I guess my questions for the chicago guys are:
- what do you need to wear for their 30 degree weather. I wear just jeans, t-shirt and jacket. Maybe a hat if it's windy. Hands in pockets of jacket to keep warm.
- is it safe to walk around with luggage in the loop? Yes. Just don't be dumb and leave it unattended
- how safe is it to walk around the loop at night but before midnight? I've never felt unsafe. Just keep walking when anyone homeless person asks for money. Also make it look like you live there and know exactly where you're going.
- how easy is it to use lyft at night in the loop? Very easy. I use Uber or taxis mostly though but have used lyft many times
- would you recommend using a bus to get to our hotel while carrying luggage? Can't answer that one. Never taken the buses. But since ubers are so cheap, I'd just take that honestly
- would you recommend the bus system in general? Sure, I have no reason why I don't use it. I just usually walk around the city and rarely use any transportation unless it's winter time or I have to go far.
- how safe is public transportation at night but before midnight? It's pretty safe depending on where you're going. There's a few spots I would NOT recommend going. My girlfriend would take the CTA while going to school downtown at night all the way till 3am. She had a few crazy stories, but for being 20 year old girl by herself, pretty okay.
Anymore questions, don't hesitate to PM me. I personally live in the burbs but go very often, have countless friends that live on the west side and North side. Girlfriend lived in South loop for 2 years as well.