5 Great Things to Do in Chicago Between Meetings

In between meetings in Chicago? Make the most of your time with our hit list of things to do in this sprawling city. By C.A. Smith.

Get your art fix

The Art Institute of Chicago has everything from Asian art to Impressionists. Its Modern Wing is a welcome place to spend a free afternoon, where the works of modernists such as Jackson Pollock, Mark Rothko and Cy Twombly make inspiring company. Exit the airy galleries (stopping at the gift shop to stock up on presents) and use the remainder of your time to stroll through Lurie Garden, designed by pre-eminent landscape architect Piet Oudolf.

Indulge in retail therapy

If you have a half-day free in your calendar, take the Blue Line “L” train to Wicker Park/Bucktown (Damen Avenue stop). Go shopping along Damen and Milwaukee avenues or hop on a bicycle from the Divvy stand (the city’s bike-share program) and cycle north to The 606, a park along a converted train line.

Set sail on a cruise

Take to the river on a Chicago Architecture Foundation boat tour. From the backstories – such as the building that had to have its entire façade replaced when the marble crumbled – to the details that define each skyscraper, the tours always deliver something new. Allow two to three hours and be sure to book ahead to get the time and date you want (midweek tends to be less crowded than weekends) or check out the foundation’s excellent walking tour options. 

Watch a pitch

This year’s pro sports excitement is fixated on the Chicago Cubs baseball team and their chances of reaching the World Series. Though still speculative at the time of going to print, hopes are high that the Cubbies will be on their way to breaking a title drought that began in 1908. Tickets might be hard to get but a 20-minute “L” ride to the Cubs’ home ground, Wrigley Field, will let you take in the atmosphere and choose from a range of bars in which to watch the game (typically about three hours long) with crowds of locals.

Chicago’s theatre district is encapsulated in the Loop but the city’s true theatrical heart is found further north in the Lincoln Park district, where Steppenwolf Theatre Company ensemble members, including Gary Sinise and John Malkovich, have been creating memorable plays for decades. Get there early and have a delicious pre-show dinner at Italian restaurant Balena, just across the street.

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