Skip to site content
Group Travel Leader Group Travel Leader Group Travel Leader

Chicago after dark

When you visit Chicago, there’s no excuse for going to bed early.

The Windy City’s world-class museums, dynamic shopping and downtown attractions keep visiting groups busy with plenty of activity during the day. After dinner, though, there’s more to discover, as the city’s entertainment culture comes to life after dark.

It would be a shame to take a group to Chicago without tapping into the great after-hours entertainment available there. Plan a classy night out at the symphony or the opera, or catch some of the best music in the Midwest at one of the city’s iconic jazz and blues clubs. The improv comedy scene in the city is legendary as well and can have your group laughing well into the night.


A Classy Night Out

As one of the largest cities in the United States, Chicago enjoys a classical music culture on par with other great music destinations around the world. Groups visiting the city can get a sample of the city’s fine performing arts by taking in a show at the Chicago Symphony Orchestra or the Lyric Opera of Chicago.

“A lot of people think that they can’t go to the symphony, like it’s a snooty thing,” said Joleen Harlan, assistant director of tourism for Choose Chicago. “But it’s really not; the people at the symphony and the opera make it a great experience and show you how accessible the music really is. You may not know the name of what you’re hearing, but you’ll love it.”

The Chicago Symphony Orchestra plays at Symphony Center, a large hall that is touted as one of the most beautiful buildings in Chicago. Harlan said that despite the venue’s size, each performance has an intimate feel.

The orchestra has played concerts all around the world and frequently sells out its regular home performances, so it’s important for group leaders to make arrangements for tickets well in advance of their trip. Harlan said the organization works well with groups but that planners may have to be flexible on the nights they attend, depending on the number of tickets remaining.

The Lyric Opera of Chicago is a bit easier for groups to attend. This organization performs great classical operas from around the world and displays subtitles so that audience members can follow along with the story.

Groups that attend the opera often enjoy the performance venue just as much as the show itself.

“The Opera House is amazingly beautiful and large, a big, grandiose experience when you come to Chicago,” Harlan said. “They can also do a building tour, where they take you through the theater and onto the stage, and talk to you about the way that opera works.”


City of Blues & Jazz

Many music lovers know Chicago as one of the nation’s foremost destinations for blues and jazz. There are countless live music clubs throughout the city, including a pair that go out of their way to create great music experiences for groups.

Just south of downtown, Buddy Guy’s Legends features nightly live music with performances by some of the city’s top blues talent.

“Buddy Guy himself plays there every January,” Harlan said. “It’s a great experience. Groups can do dinner and have food while watching the show. You can also do lunch with the musicians — that’s sometimes a nice way to fit in a show for groups that don’t want to stay up super late.”

Groups can also arrange to have meet-and-greet sessions with the artists that perform there or to have special events and private performances in rooms upstairs from the main venue.

In the city’s main entertainment district, Andy’s Jazz Club gives groups an opportunity to get close to great Chicago jazz musicians.

“They serve food as well, but it’s much more of an intimate jazz club,” Harlan said. “It’s a small venue, so you’re right up there with the jazz musicians in front of you. For groups, they can do an early-evening performance, and the musicians love talking with the groups that visit.”


Laugh Out Loud

Maybe your travelers aren’t looking for musical entertainment; they’d rather have a good hard laugh. If that’s the case, you won’t have to search far to find it in Chicago, a city that has become nationally known for its improv comedy clubs.

The most famous comedy company in Chicago is the Second City, a theater and training organization that is celebrating its 50th year in the city. The group’s alumni include many of the top names in comedy over the past few decades.

“Most of the people that you see on ‘Saturday Night Live’ came from the Second City, so it’s a breeding ground for that level of talent,” Harlan said. “They also have a huge training program there, so you can see their students performing there as well.”

Groups can visit the Second City’s theater in the Old Town neighborhood for one of two shows that take place each night. There are also daytime matinee shows and, for the truly adventurous, midnight shows.

The nature of improv comedy means that audience members participate by making suggestions to the cast or even playing bit parts onstage. For even more participation, groups can arrange to have their own classes and workshops at the Second City.

“If the group is a bunch of ones and twos, the people might not know each other, so these classes are a good way to get people moving and get to know each other,” Harlan said. “And because you’re learning about improv, it’s a nice way to train people for situations in everyday life.”

Another organization, ComedySportz Theatre, offers squeaky-clean improv comedy served to audiences in a competition-style setting.

“It’s improv played as a sport,” Harlan said. “They have two teams of improvisers that compete against each other in improv games.”

A referee introduces each game, solicits suggestions from the audience and awards points to each team according to how they perform. The referee also uses humorous props to help make sure the performers and attendees steer clear of racy material.

“If one of the improvisers says something inappropriate, the ref blows the whistle and makes the person wear a brown bag on their head for the rest of the game,” Harlan said. “They’ll even do that to an audience member.”

Brian Jewell

Brian Jewell is the executive editor of The Group Travel Leader. In more than a decade of travel journalism he has visited 48 states and 25 foreign countries.