Top 5 Things to Do in Chicago for Labor Day Weekend

The end of summer is in sight Chicago residents! Schools are back in session, the temperatures are beginning to drop lower and lower, and the sun is disappearing earlier each night. GenRealty has compiled a list of our favorite things to do in Chicago for Labor Day weekend. Time to kick back and relax and enjoy the last bits of summer, sunshine, sand, and the waves of Lake Michigan.


1. Catch a Fireworks Show on Navy Pier

Enjoy one last summer hurrah down at the lakefront with a spectacular fireworks show lighting up the skies at Navy Pier. The show begins at 10:15pm but you can get there earlier to enjoy a ride on Navy Pier’s newest addition: Centennial Wheel. There is always plenty to do and see down at Navy Pier’s 50 acre scenic boardwalk.


2. Eat Your Heart Out at a Festival

If you didn’t eat enough burgers, hot dogs, or gourmet dishes at Taste of Chicago this summer, then prepare your stomach for the remaining summer food festivals. Head on down to the waterfront at Navy Pier for the Great American Lobster Fest for seafood, fireworks, music, and family friendly entertainment. Satisfy your tastebuds with Taste of Polonia in Jefferson Park with all things Polish: pierogis, blintzes, polka music, sausages, and potato pancakes galore! Don’t forget to take a picture and tag your favorite eats on Instagram.

Great American Lobster Fest | September 2-3 | Navy Pier | $42-$140 *Hurry, tickets are selling out fast!

Taste of Polonia | September 2-5 | Jefferson Park | $5 (Before 5pm) $10 (After 5pm)

Labor day baseball

3. Support the Cubs or WhiteSox

Go Cubs! Go Sox! Whether you’re a North side or a South side fan, there are plenty of games to catch at Wrigley & Cellular or (Guaranteed Rate Field) before the end of baseball season. Put on your ball cap, grab a hot dog, peanuts, or cracker jacks, and root, root, root for the home team to win! The WhiteSox will technically be out of town during Labor Day weekend, but that shouldn’t stop you from visiting your favorite Chicago sports bar to watch them play the Twins!

Labor Day Weekend Games
September 1- 4

Chicago Cubs vs. San Francisco Giants: Games at 7:05pm and 1:20 pm

Chicago White Sox @ Minnesota Twins: Games at 7:10pm, 6:10 pm, and 1:10pm


4. Soak Up Rays and Catch Waves at the Beach

Chicago is home to some of the greatest beaches in the Midwest and offers variety to diverse beachgoers. Whether you want a day at the beach for volleyball or frisbee, a family picnic day, or to play with your best four-legged friend, Chicago has plenty of sand for everyone. Be sure to grab the sunscreen one last time, your favorite beach towel, your closest friends, and get one last swim in before the season is over!

North Avenue Beach
Montrose Beach
Foster Beach
Ohio Street Beach
57th Street Beach
63rd Street Beach
South Shore Beach


5. Shake it Off with Music

Going through Lollapalooza withdrawals? Have no fear as there are several more music festivals for you to hear! The annual Chicago Jazz Festival, North Coast Music Festival, and Chicago SummerDance will give plentiful chances to let loose, sing along, and shake off those end of summer blues! Attend any of these music festivals downtown at the Chicago Cultural Center, Millennium Park, Grant Park, and Union Park.

38th Annual Chicago Jazz Festival | September 1-4 | FREE | Kickoff at Chicago Cultural Center & Nightly performances at Millennium Park

North Coast Music Festival | September 2-4 | Union Park

Chicago SummerDance | September 2-4 | Free | Grant Park

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