This is me. There is something great about every season here. If you're not feeling good in a season figure out how to adjust your wardrobe or habits.
andrew
Make sure you're taking the L, it's the safest and least stressful way to get around. Google maps should route you through it pretty intuitively along with the signs. I'd recommend getting out of the loop. Wicker Park and Chinatown are fun places to walk around, eat, drink, etc. Rent a bike or just walk the lake front trail and hang out at the beach for a bit. I personally prefer Lou's for deep dish. Enjoy the event, I'm curious to see how it plays out.
Lincoln bus was always a mess as well. I think part of it is likely that those north side diagonals are not very wide but very popular with many destinations so the buses have to do a lot of waiting for private vehicles.
I also ride a aluminum hybrid bike from working bikes. I try to do the majority of my local trips by bike and also really enjoy group rides. I've been working to improve bike infrastructure on the southwest side. Really excited because CDOT is currently working with us and we also have a supportive alder for the first time.
I'm conflicted on Airbnb. Their product really is superior to corporate hotel chains and they've opened up areas previously unserved by traditional hotels. In my city corporate landlords, foreign investors, and disinvestment in public housing seem to be much bigger problems than Airbnb.