The Windy City transforms into a winter wonderland each holiday season, and nowhere is that magic more apparent than at Chicago's Christmas bars. For anyone seeking an intimate evening or a high-energy night out, Chicago has the perfect spot to raise a glass this season. Even better, many of the city's most beloved attractions are just moments away from these merry establishments, so it's easy to pair a festive cocktail with world-class sightseeing.
Chicago's Winter Wonderland: Holiday Bars and Festive Stops
Chicago has embraced the pop-up holiday bar trend with enthusiasm, offering locals and visitors dozens of themed venues throughout the season. From elaborate three-story establishments to intimate neighborhood spots, these bars compete to create the most memorable festive atmosphere. Many feature specialty cocktails, photo opportunities, and decor that rivals department store window displays.
What makes these experiences even more special is their proximity to some of Chicago's premier attractions. With Chicago CityPASS® tickets, you can explore iconic landmarks during the day before settling in for evening festivities. This combination lets you experience both Chicago's cultural treasures and its seasonal celebrations without zigzagging across the city.
Wrigleyville's High-Energy Holiday Headquarters
Santa Baby
Wrigleyville becomes ground zero for holiday revelry each year, and Santa Baby Christmas Bar leads the charge. This multi-level destination features wall-to-wall decorations that create an immersive holiday experience from the moment you step inside. The bar serves festive cocktails with creative names and presentations, perfect for getting into the spirit. Expect crowds on weekends, as this spot has become a Chicago tradition for those seeking an energetic celebration.
Elf'd Up
If you loved the movie Elf, you'll feel right at home at Elf'd, another Wrigleyville pop-up. With more than 1,000 elf figurines positioned throughout the space, Elf'd Up brings Buddy the Elf's enthusiasm to life. The decor includes references to iconic scenes from the film, and the drinks menu plays along with the theme. This spot attracts a younger crowd looking for Instagram-worthy moments alongside their cocktails.
River North's Dazzling Drinks & Upscale Cheer
Frosty's Christmas Bar
When it comes to Frosty's Christmas Bar Chicago, bigger is better. This three-level establishment has earned its reputation as one of the most elaborate holiday pop-ups in the city. Each floor features distinct decor and atmosphere, from intimate seating areas perfect for conversation to dance floors where DJs keep the energy high. The lighting design alone is worth the visit, with thousands of bulbs creating a glowing winter scene.
Mistletoe at Mordecai
For a slightly more refined take on the Christmas bars in Chicago, Mistletoe at Mordecai offers a winter wonderland theme with sophisticated touches. The drink menu goes beyond basic holiday flavors, incorporating seasonal ingredients into craft cocktails that would satisfy any mixology enthusiast. The elegant decor makes Mistletoe at Mordecai an excellent choice for those who want a festive atmosphere without overwhelming sensory overload.
The Nutcracker Christmas Bar
Located in the stylish Virgin Hotel, the Nutcracker Christmas Bar brings upscale holiday cheer to the River North neighborhood. Tinsel, ornaments, and thoughtful design create spaces that feel both festive and comfortable. You can expect polished service and a crowd that skews slightly older than the Wrigleyville scene. This makes it ideal for those seeking holiday spirit with a touch of sophistication.
Jack Frost Christmas Pop-Up
Jack Frost takes the pop-up concept in a different direction by incorporating a Christmas market experience alongside the bar. You'll find photo opportunities throughout, making it easy to capture memories of your evening. The larger footprint allows for multiple themed areas, so you can explore different vibes throughout the night.
Make a Night of It: What To Do Before or After Your Drink
In addition to these amazing pop-up Christmas bars, many of the attractions in Chicago also get all geared up for the holidays. Here are a few you won't want to miss on your trip:
Art Institute of Chicago
Founded in 1870, the Art Institute of Chicago houses masterpieces spanning centuries and cultures, from ancient artifacts to contemporary installations. After spending a few hours with Van Gogh, Monet, and Picasso, you'll have worked up an appetite for both dinner and those festive cocktails.
Shedd Aquarium
For something completely different, consider visiting the Shedd Aquarium earlier in your day. Located on the Museum Campus along Lake Michigan, this world-class facility houses thousands of aquatic animals. The aquarium's location offers beautiful views of the Chicago skyline, particularly as the sun sets and city lights begin to glow. From there, you can head north to your chosen holiday bar, refreshed and ready for festivities.
Skydeck Chicago
Nothing says Chicago quite like standing on The Ledge at Skydeck Chicago, the glass balconies extending from the 103rd floor of Willis Tower. If you visit during daylight hours, you'll see four states on a clear day. Or visit during sunset for the perfect prelude to experiencing Chicago's nightlife.
Shoreline Sightseeing
During clear weather, consider a Shoreline Sightseeing architecture cruise before your evening plans. These narrated tours showcase Chicago's famous skyline and architectural heritage from the unique vantage point of the Chicago River. You'll learn stories about the buildings that define this great American city while enjoying fresh air and photo opportunities. The cruise docks conveniently near downtown, positioning you perfectly for an evening exploring holiday bars.
Rather than purchasing individual tickets or coordinating multiple reservations, your CityPASS® tickets streamline the planning process. This leaves more energy for enjoying yourself at whichever festive establishments catch your eye.
Cheers to a Magical Chicago Christmas
Chicago's holiday bar scene offers something for everyone, whether you prefer elegant cocktails or all-out festive chaos. By pairing these seasonal experiences with the city's top attractions, you create a fuller picture of what makes Chicago special during the holidays. The combination of world-class museums, breathtaking observation decks, and these temporary winter wonderlands captures both the city's cultural depth and its commitment to celebration.
With Chicago CityPASS® tickets, you'll have everything you need to explore Chicago's top things to do while saving up to compared to regular admission prices. Make this holiday season one to remember — Chicago style.