Big Weekend Chicago

Coming off Sunday’s win, I’m feeling very hopeful for the Bears - dare I say optimistic 🙏 so naturally I scoured the internet for the most stylish gameday fits for the whole family. 👌🏈

Comment BEARS and I’ll send you the links

GOOD, BETTER, BEST! 🧡💙🐻

If you looked at the calendar and realized Labor Day weekend is HERE and the back-to-school madness completely distracted you from making plans… I’ve got you covered ☀️

I pulled together some of my favorite family-friendly ways to spend the long weekend around Chicago — including a few last-chance summer experiences.

Swipe through for dates, times, and the details for a final big weekend of summer 🤸✨☀️🌞

The Chicago Dogs are home against the Gary SouthShore RailCats all Labor Day weekend at Impact Field:

FRI 9/4 · 6:30 PM → Happy Friday + Stan/Stu bobblehead giveaway + kids run the bases

SAT 9/5 · 6 PM → Postgame fireworks

SUN 9/6 · 3 PM → Family Sunday with pregame catch + player autographs + $3.50 bottomless popcorn and $3.50 bottomless fountain drinks

MON 9/7 · 1 PM → Fan Appreciation Day + team photo giveaway + pregame catch and autographs

The 25th annual Bike The Drive aka Bike the Drive is Sunday, Sept. 6!

Bike DuSable Lake Shore Drive while it’s closed to cars.

Ride window: 6:30–10:30 AM
Main start + festival: Butler Field in Grant Park
Helmets required
Youth registration available

Registration is still open.

Labor Day is the FINAL day of Butterflies & Blooms at Chicago Botanic Garden

Walk among hundreds of live butterflies from around the world before the exhibit closes for the season.

Through Monday, Sept. 7
Included with Garden admission

If you missed it this summer Brookfield Zoo Chicago still has
Dinos! - featuring life-size dinosaurs throughout the zoo, plus fossil digging, photo ops + more.

Runs through Oct. 25
Included with regular zoo admission or membership

Make your own little spa date at American Girl Chicago.

Book a Girl + Doll Mini Manicure for $37 — matching mini manicures for your kiddo and her doll.

I found Labor Day weekend salon appointments still showing when I checked, so this is a fun little activity to add onto a Mag Mile day.

Pack one more picnic and squeeze in a final summer concert at Ravinia Festival ®

FRI 9/4 · 7:30 PM → Snoop Dogg + Neal Francis DJ set
SAT 9/5 · 1:30 PM → Karen Ouzounian: Mayrig
SUN 9/6 · 1:30 PM → Olga Kern, piano
SUN 9/6 · 6:30 PM → Squeeze + Adam Ant + Haircut 100

Cruise Chicago aboard the historic