Saturday Oct 10: the new Chicago Art Fair at the Mart, then the Riverwalk at sunset
A brand-new contemporary art fair inside the Mart, then a river walk to hayrides and a pumpkin patch
Cost: About $65 for two before drinks: Art Fair from $27 each, Fall Fest early-bird from $5
- 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 — Redwood Art Group's new international contemporary fair, in its first year at the Mart. Preview Wednesday, Oct 7, 5 to 8 PM; public days Thursday and Friday, Oct 8 and 9, 11 AM to 8 PM, and Saturday the 10th, 11 AM to 6 PM. Tickets from $27. Two and a half hours is a solid first pass and gets you out by 5.
- Saturday, around 5:00 PM: three-quarters of a mile east on the river The walk along the Chicago Riverwalk, south bank — Cross from the Mart to the south bank and head east. Wells Street to the Riverwalk's east end near Lake Shore Drive is about three-quarters of a mile, 15 to 20 minutes. Leave at 5 and you reach the Fall Fest well before the 6:19 sunset.
- 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 it Saturdays only (we checked), noon to 8 PM through October: river hayrides, a pumpkin patch, live music, fall beer and cocktails. Early-bird tickets from $5; buy ahead if price matters. Arrive at 5:20 for an hour of daylight on the river before the 6:19 sunset.
Why it lands: An art fair gives you two something to react to, for less than a dinner. The river walk afterward is where you decide whether the evening continues, and the Fall Fest closes at 8, so the night has a built-in end if you want one. The whole plan stays on the river, within a mile.
Weather backup: Prefer a weeknight with smaller crowds? The Art Fair runs until 8 PM Thursday and Friday, October 8 and 9. The Riverwalk Fall Fest also runs this Saturday, October 3, noon to 8.