Lake View's Halloween Runs All Week, and Each Shopping Street Gets Its Own Day
October 22, 2026
October 22, 2026
Which day is Halloween in Lake View this year? Southport holds its trick-or-treat on a Monday. Clark, Broadway, Belmont and Diversey share a midday candy route on the 31st. Halsted starts its festival that morning and holds its parade after dark. Before any of those, the dogs get a Saturday of their own.
Every one of these events comes from a different business group: Friends of Lakeview on Southport, the Lakeview East Chamber of Commerce on Broadway and Clark, and the Northalsted Business Alliance on Halsted. Each one picked its own day and hours. Laid out in order, they make a week-long calendar that starts this Saturday. Midway through it, the field next to Wrigley Field is fenced off for Christmas.
The first full day of the week is mostly for pets and small children. The Northalsted Halloween Pup Crawl runs from 10 a.m. to 2 p.m. on October 24 along Halsted, from Aldine to Cornelia. Advance registration is $5, and a brunch after-party follows on the Lark patio.
A few blocks northwest, Gallagher Way hosts its free Pumpkin Party from 1 to 5 p.m. the same day, with a magician, face painting, crafts, candy, music and pumpkin giveaways while supplies last. That afternoon is the last public event on the green space this month. More on that below.
Later on Saturday, Dance on Broadway holds a Kids Halloween Dance Party from 4 to 6 p.m. for ages 3 and up, and registration is required. On Sunday the 25th, Stolen Saddle hosts Howl-A-Ween, a dog market and costume contest, from 11 a.m. to 2 p.m., with judging at 1 p.m. Both are listed in the Lakeview East Chamber's spooky-season guide.
Trick or Treat on Southport is the one major corridor event set on a weekday: Monday, October 26, from 4 to 7 p.m. on Southport Avenue between Roscoe and Grace. Friends of Lakeview produces it, admission is free, and it goes ahead rain or shine.
The late-afternoon hours make it the after-school version of the holiday, and the street has fixed places for each activity:
That evening at 6 p.m., Konbini and Kanpai at 1433 W. Belmont Ave. holds a Halloween origami workshop, listed in Block Club Chicago's Halloween guide.
The same Monday, Gallagher Way's green space closes to the public every day from 7 a.m. to 10 p.m. through November 19 while Christkindlmarket is built. Gallagher Way says the surrounding stores and eateries stay open as usual. For the rest of the week, Halloween around the ballpark happens in the bars and storefronts along Clark.
Halloween falls on a Saturday this year, and two business groups divide the day.
From 11 a.m. to 2 p.m., the Lakeview East Chamber runs the Little Monsters Crawl. It works like house-to-house trick-or-treating, except the stops are businesses. The chamber's list has more than 100 participants across Clark, Broadway, Belmont, Sheffield, Diversey and Halsted, and many offer something for parents along with the candy. A sample by street:
The chamber's page says more businesses may be added, so check the list again Friday night.
Halsted starts at the same hour. The Northalsted Business Alliance marks the 30th anniversary of the Haunted Halsted Halloween Parade this year with an all-day festival, its first, on Halsted between Aldine and Addison. The alliance calls the parade Chicago's only Halloween-night parade, with more than 300 costumed participants. Some Little Monsters stops, including Lark at 3441 N. Halsted and Kit Kat Club at 3524 N. Halsted, sit inside the festival's footprint. That means the daytime candy route and the night festival share a few blocks.
Here is the full Saturday:
| Time | Event | Where |
|---|---|---|
| 11 a.m.–2 p.m. | Little Monsters Crawl | Clark, Broadway, Belmont, Sheffield, Diversey, Halsted |
| 11 a.m. | Haunted Halsted Fest begins | 3300–3526 N. Halsted |
| 2–6:15 p.m. | Costume contest check-in | Registration tent, east side of Halsted at Belmont |
| 5 p.m.–1 a.m. | Wrigleyville Halloween Crawl | More than 20 Wrigleyville venues |
| 7 p.m. | Parade steps off | Halsted and Belmont, north to Brompton |
| 8 p.m. | Costume contest and post-parade party | Lot at 3514 N. Halsted |
| 10 p.m. | Haunted Halsted ends | Halsted |
Watching the parade is free for all ages. Entering the costume contest costs $5, and entrants compete for $4,000 in total cash prizes. The parade goes on in rain or snow. Performers include the Chicago Full Moon Jam fire performers, the Lakeside Pride Marching Band, the Windy City Rollers and Chicago Thriller. Block Club Chicago's guide lists a free dinner buffet as part of the Wrigleyville crawl.
After the parade, the Lakeview East Chamber's guide lists three late events: Grave Rave at The River from 9 p.m. to midnight, Dolloween at Level Sporting Club from 7 p.m. to 1 a.m. with a 9 p.m. costume contest, and a 21-and-over party at Smartbar with doors at 10 p.m.
Halfway along the Broadway section of the Little Monsters route, Cesar's Killer Margaritas at 2924 N. Broadway and Royale of London at 2910 N. Broadway are both handing out candy. Across the street, 2923 N. Broadway is dark for the first Halloween in decades. Block Club Chicago reported that Royal Home Entertainment closed on October 17 after 55 years. The electronics shop was opened in 1971 by brothers Joe and John DeGuide and moved into the Broadway storefront in 1980. The Lakeview East Chamber also marked the closing with a tribute to the shop.
A route of more than 100 businesses depends on the storefronts being open. When one of the longest-running shops on the route closes, the change shows up on the map.
On Clark, the season runs one day past Halloween. Nightmare on Clark Street, a ticketed haunted house and bar pop-up at Stolen Saddle, 3505 N. Clark St., is open Thursdays through Sundays until November 1. It is 21 and over, and the ticket includes a drink.
The Lakeview East Chamber's next event starts that same Sunday. Discover Diversey runs November 1 through 15, with participating Diversey businesses offering specials, featured menu items and limited-time promotions. Nando's PERi-PERi Chicken at 670 W. Diversey Pkwy. is among the first listed. The chamber's Giver's Gift promotion also starts November 1 and runs through December 21. Shoppers submit receipts from local purchases toward a Lakeview East gift card.
Then Gallagher Way reopens with a new purpose. Christkindlmarket Wrigleyville opens Friday, November 20, at 3635 N. Clark St., with 28 local and international vendors and free admission. It stays open through New Year's Eve, a week longer than the Daley Plaza and Aurora markets, which both close on Christmas Eve. Hours are 3 to 9 p.m. Monday through Thursday, 11 a.m. to 9 p.m. Friday and Saturday, and 11 a.m. to 7 p.m. Sunday. On Thanksgiving Day it is open 11 a.m. to 4 p.m.
Each of these streets also has its own place in the city's real estate market, and the day-to-day details matter as much as the listing details. If you're thinking about a move within Lake View or nearby, or just want to talk through how one block compares with the next, Nancy Tassone is glad to share what she knows. Let's Connect.
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