Looking for the best things to do in Chicago this weekend? Halloween lands on a Saturday this year, and the city is ready. North Center starts the morning with trick or treating around the Town Square. Then Haunted Halsted throws an all day street fest before its famous parade at 7pm. On Sunday, the National Museum of Mexican Art honors Día de Muertos with a free exhibition in Pilsen. Also, set your clocks back Saturday night. Plus, CPS kids are off Monday and Tuesday, and Tuesday is Election Day. Here is everything worth your time for October 30 to November 1, 2026.
Costumes on. Let’s go.
Northcenter Halloween Trick or Treat
Saturday, October 31 | 10am to 1pm | Free | Northcenter Town Square, 4100 N. Damen Ave.
The Northcenter Chamber of Commerce runs one of the sweetest Halloween mornings in the city. More than 500 kids trick or treat around the Town Square and at shops along Lincoln, Irving Park and Damen. First, family photos with Sharon Gaietto Photography run from 10am to 11:30am for a $5 suggested donation. Then hay rides leave from Baird and Warner, 4037 N. Damen Ave., from 11am to 1pm. Costume contests start at noon, with prizes for pets, kids by age group and Best Costumed Family.
Plus, it is the last Northcenter Farmers Market of the season, open 8am to 1pm. Bring non-perishables or toiletries for the orange Chamber tent, since donations go to Common Pantry. Details at northcenterchamber.com.
Local tip: Get there at 10am for photos before the line builds. Afterward, walk up to The Bad Apple, 4300 N. Lincoln Ave., for burgers and a kid friendly lunch. Or keep it cozy at Mrs. Murphy and Sons Irish Bistro, 3905 N. Lincoln Ave. Street parking fills fast around the square. So take the Brown Line to Irving Park and walk a few blocks west to Damen.
🏡 Realtor mom take: North Center is the neighborhood families ask me about most. You get Bell and Coonley elementary schools, a real town square and Lincoln Avenue restaurants within walking distance. As a result, a well priced single family home here rarely sits. Our team works North Center every week, and we see that demand firsthand. If this is your dream neighborhood, start here and I will show you what is 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.
Haunted Halsted Halloween Fest and Parade
Saturday, October 31 | Fest noon to 10pm, Parade 7pm | Free | N. Halsted St., Aldine to Brompton
Haunted Halsted is one of the biggest Halloween parades in the country, and it is right here in Lakeview. The Northalsted Business Alliance turns Halsted into a free street fest all day. Kids get their own zone with games, Halloween crafts and blow ups. Also, more than 25 Halsted businesses hand out candy during fest hours.
Then at 7pm, the parade steps off at Halsted and Belmont and marches north to Brompton. Expect hundreds of costumed marchers and the Lakeside Pride Marching Band. Note that the street clears at 6pm, so plan to move to the sidewalk. Afterward, the costume contest starts at 8pm at 3514 N. Halsted St. Entry is $5, and there is a Youth category for kids 13 and under. Details at northalsted.com.
Local tip: Go early with little ones. The kids zone is calmest in the afternoon, and the crowd grows fast after dark. Before you walk over, grab a cinnamon roll at Ann Sather, 909 W. Belmont Ave. Take the Red, Brown or Purple Line to Belmont, a short walk from the parade start. Then claim a curb spot by 6pm and bring a blanket. It gets cold on Halsted at night.
🏡 Realtor mom take: Lakeview is home for us, and Halloween week proves why. This week, The Yeager Team was proud to sponsor Trick or Treat on Southport. By Saturday, the party moves east to Halsted. East Lakeview gives you vintage courtyard buildings, the lakefront and the Red Line. Meanwhile, West Lakeview gives you brick single family homes off Southport. Two different price points, one great neighborhood. Curious which side fits your family? Let’s talk. 👻🍬🎭
Día de Muertos at the National Museum of Mexican Art
Sunday, November 1 | 10am to 5pm | Free | 1852 W. 19th St., Pilsen
The National Museum of Mexican Art is marking 40 years of its Día de Muertos exhibition, and admission is always free. This year’s show is called Where Memory Lives: 40 Years of Día de Muertos. Expect ofrendas and artwork honoring loved ones who have passed. It is a beautiful, gentle way to talk with kids about remembering the people we love. Plus, it runs through November 29, so you can go back. Details at choosechicago.com.
Then walk over to 18th Street for the Pilsen Día de los Muertos Window Walk, open noon to 11:30pm. Students from Pilarte at Benito Juarez Community Academy teamed up with 16 local businesses on storefront art. As you go, vote for your three favorite windows. More at choosechicago.com.
Local tip: Take the Pink Line to 18th Street. The station is covered in murals, so the art starts on the platform. The museum sits inside Harrison Park, which means the kids can run before or after. For a treat, grab pan de muerto at Nuevo Leon Bakery, 1634 W. 18th St., or a hot chocolate at Café Jumping Bean, 1439 W. 18th St. Remember, the museum is closed Mondays, so Sunday is your window this weekend.
🏡 Realtor mom take: Pilsen has some of the richest culture and best food in the city, all on the Pink Line. And this Sunday, I have a reason for you to stay a little longer. Our listing at 1810 S. Racine Unit 3 is just a few blocks from the 18th Street Window Walk. We are hosting an open house from 11am to 1pm, right in the middle of your Día de Muertos day. Stop by, warm up and come see the private rooftop deck with skyline views. Want to see what else is out there in Pilsen? Let’s look together. 💀🌼🕯️
🗝️ Open House Sunday: 1810 S. Racine, Unit 3
Sunday, November 1 | 11am to 1pm | $549,900 | 2 Bed, 2 Bath, 1,400 Sq Ft
This 2018 Pilsen condo has 11 foot ceilings, white oak floors and a chef’s kitchen with a quartz waterfall island and Viking appliances. The primary suite opens to a private balcony. Then head upstairs to the expansive private rooftop deck, freshly stained this year, with Chicago skyline views. Garage parking is included. Plus, you are steps from Thalia Hall, 18th Street restaurants and the Pink Line. See it HERE
Quick Hit List: More Things to Do in Chicago This Weekend
Here is everything else worth knowing about this weekend and the long CPS break.
- 👻 Fright on Farragut | Saturday, October 31 | 11am to 4pm | Clark and Farragut, Andersonville. The 48th Ward Halloween Parade leaves Bromann Park at 10:30am, and GUS dancers perform Thriller at 2pm.
- 🎡 Halloween at Navy Pier | Saturday, October 31 | 1pm to 10pm | Free. Indoor trick or treating, a family costume contest, games and crafts.
- 🌼 Xempasúchil Día de los Muertos | Saturday and Sunday, October 31 and November 1 | 11am to 6pm | 26th Street, Little Village. Ofrendas at local businesses, free traditional food and photo booths.
- 🦖 Fright at the Field | Through Sunday, November 1 | The Field Museum, 1400 S. Lake Shore Dr. Halloween at the museum, with the return of Underground MISAdventure.
- 🚤 Creepy Cruise | Final weekend, through November 1 | Chicago’s First Lady Cruises, 112 E. Wacker Dr. A nighttime river tour of the city’s shadowy past.
- 🎭 Stage Frights! | Through Sunday, November 1 | Raven Theatre, Edgewater.
- 🧪 Jekyll and Hyde | Through November 8 | Broadway Playhouse at Water Tower Place, 175 E. Chestnut St. Book the sitter for this one.
- 🎻 Chicago Symphony Orchestra: Brahms Requiem | Friday, October 30 | 1:30pm | Symphony Center, 220 S. Michigan Ave.
- 🎬 The Rocky Horror Picture Show Spooktacular | Saturday, October 31 | 7:30pm | The Chicago Theatre, 175 N. State St. Hosted by members of the original cast. Grown ups only.
- ⏰ Clocks fall back | Sunday, November 1 at 2am. Enjoy the extra hour of sleep after a big Halloween night.
- 🏫 No school for CPS | Monday, November 2 is Parent Teacher Conference Day, and Tuesday, November 3 is Election Day. Plan for a four day weekend.
- 🗳️ Election Day | Tuesday, November 3 | Find your polling place at chicagoelections.gov. Bring the kids along so they see how it works.
Real Estate Corner: The 20 Year Rate Cycle and Why I Would Lock In Now
Here is what everyone is thinking right now. “Rates are over 7%, the election is Tuesday, so let’s just wait.” I hear it every single week. But today the 10-year Treasury climbed back above 5%, to 5.02%. That puts mortgage rates around 7.34%. It is nice to see them under 7.5%. And based on what experts are predicting, this may be the lowest number we see for a bit.
So let me share a little history. I have lived these rate cycles myself, and the pattern is hard to ignore.
My 20 Year Mortgage Rate Story
- 2005: We bought our second condo with a rate around 7%. I had only been in real estate for one year, so I did not have enough tax returns from my new career to qualify for a traditional loan. The only option was an interest only loan. Loans like that were everywhere back then.
- 2008: The market crashed. It took something catastrophic to bring rates way down again.
- 2009 to 2013: Rates slid from about 5% in 2009 to an average of 3.66% in 2012. Meanwhile, the first time homebuyer tax credit, worth up to $8,000, pulled new buyers back into the market.
- 2014: When it was time to move again, rates averaged around 4.2%. We felt great about that number and it was time to upgrade our space to a larger home.
- 2021: Twenty years after 9/11, rates plunged into the high 2s. The 30-year hit a record low of 2.65% that January.
- 2026: Here we are, back above 7%.
See the pattern? Each big drop followed a big event. I truly believe things happen in 20 year cycles. The 2008 crash turns 20 in 2028. So I think we will see a shift by then. Nobody knows what it will be. Maybe it is AI. Maybe it is something none of us see coming. Either way, I would rather own before that shift than chase the market after it.
Of course, rates are always a guessing game. That is exactly why my advice is simple. Lock in now. Then see what the new year brings, and refinance when rates come down. You can always change your rate. You cannot go back and buy the home you missed.
For buyers: Right now you have the inventory and the space to make a good decision. Fewer buyers are competing with you, and election week keeps even more on the sidelines. So stretch for the home you truly want, with a payment you are comfortable with today. Then refinance when rates fall and enjoy the savings. Keep looking. The right one will show up, and I want you ready when it does.
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. We have some great new listings coming soon! Reach out to see if one of them is in the neighborhood you are looking for. West Lakeview, Roscoe Village, Hamlin Park, Southport Corridor are all coming soon.
For sellers: Every dip in rates pulls more buyers off the fence. And the buyers touring homes Halloween week are not browsing. They are pre-approved and ready to write. Plus, you have less competition from other listings now than you will in the spring. In April, you will be one of many. Today, you stand out. We have an off market home in West Lakeview and we know how to get real qualified buyers through the door without a simple push of a button. We have 4 showings tomorrow and it is not even on the market. 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, so there is more room to make the numbers work. North Side condos, Pilsen two flats and everything in between deserve a look. And if 2028 brings the next big shift, the properties you buy now are the ones you will be glad you own. Text me now at 773.732.1063.
Let’s Talk Investment Property
Whether you are on a hay ride in North Center or catching the parade on Halsted, slow down Sunday with the ofrendas in Pilsen and stop by our open house at 1810 S. Racine from 11am to 1pm. I hope this weekend reminds you why we raise our kids here. Happy Halloween, Chicago. Enjoy that extra hour of sleep, soak up the four day weekend and do not forget to vote on Tuesday.
Enjoy Chicago, Juliana