Off the Clock
Chicago · Group activities

Group activities in Chicago.

Things to do with colleagues or clients that work for a mixed group, from easy tastings to friendly competition.

Browse ChicagoClient dinnersPrivate dining roomsGroup activities

3 picks

Checked regularly. Confirm details with the venue when you book.
Activity

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.

Client outingViewsBucket listOutdoorsEveningBig groupsRelaxed
Fits
Private charters for 2 to 250; group rate for 20 or more
Tip
Charters run April to November only; contact charter sales (847-358-1330) and add a Chicago Architecture Center docent for the river part.
Website ↗Source ↗Map ↗Checked October 22, 2026
Activity$

The Chopping Block

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.

Hands-onCollaborativeCompetitiveCreativeEveningClient outing
Fits
Private events for 6 to 50; larger groups by running events side by side
Cost
$under 30 per person (est.)
Tip
Private events have a $1,700 minimum, so it pays off best for a group of 15 or more.
Activity

Skydeck Chicago

Willis Tower, 233 S Wacker Dr, the Loop

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
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).

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