This was a weekend trip to Chicago I took in October 2019 while in the area for work. I arrived by Greyhound bus from Milwaukee and returned by the Amtrak Hiawatha.
I stayed at HI Chicago, which was by far the cheapest bed I could find in the "Loop" area of Chicago. The hostel was neat and clean and offered a free breakfast. The location was also great and I could walk everywhere over the weekend.
After catching an early morning bus from Milwaukee, I got to the Chicago Greyhound station by about 9am. First stop was to get breakfast at the very popular Lou Mitchell's. I was alone, so I found a place to sit pretty soon, but there was a long line outside for breakfast, and the restaurant was packed.
After a large breakfast of pancakes and coffee, I headed to the Willis tower to get some views of the city from Skydeck Chicago. It was a clear day and I got there before its opening time of 11 am. This turned out to be good as the queue to the top had already formed and had I waited longer, it would only have gotten worse. In any case, I got to the top after about half an hour's wait. I bought a combination ticket to the skydeck and the Art Institueas this worked out cheaper.
It was a clear day and I got to see some spectacular views of the city's skyscrapers from the top.
From there I walked east just taking in the city till I reached the Art Institute. They required you to check in all bags aside from a small purse, so if you don't need to, I would recommend not carrying any bags. Also, there was quite a line for buying the tickets, so having bought the combination ticket at Willis tower worked out well.
The Art Institue was superb and I got to see so many famous paintings! Seurat's 'A Sunday on La Grande Jatte', Van Gogh's ' Bedroom', Picasso ,Dali, Monet, Paul Gaugin, 'Nighthawks', and of course 'American Gothic'!
There was also an amazing exhibit of miniature rooms in the basement that I enjoyed very much. After spending a few hours there, I stepped out to have lunch at one of the food trucks selling Chicago-style hot-dogs (yum!)
Next stop was 'the Bean', or Cloud Gate which looked exceptionally great on that sunny day. I spent some time taking it in from all sides and from underneath and also just walked around the rest of the Milennium Park.
From there, I had a quick round of the Chicago Cultural Center. It had some free exhibits of art inside and the building itself was interesting.
From there I continued walking north on Michigan Avenue enjoying the views of the skyscrapers. Then I turned off to walk around the Chicago riverwalk which had a few places to eat and drink. Tired, I stopped and had something to drink here, just enjoying the river view, before heading back up to see the 'Magnificent Mile'. I also booked tickets for the Chicago Architecture tour for the next day. The tours for that day were sold out already, so booking in advance was a good idea.
After a day of walking, by late afternoon I was tired and I headed to my hostel, catching a Halloween Parade on the way. After putting away my bag and a bit of rest, I stepped out again to see all the skyscrapers at night along Michigan Avenue and to get some pizza for dinner.
On Sunday, after getting the free breakfast at the hotel, I started walking again towards Grant Park and the Buckingham fountain. The fountain was unfortunately turned off, but the lakefront walk was beautiful. I headed south to the Field Museum where I enjoyed going through the exhibits for the next couple of hours, especially the segment on evolution of life and human society. I would have liked to visit the Shedd aquarium as well, but I didn't have enough time.
After a lunch at the Museum cafeteria, I headed north again to be on time for my Architectural Boat tour. The tour came highly recommended to me, and I wasn't sure what I was expecting- but the boat ride was great! The tour guide on the boat was a volunteer from the Chicago Architecture Center and as we sailed along the river for the next couple of hours, he pointed out different building, their architecture styles, told us a little about Chicago's history and why the area is the way it is. I have no interest in architecture, but I still found this tour great- I would certainly recommend it. They also sold food and some snacks on the boat.
Once done with the tour, it was time for me to head back to the train station to catch my train out of Chicago.