Chicago team outing ideas
Chicago is one of the easiest cities for a team outing, with plenty of activities built for groups. These are the standouts.
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Group activities for a Chicago team outing
Each card has a group tip and a link to live prices.
Architecture river cruise
Boat tours on the Chicago River pass the city's famous skyline with a guide explaining the buildings. Probably the single best group activity in the city.
Second City show or improv workshop
Second City is one of the most famous improv theaters in the country. Groups can catch a show or book a private improv workshop, which works especially well for teams.
Cubs game at Wrigley Field
A day game at Wrigley is a Chicago group classic. Rooftop venues across the street sell group packages with food and drinks.
Deep-dish pizza tour
A walking tour that hits several pizza spots and covers why Chicago pizza turned out the way it did. A good group lunch that settles the which-place argument.
Skyscraper observation decks
Skydeck at Willis Tower has glass ledges sticking out from the building; 360 Chicago has TILT, which tips you toward the street. Quick, memorable, and easy to book.
Chicago River kayak tour
Guided kayak tours through downtown on the river. A different view of the architecture and good teamwork.
Planning tips for a team outing
How organizers keep it cheaper and calmer.
Get a firm headcount before you book. Group rates usually lock at a minimum number, and a few no-shows can push you below it.
Ask for an invoice. Most group operators will invoice a company directly, which beats expensing a dozen personal cards.
Choose activities that work for different energy levels and comfort with alcohol. A good team outing doesn't make anyone opt out.
Weekday daytime slots are often cheaper and easier to book privately than weekends.
Keep planning
More ideas in Chicago and other cities.