Chicago is one of my all time favorite cities. It has great shopping, amazing food, incredible views, and so much more. I have only been in the spring / summer time before and I definitely recommend going then. This trip was nothing short of wonderful, but Chicago has more to offer during the summer. During warmer days, there are tons of free concerts and events going on around the city. Navy Pier and all the parks are more fun. The restaurants and cafes also have their outdoor seating open during the spring and summer. Lastly, you can go on an awesome boat tour along the river to see the beautiful skyline.
So what did we do in Chicago? We ate, we shopped, and we walked around and explored the city. What more can you ask for?
Thursday night: Room service and sleep
Friday: Shopping, lunch, sightseeing, shopping, dinner, drinks
Saturday: Breakfast, sightseeing, lunch, sightseeing, shopping, dinner, drinks
Sunday: Breakfast, sightseeing, lunch, airport