I was there for like 2 days. But I made use of every hour. I stayed at an airbnb. I made sure it was on near a subway/train station. I can't recall correctly but I think the red and blue lines run either most hours of the day and night, or 24 hours. I was on one of those lines though. I bought a 3 day unlimited pass for transit. You can ride any subway line, and buses all day. I choose this option over driving or uber. I did do quite a bit in my 2 days there.
I did everything in the citypass. Some of attractions were side by side, walking distance. So there no need for a bus/train in between those attractions. Like most trips I do. I always look at the locations of each I attraction I would like to visit, and place it on a map, so I know how far each attraction is away from each other. But I would say I do that on literally all my trips now.
I had deep dish pizza at Giordano's and it was amazing. They have several different locations, so no matter where you are, I'm sure you can find a location that's not too far from you. Not sure if you've ever had deep dish pizza. Let's just say, order a smaller size pizza than you can normally finish, or maybe 2 sizes smaller. I met up with my cousin in Chicago, so I ate a pizza there with him, however we were both on our own trips. I only met up with him to eat pizza. We shared either a 6 or 8 slice pizza. I think I ordered a medium or small. Can't clearly remember. All I know is we didn't finish it. It was amazing though. Highly recommend Giordano's.
Also if you plan on seeing Buckingham fountain or cloud gate (aka the bean) which is located in millennium park. The park does close at 11pm. There is security there all night. If you go past 11pm, they will ask you to leave. I went there my first night around 11:30pm. I got there around 10pm the next night. Still a lot of people there at 10pm at night. Buckingham fountain is lit up at night with colour changing lights. Its much nicer to see at night. As for the bean, you'll probably get better photos of it in the day.
I drove to Chicago. I believe I left the GTA around 4am, and arrived around 11:30am (est time, toronto time, so 10:30am chicago time). Just remember there is a 1 hour time difference. I didn't realize that until I arrived. So you hypothetically get an extra hour. I went to Chicago on a Sunday. I ran into a lot of traffic once I arrive into the core of Chicago. I didn't realize why the traffic was so bad. Then I realized it was a Sunday, and there was a Chicago bears football game that day. I was in the vicinity of the stadium. I guess you won't have that problem though, since football season is over.
Also to note. Chicago isn't the prettiest city, some of it looks a bit rough, especially some parts just outside of the downtown core. Don't expect the train to look as nice as the trains on the TTC. We have really nice trains here in Toronto. Something I think we take for granted, until we travel to other cities with transit that doesn't look as nice. Just giving you a heads up, if you do take the transit system. I would highly recommend taking the train. Anyways good luck, hopefully I've given you some useful advice. Enjoy your travels.
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