The ceremony is a Catholic wedding mass! Catholic masses are usually around 45 mins but with the added components of a wedding, this will be closer to an hour.
The High Point is less than 15 mins from St. Norbert. Once you get close to the reception, the roads will be windy, very hilly and a bit narrow. If you are staying at a hotel after the reception, we have permission to leave cars overnight at The High Point and Uber. The area is flush with prompt Uber and Lyft transportation.
We have a hotel block at The Desmond Hotel (code TSW). It is under 15 mins from the reception venue and church. If all the rooms are booked (which I highly doubt they will be since people usually evacuate the area and flock to the beach for MDW) there is a Courtyard Mariott less than 10 from the reception.
This is a semi formal wedding and you could say the vibe is "upscale country" mixed with "garden casual". Men could wear a blazer with jeans or a suit. For women this can be flexible. No need to buy anything new, just wear what makes you feel good. Boots are welcome! MDW is a toss up weather wise. It can be super warm or chilly. Every church I have been in is also a toss up. They can be chilly or warm with all the guests. For the ceremony, I would probably have layers.