Skip to primary navigation Skip to content Skip to footer
Back to Blog

Top 10 Things to Do in Chicago Labor Day Weekend

Chicago is arguably the best city to spend your summer. From May to September, Chicago residents head to the beach to soak in some sun during the day and enjoy plenty of fireworks by night. Labor Day Weekend is the last opportunity to enjoy the summer fun before the winter chill sets in. Luckily, there are dozens of cheap, fun and free Labor Day activities in Chicago each year.

We can also thank Chicago for the holiday itself, as Chicago has deep roots in Labor Day’s history.

In 1894, in an effort to ameliorate the tension between business and organized labor after Chicago’s Pullman strike, President Grover Cleveland and Congress designated Labor Day as a federal holiday. Legislation for the holiday was pushed through Congress six days after the strike ended. Samuel Gompers, who had sided with the federal government in its effort to end the strike by the American Railway Union, spoke out in favor of the holiday.

So celebrate Labor Day in Chicago, the city that helped put this holiday on the map.

Chicago Jazz Festival

Chicago is known for its music as much as it’s known for its epic food and gangster history. Every Labor Day weekend, jazz aficionados flock to Millennium Park for the Chicago Jazz Fest. The festival is completely free (bonus!) and features both famous and up-and-coming jazz musicians.

Visit Lake Michigan

You can’t visit Chicago without making a trip to (or even on) Lake Michigan. Whether you’re enjoying a picnic on the beach or a boat ride on the water, Lake Michigan needs to make it on your “must-do” list. The only Great Lake that is located in the US in its entirety, Lake Michigan is so large, it looks more like an ocean than a lake. All summer, there are plenty of boat tours and dinner cruises that offer some of the best views of the lake — and the Navy Pier fireworks.

If cruising old-school style is more your thing, you can always rent a paddle-board, kayak or canoe too.

Navy Pier Fireworks

When it comes to its celebrations, Chicago knows how to party. The Navy Pier hosts a series of summer fireworks, synchronized to music twice a week from Memorial Day to Labor Day each summer. Be sure to make your way down to the pier for the final display on Saturday, September 1. Throw down a blanket or enjoy the show by boat. No matter what you do, get there early. Spaces fill up fast.

African Festival of the Arts

You don’t need to travel halfway across the world this Labor Day! Africa comes to you at the African Festival of the Arts. The festival features a simulated African Village that pops up in Washington Park. You can listen to African music, browse museum-quality artifacts and taste some of the flavors of Africa. This festival is also free to the general public, but some activities and shows charge a small admission fee.

Take in a Baseball Game

The Chicago Cubs happen to be out of town on Labor Day Weekend, but you can still catch the White Sox playing the Boston Red Sox at Guaranteed Rate Field on Thursday, Friday, Saturday and Sunday this weekend. On Labor Day, the White Sox will be playing the Detroit Tigers. Just make sure you don’t tell any Cubs fans how you’ll be spending your holiday.

Chicago Fringe Festival

The annual Chicago Fringe Festival was inspired by the festival of the same name in Edinburgh, Scotland. These festivals celebrate artists that feel as though they are on the “fringe” of society and entertainment. The Chicago Fringe Festival focuses on art, music, dance, theater and comedy. Tickets for each performance cost only $10 a pop. Shows this year include “She Moved Through the Fair” and “The Big Balloon Show.”

Arlington Labor Day Race

It may not be the Triple Crown, but the Arlington Labor Day Race still draws large crowds, decked out in fancy hats, each year. There are also games and activities for kids as well as live music all weekend long. The sponsor, Miller Lite, offers plenty of opportunities to cool down and enjoy a couple of refreshing brews. Pick your lucky pony, place your bets and cross your fingers that you’ll win this year’s big pot-o-money.

Take a Tour of Chicago

There are plenty of ways to enjoy the Great Outdoors and celebrate Chicago’s history. A tour of the city is a great way to explore Chicago’s past — and to gain greater insight about its present. Before you head to the Jazz Fest or the North Coast Music Festival, take Chicago’s Premier Music Bus Tour to learn about some of the musical greats that graced the Windy City.

You’d better come prepared, though. There will be a quiz: guests are invited to play “Name That Tune,” so you’d better bring your A-game.

Midnight Circus

The Midnight Circus will set up tents in McKinley Park Friday through Sunday. Midnight Circus in the Parks was founded in 2007 in an effort to bring affordable entertainment to kids of all ages and help draw communities together. The circus itself performs long after the commencement of Labor Day Weekend, but it’s historically known as one of the best activities to enjoy on Labor Day.

North Coast Music Festival

If you can’t get enough music this weekend, head to the North Coast Music Festival, featuring headlining folk, rock, hip hop and techno music. Headliners this year include Jamiroquai, DJ Snake and Miguel. Each night also features a silent disco.

There’s no shortage of things do to in Chicago on Labor Day Weekend. So grab your swimsuit, some sunblock and a few friends to celebrate the end of the summer in the city where Labor Day was invented (sort of).

What’s your favorite Labor Day activity in Chicago? Let us know in the comments below!


  • Posted in: