Weekend 101: Labor Day Weekend 2019

The bad news: this weekend marks the unofficial end of summer. The good news: you have an extra day to enjoy these final days of the season. So start making plans to dine on fresh lobster at Navy Pier, take a trip to Nashville without leaving the Chicago area, and more.

The Great American Lobster Fest

Aug. 30 to Sept. 1

The Great American Lobster Fest in Chicago
Photo courtesy of The Great American Lobster Fest.

Head out to Navy Pier to enjoy lobster flown in fresh from the East Coast, as well as live music, family activities, shopping, fireworks, and more.


Aug. 30 to Sept. 1

Nashwood in Highwood, Illinois
Photo courtesy of Celebrate Highwood.

If you can’t travel to Nashville this weekend, visit the next best thing. Highwood is transforming into Music City with more than 80 live music performances, a kids area, and Southern-inspired food and drinks.

Chicago Jazz Festival

Through Sept. 1

Chicago Jazz Festival
Photo by DCASE, City of Chicago.

Soak up the final days of summer with jazz performances under the sun or the stars at Millennium Park. Headliners include Eddie Palmieri, Cécile McLorin Salvant, and Art Ensemble of Chicago.

Labor Day Party at City Winery

Sept. 2

Labor Day Party at City Winery Chicago
Image courtesy of City Winery Chicago.

City Winery Chicago is celebrating the long weekend with an all-female lineup featuring Sadie Woods, an award-winning DJ from Chicago; Katie Kadan, who has performed at Taste of Chicago, Navy Pier, and the Fillmore Jazz Festival; and headliner Sandra Antongiorgi, a World, Latin, and Neo-Soul artist who has opened for Lizz Wright and Wynonna Judd.

More Can’t-Miss Events:

  • Don’t miss the last Friday Night Concert in Rosemont on Aug. 30 featuring performances by Bee Gees Gold and The Wayouts as well as food and drink tents from local restaurants.
  • Irish Days in Long Grove, Aug. 31 to Sept. 2, is an annual festival features Irish musicians and dance troupes, the Irish Dog Competition, Irish food, kid-friendly crafts, a Best-Looking Men’s Legs in a Kilt contest, and more.
  • Take in a baseball game with your furry friend during the Chicago Dogs’ Bark at the Ballpark game on Sept. 1. Take part in a pet parade before the game, pose for the “pawpurazzi” from Fetch Portraits, and enjoy $3 bottomless popcorn and fountain drinks.

Anna Carlson writes the weekly Weekend 101 column and monthly Recommended Events. A graduate of the University of Missouri, her work has been published in Chicago Parent, Inside Columbia Magazine, and Central California Parent Magazine. She is a proud supporter of St. Jude Children’s Research Hospital