Where should you be in Lake View at 3 p.m. on Halloween? At that hour Broadway's kids' crawl has just finished. Halsted is four hours into a block party, with three hours left before the street gets cleared for the parade. Gallagher Way is closed to the public because crews are building the Christkindlmarket. Southport had its trick-or-treat five days earlier, on a Monday afternoon.
Lake View's Halloween runs as at least four separate events, on four streets, at four different times of day. The park beside Wrigley Field opens the season and is also the first place to leave it. If you know which block runs which hour, you'll plan a much better Saturday than if you just know the dates.
Gallagher Way has the early weeks, then turns to Christmas
After the Cubs' season ended, the space next to Wrigley moved straight into a fall program. Southport Corridor News reported on October 5 that the Cubs' 2026 playoff run ended with a Wild Card sweep by the Padres. Gallagher Way's calendar puts on an outdoor screening of The Nightmare Before Christmas on October 14. A free Pumpkins & Pigskins afternoon follows on Sunday, October 18, from 11:30 a.m. to 6 p.m., with football on the video board, lawn games, and s'mores at the fire pits. After that comes Hocus Pocus on October 21, Lucky Dorr's Pups Halloween on October 22 from 4 to 9:30 p.m., and the free Pumpkin Party on Saturday, October 24, from 1 to 5 p.m.
The Pumpkin Party is the park's last event of October. The calendar shows Gallagher Way closed to the public every day from Monday, October 26, through Saturday, October 31, for Christkindlmarket build-out. So on Halloween night, the plaza most closely tied to Wrigleyville will be under construction.
It comes back as a different place. Christkindlmarket Wrigleyville runs at Gallagher Way, 3635 N. Clark St., from November 20 through December 31. 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, with holiday exceptions posted by the market. Gallagher Way also lists Winterland starting November 20, though its event page says more details are still coming.
Southport takes the Monday the park goes dark
On the same Monday Gallagher Way closes, Southport Avenue runs the only weekday event on the neighborhood's Halloween calendar. Trick or Treat on Southport is Monday, October 26, from 4 to 7 p.m., on Southport between Roscoe and Grace. Southport Corridor News lists it as free and rain-or-shine, with crafts, games, a DJ, inflatables, drinks, a pumpkin patch, and candy.
Holding it on a weekday after school means Southport's event never competes with the Saturday crowds on Halsted and Broadway. A family can do Southport on Monday and still go to everything on the 31st. The stretch is busier this fall than last. Colectivo Coffee opened its café at 3258 N. Southport Ave. on July 8. Ernesta, the custom rug brand, now has its first Chicago showroom open at 3530 N. Southport.
The weekend before belongs to dogs
The weekend of October 24 and 25 has its own focus, and it isn't on children. Counting from Thursday, three dog events fall within four days, each on a different corridor.
- Thursday, October 22, Clark and Addison. Pups Halloween at Lucky Dorr, listed on the Gallagher Way calendar for 4 to 9:30 p.m.
- Saturday, October 24, Halsted. The Northalsted Halloween Pup Crawl runs 10 a.m. to 2 p.m., with check-in at Halsted and Aldine and the route running from Aldine to Cornelia. Advance registration is $5 and includes a tote, a raffle entry, and pup swag. Miss Foozie's photo booth for registered pets runs 10 a.m. to 1 p.m., Lark starts a pup patio brunch at 11 a.m., and the raffle drawings begin at 2 p.m.
- Sunday, October 25, Clark. Howl-A-Ween, a dog market and costume contest at Stolen Saddle with 312 Markets, runs 11 a.m. to 2 p.m., with the dog contest at 1 p.m.
Saturday the 24th is the busiest day of the run-up. The Pup Crawl ends at 2 p.m., an hour after the Gallagher Way Pumpkin Party begins. The Lakeview East Chamber of Commerce also lists a Kids Halloween Dance Party at Dance on Broadway from 4 to 6 p.m. that day. Because the hours barely overlap, you can work through Halsted, Clark, and Broadway in a single day.
Saturday, October 31, hour by hour
On Halloween itself, the events are separated by time of day more than by location. The Northalsted Business Alliance has made the 30th Haunted Halsted an all-day event this year. The Lakeview East Chamber has its kids' crawl in the morning, and Wrigleyville has the night.
| Time | Where | What |
|---|---|---|
| 7:00 a.m. | Halsted, Belmont to Addison | Street parking restrictions begin, through 2 a.m. Sunday |
| 10:30 a.m. | Halsted, Belmont to Addison | Vehicle traffic prohibited, through 2 a.m. Sunday |
| 11 a.m. to 2 p.m. | Broadway, Belmont, Clark | Little Monster Crawl |
| 11 a.m. to 6 p.m. | Halsted, Aldine to Brompton | Haunted Halsted Fest |
| 2:00 p.m. | 3211 N. Halsted | Day-of parade registration opens |
| 5 p.m. to 1 a.m. | Wrigleyville | Wrigleyville Halloween Crawl |
| 6:00 p.m. | Halsted | Street cleared, fest crowd moves behind barricades |
| 7 to 8 p.m. | Halsted, Belmont to Brompton | Haunted Halsted Halloween Parade |
| 7 p.m. to 1 a.m. | Level Sporting Club | Dolloween, costume contest at 9 p.m. |
| 8 to 10 p.m. | 3514 N. Halsted | Costume contest and post-parade party |
| 9 p.m. to midnight | The River | Grave Rave |
| 10:00 p.m. | Smartbar | Doors open for the Hot B!tch Halloween Party |
The morning is mostly for families. Children on the Little Monster Crawl visit participating businesses on Broadway, Belmont, and Clark, some indoors and some outside. As of the Chamber's September 30 post, the participating businesses and map were still marked "Coming Soon." Two blocks west, the Halsted fest sets up a kids zone with games, Halloween crafts, and inflatables. It also offers daytime trick-or-treating at more than 25 Halsted businesses, over fifty vendor booths, live local music, and beer, spirits, and fall-flavored toddies for guests 21 and up with valid ID.
At 6 p.m. Halsted is cleared, and fest-goers move behind the sidewalk barricades for the parade. Northalsted describes the parade as "Chicago's only Halloween Night parade." It features more than 300 costumed participants, the Windy City Jeep Club, the Lakeside Pride Marching Band, Chicago Thriller, the Windy City Rollers, and the Chicago Spirit Brigade, and it closes with fire performers from Chicago Full Moon Jam. The costume contest has five categories: Character, Creative, Scary, Youth for ages 13 and under, and Group. Each pays $500, $200, and $100 for first, second, and third place. Entry is $5, and the parade goes on in rain or snow.
The table shows a practical problem for anyone near Halsted. Traffic is shut down from 10:30 a.m., hours before most of the crowd arrives, and parking restrictions on Halsted between Belmont and Addison start at 7 a.m. Both stay in place until 2 a.m. Sunday. Older CTA and ward detour notices still turn up in search results, but they come from earlier years. Northalsted's 2026 page is the most current source for street effects.
What runs past October 31
A few events are built to outlast the holiday. Stolen Saddle's Nightmare on Clark Street, with themed rooms and a drink included in each ticket, runs from October 10 through November 1, so it's still open the day after Halloween. Earlier in the month, Pints & Pumpkins at Pilot Project Wrigleyville on October 18 runs 11 a.m. to 3 p.m. A $10 ticket covers a pumpkin, carving tools, and cider.
The Halloween routes also run past newer restaurants worth knowing. On Broadway, WTTW listed Tilly Bagel Shop at 3162 N. Broadway with a June 27 opening. Noodleverse had opened down the block at 3139 N. Broadway by early October. On Clark, Eater Chicago reported that Apothecary, a pharmacy-themed cocktail lounge, opened May 29 at 3242 N. Clark St. Further south on Broadway, Block Club Chicago reported that Ann Sather plans to move from 3415 N. Broadway into the former Stella's Diner space at 3042 N. Broadway after renovations. No opening date has been set.
The holiday calendar follows the same staggered pattern. Christkindlmarket opens at Gallagher Way on November 20. Then Southport takes another evening of its own with the Southport Holiday Cocktail Crawl on Friday, December 4, from 5:30 to 8:30 p.m., featuring cocktail samples at local businesses, carolers, and photos with Santa.
If Haunted Halsted's parking and traffic window covers your block, it's useful to know how events like this affect a showing schedule, a move-in date, or a listing photo shoot in Lake View. Carol Collins can help you plan around the neighborhood's calendar. Book an appointment to talk through your timing.
