Northalsted Halloween Parade 

Can your Halloween costume beat out 2,000 others at Chicago's largest costume contest?

It’s getting spooky in Chicago this week. First, hit a Harry Potter–inspired dinner at Ada Street. Then on the day itself, hightail it to Boystown for a massive Halloween parade. If you’d rather leave the creepy holiday alone, sit it out at Lillie’s Q, which is now serving brunch, or at one of the dozens of talks on every subject taking place throughout Chicago as part of the Chicago Humanities Festival.

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October 18 | Now open: Restaurant
Lillie’s Q
Our favorite Chicago barbecue spot just added another perk: brunch. Now you can have Southern-inspired brunch on Saturdays and Sundays, including avocado toast (cornbread topped with avocado, pickled shrimp, radish, and a soft-boiled egg), chicken and waffles, and Southern libations such as spiked Southern sweet tea.
Locations throughout Chicago | website

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October 28 - 30 | Themed dinner
Harry Potter Halloween Feast
Ada Street is transforming into the Hogwarts Great Hall just in time for a Halloween feast. This four-course dinner (paired with cocktails) is geared toward Harry Potter’s adult fans. Expect treats like boozy butterbeer and a firewhiskey dessert cocktail. Plus, if you arrive early, you’re in for a few games of quidditch beer pong.
1664 N. Ada St., Chicago | $75 | website

October 29 - 31 | Escape the city
Mackinac Island, Michigan
Plan a last-minute long weekend to Mackinac Island, Michigan, located about seven hours from Chicago. Stay at the Grand Hotel, which claims to have the world’s longest porch—ideal for soaking up some last sun before it’s time to head inside for winter. While you’re in town, make sure to try the fudge; there are fudge and old-fashioned candy shops on nearly ever corner. Don’t worry about calories: This is a no-car community, so you’ll spend your free time walking, biking, and enjoying being active outdoors.

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Chicago Humanities Festival

October 29 - November 12 | Festival
Chicago Humanities Festival
This diverse festival hosts a wide variety of speakers throughout the nearly 100 programs taking place over the next two weeks. Don’t miss the David Bowie and Prince–themed musical tribute, or talks by political activist Gloria Steinem. New York Times columnist and Pulitzer Prize–winner Thomas Friedman will also be speaking, as will Hamilton composer and actor Lin-Manuel Miranda.
Locations vary | From $10 | website

October 31 | Halloween parade
Northalsted Halloween Parade
Don your wild, crazy, spooky, and spectacular costumes and head over to Boystown for the Northalsted Halloween Parade. Every year, this parade draws kids, families, adults, friends, and even pets, and you better believe everyone’s in costume. March in the parade or watch from the sidelines, and if your costume is especially good, enter yourself in the costume contest. More than 2,000 Chicagoans will compete to win the honor of being best dressed.
From Belmont to Addison on Halsted | Free | website

Danielle Braff lives in Chicago with her husband, two daughters, two cats, and her dog. When she’s not writing, she’s out photographing her city and running around frantically trying to fit as many events as she can into her day. You can check out her other articles at

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