I made my first ever visit to Chicago last month. Didn't stay long though, so not enough time to gather opinions about extensive neighbourhoods, transit system, etc. Arrived on a Friday evening and had dinner in the Bridgeport area, which is considered to be on the Southside of the city, but I found to be quite well maintained and had a good vibe to it. Then drove around the surrounding area for a bit at night, including the main street in Chinatown, which from the surface felt a bit like Montreal's Chinatown, albeit being a longer strip and a more Midwest feel in some of the buildings. Then drove to the southwest outskirts of the city for a cheap-ish hotel to stay the night.
Did some shopping at a nearby big box plaza in the morning afterwards, and then went to the La Grange area for Trader Joe's. The area looked pretty nice on the drive. Sort of had a Bloor West Village feel, but with more American/Midwest style architecture. Then went downtown to spend the midday, early afternoon in the Millennium Park, and the Loop area. In terms of architectural quality, and scale of everything in the area I'd say it definitely lived up to its billing. Certainly a feeling of presence and grandeur, especially on the main section of Michigan Avenue as it faces the park. Lots of people abuzz, further increased by it being the Mexican Independence Day that weekend.
We only ventured a couple street westward into the Loop and then came back out as we didn't have a lot of time. The street life gradually fades afterwards, but that's only from a small sample size of exploring in the Loop on a weekend. We then drove to the Wicker Park area. Didn't really get a chance to step out and walk, but the area had a cool vibe to it. Had some similarities to the Mile End area in Montreal.
We then left in the afternoon and headed to Valparaiso, Indiana to attend a cousin's wedding lol. Saw some parts of Ann Arbor, Michigan as well on the way back home. And also visited Nashville a couple weeks ago, but I'll leave those for future appropriate threads lol.
All in all, I would consider visiting Chicago again to see it in further detail.