Lakeview's Halloween in 2026 runs from Oct. 2 to Oct. 31, and almost nothing on that calendar is scheduled on top of anything else. Southport holds its trick-or-treat on the Monday before. The Wrigley Field plaza moves its family events earlier because the plaza closes Halloween week. Halsted marks the 30th year of its parade by taking over the whole day before it. When the holiday falls on a Saturday, each street gets a slot of its own.
The biggest change is on Halsted. The Haunted Halsted Halloween Parade has always been a nighttime event. This year it starts at 11 in the morning.
Halsted Takes the Whole Day for Its 30th
The Northalsted Business Alliance is adding a daytime event, the Haunted Halsted Fest, to mark 30 years of the parade. It runs 11 a.m. to 6 p.m. on Saturday, Oct. 31. For those hours, the five blocks of Halsted from Aldine to Brompton close to cars and become a pedestrian block party. The organizers list a kids zone with games, crafts and inflatables, daytime trick-or-treating at more than 25 Halsted businesses, over fifty vendor booths, live music and street performers. Beer, spirits and fall toddies are sold to guests 21 and older.
At 6 p.m. the street is cleared and everyone moves behind the sidewalk barricades. The parade steps off at Halsted and Belmont at 7 and ends at Halsted and Brompton around 8. Organizers call it Chicago's only Halloween-night parade. The usual groups are back: the Lakeside Pride Marching Band, the Windy City Rollers, the Chicago Spirit Brigade, the Windy City Jeep Club and the Chicago Thriller flash mob, with Chicago Full Moon Jam fire performers closing the route.
From 8 to 10 p.m., the costume contest and after-party fill the NoHa parking lot at 3514 N. Halsted. There are five categories, Character, Creative, Scary, Youth for ages 13 and under, and Group, with $4,000 in total prizes. Watching is free. Entering the contest costs $5. Registration opens online now, and day-of entries are accepted from 2 p.m. at the tent at 3211 N. Halsted. The event goes on in rain or snow.
The restaurants are planning around the full day. Lark, at 3441 N. Halsted, has a Hocus Pocus drag brunch from 11 a.m. to 3 p.m., with shows at 11:30 and 1:30 and a costume contest at each seating. Parade viewing starts at 6:30 p.m., and Lark says window seats must be booked directly with the restaurant. The Monster Mash Bash then runs from 9:30 p.m. to 3 a.m. with a $1,000 costume prize. A family could arrive at 11 a.m. and stay on the same few blocks until the parade ends at 8.
Two Daytime Trick-or-Treats, a Few Blocks Apart
Halsted's new daytime hours overlap another event. Lakeview East's Little Monster Crawl runs the same Saturday from 11 a.m. to 2 p.m., with children going from business to business along Broadway, Belmont and Clark. The Lakeview East Chamber of Commerce says some businesses will hand out treats indoors and others from tables outside. Pets are welcome too.
So for three hours, two business-district trick-or-treats run a few blocks apart. As of the chamber's Sept. 30 update, the list of participating businesses and the Google map of stops had not been posted. Until the list is out, it's hard to plan a route that covers both. Families with small children who are done by early afternoon can start with the crawl on Broadway and Clark, then walk over to Halsted, where the kids zone and the business stops run until 6.
Halsted has its own warm-up a week earlier. The Northalsted Halloween Pup Crawl is Saturday, Oct. 24, from 10 a.m. to 2 p.m. on Halsted between Aldine and Cornelia. Check-in is at Halsted and Aldine, and a 2 p.m. brunch and raffle follow at Lark.
Southport Holds the Monday
Southport doesn't compete with Halloween Saturday. Trick or Treat on Southport is Monday, Oct. 26, from 4 to 7 p.m., on Southport Avenue between Roscoe and Grace. Friends of Lakeview produces the free event, and it happens rain or shine. Lakeview SSA 27 is bringing a pumpkin patch back near Southport and Waveland, outside Coalfire Pizza. Lakeshore Sport & Fitness and Altitude Roscoe Village are supplying inflatables. For the adults walking along, there's craft beer from Corridor Brewery and wine chosen by Galleria Liquors. At 5 p.m., dancers from Gus Giordano Dance School perform "Thriller" near Southport and Cornelia, along with a GUS Company flash mob. The Lakeview Roscoe Village Chamber of Commerce says the full 2026 list of participating businesses is still to come.
The route has changed since last fall. Colectivo Coffee announced a July 8 grand opening for its café at 3258 N. Southport, and the company's café directory now lists the Southport location as open daily from 6:30 a.m. to 6:30 p.m. Ernesta has opened its first Midwest custom-rug showroom at 3530 N. Southport, in the former Claire's space. The women's boutique Bobbles & Lace is getting ready to open at 3501 N. Southport, at Cornelia, in the former UPS Store. That corner is on the same block as the "Thriller" performance. As of September, no opening date had been announced.
Southport's Halloween season actually starts almost a month earlier, at a bookstore. Three Avenues Bookshop, 3009 N. Southport, holds its first Spooky Book Fair on Friday, Oct. 2, from 6 to 10 p.m. It's adults only, open-house style and BYOB, with cider, sweets, a fog machine and giveaways. Costumes are encouraged, and the shop asks guests to RSVP.
Wrigley's Plaza Closes Halloween Week
Wrigleyville's calendar is set by Christmas. Gallagher Way's events calendar shows the plaza closed to the public from 7 a.m. to 10 p.m. every day from Monday, Oct. 26, through Halloween while the Christkindlmarket is built. That moves the plaza's free fall events earlier in the month:
- Thursday, Oct. 8: outdoor screening of Halloweentown. Gates open at 6 p.m. and the film starts at 7.
- Saturday, Oct. 10: Harvest Hangout, 11 a.m. to 5 p.m., with a petting zoo, s'mores, face painters, live music and college football.
- Wednesday, Oct. 21: Hocus Pocus, with gates at 6 p.m. and the film at 7.
- Thursday, Oct. 22: Lucky Dorr's Pups Halloween, 4 to 9:30 p.m. Costume registration closes at 7, when the dog parade begins.
- Saturday, Oct. 24: Pumpkin Party, 1 to 5 p.m., with pumpkin giveaways, crafts, face painting, performers and live music.
Gallagher Way also lists The Nightmare Before Christmas on Thursday, Oct. 29, from 6 to 10 p.m. The same calendar shows the plaza closed to the public that day from 7 a.m. to 10 p.m. for the market build. Check with Gallagher Way before planning around that screening.
Once the plaza closes, Wrigleyville's Halloween moves to the bars. The Wrigleyville Halloween Crawl starts at 5 p.m. on Oct. 31 and includes more than 20 venues, among them the Cubby Bear and Murphy's Bleachers, plus a free dinner buffet. Early-bird tickets start at $15.97. Nightmare on Clark Street returns to the Stolen Saddle rooftop at 3505 N. Clark from Oct. 10 through Nov. 1. It's a ticketed, 21-and-over Halloween bar with haunted rooms, and hours vary Thursday through Sunday. There's also a new place to eat before the crawl. Uncle John's BBQ opened in late August at 947 W. Addison, near the Addison Red Line stop. It's owned by Darryl and Andrea Townsend, who also own Dat Donut.
Lakeview's October, Date by Date
Put in order, the month falls into distinct slots. A few October events in West Lakeview along Lincoln Avenue are included too.
Date | Event | Where | Hours |
|---|---|---|---|
Fri, Oct. 2 | Spooky Book Fair, adults only | Three Avenues Bookshop, 3009 N. Southport | 6–10 p.m. |
Thu, Oct. 8 | Halloweentown outdoor movie | Gallagher Way | Gates 6 p.m. |
Sat, Oct. 10 | Harvest Hangout | Gallagher Way | 11 a.m.–5 p.m. |
Sat, Oct. 10 | Lincoln Brunch Fest | Lincoln Ave., Wellington to Diversey | From 10 a.m. |
Oct. 10–Nov. 1 | Nightmare on Clark Street, 21+ | Stolen Saddle rooftop, 3505 N. Clark | Thu–Sun, hours vary |
Sat, Oct. 17 | Lincoln Roscoe Beer Stroll | Lincoln Ave. and Roscoe St. | 3–6 p.m. |
Wed, Oct. 21 | Hocus Pocus outdoor movie | Gallagher Way | Gates 6 p.m. |
Thu, Oct. 22 | Pups Halloween | Gallagher Way | 4–9:30 p.m. |
Sat, Oct. 24 | Northalsted Halloween Pup Crawl | Halsted, Aldine to Cornelia | 10 a.m.–2 p.m. |
Sat, Oct. 24 | Pumpkin Party | Gallagher Way | 1–5 p.m. |
Mon, Oct. 26 | Trick or Treat on Southport | Southport, Roscoe to Grace | 4–7 p.m. |
Sat, Oct. 31 | Little Monster Crawl | Broadway, Belmont and Clark | 11 a.m.–2 p.m. |
Sat, Oct. 31 | Haunted Halsted Fest | Halsted, Aldine to Brompton | 11 a.m.–6 p.m. |
Sat, Oct. 31 | Wrigleyville Halloween Crawl | 20+ Wrigleyville venues | From 5 p.m. |
Sat, Oct. 31 | Haunted Halsted Parade | Halsted, Belmont to Brompton | 7–8 p.m. |
Sat, Oct. 31 | Costume Contest & After-Party | NoHa lot, 3514 N. Halsted | 8–10 p.m. |
Lincoln Brunch Fest's listing gives 10 a.m. to 3 p.m. at the top of the page, but its description says food service ends at 2. Plan to arrive before then.
The only crowded day is the last one. On Halloween Saturday, two daytime trick-or-treats, a ticketed bar crawl and Chicago's only Halloween-night parade all happen within about a mile of each other. Halsted starts clearing for the parade at 6 p.m.
If you're thinking about a move within Lakeview, it helps to know which blocks fill up on Oct. 31 and which stay quiet, and which corridors are adding new storefronts. That shapes daily life on a block as much as the floor plan does. Maria Thanasouras knows these streets block by block and is glad to walk you through them, at any time of year. Let's Connect.
