ChiVibe 
Siete Azul Chicago brings coastal Mexican mariscos to the old Chicago Diner space at 2333 N. Milwaukee Ave. in late October 2026, with purple masa shrimp empanadas, butter-lime scallops, michelada oysters and a whole grilled red snapper. Bring a bottle: it opens BYOB.
Kermess and Sip & Guzzle are open, Halloween falls on a Saturday, and November brings the Soul Train Awards and the 25th Fur Ball at The Drake: your Chicago nightlife plan for October 17 to November 1.
A runway at Navy Pier, a free afternoon on State Street, 200 open buildings, Gordo x Metro at TAO and fifty chefs at the Celebrity Chef Ball: Chicago, October 16 to 25, 2026.
Chez Poulet Chicago spins brined, air-dried chickens at 2234 N. Western Ave., with Mindy’s Bakery bread, a Comté macaroni gratin and an all-French wine shelf from Le Bouchon’s Oliver and Nicolas Poilevey. Order at the counter and grab a seat on the patio.
World Fashion Festival Chicago 2026 is on now: two runway nights at Bar Sol on Navy Pier, October 15 and 16, with seven designers from six countries and an after-party until midnight, then a free runway at Loop Arts Fest on Saturday, October 17.
The Wayman Chicago is a private indoor golf and social club landing at 1015 W Wayman St in Fulton Market, with simulators and a putting green on the first floor, a clubhouse lounge upstairs, and a rooftop restaurant on the way.
Celebrity Chef Ball Chicago returns Friday, October 23, 2026, at The Geraghty, where more than 50 of the city’s top chefs split into 13 pods and cook a different six-course menu tableside for each one. Tickets are $450 and benefit Meals on Wheels Chicago.
The Alston Chicago hosts a one-night White Truffle Dinner on Friday, October 23, 2026: five Alba white truffle courses with wine pairing, reception at 6:00 PM CT, dinner at 6:30, $395 per guest, only 20 seats on OpenTable.
All Well Chicago, the West Loop restaurant from Oriole’s Noah Sandoval and Larry Feldmeier, pairs a $145 five-course menu with a bar that serves sandwiches, fried perch and cocktails until midnight. It is a 2027 Jean Banchet Awards finalist for Best New Restaurant.
Next Chicago is serving Fashion, Grant Achatz’s 10-course couture tasting menu, through January 10, 2027. On Wednesday, October 14, 2026, Mood Fabrics brings live draping to Fulton Market for one night only.