Wow, what a great city you have, no wonder everyone raves about it! Going to make several reports, break it down into smaller posts.
Not sure if anyone caught my post, but on the morning of our long planned trip (thanks so much for your help TA people!) I woke up with food poisoning (are you kidding me)???!!! Luckily rebooked plane tickets for next day (actually SAVING $100 in the process - love SOUTHWEST!) Vacation started a day later than planned, good thing we booked such a long stay! Still got in the 10 days, could have stretched it to 2 weeks easily, no joke! Chicago has so much to do!
Overall impression - (first time visitors) Lived in LA for 10 years and are very familiar with NYC, was interested to see what Chicago would be like. Surprised it didn't seem like such a big city (i know we only saw a teeny part of it) I guess bc of the smaller sections & the way we explored those, it seems more like a bunch of smaller communities, each with their own feel, felt very comfortable. Was surprised at how clean it was, especially coming off an unending winter. Imagine it will be breathtaking as it warms up. Everyone was super friendly, but then, it's the mid-west!
The architecture is breathtaking, it was really amazing to realize that the Chicago Fire (1871) which opened the way for the city to be rebuilt & paved the way for the first skyscraper (1880-1890) was right around the time of the shoot out at OK Corral (1881) here in AZ!
Location - We stayed in the Gold Coast (The Viceroy). After exploring the city & walking by my other choices, I think we made the best choice. I would recommend that area for tourists since you are so close to everything. We mostly walked everywhere, this is where your weather is a big plus! It's so invigorating to walk in the cold (as long as it's not windy or snowing)! It was such a pleasure to walk everywhere. The whole time it was in the upper 40's-60's, perfect (in my opinion....especially when it reached the 100's back in AZ while we were in Chicago!) One thing to mention, I thought we could easily buy beer at the local Walgreen's/CVS (they sell it at all those places in AZ, but most of them did not sell it. Was a little harder to find than I thought. Then again, we have drive-thru liquor stores here in AZ!!
Safety - I know this is a big issue, just read in the paper there were 69 shootings over the last weekend. I felt completely safe in the Gold Coast/Mag Mile area. There are some homeless people but they were so out of it & cold they barely even looked up. We have way more in PHX, I guess bc of the weather. No one was aggressive...a few mumbled shouts, walked by myself several times around the area (without husband) & felt absolutely safe. Was in Wrigleyville, Old Town, River North, Lincoln Park & Wicker Park/Bucktown. All those ares felt safe, kept my eyes out of course, but didn't feel any less safe than any other city (or small town for that matter).
Getting around - Second trip to big city without renting car. We are big fans of Lyft (pricing way better & like their company policies better) used it when we weren't walking. Adding up all the rides (including to/from airport in PHX-CHI it was less than $300 for the 10 days. Way cheaper than cost of car rental, even without the parking, gas, etc. Walked miles every day, really a great city to walk in, lots to see on every block.
Will follow with reports on restaurants, attractions, etc.