Two Nights When Chicago Dresses Up: Arts in the Dark and the Haunted Halsted Parade
On the evening of Saturday, October 24, 2026, Columbus Drive fills with lantern light. Arts in the Dark is a nighttime parade built by local artists and cultural institutions — large-scale puppets, costumed performers, floats and hand-made lanterns moving through a crowd of roughly 100,000 spectators, in a new and larger downtown location on Columbus Drive. It is the city's most theatrical procession, and it is free to watch from the curb.
A week later, on Saturday, October 31, the energy shifts north to Northalsted, the historic LGBTQ+ enclave in Lakeview, for the Haunted Halsted Halloween Parade and Block Party. The block party runs through the day; the parade steps off at nightfall. Expect fire breathers, marching bands, roller skaters, live performances, and costumed people and pets. It costs nothing to attend. If you are travelling with children and want daylight instead of darkness, Washington Park hosts the Upside Down Halloween Parade the same day — a free, all-ages march lined with performances, characters and sports mascots, with free goodie bags for kids.
Ride, Walk or Crawl Through the City's Ghost Stories
Chicago tells its hauntings in several formats, so pick the one that matches your appetite.
- By boat: Haunted River Tours with Seadog Cruises depart from the downtown waterfront.
- On foot at dusk: Chicago Ghost Tours with Tours by Foot cover downtown after dark.
- With a drink in hand: the Chicago Booze and Boos Tour with Nightly Spirits is a pub crawl built around Prohibition-era and gangster tales.
- By bus: American Ghost Walks runs The Devil In The White City Bus Tour, themed on the serial killer and the World's Fair.
- Inside historic houses: the Jane Addams Hull-House Museum runs October ghost tours referencing legends such as the Devil Baby and the lady in white; Glessner House in the South Loop offers ghost tours of the Prairie Avenue Historic District and annual Edgar Allan Poe readings on Halloween night.
Pumpkins, Mazes and a Zoo After Dark
Jack's Pumpkin Pop Up, running September 19 to November 1, 2026, bills itself as the largest outdoor Halloween experience in Chicago: a corn maze (the city's largest), a pumpkin patch, food trucks, carnival games, axe throwing, a mechanical bull, pig racing, fortune telling and photo ops, open to all ages.
Fall Fest at Lincoln Park Zoo runs September 25 to November 1, 2026, with pumpkin patch photos, live pumpkin carving and performers. Two dates to plan around: Spooky Zoo on October 27, when the zoo hosts trick-or-treating, and Zoo Brews on October 23–24, an adults-only craft beer and cider tasting where costumes are encouraged.
At the Chicago Botanic Garden, Night of 1,000 Jack-o'-Lanterns runs October 7–25, 2026 — hundreds of hand-carved, glowing pumpkins, some weighing over 150 pounds, with fall snacks and drinks on offer.
Día de Muertos in Pilsen and a Month of Screens and Stages
The National Museum of Mexican Art in Pilsen opens its 40th annual Día de Muertos exhibit on September 20, and it runs through December. The free Day of the Dead Xicágo event transforms the museum and the nearby park, and the neighbourhood itself fills with decorations and homemade altars, including a giant ofrenda. This is the city's most grounded seasonal tradition, and it is a walk through a living neighbourhood rather than a ticketed attraction.
For stages and screens, October is dense. Jekyll & Hyde, a gothic pop-rock musical, makes its Broadway in Chicago debut September 8 to November 8, 2026. The Rocky Horror Picture Show Spooktacular Tour plays the Chicago Theatre for one night only on October 31, 2026 — a 4K restoration screening hosted by original cast members. Steppenwolf Theatre's House of the Exquisite Corpse returns for a sixth season October 8 to November 1, 2026, a puppet haunted house built by six artist teams around the theme "lullabies." Raven Theatre in Edgewater hosts Stage Frights!, ten new short horror plays by Sandbox Theatre Collective, October 23 to November 1, 2026. The Newport Theater in Lakeview runs Halloween burlesque and cabaret throughout October, including Nightmare at The Newport, Occult Cabaret and Halloween Cirque Burlesque. Death Toll: A Halloween Drinking Game Sketch Show plays the Cornservatory October 16–31, 2026 — interactive sketch comedy, BYOB.
Film fans have three anchors: the Chicago Horror Film Festival, now in its 28th year, at Landmark Century Centre Cinema in Lakeview, October 2–4, 2026; Music Box of Horrors at the Music Box Theatre on October 24, 2026, a 24-hour horror marathon with actor and director appearances; and Chi-Town Movies Drive-In in Pilsen, screening classic and new horror throughout October.
Museums for the Macabre, and Where to Eat Between Them
The International Museum of Surgical Science occupies a Gold Coast historic mansion and tells the history of surgery through art, books and instruments. The Medieval Torture Museum in the Loop is an interactive historical museum with more than 100 devices. Both make a good daytime counterweight to a night of parades.
For food, follow the season rather than a single address: the fall snacks and drinks at the Chicago Botanic Garden's jack-o'-lantern nights, the food trucks parked at Jack's Pumpkin Pop Up, and the craft beer and cider tastings at Lincoln Park Zoo's Zoo Brews are the reliable October eating and drinking occasions the city puts on. In Pilsen, build your Día de Muertos visit around the neighbourhood's own restaurants and bakeries while you walk the altars and decorations.
Start with the two Saturdays: book your travel around October 24 for Arts in the Dark on Columbus Drive, or October 31 for Haunted Halsted in Lakeview and the family parade in Washington Park. Then layer in a ghost tour, a pumpkin night and a Pilsen afternoon, and check each venue's schedule as October approaches — many of these runs begin in September and sell out well before the leaves turn.