Chicago Summer Weekend, Chicago, Illinois

For years, Chicago was a regular business destination for me, but those trips rarely allowed time to truly explore the city. On one occasion, we decided to stay for a long weekend, and that’s when we discovered just how much Chicago has to offer-amazing food, countless activities, and a vibrant downtown that makes walking the best way to get around. The city's dynamic energy, paired with its rich history, culture, and architecture, quickly won us over, and we were eager to return.

When the opportunity to visit again came up, we couldn’t resist. Our first stop? Pizza, of course! While the famous deep-dish is a must-try, this time we opted for a slice by the Chicago River on a sunny day, and it was the perfect start to our trip. Chicago truly has something for everyone, from its iconic skyline and museums to the bustling riverwalk and hidden gems around every corner. Here are just a few highlights to consider for your own visit.

Chicago has a Riverwalk, along the Chicago River. There are tons of open air restaurants along the walk. There are also beautiful town homes and high rise condos, that I am sure are where you pay for the view.

You can rent any kind of water vessel along this river. From Kayaks to Luxury Yachts and everything in between we saw tons of activity on the water. This was actually about 7:30 on a beautiful summer evening. It seemed everyone was out. ...... (follow the instructions below for accessing the rest of this article).