Three–Day Group Trip in Chicago

Chicago has two airports – both within an hour of the city center – making travel to the city easy and accessible for all groups. I recommend staying in the center of the action – many great hotels are available in The Loop, River North and Magnificent Mile areas near the lakefront and Chicago Riverwalk.

Maybe your group knows each other well or maybe they need to break the ice. Either way, SPIN Chicago is a great place to blow off steam on night one and has something for everyone. SPIN is a ping-pong social club, offering games of all kinds, multiple bars and a large menu to choose from. They have a variety of private or semi-private spaces if your group prefers, and they offer the option to bring in a ping-pong pro to either teach some tournament skills or school the amateurs in your group. If you want a true Chicago meal, head up the street to Pizzeria Uno or Lou Malnati’s for deep-dish pizza. If your crew is looking for a nightcap, head across the river to Raised, an Urban Rooftop Bar for craft cocktails and views up and down the Chicago River.

Whether it's a meeting or a celebration bringing your group to Chicago, there are many great ways to spend the day. If you’re not beholden to a meeting or agenda during the day, it's a great time to spend bouncing around some of the city’s best museums. Stop by the Bean in Millennium Park on your way to the Art Institute of Chicago or keep going up the lakefront through Grant Park towards the Field Museum and Shedd Aquarium.

All those museums will mean a lot of walking, so take a load off at your hotel for a bit in the afternoon before heading out for the evening. If you want your guests to have a night they’re sure to remember, start off with a delicious dinner on the river at Smith and Wollensky.

Then, hire a private charter bus to take your group to catch a game! If you happen to be visiting during baseball season, Chicago Cubs games are excellent group activities that sell group tickets for all price points, from bleacher seats to private suites. If it’s not baseball season, I hope you’re lucky enough to overlap with a Chicago Bears or Blackhawks game. Chicago sports fans are notoriously passionate and any sporting event will allow your group to experience Chicago in a special way.

After a full day of adventuring around the city, on day three, I recommend sticking close to the hotel and seeing the sites of Chicago on a famous Chicago River architecture tour. Experienced guides will talk you through the city’s history and architecture. After your tour, take a walk along the Magnificent Mile to do some shopping or take your group along the riverwalk to City Winery Riverwalk, where you can grab a drink and watch the boats go by before you have to fly home!