The very best Chicago spots to find Instagram-worthy decorations, full-sized candy bars, and plenty of family fun on Halloween
Grab your biggest treat bag, and get your bell-ringing fingers ready. Halloween is upon us. However, with All Hallows Eve falling on a Monday this year, trick-or-treating won’t likely start until the grown-ups are home from work. Considering that late timing—plus the ever-present threat of snow in October—it might make sense for parents of little kids to take their pint-size ghouls and goblins to one of the formally organized daytime events on the weekend prior.
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Whatever your family decides to do, there are frights and delights from A to Z (or, rather, Andersonville to Lincoln Park Zoo)—so many, in fact, that you might need a second bag to carry your candy haul. We know which neighborhoods and events you should hit this Halloween to find the fewest tricks and the best treats. These 15 spots throughout Chicago are guaranteed to be well worth a costumed visit.
Related: The Best Local Costume Shops For Your Family’s Last-Minute Halloween Needs
At Halloween on Catalpa, you can not only get a head-start on Halloween but also on flu season! On Oct. 29 from 10 a.m.-4 p.m. on Catalpa between Clark St. and Ashland Ave., various family activities will be available including a DJ, a 360 degree photo booth, and costumes contests. The very inclusive event ensures everyone gets a free pumpkin, caramel apple, and toys. Gluten-free candy bags will be available, and families with sensory sensitivities and disabilities will receive priority access from 10 a.m.-11 a.m. Walgreens will be on site offering free flu shots, COVID-19 vaccinations, and boosters. It is here that you can pick up your map of the nearly 50 Andersonville businesses handing out candy to trick-or-treaters.
Long before the pandemic inspired candy givers to get creative with their distribution tactics, the Booena Park Safe Trick-or-Treating event always went above and beyond to make trick-or-treating uniquely interactive. Case in point, the use of dryer hoses to send candy down from upper-level units. Since the pandemic they have only upped their game and have been encouraged to do so again this year with prizes for the best remote candy delivery and the best and scariest decorations. Kenmore Avenue is closed from Irving Park to Montrose from 6 p.m.-8 p.m. on the 31st. Insider Tip: If you head out towards the end, residents tend to offer candy by the handful!
For a different spin on trick-or-treating, check out the Edison Park Trunk or Treat event taking place on Oct. 27 from 4:30 p.m.-6:30 p.m. Collect candy from 60 different decorated vehicles at this free neighborhood event. The first 350 kids will receive a complimentary trick-or-treat bag, and each goodie bag will contain a dining coupon to a local restaurant to be used that night only. There will also be a DJ, bounce houses, face-painting, and a balloon artist on stilts.
Visit the over-the-top, professionally decorated mansions on Goethe Street from Dearborn to Astor. Here you will find full size candy bars and even plush toys as the generous treats being passed out.
Year-round, Hyde Park has that East Coast autumn vibe, and Halloween is when it really shines. The setting of hordes of kids going mansion door to mansion door of the tree-lined streets could be taken straight out of a Hollywood movie. Check out Harper Avenue between 57th and 59th Streets. Go early to avoid the crowds!
While Lakeview is another great area in which to trick-or-treat come Halloween night, there are two organized events before Old Hallow's Eve not to be missed. Trick-or-Treat on Southport will take place one week earlier on October 24th from 4 p.m.-8 p.m. In addition to trick-or-treating at local businesses, there will be other family-friendly activities including a DJ, inflatables, and a pumpkin patch. There's even a craft beer tent and lots of business discounts for the well-deserving parents!
On Oct. 30, from 12 p.m.-3 p.m. join The Little Monsters Crawl around the streets of Lakeview, (mostly Clark St. and Broadway), to collect candy and treats, for all ages, from local businesses.
Burling St., located between Fullerton and Diversey, blocks off party-style on Halloween night, offering visiting trick-or-treaters a night of fun and candy galore. Your best bet is to hop on a bus, or jump on the "L" as evening parking can be tricky. This is destination trick-or-treating at its finest; it's particularly fun to get a glimpse of the homes all open and welcoming to the sounds and little feet of kids on the spookiest, silliest night of the year.
On Oct. 22 from 10 a.m.-1 p.m. (or while supplies last), the Lincoln Park Zoo will host a free Spooky Zoo event. This year’s event will offer trick-or-treating on zoo grounds and family-friendly entertainment.
Related: Our Ultimate Guide to Chicago-Area Pumpkin Patches
Ravenswood has become known for its "full-size chocolate bar houses." Even kids from neighboring Lincoln Square flock to the streets of Ravenswood to score these rare finds. Check the week's weather forecast, and if its not looking too good for Halloween night, head to Lincoln Scared Ravenswoooood the day before from 11 a.m.-1 p.m. when participating businesses in both Lincoln Square and Ravenswood will be passing out candy. Check the Chamber of Commerce's website for maps for both neighborhoods.
Bernard Street between Fullerton and Wrightwood might as well be deemed the honorary Halloween-town. Families go all out in decorating their homes for the season. People travel in from far and wide on the 31st to admire the spectacle and get in on all that candy!
On Oct. 29, from 10 a.m.-1 p.m., don your most creative costume and hit the streets of Lincoln, Damen, and Irving in NorthCenter to collect sweet treats and other prizes. Pick up your map, and drop of non-perishable food and toiletry donations for Common Pantry, at the NorthCenter Town Square. Be sure to return back to the square for the annual costume contests, refreshments, and free Halloween-themed crafts with Macaroni KID.
On Oct. 31, Alderwoman Maria Hadden's office is offering a safe and easy way to trick-or-treat in the 49th Ward. The Candy Crawl will begin at the Alderwoman's office at 1447 W. Morse Ave. at 4 p.m. and conclude at 7 p.m. They will provide a bag for collecting treats and a map of participating businesses along the Morse and Glenwood Corridor that are just waiting to satisfy every sugar tooth.
One of the most family-friendly neighborhoods in Chicago, Roscoe Village is the perfect place to spend Halloween night. Most blocks are lined with side-by-side, single-family homes, making it easy to earn a handsome loot without too much walking. You'll find the owners of said houses, gathered together by outdoor fire pits in this tight-knit community, enjoying the evening as much as the kids. If you want to get a head-start on the Trick-or-Treating, join the Roscoe Village Halloween Block Party on Sunday, Oct. 23rd from 12 p.m.-4 p.m. Roscoe Street will be closed to traffic while businesses between Damen and Hoyne will be handing out candy to all the costumed creatures. You'll also find kid's activities in the center of the road.
The Wicked West Trick or Treat will take place on Oct. 31. Commercial Park (1845 W. Rice St.) will host a Halloween Parade and After-Party from 2 p.m.-3:15 p.m. immediately followed by safe and family-friendly trick-or-treating around the local retail businesses and restaurants.
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Purchase tickets and reserve a time slot to trick-or-treat at The Bucktown Green (1714 N. Hoyne Ave.) on Oct. 30 from 1 p.m.-5 p.m. There will be 25 booths to visit.
From near and far, people flock to Wilmette, specifically Lake Ave., east of Green Bay Rd., to see huge historic homes transformed into haunted houses with spider webs, ghosts, and goblins. The trick-or-treat theory of big houses equals big candy haul is certainly the case here. Trick-or-treat hours in Wilmette are 4 p.m.-8 p.m. on the 31st.