Trick-or-Treating in Cold and Rainy Chicago

Raise your hand if you saw the forecast for Thursday and secretly cursed yourself for living in Chicago? Well, now that we have gotten our anger out, it’s time to prepare for the frigid Halloween temperatures (I’m just going to ignore the snow part of the forecast, ok?). While I can’t promise that your child won’t fight you about costume alterations, I can help you stay warm and dry (ish) on Thursday. Here are my tips for trick-or-treating in cold and rainy Chicago:

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Trick or Treating in Chicago Tip #1: Dress in Layers

As a tried and true Chicagoan, I spent many Halloweens trick-or-treating with a coat over my costume and I was NOT happy. So, with a few days left to spare, go on a Target run and stock up on layers your child can wear UNDER his or her costume. I’m talking about fleece leggings, long underwear, furry socks, turtlenecks—get creative!

And since the colder temperatures are just beginning to arrive across Chicagoland, there are still tons of hats and gloves to choose from that will actually coordinate with your child’s costume like these Disney character themed winter accessories.

Have a princess on your hands? Well, don’t forget that princesses wear robes (that you can also utilize all winter long). Sports athlete? They wear warm up gear, don’t they?!?! With a little creative thinking (and persuasion), you can most likely convince your child to add a layer or two.

Lastly, stock up on hand and feet warmers. ‘Nuff said.

Trick or Treating in Chicago Tip #2: Be Strategic with Your Outdoor Time

Instead of going to every house in the neighborhood, stake out the most festive houses to hit before you go out into the cold. That way you can still enjoy the trick-or-treating fun but don’t spend as much time freezing outside. And I mean, if someone is going to totally deck out their home, most likely they will give out the LARGE SIZE CANDY BARS!

In the city? I highly recommend Ravenswood Manor (take the Brown line to Francisco) on Wilson between Sacramento and Manor. Two blocks in Logan Square, 2400-2500 Bernard Street between Wrightwood and Fullerton have epic decorations and a wonderful neighborly vibe that will leave you feeling so warm and fuzzy that you won’t even notice the chilly temperatures. Edgebrook also has an impressive display of Halloween houses and you can check out (and vote) on the massive list here.

In the suburbs? Use this updated list of decked out houses to guide your short and sweet trick-or-treating. If you are looking for the biggest bang for your buck, I highly recommend Park Ridge because of its ample displays throughout the community. 

Trick or Treating in Chicago Tip #3 :Seek Out Indoor Goodies

From libraries to malls to schools, there are lots of different INDOOR trick-or-treating options. Just be sure to check the hours and dates carefully before heading out since some of these events aren’t on actual Halloween. Simply search “indoor trick or treating” and your neighborhood/town to help guide your plans.

Over 100 local businesses in Wicker Park, Bucktown, West Town and Logan Square will host a neighborhood trick-or-treat event the afternoon of Halloween, not only handing out candy to kids but also giving coupons, freebies, and other deals to families. Even better? Mr. Dave will be rocking out at a free concert. Click here for more details.

For older kids who are in search of a thrill, head to the Halloween City in Niles to go through their totally FREE and utterly CREEPY Haunted House designed in collaboration with the 13th Floor Chicago. The last room is definitely the scariest, and watch out for the live actors coming to scare you!

Trick or Treating in Chicago Tip #4: Attend a Halloween Party Instead

Don’t even want to bother with trick-or-treating in the snow? No worries! 

There are many family friendly events to choose from, including “This Little Kid Ghoulish Goblin Gathering” at the Little Goat Diner. There will be music, crafts, games, pumpkin painting, and a cash bar for adults.

Another option? Head to the Auditorium Theatre for a viewing of “The Nightmare Before Christmas” performed live-to-film by the Chicago Philharmonic. Dress in costumes and take advantage of the pre-show festivities like trick-or-treating and other fun Halloween themed activities before the movie screening begins. 

And if all else fails, pop in some frozen pizzas, turn on the music, and let your kids and their friends raid your candy bin while you stay warm and cozy on the couch. Total win-win.

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Trick or Treating in Chicago Tip #5: Make a Warm Roadie

Yes, that’s right, I’m advocating walking (NOT DRIVING) around town with a spiked apple cider or grown up hot chocolate because you are going to earn it!

Don’t forget to check out my tips on simplifying Halloween and creating a not-so-spooky celebration if Charlie Brown is more your style.

Happy Halloween!


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