My uncle lived near Chicago and had always talked about the beautiful city and its incredible food when I was growing up. I believe I was about 8 years old when I first felt the deep desire to go to Chicago. In 2021, I finally had the privilege of traveling to one of my dream cities – Chicago, and it remains one of my favorite destinations.
As to why it took me this long to get here? Not sure, but you best believe we are always planning our next Chicago trip! Chicago definitely hits the top of my list of must-travel places in the United States. It’s unique and incredibly beautiful, and the food is insanely good!
I always have such a great time in Chicago, and I am happy to be sharing this guide with you. It’s perfect for a first-time traveler to Chicago, but has plenty of unique options for seasoned travelers too. We love to visit with Husdon, so I’ve made special mention of where you can and cannot bring your pets in the city in case you also want to travel with your dog.
My Recommendation
My personal favorite time to visit Chicago is late September. The crowds are not too bad, the weather is warm in the morning and just the right amount of chill at night. This is the perfect time to get some lake time in the morning and hit a rooftop bar at night!
