The Gallagher Way lawn will be fenced off by the time most Lakeview kids put on their costumes. From Monday, Oct. 26, the green space next to Wrigley Field closes to the public from 7 a.m. to 10 p.m. daily so crews can build the Christkindlmarket. That closure runs through Nov. 19, while the shops and restaurants around the plaza stay open. The market opens Nov. 20 and runs through Dec. 31.
That date shapes the rest of the month. Halloween falls on a Saturday in 2026, and the neighborhood's calendar is set up so its big events don't compete. Gallagher Way holds most of its programming in the first three weeks. Oct. 24 is the Saturday for dogs and small children. Southport holds its trick-or-treat on a Monday. Halsted gets Halloween itself, from morning to after midnight. If you live here, you can attend nearly all of it without two events landing in the same hour.
Gallagher Way Front-Loads the Month
Most of the ballpark plaza's fall programming takes place before Oct. 26. It's a mix of free outdoor movies and football Sundays, and almost none of it needs a ticket.
- Pumpkins & Pigskins, Sundays Oct. 4, 11 and 18, from 11:30 a.m. to 6 p.m. On Oct. 11, the Bears-Packers game is on the video board at noon, with lawn games and fire-pit s'mores. It's free and doesn't need an RSVP. The Oct. 18 detail page still mentions Oct. 11 in its text, but the official calendar lists Oct. 18.
- Toyota Movie Nights: Halloweentown on Thursday, Oct. 8, from 6 to 10 p.m. The Nightmare Before Christmas on Wednesday, Oct. 14, and Hocus Pocus on Wednesday, Oct. 21. All three are free, and the two Wednesday shows open gates at 6 p.m. and start the film at 7.
- Harvest Hangout, Saturday, Oct. 10, from 11 a.m. to 5 p.m.
- Lucky Dorr Presents Pups Halloween, Thursday, Oct. 22, from 4 to 9:30 p.m. Costume registration runs from 4 to 7, the parade starts at 7 and judging is at 9:30.
- Pumpkin Party, Saturday, Oct. 24, from 1 to 5 p.m., with family activities and pumpkin giveaways.
The Pumpkin Party is the last event on the lawn before the build-out starts. If you have a movie night or football Sunday in mind, it has to happen before the fencing goes up.
The Bars Run Their Own Calendar, Mostly on Weeknights
While Gallagher Way fills its lawn, the Lakeview East bars and venues take the weeknights. The Lakeview East Chamber's 2026 spooky-season guide lists:
- Horror-movie trivia at Lark on Wednesday, Oct. 7, and Twilight trivia on Oct. 14, both from 7 to 9 p.m.
- Pumpkin Bowling at Duffy's Tavern on Thursday, Oct. 15, with sign-ups at 7 p.m.
- Practical Magic Trivia at Budweiser Brickhouse Tavern on Wednesday, Oct. 21, at 7:30 p.m.
- A pumpkin-carving and dog-costume contest at Replay Lakeview on Thursday, Oct. 22, at 7 p.m.
The Nightmare on Clark Street pop-up at Stolen Saddle runs from Oct. 10 to Nov. 1, so it covers the whole stretch. Northalsted's Movies in the Parking Lot series also has a seasonal pick. Clue was rained out on Sept. 30 and now shows Wednesday, Oct. 7, at 8 p.m. at 3514 N. Halsted, with a preshow at 7:30.
October 24 Is the Saturday for Dogs and Little Kids
With Halloween itself taken up by Halsted's big event, the Saturday before has become the day for dogs and young families. Here's what's on that day:
| Time | Event | Where |
|---|---|---|
| 10 a.m.–2 p.m. | Northalsted Halloween Pup Crawl, $5 advance registration | Halsted sidewalks, Aldine to Cornelia |
| 11 a.m. | Pup Crawl patio brunch | Lark, 3441 N. Halsted |
| 11 a.m.–12:30 p.m. | Halloween donut decorating, $25 kit | Stan's Donuts & Coffee, 3300 N. Broadway |
| 1–5 p.m. | Pumpkin Party | Gallagher Way |
| 2 p.m. | Pup Crawl costume contest and raffle | Northalsted |
| 4–6 p.m. | Kids' Halloween dance party, registration required, ages 3+ | Dance on Broadway |
This is the 12th year of the Pup Crawl. Check-in is at Halsted and Aldine, and registration comes with a tote, a raffle entry and pup swag. The 44th Ward's Oct. 1 newsletter also lists a pumpkin giveaway on Oct. 24 but doesn't give a time or place yet.
The dog events continue Sunday, Oct. 25, with Howl-A-Ween at Stolen Saddle. It's a dog market run with 312 Markets from 11 a.m. to 2 p.m., with a costume contest at 1. Between Lucky Dorr on Thursday, the Pup Crawl on Saturday and Howl-A-Ween on Sunday, a dog in costume could attend three judged events in four days.
Southport Takes a Monday
Trick or Treat on Southport is on Monday, Oct. 26, from 4 to 7 p.m., rain or shine. That puts it five days before Halloween and away from everything on the 31st. Friends of Lakeview produces it, and it runs along Southport Avenue from Roscoe to Grace.
The organizers have published a detailed plan. Lakeview SSA 27 is bringing back a pumpkin patch near Southport and Waveland outside Coalfire Pizza. Lakeshore Sport & Fitness and Altitude Roscoe Village are providing inflatables. For adults, Corridor Brewery is pouring craft beer and Galleria Liquors is choosing the wines. At 5 p.m., dancers from Gus Giordano Dance School perform "Thriller" near Southport and Cornelia, along with a GUS Company flash mob. The list of participating businesses for 2026 hasn't been posted yet.
The Chicago Park District has one more weekday event close by. Sheil Park, at 3505 N. Southport, hosts a Halloween Pickleball Boo Bash on Tuesday, Oct. 27, from 9:30 a.m. to 2 p.m. It's for players 55 and older, at $10 per co-ed team of two. The family movie listed for Sheil on Oct. 29 has been canceled.
On the 31st, the Events Take Turns by the Hour
On Halloween, Lakeview's events run in shifts by time of day and by street. Haunted Halsted is marking its 30th year by adding a daytime festival before the parade. That's the reason Halsted takes up most of the day.
| Time | What's happening | Where |
|---|---|---|
| 11 a.m.–2 p.m. | Little Monsters Crawl, business-to-business trick-or-treating | Broadway, Belmont and Clark |
| 11 a.m.–6 p.m. | Haunted Halsted Fest | Halsted, Aldine to Brompton |
| 2–6:15 p.m. | Parade bib check-in and day-of costume registration | Registration tent, 3211 N. Halsted |
| 5 p.m.–1 a.m. | Wrigleyville Halloween Crawl | Wrigleyville bars, 3554 N. Clark listed |
| 7–8 p.m. | Haunted Halsted Halloween Parade | Halsted & Belmont to Halsted & Brompton |
| 8–10 p.m. | Costume contest and post-parade party | NoHa parking lot, 3514 N. Halsted |
| 9 p.m.–midnight | Grave Rave | The River |
| 10 p.m. doors | Hot B!tch Halloween Party | Smartbar |
The new daytime fest turns five blocks of Halsted into a pedestrian-only block party. It includes a kids' zone, daytime trick-or-treating at more than 25 Halsted businesses, over 50 vendor booths and live music. 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 for the parade. Fodor's has ranked the parade among the top 10 Halloween celebrations in the U.S. This year's lineup includes the Lakeside Pride Marching Band, Chicago Thriller, the Windy City Rollers, the Chicago Spirit Brigade and the Windy City Jeep Club. Full Moon Jam closes the parade with fire performers.
Entering the costume contest costs $5. Prizes total $4,000, with $500, $200 and $100 awarded in each of five categories: Character, Creative, Scary, Group, and Youth for ages 13 and under. Watching is free and open to all ages, and the parade goes on in rain or snow.
Families who want a smaller event than the Halsted fest can do the Little Monsters Crawl in Lakeview East the same morning. Some businesses hand out treats indoors and some set up tables outside, and dogs are welcome too. The Chamber says its list of participating businesses and a map are coming soon.
The Tow Zones Start Before the Fest
If you live near Halsted, the timing that matters most comes before the first costume shows up. Street parking is banned from 7 a.m. on Saturday, Oct. 31, until 2 a.m. on Sunday, Nov. 1, and cars left there will be towed. Car traffic is banned from 10:30 a.m. over the same stretch until 2 a.m. The affected blocks are:
- Halsted, 3200 to 3600 north, Belmont to Addison
- Melrose, 720 to 758 west
- Aldine, 800 to 830 west
- Buckingham, 720 to 820 west
- Roscoe, 732 to 820 west
- Newport, 800 to 840 west
- Cornelia, 732 to 820 west
- Brompton, 743 to 800 west
If your car is parked on one of those blocks overnight on Friday, Oct. 30, it needs to be moved before 7 a.m. Saturday. That's four hours before the fest opens. Pets can watch or march in the parade if they're leashed or carried. For more on how Halsted, Southport and Wrigleyville each work as their own part of the neighborhood, read our guide to Lakeview's micro-neighborhoods or visit our Lakeview neighborhood page.
Knowing which block closes when is the same street-by-street knowledge Stephanie Turner uses to value homes along Halsted, Southport and Clark. If you'd like to understand what your Lakeview home is worth, book a consultation and we'll go through it block by block.
This article is general information, not legal, tax or financial advice. Consult a qualified professional about your situation.
