Things to do in Chicago this weekend
Explore the best events and things to do in Chicago, from parties and live shows to pop-ups, community events, and more.Updated September 23, 2026
(CHICAGO) TOUCH GRASS WALK CLUB: MATCHA EDITION
Sun at 10am · Chicago
hello chicago!!
addicted to your phone? stressed from work? tired of having no friends?
you need to touch some grass.
touch grass walk club is a social walking club with roots in san francisco, built around a very simple concept: getting off our phones, getting outside, and meeting cool people along the way. i recently moved to chicago and am SO excited to bring touch grass with me and start a new chapter in the city <3
expect themed walks every month, excuses to explore chicago, and many opportunities to make friends without having to ask someone on bumble bff if they want to get coffee.
FOR OUR FIRST CHICAGO WALK: BIG BACKS DRINK GRASS 🍵
for all you big backs out there, we’re kicking things off with a matcha crawl
we’ll spend ~2 hours walking around wicker park + surrounding neighborhoods and hitting 3 matcha-themed stops:
SIP → EAT → SWIRL
matcha drink. matcha treat. matcha soft serve. you get it.
after the crawl, we’ll hang around and mingle so you can actually talk to the people you just spent 2 hours walking around chicago with (bc i know some of u people desperately need friends) (i am people)
official crawl stops will be announced as they are confirmed
important note: everyone will purchase individually at each stop, so come HUNGRY or bring friends if you want to split things and try more stuff.
come alone. bring a friend. bring your hinge date idgaf. just get out of your house and feel the sun on your skin before the blistering winter.
very excited to assemble chicago’s matcha lovers for a day of eating, walking, yapping, and touching grass. see you there 🍵🌱RSVP Here
Art Show Opening
Sat at 2pm · Chicago
Solo Art Show about time and beyond time. Things are always becoming something else.
Join me for an afternoon of new work exploring time, transformation, and the space between what something was and what it becomes.
Come see a new collection of acrylic paintings and prints, enjoy drinks and light bites, and spend as little or as much time as you like.
Works and prints will be available for purchase, with pieces priced at $300 and under. An approachable way to start collecting art, or simply find something new for your space.
Come as you are. Stay as long as you want.RSVP Here
$10 & Under Market
Sun at 12pm · Chicago
312 Markets is turning two and celebrating with their signature $10-and-under pop-up with clothes, jewelry, art, tarot, and handmade goods from Chicago small businesses, plus coffee and food on site
First 50 shoppers score a free tote!RSVP Here
That's So Y2K!: Cafe Edition
Sat at 11am · Chicago
We’re taking it back to the 2000s for the day ☀️💿
That’s so Y2K takes over Lit Cafe for the ultimate ✨cafe experience✨ brought to you by King Inesse & DJ Cher
Infused (+non-infused) pastries, coffee, matcha, & more 🍃🍵
Bring your friends— we’ll have all throwback pop + R&B hits you need… plus GIVEAWAYS🎁
FREE ENTRY w/ RSVPRSVP Here
Garage ahh House Show
Sat at 6pm · Chicago
Join us for an outdoor show in Wicker Park!
We’ll have local band VRTUE playing some live tunes, right on the deck of our wonderful hosts’ garage-esque abode.
WHEN:
- Saturday, September 26th
- 6 PM: Doors open - come hang!
- 7 PM: Show start
- 8 PM: Show end
WHERE:
- 1028 N. Marshfield Ave
- The show is in the backyard
- Greeter will be near the entrance
TICKETS:
- $10 admission
- Pick up an event wristband upon arrival
- Jason is handling payments! Please shoot Jason (one of the hosts) a Venmo or Zelle to RSVP
- Venmo: Jason-Inumerable
- Zelle: (847) 704-2415
- Prefer Cash? Feel free to reach out to Jason/the band directly.
REFRESHMENTS:
- Drinks and snacks available for purchase
- BYOB as well
QUESTIONS?
- DM @vrtueband on Instagram
- Kyle (847-848-1328)
- Jason (847-704-2415)
We have limited space so grab your spot while ya can. Hope to see you there!RSVP Here
Kelley Cole @ The Shrine Chicago
Sat at 6:30pm · Chicago
Pass Down Magazine Presents: big ole indie rock house show. Featuring touring artist Kelley Cole from Nashville and local acts Sports Boyfriend, Iris Blue and daarling.
check out the official playlist so ur ready to party 🖤
rsvp for the address or dm @thekelleycole (insta).RSVP Here
ROOM TONE: Evan G & Leja Hazer
Fri at 9pm · Chicago
Elevated and soulful dance music for lovely people.
This month’s guest selector is Leja Hazer, whose signature style blends deep grooves from jazz, house, soul, and funk with a touch of classic Chicago grit.
$5 cover | 21+RSVP Here
end of summer yard sale <3
Sat at 10am · Chicago
please join us for our end of the summer yard sale! 🛍️🌷🩷
bring a tote bag! 👜 we will have tons of….
🎽 clothing (ranging from xs-xl) (femme, masc, unisex)
💍 jewelry
🪞 home goods
+ sweet little oddities we no longer have space for! 🥲
all things ranging from $1-$20!
there will also be a bin of FREE baby items including clothing, bottles, and formula! 🍼
📍directions📍
🏦 (chase bank) 🏠🏠📍(backyard sale!)
once you arrive at 1538 w henderson st, locate the white gate on the right. walk all the way down and you will find the sale in our backyard!
🔔 please be respectful of our neighbors and don’t knock on the front door! thank you!!! <3RSVP Here
Figure Drawing (Ballerina) | LakeFront
Sat at 11am · Chicago
Bring a sketchbook and join us at stone ramps on Lakeview portion of the Lakefront to sit for a morning of figure drawing with a live ballerina.
We'll meet near the water behind the AIDS Garden (giant green stick figure statue), to sketch a ballerina with the lake as the backdrop. All skill levels are welcome, from complete beginners to experienced artists. No instruction, no pressure; just draw, experiment, and enjoy the morning.
At 12:00 PM we'll do a sketchbook throwdown (everyone lays their sketchbooks out on the ground so we can walk around and see what everyone created).
📍 Concrete Ramps on Lakefront; Lakeview portion
🗓️ Saturday, September 26 • 11 AM
Bring whatever supplies you've got; pencil, pen, charcoal, watercolor, iPad, or a full easel. Come draw with us.
Complete our survey to claim a free Rendr sketchbook at arrival, courtesy of Crescent Brands: https://forms.gle/M2jkPhvhT5W8Nh7K9RSVP Here
Q4 Reset | Picnic at Obama Center🧺
Sun at 1pm · Chicago
As we wind down summer and get ready to step into Q4, it’s the perfect time to pause, reconnect with our goals, and get intentional about how we want to finish the year.
Join us at the Obama Center Great Lawn for an afternoon of goals, connection, and community as we reset, refocus, and lock in for the final quarter of the year.
Bring your picnic blanket, your favorite snacks, and whatever you like to use to capture your thoughts — whether that’s a journal, laptop, iPad, or phone.
Come solo or bring a friend. Either way, there’ll be space to connect, reflect, and set some goals Q4!
What to bring:
🧺 A picnic blanket or lawn chair
🥐 Your favorite snacks or lunch
📝 Whatever you like to take notes on
✨ Your goals, ideas & an open mind
📍 Obama Center Great Lawn | Chicago
📅 September 27, Last Sunday Funday of the quarter!
⏰ 1–3 PM
Let’s reset. Let’s connect. Let’s lock in. 🔒
Hosted by The Elevate BoxRSVP Here
Mid-Autumn Mini Market! 🏮✨
Sun at 1pm · Chicago
Last Place on Earth is celebrating the season with a free Mid-Autumn Mini Market in Wicker Park
It will be an afternoon of local art, vendors, and more. No ticket needed, just RSVP and come support local creators!RSVP Here
Indie Music Festival
Sat at 7pm · Chicago
Porchlight Fest is back with a stacked indie lineup, Hannah Sandoz, Gerfety, Doc Mino, and more, with every dollar of profit going to Avondale Mutual Aid
Address goes out to ticket holders only, so grab yours before the night sells out!RSVP Here