Travel
We will provide a few hotel options. If you want to book right away, the wedding venue is in the "West Loop" neighborhood of Chicago, but most hotels are a quick Uber ride away. If you want more of a Chicago experience, the best neighborhood would be River North/Streeterville.
In terms of airports, both are pretty equally distanced. Midway is the smaller airport (for Bay Area travelers, compare to Oakland Airport) and is the primary airport for Southwest. O'Hare is the big international airport (for Bay Area travelers, compare to San Francisco Airport), so while there are more options it is busier.