Chicago transforms into a glittering wonderland during the holiday season.
From neighborhood light shows and festive pop-ups to cozy local shops and seasonal cocktails, there are plenty of opportunities to celebrate.
At Thomas Law Offices, we have handpicked the best experiences for families, friends, or anyone looking for a little extra holiday cheer.
Holiday Events
Chicago takes holiday cheer very seriously, and the city’s most beloved traditions only get better each year. From European-style markets to glowing gardens and festive pop-ups, these events bring the magic of the season to life for families, date nights, and anyone craving a little winter wonder.
Christkindlmarket
Nov 21 – December 24, 2025
You can step into a European Christmas village right in Daley Plaza. This beloved German-style market overflows with hand-carved ornaments, intricate nutcrackers, warm glühwein, and delicious holiday treats. This is the perfect spot to shop for one-of-a-kind gifts while soaking in live music and the glow of festive lights.
ZooLights at Lincoln Park Zoo
Nov 21, 2025 – Jan 4, 2026
Millions of sparkling lights glimmer across the zoo grounds. From life-sized animal lanterns to twinkling pathways, this display combines Chicago’s love of winter with the wonder of wildlife. With a hot cocoa in hand, families and friends can stroll past illuminated enclosures and holiday-themed installations at this year’s ZooLights.
Lightscape at Chicago Botanic Garden
Nov 14, 2025 – Jan 4, 2026
If you want to experience an enchanting nighttime stroll through illuminated forests, magical tunnels of light, and dazzling gardens, Lightscape at Chicago Botanic Garden is the place. Each display is designed to inspire awe and create perfect photo moments, all while supporting a beloved Chicago institution.
One of a Kind Holiday Show
Dec 4 – 7, 2025
The One of a Kind Holiday Show is a haven for unique gifts and artisan treasures. This show features hundreds of local makers. From handcrafted jewelry and ceramics to quirky decor, you can find treasures you won’t see anywhere else.
Wrigleyville Wonderland
November – January
The neighborhood transforms into a collective holiday spectacle. At the Wrigleyville Wonderland, each bar and pop-up is decked with festive lights, themed drinks, and winter cheer. This is the perfect spot to experience Chicago’s holiday nightlife with a local twist.
Neighborhood Light Shows
If you love crisp winter air and twinkling displays, Chicago’s neighborhoods know how to put on a show. These local favorites range from over-the-top home displays to guided light tours and drive-thru experiences that let you soak in the glow without ever leaving the warmth of your car.
Light of Christmas – Chicago Drive-Thru
You can cozy up in your car and enjoy a synchronized, dazzling holiday display at Rate Field. This event is perfect for families or large groups. The drive-thru show combines music, lights, and plenty of holiday cheer without ever leaving your vehicle.
Chicago Holiday Lights Trolley Tour
Let someone else do the driving! This guided trolley tour winds through some of Chicago’s most festive neighborhoods, giving guests an insider’s view of the city’s holiday lights, decorations, and local charm.
Candy Cane Lane – Sauganash & Edgebrook
These Northwest Side streets are legendary for their sparkling holiday displays. Families and friends can stroll or drive past elaborately decorated homes, featuring lights, inflatables, and festive scenes that have delighted locals for decades. For organized tours, the Edgebrook-Sauganash Chamber of Commerce offers trolley rides.
Places to Buy Gifts
Skip the big-box stores and support Chicago’s vibrant community of makers, artists, and family-owned shops. These small businesses offer thoughtful gifts you won’t find anywhere else. Remember that shopping local helps keep the city’s creative spirit shining bright.
Neighborly
This charming boutique focuses on fair trade, eco-friendly, and handmade gifts. From artisan candles and home goods to quirky stationery, everything supports local or small-scale creators. The shop itself radiates holiday cheer with cozy displays and thoughtful gift ideas.
SOW (Stacker of Wheat)
This boutique in Lincoln Park showcases handmade goods from Chicago artisans and small-batch creators. Think jewelry, home textiles, art prints, and quirky gifts that feel personal.
Randolph Street Holiday Market
This seasonal market is a paradise for handmade and artisan goods. Browse jewelry, ceramics, prints, and festive décor, while enjoying live music and holiday treats from local vendors.
Hazel Chicago
Hazel transforms into a holiday wonderland every December. You can find luxe ornaments, winter candles, beautifully wrapped gift boxes, and stylish accessories that feel tailor-made for the season.
Dusty Groove
For the music lover in your life, nothing beats a perfectly selected record under the tree. Dusty Groove has rare vinyl, classic albums, and collector finds that make unforgettable gifts, especially when paired with a handwritten note and hot cocoa.
Aroma Workshop
One of the most unique holiday gifting experiences in Chicago. You can create custom perfumes, candles, or scent kits. Aroma Workshop has perfect romantic gifts, best-friend gifts, and gifts for anyone who loves a personal touch.
Foursided
Foursided is the perfect place for whimsical Christmas finds. You can find vintage-style prints, holiday cards, quirky ornaments, framed art, and stocking stuffers with personality. Your most fun, festive gifts will come from here.
Milk Handmade
If your holiday list includes fashion lovers or anyone who appreciates handmade pieces, Milk is a gem. Their winter accessories, handcrafted jewelry, and cozy small-batch clothing make beautiful, thoughtful gifts.
Bars & Restaurants
Whether you’re looking for festive cocktails, themed pop-ups, or cozy spots to warm up after a long day of shopping, Chicago’s holiday dining scene delivers. These local favorites pair great food and drinks with twinkling décor and an atmosphere that makes every night feel like a celebration.
Elf’d Up (Stretch Bar & Grill)
If you ever wanted a holiday movie to come to life, this is your chance. Thousands of elves, themed cocktails, and festive comfort food create a truly immersive experience. Elf’d Up is perfect for friends or family; it’s a pop-up that combines humor, nostalgia, and holiday spirit.
Jingle Junkie
Jingle Junkie is a ski-lodge-inspired bar bursting with holiday cheer, featuring cozy décor, seasonal cocktails, and a festive outdoor patio. It’s the ultimate spot for a merry night out or Instagram-worthy photos.
Tinseltown at The Pink Squirrel
Amidst thousands of twinkling lights, Tinseltown at The Pink Squirrel is a pop-up bar that adds playful holiday flair to Logan Square. You can enjoy cocktails, duckpin bowling, and a cozy atmosphere that feels like stepping into a Christmas card.
Frosty’s Christmas Bar
Life-sized nutcrackers, larger-than-life Santas, and whimsical décor create a magical escape at Frosty’s Christmas Bar. Cozy up with holiday cocktails while soaking in the playful festive energy.
8 Crazy Nights
You can celebrate Hanukkah in style at the Graystone. There is plenty of blue-and-white décor, festive food, and themed cocktails.
Sheraton Sleigh Bar
This cozy holiday pop-up inside Sheraton Grand Chicago features twinkling lights, festive drinks, and perfect bites for winter evenings.
Christmas Tree Farms
Bring a little fresh-pine magic into your home. These local tree farms and lots offer everything from cut-your-own experiences to beautifully curated evergreens, wreaths, and garlands, all with that welcoming, family-run charm.
Ben’s Christmas Tree Farm
Nothing beats choosing your own tree straight from the farm. Ben’s offers a wide variety of evergreens and a warm, family-run atmosphere. Kids can enjoy wagon rides, and the whole family can snap memorable holiday photos.
Abbey Farms
Located in Aurora, this charming farm invites visitors to pick, cut, and decorate their perfect Christmas tree. Along with fresh wreaths and garlands, Abbey Farms brings countryside magic just a short drive from Chicago.
Ivy’s Christmas Trees
This Christmas tree lot offers a personal touch that big box stores can’t match. Friendly staff, high-quality trees, and a festive atmosphere make it a joy to shop locally.
Volunteer Opportunities
The holidays are a perfect time to give back. These local organizations make it easy to spread kindness and brighten the season for Chicago families. Whether you’re delivering meals, decorating community spaces, or helping with local drives, your time makes a difference.
Christmas Cheer Foundation
You can deliver meals and gifts to those in need. At the Christmas Cheer Foundation, you can join local volunteers to make the season brighter for Chicago families.
Chicago Cares
You can connect to countless volunteer opportunities, from decorating for seniors to assisting at food pantries. All these opportunities support Chicago neighborhoods in festive ways.
Have a Happy Holiday Season
Chicago’s holiday season is a magical mix of lights and unforgettable experiences. You can support small businesses and create festive memories that will last a lifetime. From holiday markets to immersive pop-ups and volunteering, the city is ready to welcome you with open arms and twinkling lights.
All of us at Thomas Law Offices hope the season brings you comfort, connection, and time to reflect on what matters most this time of year.
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