Looking for the best things to do in Chicago this weekend? This is the weekend before Halloween, and the city goes all in. Lincoln Park has two full days of trick or treating. Lincoln Square turns into Lincoln Scared on Sunday morning. Then Arts in the Dark lights up Columbus Drive on Saturday night. Plus, the fun keeps going Monday with Trick or Treat on Southport, and The Yeager Team is a proud community sponsor this year. Here is everything worth your time for October 23-26, 2026.
Grab the costumes. Let’s go.
Lincoln Park Spooktacular
Saturday and Sunday, October 24-25 | 1pm to 4pm | Free | 40+ Businesses Each Day
The Lincoln Park Chamber of Commerce runs this one, and it is two different routes on two different days. On Saturday, kids trick or treat along Lincoln Avenue from Diversey to Webster. Then on Sunday, the route moves to Clark Street from Armitage to Diversey, plus Diversey from Lakeview to Orchard. More than 40 businesses hand out candy each day. Route details at lincolnparkchamber.com.
Local tip: End Saturday’s route at Oz Park, right where Lincoln meets Webster. The Tin Man and Dorothy statues are the best free costume photo op on the North Side. Let the kids burn off the sugar on the playground before you head home.
On Sunday, refuel along the Clark Street route. KALA Modern Greek is an easy, casual lunch for the whole crew. Meanwhile, Maison Parisienne is the croissant and coffee stop that gets parents through the second half of the route.
🏡 Realtor mom take: Two days of trick or treating on two of the most walkable streets in the city. That is Lincoln Park in one sentence. Just a few blocks away, our condo on Armitage went under contract with multiple offers this month. This is exactly what buyers are paying for. You walk out the door and the neighborhood is the activity. If Lincoln Park is on your list, start here and I will show you what is actually available right now. 🎃🍬
Not sure where to start? Fill out a quick form and I will send you a curated list of homes that match what you are looking for, including off-market options.
Lincoln Scared and Ravenswoooood
Sunday, October 25 | 11am to 1pm | Free | Lincoln Square and Ravenswood Businesses
On the Sunday before Halloween, the Lincoln Square and Ravenswood business district becomes Lincoln Scared and Ravenswoooood. Kids trick or treat between participating shops all morning. Then stop at The Perfect Cup at 4700 N. Damen Ave., where Concordia Place sets up pumpkins and decorating supplies right out front. Pumpkins are limited, so go early. It is rain or shine, and treats are available while supplies last. Participating businesses and maps at lincolnsquare.org.
Local tip: Take the Brown Line to Western and you are steps from Giddings Plaza. Grab a pastry at Café Selmarie, right on the plaza. Then let the kids pick a treat at Gene’s Sausage Shop on Lincoln Avenue for the walk home. Pro move: Lincoln Scared wraps at 1pm, and Lincoln Park Spooktacular starts at 1pm. Do both and call it the Sunday double header.
🏡 Realtor mom take: Lincoln Square has the Old Town School of Folk Music, the Brown Line, a real town square and block after block of classic brick homes on tree lined streets. Families find it and they do not leave. So when a well priced home hits here, it moves. If you want to know what is coming up before it hits the market, let’s talk. 🍂👻
Arts in the Dark Halloween Parade
Saturday, October 24 | 6pm to 8pm | Free | Columbus Drive, Balbo to Jackson
Arts in the Dark is back for its 12th year, and it is moving home. The parade returns to its original spot on Columbus Drive, stepping off at Balbo and marching north to Jackson. Think glowing floats, giant puppets, dancers and performers from every corner of the city. Organizers expect more than 100,000 people. Food trucks line the east side of the route and vendors set up on the west side, so come early and eat there. Also, costumes are strongly encouraged for the crowd, not just the parade. Details at choosechicago.com.
Local tip: Skip driving. Take the Red Line to Harrison and walk east into Grant Park. Buckingham Fountain sits right near the start of the route, so it makes an easy meeting spot if your group splits up. Bring glow sticks for the little ones. It gets dark fast in late October.
🏡 Realtor mom take: Families in the South Loop and Printer’s Row walk to this. Grant Park is their front yard, and nights like this are the payoff. You get space, lake views and a commute measured in minutes. If you have been curious about downtown living with kids, reach out and I will walk you through it. 🎭✨
Monday Bonus: Trick or Treat on Southport
Monday, October 26 | 4pm to 7pm | Free | Southport Avenue, Roscoe to Grace | Rain or Shine
Halloween in our neighborhood starts on a Monday. Trick or Treat on Southport takes over Southport Avenue from Roscoe all the way to Grace. Dozens of local businesses hand out candy. A pumpkin patch sets up near Southport and Waveland, right outside Coalfire Pizza. Inflatables come from Lakeshore Sport and Fitness and Altitude Roscoe Village. Then at 5pm, dancers from Gus Giordano Dance School perform Thriller near Southport and Cornelia. Friends of Lakeview produces the event, and The Yeager Team is proud to be a community sponsor this year. Come Visit our Tent by the Music Box! More at lakeviewroscoevillage.org.
Local tip: Leave the car at home. The Brown Line Southport stop drops you just south of the corridor. Start there, walk north and time it so you catch Thriller at 5pm. Then finish at the Music Box Theatre, the 1929 movie palace that makes every Southport walk feel like old Chicago. Need a warm drink for the grown ups? Bake House at Southport and Grace has you covered.
🏡 Realtor mom take: Southport is home for us, and this is one of my favorite nights of the year. It is also one of the corridors our buyers ask about most, and for good reason. You get a real main street, a neighborhood school at the end of the block and single family homes within walking distance of all of it. Come find The Yeager Team along the route by the Music Box Theater on Monday. We will have candy, a spin-the-wheel game with prizes and we would love to meet you. Thinking about a move to Lakeview or North Center? Start the conversation here. 🎃🖤
Quick Hit List: More Things to Do in Chicago This Weekend
Here is everything else worth knowing about this weekend.
- 🎬 Chicago International Film Festival | Final weekend, through Sunday, October 25 | Multiple venues. Last call for North America’s longest running competitive film festival.
- 🦁 Lincoln Park Zoo Fall Fest | Fridays through Sundays, through November 1 | Free. Pumpkins and fall fun at the best free destination in the city.
- 🍻 Zoo Brews: Howls and Growls | Friday and Saturday, October 23-24 | 6:30pm to 10pm | Lincoln Park Zoo | Adults only. Book the sitter.
- 🎃 Slightly Spooky October at Navy Pier | Saturday, October 24 | Free Halloween movies in Crystal Gardens.
- 🛍️ Chicago Fall Market by Markets for Makers | Saturday and Sunday, October 24-25 | Artifact Events, 4325 N. Ravenswood Ave. Get a jump on holiday gifts from local makers.
- 👻 Gompers Park Ghoulfest | Saturday, October 24 | Costume parade, trunk or treat, games and crafts.
- 💀 Día de los Muertos in Pilsen | Saturday, October 24 | One of the most beautiful neighborhood celebrations of the season.
- 🛒 Meet Me on Milwaukee | Sunday, October 25 | 10am to 4pm | Wicker Park | Free.
- 🏀 Chicago Bulls vs. Washington Wizards | Saturday, October 24 | United Center.
- 🎸 Tedeschi Trucks Band | Friday, October 23 | 7:30pm | The Chicago Theatre, 175 N. State St.
- 👻 Hamilton Elementary Boo Bash | Saturday, October 24 | 1pm-4pm | Hamilton Turf Field 1650 W Cornelia Ave
Real Estate Corner: Everyone Is Waiting on Rates, and That Is Your Opening
Here is what I hear every single week right now. “We are just going to wait until rates come down.” I get it. The 30-year fixed averaged 7.40% last week, according to Freddie Mac. That number feels heavy.
But here is the flip. Whether the rates drop in the new year or not, people will still move. And with that is the spring market. Packed open houses. Twelve offer weekends. Escalation clauses. So right now is the quiet before that rush. A high rate will feel uncomfortable temporarily, but getting in now before the home price is even higher will be the biggest impact. You will adjust and that rate will eventually come down.
For buyers: Right now you have the inventory and the space to make a good decision. Fewer buyers are competing with you. The sellers listing in late October are serious. In addition, you can refinance later if rates drop, but you cannot go back and buy the home you missed. So keep looking. The right one will show up.
Not sure where to start? Fill out this form and I will send you a curated list of homes that match exactly what you are looking for, including off-market options.
For sellers: The buyers touring homes the weekend before Halloween are not browsing. They are pre-approved and ready to write. Meanwhile, you have less competition from other listings than you will in the spring. When the spring rush hits, you will be one of many. Today, you are the one they are choosing. We would love to sell your home, and we are always grateful for the opportunity to work together.
Curious what your home is worth right now? Fill this out and I will send you a custom value estimate and a selling game plan for your neighborhood. Want your home value instantly? Click here.
Thinking of Selling? Let’s Talk
For investors: Now through the end of the year is your season. Fewer buyers are bidding, which means more room to make the numbers work on the North Side. If you are adding to your portfolio or buying your first investment property in the city, the next 60 days are the move. Text me now at 773.732.1063.
Let’s Talk Investment Property
Whether you are trick or treating on Lincoln Avenue, decorating pumpkins in Lincoln Square or watching glowing floats on Columbus Drive, I hope this weekend reminds you why we raise our kids here. Then come find us on Southport Monday night. We will have the candy ready.
Enjoy Chicago, Juliana