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The Big City Blog: Jack’s Pumpkin Nights, Seadog haunted cruises and more Chicago Halloween fun

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By Trent Modglin

For a fun, new Halloween pop-up experience complete with carnival games, bounce houses, live performances, nighttime light displays, food trucks and a beer and cider-stocked bar inside of a giant corn maze, head to the two-acre lot near Goose Island for Jack’s Pumpkin Nights. Perfect blend of entertainment for the kids during the day and the adults (and a bit of a singles scene) later in the afternoon into the evening. With plenty of fall-themed props, Instagrammable photo opportunities abound. Open daily through Nov. 4. 1467 N. Elston. Tickets available at

Docked on Navy Pier is Seadog Cruises, which changes things up from their summer high-speed adventures across Lake Michigan to offer a spooky 75-minute narrated tour this month based on the city’s urban legends and haunted history. Cruising the river at night is quite an experience on its own, but add in a costumed narrator and true haunted tales of Chicago makes it all the more perfect this October. Bring the blankets and settle in for some unique fun. We even brought the kids and they’re still talking about it. 888-636-7737.

A regular staple for families every October in Chicago is Lincoln Park Zoo’s Fall Fest, with a Ferris wheel, games, live music, a pumpkin patch, corn maze, inflatable obstacle course and plenty of fall-themed animal entertainment. Fall Fest runs Fridays-Sundays through Oct. 28 and is open till 8 p.m. on Saturdays. Held in conjunction with Fall Fest is Spooky Zoo 2018 on Oct. 27, which is a safe alternative to trick or treating from 10 a.m.-1 p.m. 2200 N. Cannon Dr.

If you want to let a sleek, modern machine propel you around town while listening to eerie stories of Chicago’s haunted past, check out Absolutely Chicago Segway( or Steve’s Segway Tours (

Navy Pier has plenty going on this Halloween season, including a haunted maze, fireworks, free outdoor films and musical performances.

For adult-themed hotel parties that will be the talk of the town on Saturday, Oct. 27, head to the Chicago Athletic Association’s Underworld’s Fair, the Drake Hotel’s Masquerade Ball or the Congress Plaza’s Haunted Halloween Ball.

Join a massive Thriller dance party, or just enjoy the hundreds of elaborately costumed marchers at the 22nd annual Haunted Halsted Halloween Parade in Boystown at 7:30 p.m. on Oct. 31. Some $4,000 is given away in cash and prizes at the costume contest. Halsted and Belmont.

Need to get in the spirit of the season? For more than 50 years, Fantasy Costumes in Portage Park has been the sought-after destination in Chicagoland for the largest selection of costumes, wigs, hats, masks, decorations, makeup and accessories. Specializing in rare and hard-to-find items, perfect for any budget and carrying more than one million items in its block-long store, you’re certain to find something special for your Halloween plans in the Windy City. And they deliver too. 4065 N. Milwaukee.