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Chicago’s January Calendar of Events

January might not be the most active month of the event calendar, but there are some fun event geared toward locals.

Things to Do in Chicago in January:

Silver Skates

When: TBD
Neighborhood: Hyde Park
Address: Midway Plaisance Ice Rink

A speed skating competition for children (6 and up) and adults that takes place at the Midway Plaisance ice rink each January.


When: November 11, 2022 – January 8, 2023
Neighborhood: Glencoe
Address: Chicago Botanic Garden, 1000 Lake Cook Road, Glencoe

An event where an illuminated walking trail and light installations take over the grounds of the Chicago Botanic Garden. Tickets sell out every year – they go on sale June 8th.

Garfield Park Conservatory Winter Flower Show

When: TBD
Neighborhood: Garfield Park
Address: Garfield Park Conservatory

The Winter Flower Show starts in late November and is open until early January.

Eataly Cheese and Wine Fest

When: TBD
Neigborhood: Streeterville
Address: Eataly

Eataly’s events are not to be missed. This wintertime event focuses on letting guests taste 15 different wine and cheese pairings.

Chicago International Puppet Theater Festival

When: TBD
Address: Theaters across Chicago

An 11 day event that takes place over the course of 11 days each January that includes performances, workshops, artist instensives, free neighborhood events and symposia.

The Cub’s Convention 

When: TBD
Neighborhood: Streeterville
Address: Sheraton Grand Chicago

After two years of cancellations, the Cubs plan to bring back their annual convention in 2023.


When: TBD
Neighborhood: South Loop
Address: McCormick Place

The White Sox’s annual fan event brings fans, players, coaches, and staff together to celebrate the team.

Fillet of Solo Festival

When: TBD (mid-January through mid-February)
Neighborhood: TBD
Address: TBD

A storytelling festival hosted by the Lifeline Theater that features storytelling collectives and solo performers.