Five Things to Do in Chicago This Valentine's Weekend

From a film festival to a Galentine's party, there's something for everyone in the Windy City.

Published on Feb. 12, 2026

This weekend in Chicago, you can attend a film festival about messy relationships, celebrate Galentine's Day with your best friends, watch a Valentine's Day fireworks display, shop at an artisan market, or enjoy a night of comedy and caviar.

Why it matters

Chicago is offering a variety of events and activities to keep residents and visitors entertained during the Valentine's Day weekend, catering to singles, couples, and groups of friends alike.

The details

The 'Crying at the Shed' film festival at the Salt Shed will screen movies about 'messy and meaningful relationships' like Licorice Pizza, Her, and Beginners, as well as a family-friendly screening of Lady and the Tramp. Punch Bowl Social in West Loop is hosting a Galentine's Party with tarot readings, crafts, and a caricature artist. Navy Pier will have a free Valentine's Day fireworks display over the lakefront. The Chicago Artisan Market returns to Artifact Events in Ravenswood, featuring 100 local vendors. And Le Bouchon is offering a 'Comedy and Caviar' event with sparkling wine and chef-curated snacks.

  • The 'Crying at the Shed' film festival runs from February 12-14.
  • The Galentine's Party at Punch Bowl Social is on February 13.
  • The Valentine's Day fireworks display at Navy Pier is on February 14 at 9 p.m.
  • The Chicago Artisan Market takes place on February 14-15.
  • The 'Comedy and Caviar' event at Le Bouchon is on February 15.

The players

Salt Shed

A venue hosting the 'Crying at the Shed' film festival.

Punch Bowl Social

A West Loop venue hosting a Galentine's Party.

Navy Pier

A Chicago landmark hosting a free Valentine's Day fireworks display.

Artifact Events

An event venue in Ravenswood hosting the Chicago Artisan Market.

Le Bouchon

A restaurant offering a 'Comedy and Caviar' event.

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The takeaway

Chicago is offering a diverse array of events and activities this Valentine's Day weekend, catering to singles, couples, and groups of friends looking to celebrate the holiday in unique and memorable ways.