Things To Do
Chicago Architecture Boat Tour
Cruise the Chicago River and learn the history of the buildings that make up the skyline. If you only have time for one thing, this is the thing to do. There are multiple options for boat tour companies, but we strongly recommend First Lady as they are partnered with the Chicago Architecture Center and have excellent tour guides.
Chicago Jazz Festival
The 2026 Chicago Jazz Festival is a free, four-day event from September 3–6, 2026, featuring local, national, and international artists, largely centered in Millennium Park. It is a premier Labor Day weekend tradition highlighting diverse jazz styles, produced by DCASE and the Jazz Institute of Chicago.
Lincoln Park Zoo
The Lincoln Park Zoo is free and easy to get to via public transportation or rideshare apps.
Michigan Avenue
Explore the Magnificent Mile (Michigan Ave), which offers a wide range of shopping, restaurants, and experiences in the heart of Chicago's downtown.
Walk / Bike Down Lakeshore Path
Would recommend starting at North Ave Beach and walking or biking north up to Lincoln Park. City Bike Rentals (Divvy Bikes) are available for rent along the lakeshore.
Taste of Chicago Food Festival
The 46th annual Taste of Chicago is bringing some of the city’s most iconic bites to lakefront Grant Park, with free entry to all guests. The event will include dozens of Chicago’s favorite food vendors, representing the astounding diversity of Chicago’s acclaimed culinary scene. Attendees can also enjoy live music performances, community dance lessons, family-friendly activities, interactive pop-ups, and so much more.
(Thursday Night Only) Cubs Game at Wrigley Field
See the iconic Chicago Cubs play the Milwaukee Brewers at Wrigley Field at 6:40pm on Thursday September 3rd