A Complete Chicagoland Holiday Bucket List
Hi, I’m Haley, a Chicago North Shore resident, mom to a preschooler, and a realtor helping people find (and create!) their dream homes.
Growing up on the North Shore, the holidays were always filled with little traditions that made this season feel magical, like drinking hot cocoa at the Chicago Botanic Garden Lightscape and walking through the Christkindlmarket in the city.
Now, getting to experience all of these again with my daughter has made them even more special. The same places I loved as a kid have become our own family traditions.
So whether you’re new to Chicagoland or you’ve lived here your whole life, here’s my complete holiday bucket list of local favorites. These are the events I grew up with, still go to today, and truly believe make this area such a magical place to call home.
Lightscape at the Chicago Botanic Garden – Glencoe, IL
November 14, 2025 – January 4, 2026. Lightscape at the Botanic Garden is a must every holiday season. I’ve been going since I was a kid, and now I get to take my daughter — it’s honestly just as magical as I remember. Bundle up, grab some hot cocoa, and take your time walking the path. It’s always one of my favorite nights of the season.
Christmas Around the World and Holidays of Light at the Museum of Science and Industry – Chicago, IL
Nov. 8, 2025 – Jan. 5, 2026. Christmas Around the World at the Museum of Science & Industry is one of those Chicago traditions that never gets old. It’s the perfect indoor holiday outing when you want something festive (and warm!). If you’ve never been, it’s such a fun way to see how different cultures celebrate the season.
Tea at Deer Path Inn Hotel – Lake Forest, IL
Afternoon tea is one of my absolute favorite holiday traditions. The English Room at the Deer Path Inn just nails it — cozy vibes, great tea, and the best little treats.
They do seatings Wednesday–Saturday at 2:00, 2:30, and 3:00 pm, and it always feels like the perfect slow, festive break in the middle of the season.
Drinks/Dinner at Chief O’Niells or Butch McGuire’s – Chicago, IL
For something a little more grown-up, I love grabbing dinner or drinks at Chief O’Neill’s or Butch McGuire’s during the holidays. Both places go all-in on the festive decor — lights everywhere, cozy vibes, and that fun, slightly chaotic holiday energy.
Pictures at The Home Alone House – Winnetka, IL
One of my favorite little holiday traditions is stopping by the Home Alone house in Winnetka for a quick photo. It’s such an easy, feel-good outing — especially if you grew up watching the movie a million times like I did.
Reindeer Happy Hour at Chalet – Wilmette, IL
Thursday, Dec 4th + Dec 11th from 5-7. Reindeer Happy Hour at Chalet is such a fun little North Shore tradition. You get to visit Santa’s reindeer before they “head back to the North Pole,” and the whole thing just feels super festive. You can hang out in the garden with holiday music, hot cocoa, wine, beer, and cookies. It’s simple, cute, and always a hit with kids (and honestly, adults too).
Christkindlmarket – Wrigleyville
Christkindlmarket Wrigleyville is one of my favorite spots to squeeze in a little holiday magic. It’s smaller than the downtown market, but that’s what makes it so fun. You still get the mulled wine, the handmade ornaments, the pretzels, and all the cute little vendors, just without the massive crowds.
Christkindlmarket – Downtown Chicago
Christkindlmarket Downtown is the classic Chicago holiday experience. It’s busy and a little chaotic, but in the best way. You’ve got the twinkly lights, the wooden vendor stalls, the hot spiced wine, the handmade ornaments, the pretzels… all the iconic Christkindlmarket things. It’s right in the heart of the Loop and feels like stepping into a little European Christmas village.
Illumination at The Morton Arboretum – DuPage County, IL
Saturday, November 15, 2025 – January 3, 2026. Illumination at The Morton Arboretum is such a cool change of pace from the usual holiday lights. Instead of big displays, the trees themselves are the show — all lit up with color, music, and interactive light effects as you walk through the paths.
Sip & Skate – Glencoe, IL
Sunday, December 7th, 4:15 – 7pm. Clients, friends, and biggest supporters — this one’s for you! Join me for Sip & Skate, a little holiday thank-you party filled with ice skating, s’mores by the fire, photos with Santa, and hot cocoa (or hot toddies) to keep you warm. I’ve rented out my favorite local rink and party room just for us — it’s my way of saying how much I appreciate you this season. This is a FREE event, but space is limited. Please RSVP to save your spot!
Willow Hill Lights Drive Thru – Northbrook, IL
Open 5pm Nightly | November 14th – January 4th. This drive-thru holiday light show takes you along a 2.5-mile route filled with more than a million lights, three glowing tunnels, and a giant 30-foot Christmas tree
Metra Holiday Train – Chicago IL
Metra runs its festive Holiday Trains every December, complete with decorations and holiday characters onboard. Rides are just $10 and run on the Metra Electric, BNSF, Milwaukee District West, Rock Island, and UP Northwest lines. The Metra Electric trips are extra fun — your ticket includes entry to a mini North Pole inside Millennium Station with treats, music, games, and activities for kids. Dates are Dec 6, Dec 13, and Dec 20. Tickets drop Nov 17 at noon and sell out fast. It's an easy, family-friendly holiday outing if you're near one of the participating lines.
CTA Holiday Train – Chicago, IL
The CTA Holiday Train is one of my favorite Chicago holiday traditions. It’s a fully decked-out six-car train covered in lights, garland, and all the festive decor you can imagine. It runs from late November through late December on every CTA line (just check the schedule online).
Hotel Zachary Winterland Escape– Wrigleyville
Hotel Zachary always feels extra magical during the holidays, and their Winterland Escape package makes it even better. You get an overnight stay in one of their premium rooms, drink vouchers at Alma, Christkindlmarket mugs, Hotel Zachary winter hats, and admission to Winterland’s ice rink. Skating runs daily from November 23 to December 31, 2025. It’s such a fun little holiday getaway right in the city.
Holiday Magic at Brookfield Zoo – Brookfield, IL
November 21-23 and 28-30, 2025; December 4-7, 11-14, 18-21 and 26-31, 2025; January 1-4, 2026. Holiday Magic at Brookfield Zoo is such a fun one for families. The whole zoo is covered in lights, big displays, and tons of photo spots — it’s one of the longest-running holiday light shows in Chicagoland. Kids love seeing the animals after dark, the giant trees, and all the glowing tunnels. It’s an easy, festive night out and always feels super nostalgic.
