Downtown & River North

1. Saturday, Oct 10, 2:30 PM: Saturday is the short day, 11 AM to 6 PM Chicago Art Fair, the Merchandise Mart, 222 Merchandise Mart Plaza — This is a new international contemporary art fair from Redwood Art Group, in its first year at the Mart. It opens with a preview on Wednesday, October 7, from 5 to 8 PM. Public days are Thursday and Friday, October 8 and 9, 11 AM to 8 PM, and Saturday the 10th, 11 AM to 6 PM. Tickets start at $27. The fair's own visit page, Time Out and Chicago Gallery News all carry the same schedule. We have not seen an exhibitor count, so we are not printing one. Two and a half hours is enough for a first pass, and it gets you out by 5.
2. Saturday, around 5:00 PM: three-quarters of a mile east on the river The walk along the Chicago Riverwalk, south bank — Cross the river from the Mart to the Riverwalk on the south bank and head east. By our map math it is about three-quarters of a mile from Wells Street to the Riverwalk's east end near Lake Shore Drive, roughly 15 to 20 minutes. Walking it at 5 PM gets you to the Fall Fest well before sunset, which is about 6:19 by our calculation.
3. Saturday, Oct 10, 5:20–8:00 PM: Saturdays only, noon to 8 Riverwalk Fall Fest at Island Party Hut, Chicago Riverwalk between Columbus Dr and Lake Shore Dr — Island Party Hut runs this on Saturdays only, from noon to 8 PM through the end of October: hayrides on the river, a pumpkin patch, live music and fall beer and cocktails. Chicago on the Cheap, WGN and the Eventbrite listing all give the Saturday-only schedule. Early-bird tickets are listed from $5. We did not see a gate price, so buy ahead if the price matters to you. Arriving at 5:20 gives you an hour of daylight on the river before the 6:19 sunset.

Why it lands: An art fair gives two people something to react to, and it costs less than a dinner. The river walk afterward is a natural point to decide whether the evening continues. The Fall Fest closes at 8, so the night has a built-in end if you want one. Both venues sit on the river, so the whole plan stays within a mile.

Weather backup: The Art Fair is open until 8 PM on Thursday and Friday, October 8 and 9, if you would rather have a weeknight with smaller crowds. The Riverwalk Fall Fest also runs this Saturday, October 3, from noon to 8, though this week's Move is on the North Side.