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Best Things To Do This Week

These are the best things to do in Chicago the week of September 19, 2022.

You might want to bookmark this page. We will be updating it each week. If you want to make plans for next week – check our listing of the best things to do in Chicago next week.

Things to Do in Chicago This Week:

Andersonville Vintage Market

When: September 21, 2022, 10 am – 3 pm
Neighborhood: Andersonville
Address: Catalpa Street between Ashland and Clark

During the Andersonville Vintage Market the neighborhood’s vintage and antique stores take over a stretch of Catalpa Street between Ashland and Clark.


When: September 22, 2022
Neighborhood: The Loop offers the best viewpoints
Address: Any East-West Street

Chicagohedge is an event when the sunrise and sunset happen to align with the skyline. It happens twice a year, usually around the spring and fall equinoxes. This event the perfect way to say farewell to summer and hello to fall.

Chicago Gourmet

When: September 22-25, 2022
Neighborhood: The Loop
Address: Millennium Park

A weekend-long event showcasing some of Chicago’s best restaurants. Guests can try bites from dozens of restaurants, taste wines, and watch cooking demonstrations from well-known chefs. Purchase tickets in advance since events do tend to sell out.

Hyde Park Jazz Festival

When: September 24-25 2022
Neighborhood: Hyde Park
Address: Midway Plaisance Park
Cost: $10 suggestion

An event dedicated to supporting jazz music. The 2022 has not been announced yet but the 2021 event showcased over two dozen bands.

West Town Art Walk

When: September 23-24, 2022
Neighborhood: West Town
Address: throughout West Town

An event hosted by West Town galleries, home stores, and garden shops that celebrates local art with walking tours and special events.

Kyiv City Ballet of Ukraine

When: September 24 and 25
Neighborhood: The Loop
Address: Auditorium Theater, 50 E. Ida B. Wells Drive

The Kyiv City Ballet left for a tour the day before Ukraine was invaded and hasn’t returned home. The ballet company is performing a program that includes a new piece titled Tribute to Peace. They will be in Chicago for two nights only.

Revolution Brewing Oktoberfest

When: September 24-25, 2022
Neighborhood: Logan Square
Address: 2323 North Milwaukee Ave

This beer-centric street festival features live music and Revolution Brewery’s seasonal Oktoberfest beer. In the past, metal bands played on Friday.