Not every team outing hits the mark. You’ve got the sporty types, the social drinkers, the quiet creatives—and somehow you’re supposed to plan something everyone enjoys? That’s a tall order. But the good news is, Chicago has plenty of options that make it easy to please the whole crew.
Let’s be real: not every team outing is a hit. One person’s ideal event is another’s social nightmare. The best team events hit that sweet spot. It should be low lift for planners, fun for everyone, and just the right amount of interaction.
That’s what this list is all about.
We pulled together 10 great options for 2025 that cover a full mix of interests. Some are active, some are chill. Some get you outside, others keep it cozy.
And if you’re just here looking for the one with cold beer, great space, and built-in games that aren’t over-the-top competitive? Head straight to Navigator Taproom. That’s the one that covers all your bases. Obviously! We’re the ones that wrote this article. Of course we were going to list ourselves first.
Navigator Taproom Taproom + Self-Pour + Games
Navigator Taproom is the dream scenario for anyone who’s ever had to plan a team event. It’s built for connection, with 48 self-pour taps, flexible seating, and built-in games like shuffleboard and giant Jenga. You don’t need a long itinerary or multiple locations — just show up, swipe a card, and let people move at their own pace. There’s no waiting around for bartenders, and no complicated setup.
Food and entertainment are available as part of their event packages, so you can host a complete experience with one point of contact. Planners get clear pricing, fast responses, and a space that feels fresh while bringing everyone together.
2211 N Milwaukee Ave, Chicago, IL 60647
Chicago Pizza Tours Food-Centric + Bus Tour
This is the tour you book when your team just wants to eat and relax. Chicago Pizza Tours takes your group to 3–4 local pizzerias across the city in a private bus, mixing deep dish, tavern-style, and more along the way. It’s guided, entertaining, and super easy to plan. Since everyone ends up full and happy, it’s one of the safest bets out there.
615 N State St, Chicago, IL 60654
Flight Club High-Energy Social
If your team wants a mix of competition and cocktails, Flight Club is a sure bet. This isn’t your dive bar darts setup. It’s tech-enhanced social darts with instant replays, team scoreboards, and a buzzy vibe. Groups can book semi-private booths, and food service runs all night. It’s just the right amount of structure to feel like an event without ever getting too formal.
111 W Wacker Dr, Chicago, IL 60601
Bottle & Bottega Creative + Low-Key
Not every team wants noise and neon. Bottle & Bottega offers a relaxed, wine-friendly environment where people can unwind while making art. You’ll get a guided painting session with all materials included. No experience necessary. It’s one of those events where even the shyest team members get involved, and everyone leaves with something they made.
1241 N Clybourn Ave, Chicago, IL 60610
Royal Palms Shuffleboard Club Throwback Game Night
Royal Palms has all the ingredients of a great outing: retro shuffleboard courts, tropical cocktails, and vintage Miami vibes. The space is huge, the music’s always good, and the optional food truck rotation keeps things interesting. Planners love it because there’s plenty of room to mingle, drink, and casually compete without needing a schedule or itinerary.
1750 N Milwaukee Ave, Chicago, IL 60647
Underground Donut Tour Sweet + Easy Walk
This is for the teams who bond best over sugar. The Underground Donut Tour is a casual, guided walk that stops at some of Chicago’s best donut shops, with samples at every stop and stories about the city in between. It’s low-key and great for mixed-age teams who don’t want anything too structured. Plus, it ends with a sugar high everyone can agree on.
Starts near 50 W Randolph St, Chicago, IL 60601
SPIN Chicago Casual Competition + Drinks
SPIN takes ping pong and makes it feel cool. Located just off the Riverwalk, this place has a clean, urban vibe and enough tables to accommodate groups of all sizes. Games are easy to jump into, and the drink menu and lounge setup give it more of a cocktail party feel than a sports bar one. It’s a good balance between doing something and just enjoying each other’s company.
344 N State St, Chicago, IL 60654
Team Graffiti Bold + Visual
This outdoor art experience is unlike anything else in the city. Your team works with a professional graffiti artist to sketch, spray, and bring a group mural to life. It’s hands-on, collaborative, and surprisingly easy to pull off even if no one has painted before. You can book it in parks, rooftops, or even company parking lots. It’s visual, memorable, and totally different.
Mobile, location varies
Lucky Strike Social Big Group, Arcade Vibe
If you’ve got a large team and want something high-energy but unfussy, Lucky Strike is an easy win. There’s bowling, billiards, ping pong, and over 100 arcade games to keep everyone moving. You can rent a few lanes or a whole lounge area, and the food and drink packages are flexible. It’s especially great for team celebrations or onboarding events where people don’t know each other yet.
322 E Illinois St, Chicago, IL 60611
Planning something your whole team will love doesn’t have to be complicated. Whether you go bold with murals, laid-back with boat views, or all-in on ping pong and pints, Chicago’s got the options.