Trip planner · Chicago

Chicago in October 2026.

What's on, what to book ahead, and where to take colleagues and clients during a business trip to Chicago this month.

On the calendar

6 dates to plan around

Our rule of thumb for groups. Individual venues vary, so confirm when you call.

Groups of 10 or more: book a private room 3 to 4 weeks ahead in a normal week.
Conference weeks: book as soon as your dates are set. Each conference guide shows our book-by date.
Game nights near the arena: book pregame dinners at least a week ahead.
Holidays: many restaurants close or switch to set menus, so confirm hours before you book.

Pick one, book two places, done

15–60 people · $$$$

5:00 PMSwift & Sons · Early steak dinner in the Wellington Room in Fulton Market
6:30 PMShort cab ride west to the United Center
7:00 PMBulls vs Wizards, Sat Oct 24

6–28 people · $$$$

6:30 PMMoody Tongue · Michelin-starred tasting menu with beer pairings in the Dining Room, a short walk from McCormick Place

20–65 people · $$$$

6:00 PMChicago's First Lady architecture cruise · Private evening charter on the river from the Riverwalk dock
8:00 PMPrime & Provisions · Walk along the river to dinner in the River View Room