Flight
O'Hare is definitely the easiest as it is only a short car ride (25 minutes) from the hotel, venue, etc. If traveling with Southwest, you'll have to fly into Midway which is approximately an hour distance.
Hotel
Check-in: Friday, October 1, 2021. Check-out: Tuesday, October 5, 2021. Last Day to Book: Friday, September 10, 2021 Rate: $109. Breakfast for two included in the rate and round-trip shuttle service to The Haight.