34 Festive Chicago Holiday Party Ideas You Must Try in 2024

As the winds turn crisp in Chicago and twinkling lights adorn the cityscape, it’s time to delve into the heartwarming world of holiday parties.

Of course, any festive celebration calls for a stunning location, and as December approaches, the pressure to create a truly enchanting experience intensifies. But fret not! We’ve scoured the city’s vast options to handpick a selection of bookable venues that will take your party to a whole new level.

Just as Kevin McCallister turned an ordinary home into a holiday wonderland in Home Alone, we’re here to guide you in transforming Chicago into your personal festive playground.

Read on to discover a sleigh-full of creative and captivating holiday party ideas in Chicago that will turn your celebrations into cherished memories. Whether you’re a local Chicagoan seeking fresh inspiration or a visitor looking to experience the Windy City’s festive spirit, we’ve got you covered.

So, grab a mug of hot cocoa, snuggle into your coziest sweater, and let’s unwrap the magic of Christmas in Chicago!

🎄 Classic Holiday Party Ideas

Let’s start with some ideas for those who love a traditional approach to holiday celebrations. Whether you’re planning an elegant party or you’re looking for something laid-back, we’ve got plenty of options to inspire you.

1. Traditional Holiday Feast at Aboyer

📍 Location: 64 Green Bay Road (Glencoe)
💰 Price: from $80 per person
🧑‍🤝‍🧑 Capacity: up to 80 people

Ready to serve up a feast worthy of the holiday season? Embrace the spirit of togetherness with a traditional holiday banquet in one of Chicago’s premier dining establishments. Treat your team to an evening of gourmet culinary delights, basking in the ambiance of a city renowned for its diverse food culture.

This isn’t just a meal; it’s an experience. One that incorporates the spirit of the season with the pleasure of good company and great food. A traditional holiday feast in Chicago can turn a standard company party into an unforgettable celebration. Imagine a banquet table spread that would make even Scrooge crack a smile! Now, who’s ready to pass the gravy?

💡 Pro tip: If you prefer organizing the festive dinner in your office space rather than renting a venue, consider hosting it potluck-style. Sharing homemade dishes will surely be an amazing bonding experience and a money-saver.

2. DIY Ugly Sweater Party at Replay Lincoln Park

Now, who’s ready to unleash their creativity and holiday cheer in equal measure? A DIY ugly sweater party is your chance to combine festive fun with a dash of friendly competition. It’s a party theme that encourages everyone to let their guard down, don their most extravagant holiday attire, and bask in the joy of the season.

Host this playful event at your office, or at a relaxed venue like Chicago’s Replay Lincoln Park. This arcade bar provides a fun and vibrant backdrop for your celebration, featuring a multitude of games and plenty of space to showcase those wonderfully outrageous sweaters. You might even crown the Ugliest Sweater of the Night! So, let’s get creative, and remember—the more tinsel, the better!

📍 Location: G2833 North Sheffield Avenue (Lincoln Park)
💰 Price: from $30 minimum spend
🧑‍🤝‍🧑 Capacity: up to 400 people

🎄 DIY ugly sweater tips:

• Embrace the glitter: Glitter glue or glittery fabric paint can add a festive touch to any sweater. Draw holiday shapes like trees, snowflakes, or reindeer and fill them in with sparkles.
• Go 3D: Don’t limit yourself to the surface of the sweater. Attach small ornaments, tinsel, or even a stuffed reindeer or Santa for a truly standout piece.
• Light it up: Battery-operated Christmas lights can be sewn or glued onto your sweater for a truly illuminating look. Just make sure you can easily remove the battery pack for washing!
• Pom-poms and bells: These craft store staples can be easily sewn or glued onto your sweater. They’re perfect for simulating snowballs or jingle bells.
• Use felt: Felt is inexpensive and easy to work with. Cut out shapes or letters and attach them to your sweater with fabric glue or a needle and thread.
• Don’t forget the back: Many people only decorate the front of their sweater, but adding some decorations to the back can add an element of surprise and extra laughs.
• Make it a group activity: If you’re hosting the party, consider setting up a DIY ugly sweater station with supplies like glue guns, felt, glitter, and scissors. It’s a fun activity and can be a great icebreaker!

3. Holiday Movie Marathon at Chicago Theater Works

When it comes to feel-good festivities, nothing quite matches the joy of cozying up with your favorite holiday classics. A holiday movie marathon invites your team to revisit the films that define the season, all while enjoying each other’s company and a steady supply of popcorn.

To make it even more special, you could organize a private screening at a venue like Chicago Theater Works in Lakeview. Deck the halls, screen blockbusters such as While You Were Sleeping, Home Alone, or It’s a Wonderful Life, and let the magic of these heartwarming stories set the tone for an unforgettable holiday celebration.

📍 Location: 1113 West Belmont Avenue (Lakeview)
💰 Price: from $250 hire fee
🧑‍🤝‍🧑 Capacity: up to 200 people

💡 Pro tip: While preparing the repertoire, you can ask guests to vote for their favorite holiday movies. To spice it up, prepare a game of bingo, where everyone will have to watch out for holiday-related phrases, bits of dialogue, or specific scenes in the movies. Don’t forget to set up a concession stand with snacks and drinks!

4. Christmas Ball at The Ballroom at The Woman’s Club of Evanston

Your colleagues, decked out in their festive finery, waltz across the spacious, beautifully lit dance floor. The room is filled with the sounds of a live band playing holiday classics, and the air is buzzing with laughter, conversation, and the clink of champagne glasses. 

This isn’t just another corporate holiday party—it’s a chance to create a truly magical that perfectly captures the spirit and beauty of the holiday season.

So, step into a world of timeless elegance with a holiday ball at a distinguished ballroom, such as the one at The Woman’s Club of Evanston. With its stunning architectural detail and grandeur, this venue offers the perfect setting to create a night of glamor, sophistication, and festive cheer for your team.

📍 Location: 1702 Chicago Avenue (Evanston)
💰 Price: from $5000 hire fee
🧑‍🤝‍🧑 Capacity: up to 250 people

💡 Pro tip: Step it up by picking a theme, such as a holiday masquerade ball (a time-honored tradition dating back to the Middle Ages!). The dress code is elegant, formal wear. Everyone should wear masks to add an element of mystery and intrigue—you can even have a grand reveal at midnight when everyone will remove their masks.

5. Drinks and Carol-oke at Green Light Pub & Karaoke

Shake things up this festive season with an unforgettable party at the Green Light Pub & Karaoke. This is where your team can unleash their inner Mariah Carey or Michael Bublé and celebrate the holidays with a bit of song, dance, and good-natured fun. 

Located in the heart of Chicago, Green Light offers private karaoke rooms for  groups of 6 to 20. Picture your colleagues belting out festive favorites, a pint in hand, laughter filling the room! It’s a light-hearted, spirited alternative to a traditional holiday gathering, and one that will surely be remembered for years to come. After all, nothing says holiday spirit like a rousing chorus of Jingle Bell Rock!

📍 Location: 2519 West Peterson Avenue (Peterson Park)
💰 Price: from $15 hire fee
🧑‍🤝‍🧑 Capacity: up to 70 people

6. Holiday Wine Tasting at Lush Wine & Spirits

Immerse your team in a world of refined flavors with a holiday wine-tasting event at Lush Wine & Spirits. With their stellar collection of wines and spirits, it’s the ideal spot to bring together loved ones and colleagues.

Lush takes wine appreciation to a whole new level, maintaining their ambiance at a cellar-like 62°F to ensure every bottle is at its prime. And don’t fret about the winter chills; they’ve got these cozy polar fleece shawls to wrap you in warmth.

Whether it’s an intimate gathering or a grand holiday celebration, Lush promises an experience that’ll have everyone raising their glasses in holiday cheer. Here’s to making merry memories!

📍 Location: 1412 West Chicago Avenue (West Town)
💰 Price: from $1500 minimum spend
🧑‍🤝‍🧑 Capacity: up to 100 people

7. Winter Wonderland Party at Navy Pier

Embrace the magic of the season with a Winter Wonderland party at Navy Pier. This iconic Chicago landmark transforms into a dazzling holiday spectacle each winter, offering an enchanting backdrop for your company party.

After you’ve explored Navy Pier’s holiday attractions, enjoy a celebratory dinner at Bar Sol, an upscale restaurant with stunning views of Lake Michigan. With its stylish interior and an excellent selection of food and drinks, it’s the perfect place to celebrate while surrounded by twinkling lights and festive displays. It’s a party that’s sure to leave your team spellbound!

📍 Location: 700 East Grand Avenue (Near North Side)
💰 Price: from $750 hire fee
🧑‍🤝‍🧑 Capacity: up to 300 people

8. Relaxing Evening by the Fire at Charcoal Factory Loft

Want to give your team a holiday party that feels more like a cozy retreat? Consider a relaxing gathering by a fireplace at the Charcoal Factory Loft. This rustic, chic venue in Chicago offers an intimate, warm setting that is just perfect for a low-key, comfortable holiday celebration.

Picture your colleagues unwinding by the fire, hot cocoa, or mulled wine in hand, exchanging stories and laughter as the snow falls gently outside. The relaxed ambiance of the venue makes it feel less like a corporate event and more like a gathering of close friends—perfect for celebrating the holiday season together in a soothing, homey way.

📍 Location: 1684 North Ada Street (Wicker Park)
💰 Price: from $550 hire fee
🧑‍🤝‍🧑 Capacity: up to 100 people

9. Chic Holiday Party at Pops for Champagne

Step up your holiday party game with a chic evening of jazz music and bubbles at Pops for Champagne. This upscale Chicago venue is known for its extensive champagne list and live music, making it the ideal place for a stylish, sophisticated holiday celebration.

Your colleagues will be treated to the smooth sounds of jazz as they sip on premium bubbly, creating a festive atmosphere that’s full of elegance and cheer. The combination of world-class music, exquisite drinks, and the glitz and glamor of this champagne bar is sure to make your holiday event a sparkling success!

📍 Location: 601 North State Street (River North)
💰 Price: from $35 per person
🧑‍🤝‍🧑 Capacity: up to 75 people

⛄ Unusual Holiday Party Ideas

If you want to put a creative spin on holiday traditions and wow your guests with an out-of-the-box party, these ideas are for you!

10. An Unusual Dining Experience at 2D Restaurant

This holiday season, step into a unique world where life imitates art with a 2D dining experience at the one and only 2D Restaurant in Lakeview! This one-of-a-kind venue takes dining to a whole new dimension, transforming your company’s holiday celebration into a whimsical, immersive experience.

As you enter, you’ll feel like you’ve walked into a flat, monochrome comic strip. The stark black-and-white interior creates an illusion of two-dimensionality, providing a surreal backdrop for your festive feast.

Imagine your team seated amidst this playful setting, enjoying a delicious meal while reveling in the joy of a holiday party that’s anything but ordinary. With the 2D Restaurant, you’re not just hosting a holiday event, you’re creating a captivating story straight out of a comic book!

📍 Location: 3155 North Halsted Street (Lakeview)
💰 Price: from $1960 minimum spend
🧑‍🤝‍🧑 Capacity: up to 38 people

11. Victorian-Era Christmas Party at Epiphany Hall

Immerse your team in an age of elegance with a historic-themed holiday party at the iconic Epiphany Hall. This venue, part of the Epiphany Center for the Arts, dates back to 1885 and is an officially recognized local and national landmark. Designed by the acclaimed architectural firm Burling and Whitehouse, the venue impresses with its Richardsonian Romanesque exterior and intricate Eastlake Style interiors.

The heart of your festive celebration will be surrounded by breathtaking Queen Anne details, decorative terracotta tiles, and Venetian glass mosaics designed by Tiffany. Amidst these historic elements, your colleagues will dine and revel under grand arched trusses that frame the room, offering a truly unique holiday experience that blends modern-day comfort with the undeniable charm of this historic gem.

📍 Location: 201 South Ashland Avenue (West Loop)
💰 Price: from $7500 hire fee
🧑‍🤝‍🧑 Capacity: up to 946 people

💡 Pro tip: For an authentic feel, why not ask your guests to dress in period-style attire?

12. A Progressive Dinner Tour at Multiple Restaurants

This holiday season, take your team on a culinary adventure with a progressive dinner tour. The concept is simple yet exciting: rather than having multiple courses at one restaurant, you’ll savor each course at a different locale, experiencing the vibrant food scene of Chicago one delicious bite at a time.

Sample itinerary: Begin your evening with appetizers at a trendy spot in River North, follow it with main courses at a renowned steakhouse in the Loop, and cap off the night with decadent desserts at a cozy bakery in West Town. It’s a moving feast that’s sure to provide your team with a memorable and scrumptious holiday celebration.

💡 Pro tip: Just as Lucy (Sandra Bullock) commutes in the CTA in While You Were Sleeping, invite your party-goers on an “El-train mystery tour.” Start at one restaurant for appetizers, then hop on the El-train to another location for the main course, and finally end up at a dessert bar. All the while, keep the next destination a secret to add to the suspense and excitement.

🍽️ Some of our favorite restaurants in Chicago:

• Wildfire, 📍 River North. A retro-chic steakhouse in Chicago known for its signature dishes like Horseradish Crusted Filet Mignon, Macadamia Nut Crusted Halibut, Wildfire Chopped Salad, and Cedar Planked Salmon.
• Roberto’s Ristorante & Pizzeria, 📍 Elmhurst. A family-owned Italian restaurant in Chicago that is famous for its authentic Neapolitan-style pizzas and wide range of traditional Italian dishes.
• Tanta Chicago, 📍 River North. A vibrant restaurant that brings the flavors of Peru to Chicago. It offers a diverse menu with a unique blend of traditional Peruvian ingredients and innovative culinary techniques.

13. Xmas Dance-Off at Chicago Dance Factory

Let the rhythm of the season take over with a Christmas dance-off at Chicago Dance Factory. This renowned dance studio, nestled in the heart of the Windy City, offers the perfect stage for your team to unleash their inner dancing stars and let loose this holiday season.

Picture your colleagues swaying to the beat of festive tunes, engaging in friendly dance-offs, and even learning a few new moves from professional instructors. It’s a high-energy, unforgettable way to celebrate the holidays, filled with laughter, fun, and a lot of festive grooving!

📍 Location: 219 West Saint Charles Road (Villa Park)
💰 Price: from $250 hire fee
🧑‍🤝‍🧑 Capacity: up to 60 people

14. Christmas Cheers at Ravinia Brewing Company

Raise your glasses to the holiday season with a beer-tasting event at Ravinia Brewing Company. This locally loved brewery, known for its amazing selection of beers, offers an enticing journey into the world of hops, malts, and brewing craftsmanship right in Chicago.

Your team will enjoy a curated selection of Ravinia’s finest brews paired with flavorful Mexican street food. In addition, the restaurant’s urban interior with bright colors and unique design will help you create a relaxed and friendly atmosphere (you can sit on swinging benches—how cool is that?!). So, bring in the holiday cheers!

📍 Location: 2601 West Diversey Avenue (Avondale)
💰 Price: from $80 per person
🧑‍🤝‍🧑 Capacity: up to 150 people

15. The Season of Giving: Charity Gala at Lacuna Events by LM

Celebrate the spirit of giving this holiday season by hosting a charity gala at an elegant venue such as Lacuna Events by LM in the Lower West Side. Partner with a local charity organization and create a meaningful holiday event that is not just about celebrating, but also about making a difference in the community.

Set amidst the eclectic charm of Lacuna, your gala can include fundraising activities like silent auctions and raffles. Imagine your team, dressed in their festive best, engaged in friendly bidding wars, with all proceeds going to a good cause. This is a heartwarming, fulfilling way to embrace the true spirit of the holidays—celebrating joy, community, and the power of giving back.

📍 Location: 2150 South Canalport Avenue (Pilsen)
💰 Price: from $115 per person
🧑‍🤝‍🧑 Capacity: up to 500 people

16. Holiday Club Night at Joy District

Unleash the holiday spirit with a high-energy Xmas party at one of the city’s hottest dance clubs! Joy District is a pulsating nightlife spot in River North known for its lively atmosphere and captivating music. If you’re looking for a sure-fire way to add a dose of groovy fun to your holiday celebrations and get your team up on their feet—this is it!

The club’s electrifying atmosphere and powerful sound system promise an unforgettable night. As your team hits the dance floor and moves to the beat of the hottest tracks, they’ll be creating holiday memories filled with laughter, camaraderie, and a touch of festive wildness. Celebrate this holiday season with the rhythm of joy at Joy District!

📍 Location: 112 West Hubbard Street (River North)
💰 Price: from $5000 minimum spend
🧑‍🤝‍🧑 Capacity: up to 350 people

17. Have Yourself a Polish Little Christmas at Staropolska Restaurant

Chicago is home to one of the largest Polish communities outside of Poland, and the Polish influence is deeply ingrained in the city’s cultural fabric. If you fancy something unique this holiday season, embrace the warmth and richness of Polish tradition with a festive celebration at Staropolska Restaurant!

Located in Logan Square, this beloved eatery is renowned for its authentic Polish cuisine and cozy, inviting atmosphere, making it an ideal venue for a distinctive, culturally-rich holiday party. Your team will delight in a traditional Polish feast, featuring dishes like pierogi stuffed with sauerkraut and mushrooms, red borscht with uszka (small, ear-shaped dumplings), and carp. 

As you break bread together, surrounded by the warm decor and hospitable charm of Staropolska, you’ll experience the joy of the season through the lens of Polish heritage. It’s a heartfelt, flavorful way to experience a different side of Christmas and broaden your festive horizons.

📍 Location: 3030 North Milwaukee Avenue (Logan Square)
💰 Price: from $37 per person
🧑‍🤝‍🧑 Capacity: up to 70 people

18. Tropical Getaway at Pau Hana Lounge

Escape the chill of the Windy City and embrace the warmth of a tropical holiday at Pau Hana Lounge. This exotic oasis, renowned for its Hawaiian delights, will serve as your festive sanctuary where vibrant beach vibes meet Yuletide cheer. 

Surrounded by original decor and the infectious spirit of aloha, your team will be whisked away to an island paradise. Clad in Hawaiian shirts and leis, they’ll savor an array of tropical treats and signature cocktails. So, swap the snowflakes for sand, and replace the cold with the warmth of holiday laughter!

📍 Location: 334 Georgetown Square (Wood Dale)
💰 Price: from $2000 minimum spend
🧑‍🤝‍🧑 Capacity: up to 180 people

19. Holiday Cheer on Wheels with Party Bus Express

Why stay stationary when you can celebrate on the move? Switch things up this festive season, with a party bus experience from Chicago Limo Party Bus. This reputable company provides luxury transportation decked out with all the amenities you need for an unforgettable mobile celebration. 

Your team will climb aboard a stylish, well-equipped party bus, where the festive ambiance is as palpable as it would be at any top-notch venue. Enjoy music, drinks, and laughter as you cruise through the twinkling cityscape of Chicago. It’s a dynamic, exciting way to revel in the holiday cheer—one that keeps the party rolling, literally!

📍 Location: Chicago
💰 Price: from $225 hire fee
🧑‍🤝‍🧑 Capacity: up to 20 people

💡 Pro tip: You can also rent the party bus as a mode of transportation between different venues or activities! Remember the progressive dinner tour we mentioned earlier? You can also plan a bar crawl or a tour of Chicago’s top holiday attractions! (Pssst! We’ve got some hints coming up in the Must-Do Festive Activities in Chicago section of this article!).

20. DIY Cooking Workshop at BLOCK | 25

Stir up some festive cheer with a DIY cooking workshop! This hands-on approach to a holiday celebration offers your team the chance to roll up their sleeves and create their own culinary masterpieces.

In the inviting atmosphere of a professional kitchen, your team will bond over the shared joy of preparing and cooking a holiday meal together. This holiday party is not just about feasting but the fun and camaraderie of making the feast itself. A truly delicious way to celebrate!

📍 Location: 2521 North Halsted Street (Lincoln Park)
💰 Price: from $300 hire fee
🧑‍🤝‍🧑 Capacity: up to 70 people

💡 Pro tip: There are a few ways to go about this idea. You can follow online tutorials or ask your teammates for traditional recipes they make every Christmas and pick a few that you will recreate together. Alternatively, you can book a cooking class or hire a professional chef who will guide you step-by-step and let you in on useful kitchen hacks.

21. Christmas in New Orleans at Nola Bar & Kitchen

Did you know that New Orleans is just around the corner? Nola Bar & Kitchen brings the rich flavors and lively spirit of Bourbon Street right to the heart of Chicago! This hotspot offers an immersive cultural experience that’s as exciting as the city it pays homage to.

As your team mingles amidst the enchanting decor, they’ll be treated to the taste of Nola’s exquisite Creole and Cajun cuisine, bringing a unique twist to your holiday feast. Add in some jazz tunes, a round of signature Sazerac cocktails, and that unmistakable New Orleans zest, and you’ve got yourself a holiday party that’s as lively and colorful as the French Quarter itself.

📍 Location: 3481 North Clark Street (Wrigleyville)
💰 Price: from $4300 minimum spend
🧑‍🤝‍🧑 Capacity: up to 90 people

22. A Festive Golf Tournament at Various Locations

Do you want to organize an intriguing and interactive holiday gathering? Mix business with pleasure as you tee off the holiday season with a festive golf tournament! Rent an indoor golfing venue with state-of-the-art simulators that provide a realistic and thrilling experience, and prepare for a friendly holiday competition amongst your team.

As they swing their clubs and toast their victories, they’ll be creating holiday memories that are on par with the best! It’s an inventive way to incorporate sport, camaraderie, and holiday cheer all in one go.

⛳ Our favorite indoor golfing venues in Chicago:

• Game of Irons, 📍 Oak Brook. With 16 bays and more than 18,000 square feet, this is Chicago’s largest indoor golf facility, also featuring a full restaurant and bar.
• X-Golf Kildeer, 📍 Kildeer. The venue provides 8 best-in-class golf simulators suitable for players of all skill levels, as well as signature food and cocktails.

23. Holiday Bowling at Various Locations

Trade the traditional holiday party for a lively spin on the lanes! Bowling provides a fantastic mix of friendly competition and playful interaction, guaranteed to bring everyone together in a festive spirit.

Amidst the clatter of falling pins and echoes of triumphant cheers, your colleagues will have the chance to showcase their skills (or lack thereof, like me 😂) in a sport where enthusiasm trumps expertise. Fueled by the thrill of the game and the warmth of shared laughter, your team’s bond will strengthen, strike by strike. Choose this party idea for a festive celebration full of energy, excitement, and a little friendly rivalry.

🎳 Our favorite bowling venues in Chicago:

• Timber Lanes Bowling Alley, 📍 North Center. A classic, eight-lane bowling alley in Chicago, known for its vintage charm, league play, and friendly, laid-back atmosphere.
• Kings Dining & Entertainment, 📍 Rosemont. A modern, upscale venue in Chicago offering a unique combination of bowling, dining, and entertainment with gourmet food and cocktails.
• Skyway Bowl, 📍 South Chicago. A historic, black-owned bowling establishment in Chicago’s 10th Ward with old-school vibes, 36 USBC regulation lanes, a pro shop, and a sports bar.

24. Holiday Bouldering Adventure at Brooklyn Boulders

How about an interactive event that will have your team reaching new heights together? Spice up your celebration with an exhilarating bouldering adventure at Brooklyn Boulders, a popular climbing gym in the West Loop.

In this dynamic setting, your team will navigate their way up and around the boulders, cheering each other on as they tackle each new challenge. In between climbs, they can unwind, mingle, and share their experiences, forging connections in a fun and unconventional way. As they ascend the climbing walls, they’ll also be building stronger bonds with each other.

📍 Location: 100 South Morgan Street (West Loop)
💰 Price: from $50 per person
🧑‍🤝‍🧑 Capacity: up to 400 people

25. Gaming Holiday Party at Midlane Esports

Inject a pulse of electrifying excitement into your holiday festivities at Midlane Esports, Chicago’s gaming hotspot. Nestled in vibrant Logan Square, it’s a fusion of advanced gaming tech, congenial atmosphere, and holiday cheer that promises an unforgettable gaming-themed party.

Engage your team in dynamic virtual tournaments, cheer each other on, and savor the camaraderie that blossoms over laughter and libations. This celebration blends gaming euphoria and holiday magic, fostering team connections while igniting a childlike love for games.

📍 Location: 2741 North Milwaukee Avenue (Logan Square)
💰 Price: from $150 per person
🧑‍🤝‍🧑 Capacity: up to 100 people

26. Blues Night at Rosa’s Lounge

Slide into a soulful rhythm this holiday season with a blues night at Rosa’s Lounge, Chicago’s legendary blues hub. Conveniently located in West Town, Rosa’s welcomes your team into a harmonious fusion of toe-tapping live blues music and festive spirit, setting the stage for a truly memorable celebration.

Your team will lose themselves in the infectious blues beats of the city’s top musicians, their shared laughter and camaraderie flowing as smoothly as the melodies. Sink into a symphony of holiday cheer and bluesy indulgence that will strike a chord with your team and create a timeless tune of holiday memories.

📍 Location: 3420 West Armitage Avenue (West Town)
💰 Price: from $3000 minimum spend
🧑‍🤝‍🧑 Capacity: up to 100 people

❄️ Must-Do Festive Activities in Chicago

The enchanting holiday spirit engulfs all of Chicago in the winter months. From shimmering light displays to vibrant holiday markets, these iconic events provide the perfect backdrop for a corporate holiday party and team-bonding experiences.

27. Go Ice Skating

Embrace the chilly charm of Chicago’s winter and glide into a world of icy delight with a team outing at the iconic Millennium Park ice rink. Located in the heart of our beloved city, this rink becomes a vibrant tableau of twinkling holiday lights, laughter, and camaraderie during the festive season, offering your team an enchanting and invigorating experience.

Just a stone’s throw away, you’ll find the Maggie Daley Ice Ribbon, a unique skating destination that twists and turns through the park’s mesmerizing winter landscape. If you’re looking for a captivating holiday activity that embodies the magic of a true Chicago winter—this is it!

28. Visit the Christkindlmarket

The Christkindlmarket probably doesn’t need an introduction. This beloved Chicago holiday staple whisks you straight into the heart of a European Christmas village, with a tapestry of traditions to explore!

Revel in the festive bustle as you wander through the market’s labyrinth of wooden stalls, brimming with artisanal crafts, festive decorations, and gastronomical delights. The aroma of sizzling sausages, sweet pastries, and warm, spiced Glühwein pervades the air, adding an extra dash of holiday charm to your company outing.

The Christkindlmarket also offers a unique team-bonding platform as you navigate the cultural kaleidoscope together. Witness the joy in discovering one-of-a-kind holiday trinkets, the friendly competitiveness in haggling for the best price, and the shared satisfaction in tasting traditional German holiday treats.

29. Christmas Around the World and Holidays of Light

Gift your team a multicultural holiday journey by visiting Christmas Around the World and Holidays of Light, a dazzling annual spectacle held at the Museum of Science and Industry.

This enchanting exhibit fills your senses with the festive spirit as you explore a forest of more than 50 trees, each adorned with unique ornaments representing diverse global traditions. The gleaming lights and beautifully detailed decorations serve as a breathtaking backdrop for a corporate outing steeped in cultural richness and holiday cheer.

So, take this voyage around the world and infuse the holiday season with a deeper sense of unity and appreciation for global festivities.

30. Christmas Club Chicago

Experience the ultimate festive celebration at Christmas Club Chicago, the city’s premier holiday pop-up bar. Infuse your holiday gathering with a jolly spirit as you step into this winter wonderland, where every corner brims with Christmas cheer.

The vibrant atmosphere, adorned with twinkling lights and nostalgic holiday decor, sets the perfect backdrop for a memorable corporate soiree. Sample holiday-themed cocktails, groove to classic Christmas tunes, and participate in joyous yuletide activities.

Beyond the merriment, Christmas Club Chicago offers a bonding experience infused with laughter, shared stories, and holiday nostalgia.

📍 Location: 3460 North Clark Street (Lakeview)
💰 Price: from $2000 minimum spend
🧑‍🤝‍🧑 Capacity: up to 300 people

31. Comedy and Cocktails Night

Kick off your holiday festivities with a comedy and cocktails night in the vibrant heart of the city. Start the evening with a pre-show cocktail gathering, where your team can mingle over festive libations, setting the tone for a night filled with laughter and camaraderie. Let the clinking glasses and lighthearted banter act as a prelude to the evening’s main entertainment.

Guide your team to a holiday-themed comedy show or, for a twist, an improv comedy night! The infectious laughter and shared amusement at the jokes and skits create an environment where work stresses evaporate, replaced by light-hearted enjoyment. The result? A holiday memory that is as refreshing as the cocktails and as unforgettable as the punchlines.

😂 Our favorite places to see comedy shows in Chicago:

• iO Theater, 📍 Lincoln Park. Although it’s well-known for improv shows, iO Theater frequently showcases holiday-themed sketch and improv shows during the festive season.
• The Second City, 📍 Lincoln Park. This iconic Chicago comedy institution typically puts on a variety of holiday-themed shows throughout the season. Check out their mainstage or e.t.c stage for a rotation of hilarious, festive performances.
• The ComedySportz Theatre, 📍 North Side. Known for its competitive improv shows, ComedySportz usually offers fun holiday-themed performances. It’s a great choice for interactive and family-friendly humor.
• The Annoyance Theatre & Bar, 📍 Lakeview. Famous for its unconventional and quirky performances, The Annoyance often hosts unique holiday-themed shows that provide a distinct twist on the usual festive fare.
• Laugh Factory, 📍 East Lakeview. This renowned comedy club often features holiday-themed stand-up performances by both local comedians and nationally recognized performers.

32. Holiday Jazz Night

Indulge in a smooth holiday jazz night in Chicago, a city renowned for its rich musical heritage. Begin the evening at one of the city’s iconic jazz clubs, such as Jazz Showcase or the Green Mill. As your team unwinds in the club’s cozy atmosphere, the sweet melodies of holiday jazz tunes will fill the air, creating an elegant backdrop for your gathering.

Under the soft glow of stage lights, let the music guide your night, with skilled jazz musicians putting their unique spins on festive classics. This immersive experience, amplified by the occasional clink of cocktail glasses, strikes a chord of unity and shared enjoyment.

33. A Night of Lights: Luminaria Celebration

Delight your team with the visual spectacle of Lightscape at the Chicago Botanic Garden! As you explore this enchanting landscape, the radiance of thousands of lights fosters a serene and captivating opportunity for team bonding, while the harmonious mixture of luminous light and peaceful nature forms a timeless holiday memory.

Following your luminous exploration, direct your gaze towards Navy Pier’s dazzling Light Up the Lake to continue your night of lights. Against the backdrop of Lake Michigan, the shimmering reflection of festive lights adds another layer of holiday charm to your outing. This dual adventure of lights, blending natural beauty and urban brilliance, promises an unforgettable holiday experience.

34. Holiday Lights Trolley Tour Party

Gift your team a mobile feast of festive visuals with a Holiday Lights Trolley Tour. Journey through Chicago’s illuminated streets, soaking in the city’s holiday magic from the cozy confines of your private trolley. As you navigate the urban winter wonderland, this unique experience fosters team camaraderie amidst the sparkle and cheer.

Witness the city’s iconic holiday displays, from Michigan Avenue’s glittering storefronts to Lincoln Park’s ZooLights extravaganza. Amidst the oohs and aahs, share stories, laughter, and maybe a flask of hot cocoa, making the trolley not just a mode of transport but a mobile celebration hub.

🎁 Wrapping Up the Holiday Cheer

The Windy City offers a treasure trove of experiences to make your annual holiday party memorable. From a 2D dining experience to an enchanting evening under the stars at Lightscape, the diversity of these experiences is as captivating as Chicago itself.

In this city of broad shoulders and bright lights, each street corner and venue is brimming with the potential to make your corporate holiday party a unique and joyous event. So explore more options on Tagvenue, step out into the vibrant Chicago night, and plan a celebration that mirrors the beauty and festivity of the holiday season. 

Here’s to unforgettable celebrations, laughter-filled nights, and a festive spirit that lights up the Chicago skyline!

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