As a lifelong Chicagoan, I find the holiday season to be one of the most magical times in the city. Some years bring light flurries of snow, and other years stay a little warmer, but no matter the weather, Chicago goes all out for the holidays. Whether it’s a festival of Christmas trees or a candlelit tour through one of the city’s most storied homes, there’s truly something for everyone.
So here is my lifelong Chicagoan’s guide to the season, written for anyone who wants a Christmas in the city that isn’t so on the nose. Don’t get me wrong, a few classics made the list, but you’ll also find Gilded Age mansions, afternoon teas, baking classes, a little filth, and my favorite cozy spots to eat and drink.
Gilded Glamour and History
If your idea of the holidays involves a little sparkle and a lot of history, this is where Chicago really shines. Between Gilded Age mansions decked out for the season and an evening at the symphony, these are the experiences for anyone who wants their Christmas to feel elegant, a little old-world, and far less crowded than the usual holiday hot spots.
The Driehaus Museum at Christmas
The Driehaus Museum is one of the best places to see Christmas decorations in Chicago, and it’s the perfect backdrop for a very glamorous holiday. Every year, the museum decks itself out to the nines with some of the most stunning holiday displays in the city.
The Richard H. Driehaus Museum explores the art, architecture, and design of the late 19th century, with a focus on the Gilded Age. It’s tucked just off the Mag Mile at 40 E. Erie St. in the Nickerson Mansion, a home turned museum that’s been meticulously restored after years of neglect. The house itself is full of grand rooms with intricate woodwork, marble, stained glass, and enough little bits for you to really get lost in. My personal favorite is the gallery with a truly magnificent stained glass dome. I could stare at it forever.
As far as holiday decor goes, this place puts up several large Christmas trees that are lavishly decorated with everything from pearls to velvet bows. Seriously, if you are really into glamour or history, this is an absolute must. On select weekends, the museum also hosts its Drie-cember holiday market, full of local vendors selling vintage jewelry, handmade gifts, and local art, so check the dates before you go. They also have Victorian-Yuletide ghost stories, and even carolores.
General admission is $23, with discounts for students and seniors, and kids 12 and under and military members get in free. If you want to save a little, the museum offers pay what you wish admission on Wednesdays from 4 to 7 p.m. Just know it’s closed Mondays and Tuesdays, so plan accordingly.
Christmas Candlelight Tours at Glessner House
If it seems like I really like old houses, well, I do. I find them beautiful and charming in their own right, and they come with the added bonus of being far less crowded than some of the city’s other festive attractions. You really get to experience the season and the beauty of it while also learning something new.
The Christmas Candlelight Tours at Glessner House are one of the most charming holiday traditions in Chicago. The house sits in the South Loop and is a National Historic Landmark, and every December it’s decorated just as it would have been in the late 19th century. There’s a 10-foot tree decorated with period ornaments, toys, and holiday crafts, Christmas music performed on the Glessners’ Steinway piano, and the dining table set for an eight-course Christmas feast. My invite must have gotten lost in the mail!
The tours are about an hour long and led by a museum docent, and each time slot is capped at just eight people, so it feels really intimate. Afterward, you get to enjoy some hot cider and cookies. Tickets were $20 last year, and the tours only run on a couple of weekends in December, so book early.
Merry, Merry Chicago! at the Chicago Symphony Orchestra
Time to get dressed in your very best and head out for an evening of glamour. Every year, the Chicago Symphony Orchestra puts on Merry, Merry Chicago!, its annual holiday concert at Symphony Center, and it’s one of the most elegant ways to celebrate Christmas in Chicago.
Members of the Chicago Symphony Orchestra and the Chicago Symphony Chorus perform a mix of beloved carols, popular seasonal songs, and a few holiday surprises, all inside a lavishly decorated Orchestra Hall. There’s something about hearing holiday music played by a world-class orchestra in a room that grand that just hits differently.
I’ll also add that this is by far the perfect event to dress up for. But on your best and make a night of it. I love grabbing a cocktail before, or if it’s really in the budget, heading to Bazaar Meat. The have a theater tasting menu for $95 a person. I have found it to be quite a good deal for the price, and you don’t have to be seeing any specific show.
Holiday Afternoon Tea in Chicago: An Experience Steeped in Tradition
I am a woman who loves all forms of pleasure, and for me, one of the greatest pleasures is afternoon tea. There’s so much tradition, service, and attention to detail that goes into it. Teas vary quite a bit by budget, so here are my favorite holiday afternoon teas in Chicago, depending on the experience you’re after. But if you want my full guide, check this one out!
My Overall Pick: The Ritz-Carlton, Chicago
For Christmas, the Ritz-Carlton is my top pick if you’re looking for an experience where you can really sit back, relax, and take in beautiful views of the city. Tea is served in the Café Atrium of the hotel, which sits in Water Tower Place right off the Mag Mile. If you book the last seating of the afternoon, you can watch the Christmas lights slowly start to come on.
Best for Families and First-Timers: The Drake
If you’re bringing the family or it’s your first afternoon tea, I’d suggest the Drake. Afternoon tea at its Palm Court is a true Chicago tradition, and Princess Diana even stopped by during her visit to the city. It’s also the most accessible and kid-friendly of the nice hotel teas. During the holidays, a harpist plays at every seating, and carolers perform on select dates through Christmas. You’re seated right by the fountain, surrounded by holiday florals, with views of the lobby Christmas tree and gingerbread display.
Best for Going All Out: The Langham
And if you really want to ball out in luxury, head to the Langham. It’s stunning and a true experience, full of pomp and circumstance. Tea is served in the hotel’s Pavilion, and the Langham’s afternoon tea tradition goes all the way back to its London hotel in 1865. They also love to get experimental, with themed holiday teas that make the whole thing feel really creative. After tea, I’ll make my way to the hotel bar, which overlooks the Chicago River. They make a killer martini!
Holiday Baking and Cooking Classes in Chicago
One of my favorite low-stakes things to do with friends is take a baking or cooking class. The great thing about Chicago is that there’s no shortage of options, each with its own vibe. Classes also make such a thoughtful holiday gift if you’re stuck on what to give someone this year. It’s an experience you can share together, and it beats another thing collecting dust on a shelf. For more gift ideas, check out my Nice List.
Bettie’s Chicago
Bettie’s Chicago in River North has an incredible ambiance, with a retro 1950s feel to the decor that makes the whole experience extra charming. It’s run by Kristin “Baker Bettie” Hoffman, a trained chef and cookbook author who’s great at breaking down the techniques and science behind baking. They offer a variety of holiday classes on both the sweet and savory side, from yule log cakes to holiday pies and breads. Classes come with snacks and drinks to enjoy during the downtime, so you can socialize while your bakes are in the oven.
Sur La Table
Now, one of my favorites has to be Sur La Table. I think they have the best variety of classes. They have regular classes throughout the year, like steak frites or a French feast, but they also do a ton of really good seasonal ones, both sweet and savory. On the sweet side, you can learn to make cookies for your holiday cookie box, holiday macarons, holiday pies, croquembouche wreathes, yule logs, and holiday candy. For something savory, there’s holiday breakfast, pizza shaped like a Christmas tree, tamales, and heartier winter pastas. You can even learn to make a rack of lamb!
The workshops are always really fun and great for any skill level. They have locations in the Gold Coast and in suburban Skokie, with a ton of different dates and times. I’ve taken some of their Mediterranean classes, and it’s always a really fun time.
Bon Vivant
If you really want to tap into your creative side, look to Bon Vivant in Albany Park, which specializes in cakes and pastries. They have several holiday classes featuring vibrantly colored cakes, kitschy cookies, and the type of sweets you could only dream of. They also have a Hanukkah focaccia class that offers a sweet and savory option. All classes come with some bites that are quite fantastic. Spots fill up fast, and to be transparent, the space is a bit small, so it can sometimes be hard to hear over everyone talking. Just something to take into consideration
Naughty, Nice, and a Little Filthy: Festive Nights Out in Chicago
Not every holiday plan has to be wholesome. If you’re looking for something a little more grown-up this season, these are my favorite festive nights out in the city, whether you’re feeling a bit naughty, a bit nice, or somewhere in between.
Wreath Making at Flowers for Dreams
If you want to bring a little bit of the season home with you, book a wreath workshop at Flowers for Dreams. Their West Town studio hosts holiday wreath classes, and they offer several other floral classes throughout the year. In this class, you build a fresh-cut evergreen wreath with your choice of dried accents, holiday berries, and ribbon. If your style is a little more rustic, or you can’t have greenery at home, there’s also a Woodland Wreath Workshop that uses a grapevine frame. Flowers for Dreams has some of the best greenery and florals around, and they’re very dedicated to sourcing them ethically and giving back to the community. In all honesty, they’re one of my favorite businesses in the city.
A John Waters Christmas
Perhaps you’re in search of some filth. Well, then you’ll want tickets to A John Waters Christmas, his annual holiday tour. It’s debaucherous. There’s typically a Q&A session, plus a delivery that’s part storytelling, part monologue, and part stand-up. It’s very much for the fans, and something you have to have the right disposition and appreciation for. The Chicago show is typically at a pretty small venue, so it feels like a really intimate moment with just you and a bunch of other weirdos who share your interests. I personally wouldn’t suggest it if dirty humor isn’t your thing.
Naughty or Nice at the Museum of Science and Industry
Every year in early December, the Griffin Museum of Science and Industry closes for the evening and then reopens after hours for its Naughty or Nice event. This is the closest I’ve come to experiencing ’90s Chicago. It feels so nostalgic, and it’s so much fun. There’s a DJ who remixes classic Chicago house hits with holiday favorites, so you can go from “The Percolator” straight into Mariah Carey’s “All I Want for Christmas Is You.” I mean, who doesn’t want that?
The event is 21 and up, and the exhibits are open, including Christmas Around the World and Holidays of Light, the museum’s famous display of trees decorated by Chicago’s cultural communities. It’s a great time to enjoy the museum with far fewer crowds because attendance is capped. I’ve never found it overly crowded. I’m not waiting in lines, and I’m not feeling rushed, which makes it so much more enjoyable.
There are alcoholic and non-alcoholic drinks, and you can maybe even meet Santa. People usually dress festive but still casual and comfortable. Tickets are usually around $35, and it’s a great event if you just want to have fun and enjoy something a little more adult.
Sip and Script
Sip and Script holds calligraphy events year-round, but during the holiday season they host a few that focus on perfecting your penmanship for things like ornaments and place settings. I think it’s a really fun way to learn the basics of calligraphy. One of my biggest takeaways is that there are a ton of different calligraphy styles, and most people end up developing their own that flows naturally with their handwriting. There’s no right or wrong way to do it, and you leave with better penmanship and a starter kit to keep, plus an ornament you lettered yourself.
There’s usually some alcohol too, just for a little added fun. It’s honestly a great place to meet new people and make friends, or to bring your friends along. Either way, you’ll meet someone cool who shares your interests, and calligraphy is such a lost art.
Bonus: Chicago Mahogany Tours
There isn’t a Christmas version of this bus tour, but if you’re visiting Chicago, I highly recommend booking one of the Chicago Mahogany Tours. They’re led by Shermann “Dilla” Thomas, an incredible Chicago urban historian you might know from TikTok as @6figga_dilla. His tours highlight neighborhoods on the South and West Sides that are often overlooked, including Black and Latino communities. You learn so much about the history of these neighborhoods and really get an in-depth feel from a lifelong local, which helps you understand the bigger picture of Chicago and how it connects to national history.
My personal favorite is the Bronzeville tour. It’s a little music-heavy (Bronzeville is considered the birthplace of gospel music), and I just really love music, so it’s my favorite. I think it’s really worth it. The bus is also very comfortable, so if that’s something you’re concerned about, I highly recommend it.
Where to Eat and Drink in Chicago During the Holidays
There’s a variety of festive spots to eat and drink in Chicago during the holidays, across all price points. Here are my personal favorites, plus one that I think is worth visiting with a bit of a caveat. I’ll also add that Chicago has a ton of themed Christmas pop-up bars, namely in Wrigleyville. But honestly, I find them to be a bit of a rip-off. They tend to be pricey and overcrowded, and they really just feel like an upcharge at every opportunity.
Club Lucky
Club Lucky in Bucktown is a Chicago classic. It’s one of the better Italian restaurants in the city, and it really goes all out for the holidays. The bar area is covered in handmade snowflakes set against a retro bar lit with red and green lights. The main dining room has old-school dining booths decked out with big, beautiful garlands and wreaths, which give it that 1940s supper club feel. As for the food and drinks, it really holds its own. I’ve never had a bad meal, and I’ve been going since Obama’s first term. My personal favorites are the fried calamari, any of their pastas in vodka sauce, and of course spumoni for dessert, all accompanied by your martini of choice. I’m a filthy gin martini kind of woman, and they excel at them. This is hands down my favorite place to go for Christmas.
Drinking Chocolate Flights at Katherine Anne Confections
If you haven’t had drinking chocolate, it’s definitely worth trying. It’s much thicker and richer than hot cocoa. Katherine Anne Confections, with locations in Logan Square and Irving Park, offers a flight of three, so you can pick your favorites. Mine are the salted caramel, Mexican, and milk chocolate. Each one has its own flavor profile and comes topped with a marshmallow. Honestly, the flight is small enough to split with someone, and while you’re there, you can pick up some truffles for all your holiday hosts.
Blue Line Lounge & Grill
Blue Line is such an experience, and it reminds me a lot of what Wicker Park used to be like. It sits right under the Damen Blue Line stop and is styled like an old-school railroad dining car, with a bit of an art deco vibe. For the holidays, they go all out with red and green lights everywhere and festive cocktails, and they play old black-and-white holiday movies in the back. The cocktails definitely aren’t made with your highest-grade liquor, and as the night goes on, the crowd gets real local. But it’s charming and fun, and it always ends up on my calendar. They also have a full-service kitchen. I recommend going on a Wednesday, when they have heavily discounted martinis.
Lady Gregory’s
Head over to Andersonville for some charming pub fare with a side of warm and cozy Christmas. The restaurant brings in plenty of garland for the season. Personally, I don’t think there’s anything bad on the menu, but it is heavier fare. Afterward, take a stroll around Andersonville to walk it off and enjoy the neighborhood’s holiday lights.
Chief O’Neill’s Pub
I have to say, Chief O’Neill’s in Avondale really goes all out for Christmas. The decorations are everywhere, with giant ornaments, glitzy lights, and garland. I came here during the holiday season and will admit it wasn’t for me. Maybe it was an off night for the kitchen, or maybe I ordered wrong, but there were a lot of issues. I know it gets really crowded during the holidays, so maybe it’s worth trying again. If you go, I’d say come for the decor and a drink.
Venturing Outside the City: A Home Alone Weekend on the North Shore
If you’re looking to make a weekend of it, might I suggest a North Shore getaway, or what I’m dubbing the Home Alone experience. Start with a stay in the Home Alone Suite at the Graduate in Evanston. It recreates the McCallisters’ master bedroom right down to the four-poster bed, and it comes stocked with Kevin’s favorite snacks and the movies on demand. I did a full tour of it on my YouTube.
From there, head around the North Shore to see the Home Alone house in Winnetka (just remember it’s a private home, so admire it from the street), the church in Wilmette where Kevin hides in the nativity scene, and Hubbard Woods in Winnetka, the little town square where Kevin buys his toothbrush. You could also take a drive up to Lake Forest for afternoon tea at the Deer Path Inn, a charming English-style inn that does holiday-themed teas all season, and then do some shopping around their downtown, which is wonderfully lit up for the holidays. End with a drive back to the hotel to look at the holiday lights.
I did this one year, and it was really magical. I even used my Pura car diffuser to make my entire car smell like Christmas trees.
Where to Stay in Chicago for the Holidays
If you’re coming in from out of town (or just want a festive staycation), here’s where I’d book, depending on your budget.
Splurge Pick: The Langham or the Four Seasons
For a beautiful holiday experience, I’d recommend the Langham. They decorate their lobby exceptionally, and the service is lovely. The front desk staff has always been so kind to me, and they’re meticulous about cleaning the rooms. The sheets are really comfortable, and the mattresses are fairly firm. They’re not the firmest I’ve had, but not bad for someone like me who loves a firm mattress. Plus, it’s in a great location right on the river, steps from the Mag Mile, and you’re already in the building for tea and a martini.
The Four Seasons is for the Home Alone fans. It’s where the Home Alone 2 pool scene was filmed, where Kevin infamously loses his swim trunks. The movie claims it’s the Plaza, but a lot of scenes were actually filmed in and around Chicago.
Midpoint Pick: The Pendry
This one really depends on prices. The Pendry’s rates vary a lot by room level and time of year, but it’s located in the iconic Carbide & Carbon Building, the art deco skyscraper with the gold-topped tower on Michigan Avenue. Legend has it that it was designed to look like a champagne bottle. It feels so glamorous and otherworldly, with lots of nice little touches, and the hotel bar has very knowledgeable staff. You’re right in the center of the city, near the Art Institute and the Mag Mile shopping.
Affordable Pick: The Thompson
Prices here depend on the time of year too, but the location is great. It’s in the Gold Coast, which is a little quieter, so you get a downtown holiday feel with a bit of a neighborhood vibe. It’s close to Oak Street, the Mag Mile, and the Drake, so if you want to shop, this is the pick. It’s cozy while still feeling elevated, and when I stayed there, it had some of the best room service I’ve ever had. That was many years ago, so I can’t promise it’s still the case, but it was really nice.
Outside the Loop Pick: Hotel Sophy
Hotel Sophy in Hyde Park is a boutique hotel with a ton of character, just a short trip from the Museum of Science and Industry. What I really love is how much art there is throughout the hotel. It’s stunning. I’ve stayed there a couple of times for staycations, and it feels comfortable and homey while still feeling like an escape. The suites are great bang for your buck, and they come with cute little record players.
Happy Holidays from Chicago
There you have it, my lifelong Chicagoan’s guide to the most wonderful time of the year in this city. Whether you’re sipping tea under the Christmas lights, belting out house remixes at the Museum of Science and Industry, or tracking down Kevin McCallister’s old haunts, I hope this guide helps you find a little magic (and maybe a little filth) this season.
