Checked regularly. Confirm details with the venue when you book.
ActivityTickets from $57; charters from about $1,500 an hour
Chicago's First Lady architecture cruise
Chicago Riverwalk, 112 E Wacker Dr, the Loop
The official Chicago Architecture Center river cruise, a 90-minute trip led by the center's volunteer docents. Groups can also charter a boat for a private evening on the river.
Private charters for 2 to 250; group rate for 20 or more
Cost
About $57 per person
Tip
The 2026 season runs to December 20. Call charter sales (847-358-1330, weekdays 9 to 5). A Chicago Architecture Center docent on a charter costs $500 extra. The group rate for 20 or more applies to some daytime cruises Sunday to Thursday, booked a week ahead.
4747 N Lincoln Ave, Lincoln Square · about 25 min by cab from the Loop
A cooking school running since 1997, with hands-on classes and private cooking parties. Colleagues cook a multi-course meal together, with a competition format on offer.
The observation deck on the 103rd floor of Willis Tower, with The Ledge glass boxes. Groups of 20 or more get discounted tickets, and a 99th-floor space hosts private events.
ViewsBucket listEveningPregameLow effortBig groups
Fits
Group tickets from 20 guests; 99th-floor event space 50 to 300 seated or 400 standing
Cost
About $32 per person
Tip
Book group tickets at least 14 business days ahead through sales@theskydeck.com; winter hours run 9 AM to 8 PM (9 PM Saturdays).
700 S Wabash Ave, South Loop · about 10 min by cab from McCormick Place
Buddy Guy's own blues club, with live music Wednesday to Sunday and his guitars and awards on the walls. Cajun food and a warm room make an easy winter night out for a group.
Groups of 25 to 550; largest room 270 seated or 550 standing; full buyout possible
Cost
$30–60 per person (est.)
Tip
It takes no table reservations and tables fill by 6 to 7 PM on weekends, so arrive early or book a private event for a group. Shows after 8 PM are 21 and over.
111 W Wacker Dr, the Loop by the Riverwalk · about 15 min by cab from McCormick Place
Social darts with automatic scoring on 14 playing areas, plus two bars and a restaurant. Colleagues play team games side by side, and it runs indoors all winter.