Chicagoland

🍸 Prancer’s Pub
2815 Jorie Boulevard, Oak Brook, IL 60523
Dates Coming Soon
A stylish lakeside holiday pop-up inside the Hyatt Lodge, featuring festive cocktails, seasonal bites, and cozy mid-century dècor. More info

🍭 Cocktails & Candy Canes Pub Crawl
9 South Park Avenue, Lombard, IL 60148
Starting December 13, 2025
A fun downtown Lombard holiday pub crawl with festive drinks, swag bags, and charitable giving. More info

🍨 JoJo’s Shake Bar
5 Jackson Ave, Naperville, IL 60540
Dates & Times Vary
A holiday wonderland with over-the-top décor, seasonal shakes, spiked ciders, and themed events. More info

❄️ Baby It’s Cold Outside at Hey Nonny
10 S Vail Ave, Arlington Heights, IL 60005
December 9, 2025 |  6:00 PM
A 1960s-style holiday dinner party with a curated multi-course meal, cocktails, and festive retro ambiance. More info

Chicagoland

🏠 Home Alone Pop-Up Bar
1 N Vail Ave, Arlington Heights, IL 60005
Opened November 12, 2025
A playful holiday pop-up inspired by Home Alone, filled with themed décor, iconic scenes, and specialty drinks. More info

⛄ Creamery Igloo Experience
506 E St Charles Rd, Lombard, IL 60148
Wednesday–Sunday | 4:00 PM — 9:00 PM
Enjoy a 45-minute private session and leave with a take-home Ice Cream Truck featuring two pints you choose. More info

🍺 Noon Whistle Brewing Pints & Presents
800 E Roosevelt Rd, Lombard, IL 60148
November 23, 2025 | 12:00 PM — 5:00 PM
Start the season with festive drinks, great brews, and unique local finds! More info

🎄 The Ugly Sweater Bar Crawl
Chicago, IL
December 13, 2025
Join Bar Crawl Live! at all your favorite bars pubs and clubs for the best ugly sweater pub crawl in the city. More Info

Chicago

🎅 Santa Baby Bar
3505 N Clark St, Chicago, IL 60657
Starting November 21,  2025
A multi-room holiday pop-up with over-the-top décor, themed cocktails, boozy milkshakes, and endless photo ops. More Info

🧝 Elfd Up
3485 N Clark St, Chicago, IL 60657
November 8, 2025 – January 1, 2026
A high-energy Elf-inspired pop-up loaded with elves, themed drinks, Buddy’s Breakfast Pasta, and immersive décor. More Info

⛄ Frosty’s Christmas Bar
809 W Evergreen Ave, Chicago, IL 60642
Dates Coming Soon
A massive holiday pop-up with multiple bars, DJs, dancing, festive cocktails, and life-size décor. More Info

❄️ Jack Frost Fulton Market
170 N Green St, Chicago, IL 60607
November 22, 2025 – January 3, 2026
An outdoor winter pop-up featuring ice skating, holiday cocktails, bumper cars, and festive photo ops. More Info

🕎 Chicago’s Hanukkah Bar
3441 N Sheffield Ave, Chicago, IL
Starting November 21, 2025
A lively Hanukkah-themed pop-up featuring traditional décor, themed cocktails, games, and seasonal celebrations. More Info

Chicago

🍹 Sippin’ Santa
2834 River Road River Grove, IL 60171
Starting November 18, 2025
A tropical tiki-holiday mashup with festive island-style cocktails and cozy seasonal vibes. More Info

🎁 Crawl to Christkindlmarket
3658 North Clark Street Chicago, IL 60613
November 28, 2025 – December 31, 2025
A holiday bar crawl through iconic Chicago neighborhoods ending at the famous Christkindlmarket.More Info

🦌 Rudolph’s Bar
85 E Wacker Dr, Chicago, IL 60601
November 22, 2025 – January 25, 2026
A rooftop holiday bar with panoramic views, heated igloos, festive cocktails, and cozy seasonal ambiance. More Info

🎄 The Official Christmas Bar Crawl
Chicago, IL
December 20, 2025 4PM-12AM
A city-wide crawl featuring multiple festive stops, holiday drinks, and themed entertainment. More Info

Did we miss a holiday pop-up bar or festive cocktail experience? 🍸✨

Our goal is to make it easier for you to discover the best seasonal pop-ups — from cozy heated igloos and retro-themed dinner parties to high-energy movie-inspired bars and festive pub crawls across Chicagoland and Chicago! 🎄

By exploring and supporting these local favorites, you help strengthen our community and keep small businesses thriving throughout the holiday season. 🤎

This season, sip, celebrate, and create unforgettable memories with friends, family, or that special someone — all right here at home. 🎁🏙️

-Brandon Blankenship, Founder of Living Chicago Suburbs & Realtor at Keller Williams Premiere Properties