10 Best Things to Do in Chicago and DuPage This Weekend: October 30-November 1, 2026
CHICAGO— Halloween lands on a Saturday this year, and Chicagoland is making the most of it.
Chicago has a massive Halloween parade in Northalsted, an after-hours night with SUE at the Field Museum, Rocky Horror at the Chicago Theatre, pumpkin-filled fall attractions, and spooky cruises along the river.
In DuPage County, you can take your costumed dog to Morton Arboretum, trick-or-treat through Downtown Wheaton, shop a Halloween flea market until midnight, or hear spooky music played on Naperville’s 72-bell carillon.
Here are 10 things worth checking out from Friday, October 30 through Sunday, November 1, 2026.
1. Haunted Halsted Halloween Fest & Parade
When: Saturday, Oct. 31, festival begins at noon; parade at 7 p.m.
Where: North Halsted Street, Northalsted
Admission: Free
Chicago’s Halloween night parade celebrates its 30th anniversary with an expanded all-day street festival this year.
The daytime event runs along Halsted between Aldine and Addison with 50+ vendors, live entertainment, family activities, trick-or-treating at more than 25 businesses, and a kids zone. At 7 p.m., more than 300 costumed participants take over the street for the parade, followed by a costume contest and post-parade party with $4,000 in prizes.
For people who want one big Halloween event Saturday, this is probably the easiest choice.
2. Boo with SUE at the Field Museum
When: Friday, Oct. 30, 6-9 p.m.
Where: Field Museum, 1400 S. DuSable Lake Shore Drive
Admission: $40 non-members; $36 members
The Field Museum stays open after hours Friday for Family Field Nights: Boo with SUE.
The all-ages event combines Halloween with science, giving families an evening inside the museum rather than another outdoor trick-or-treating event. An optional Nocturnal Garden Walk is also available for $55 for non-members and $50 for members.
If the weather turns cold or rainy, keep this one on the shortlist.
3. The Rocky Horror Picture Show Spooktacular Tour
When: Saturday, Oct. 31 at 7:30 p.m.
Where: The Chicago Theatre, 175 N. State St.
Admission: Ticketed
Halloween night at the Chicago Theatre gets appropriately weird.
The Rocky Horror Picture Show Spooktacular Tour features a screening of the cult classic in a new 4K restoration, along with a live shadow cast, audience participation, original cast appearances, and a costume contest. Doors open at 6:30 p.m.
For adults who would rather spend Halloween inside a historic theater than at a nightclub, this is one of the weekend’s more distinctive options.
4. Jack’s Pumpkin Pop-Up: Final Weekend
When: Friday-Sunday, Oct. 30-Nov. 1
Where: 1265 W. Le Moyne St., Chicago
Admission: Ticketed; prices vary by entry time and package
This is the final weekend of the 2026 season at Jack’s Pumpkin Pop-Up.
The outdoor fall attraction packs in more than 10,000 pumpkins, a corn maze, carnival games, photo installations, food trucks, seasonal drinks, gem mining, and axe throwing for guests 18 and older. It is open to all ages.
Friday sessions run into the evening, while Saturday and Sunday offer daytime and nighttime entry windows.
5. Creepy Cruise on the Chicago River
When: Friday through Sunday, select sailings Oct. 30-Nov. 1
Where: Chicago’s First Lady Cruises, 112 E. Wacker Drive
Admission: Tickets start at $46
If you have already done Chicago’s architecture tours, try the haunted version.
The 90-minute Creepy Cruise explores stories involving mysterious sightings, mobsters, historic tragedies, and other darker pieces of Chicago history while sailing the river at night. Boats include both open-air and enclosed seating and operate rain or shine.
This is an easy date-night choice if you want Halloween atmosphere without committing to a costume party.
6. Balourdet Quartet at Wentz Concert Hall
When: Friday, Oct. 30 at 7:30 p.m.
Where: Wentz Concert Hall, 171 E. Chicago Ave., Naperville
Admission: $15
Not everything this weekend has to involve pumpkins.
North Central College welcomes the Balourdet Quartet, recipients of the 2024 Avery Fisher Career Grant, for a chamber music performance with pianist Susan Chou.
The program includes Beethoven’s String Quartet Op. 18, No. 3 and Dvořák’s Piano Quintet Op. 81.
The Downtown Naperville location also makes this easy to pair with dinner before the concert.
7. Howl-o-Ween at The Morton Arboretum
When: Saturday, Oct. 31, 9 a.m.-noon
Where: The Morton Arboretum, 4100 Illinois Route 53, Lisle
Admission: Arboretum admission plus $7 per guest dog; $6 per member dog
Halloween morning belongs to the dogs in Lisle.
Howl-o-Ween includes costumed dog parades, a canine costume contest, trick-or-treating, complimentary pup cups, pet-friendly vendors, and fall photo opportunities among the Arboretum’s trees.
The first dog parade starts at 10 a.m., followed by the costume contest around 10:30 and a second parade at 11:15.
Dogs can stay on the Arboretum grounds with their owners until sunset.
8. Downtown Wheaton Trick-or-Treating
When: Saturday, Oct. 31, 10 a.m.-noon
Where: Downtown Wheaton
Admission: Free
For families with younger children, Downtown Wheaton offers an easy Halloween morning before neighborhood trick-or-treating begins later in the day.
Participating Downtown businesses will hand out candy to costumed children from 10 a.m. to noon. Wheaton’s regular residential trick-or-treating hours then run from 3:30 to 7:30 p.m.
The Wheaton French Market is also open nearby from 8 a.m. to 2 p.m., so parents can combine both into one trip Downtown.
9. Wheaton Haunted Halloween Flea Market
When: Saturday, Oct. 31, 3 p.m.-midnight
Where: DuPage County Fairgrounds, 2015 Manchester Road, Wheaton
Admission: $10; children 12 and under free with an adult
This one gets stranger as the evening goes on.
The 13th annual Wheaton Haunted Halloween Flea Market keeps the DuPage County Fairgrounds open until midnight with vendors selling antiques, collectibles, unusual finds, and plenty of Halloween-themed merchandise.
Guests are encouraged to shop in costume, parking is free, and tickets are sold at the event.
It is a good option for anyone who prefers treasure hunting to another traditional Halloween party.
10. SCARE-illon at the Millennium Carillon
When: Saturday, Oct. 31 at 7 p.m.
Where: Millennium Carillon at Rotary Hill, 443 Aurora Ave., Naperville
Admission: Free
Halloween music sounds very different when it is being played on 72 bells.
Naperville City Carillonneur Tim Sleep will perform a 50-minute Halloween-themed concert from the Millennium Carillon while visitors listen from Rotary Hill and along the Naperville Riverwalk.
Bring a chair or blanket, finish trick-or-treating a little early, and use this as a relaxed way to close out Halloween night.
Halloween Weekend Is Packed Across Chicagoland
The biggest challenge this weekend may be choosing what not to do.
For a major Chicago celebration, Haunted Halsted is the obvious Saturday-night centerpiece. Families have strong options at the Field Museum, Morton Arboretum, and Downtown Wheaton, while couples can choose between a river cruise, Rocky Horror, or chamber music in Naperville.
And if you want something completely different, there is always the option of shopping a flea market at 11:30 p.m. on Halloween.
Event schedules, ticket availability, and weather plans can change, so check the organizer’s latest information before heading out.
Exploring Chicago or the Western Suburbs This Weekend?
Events are one of the easiest ways to experience how a neighborhood feels beyond its real estate listings.
The Cory Tanzer Group at Option Premier helps buyers and relocation clients compare communities across Chicago, the North Shore, and the Western Suburbs, including housing, walkability, transit, restaurants, parks, and the everyday lifestyle surrounding each property.
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