- Event Overview
About
Chicago, IL
Ugly Sweater Pub Crawls
Chicago’s Ugly Sweater Pub Crawl brings the City of Broad Shoulders’ bar culture and Midwest holiday spirit to the holiday sweater tradition. Wicker Park and the surrounding neighborhoods have developed into one of the most celebrated bar scenes in America and on ugly sweater night the combination of Chicago’s beloved creative culture, the world-class bar quality, and the excellent local bars creates a holiday celebration with a Chicago energy that is genuinely one of the best ugly sweater crawl experiences in the country.
Our Chicago route moves through Wicker Park and the surrounding bar district, stopping at venues that represent the full quality of what Chicago’s extraordinary bar scene has built. The ugly sweater competition in Chicago draws on the creative energy of a world-class city and the entries reflect that Second City combination of comedic tradition, architectural excellence, and genuine Chicago holiday passion.
December in Chicago is cold, typically ranging from 18 to 28 degrees at night, with the famous Lake Michigan wind. The Windy City in December has a spectacular energy with the Magnificent Mile lit up for Christmas and the neighborhoods creating their own holiday magic. Chicago ugly sweater night has the scale and quality of America’s greatest Midwest city.
Our hosts manage the Chicago route with local knowledge. Specials are confirmed, wristbands handle entry at every stop, and the ugly sweater contest brings Second City creativity to the holiday season.
Event Detalis
Everything you need to know about the Chicago Ugly Sweater Bar Crawl.
VIP Wristband
Largest Pub Crawl Event
Top Chicago Ugly Sweater Bar Crawl
40,000+ Attendees
Thousands join the annual Chicago Ugly Sweater Bar Crawl
100+ Participating Bars
Organized Event
- What's Included
What You Get With a Pub Crawl Ticket
Pub crawls for the biggest party holidays. Choose your event and join the party in 100+ cities across the USA.
Ugly Sweater Contest
The most outrageous sweater wins a prize.
Welcome Drink at Check-In
Included with your ticket.
Drink Specials at Every Stop
Exclusive holiday pricing throughout the route.
Official 2025 Wristband
One wristband for every venue on the crawl.
On-Site Hosts
Our team manages the route and the sweater competition.
VIP Entry at Select Venues
Priority access at participating bars.
Holiday Party Gear
Festive accessories at check-in.
Pub Crawl Route
The crawl covers the best bars in the city’s top bar neighborhood.
Participating Venues on the Pub Crawl Route
The 2026 Chicago Ugly Sweater Bar Crawl route runs through State Street / Capitol Square. All stops within walking distance. Full lineup sent to ticket holders before the event.
How the Pub Crawl Works
Four simple steps to join the Chicago Ugly Sweater Bar Crawl and start bar hopping.
Purchase at pubcrawls.com.
7:00 PM. Address with ticket confirmation.
Welcome drink, wristband, holiday gear. Route starts at 7:30 PM.
Hosts guide the group through venues all evening.
Event Agendas
Your complete Chicago Ugly Sweater Bar Crawl timeline from check-in to after-party.
Frequently Asked Questions
Everything you need to know about the Chicago Ugly Sweater Bar Crawl.
Where does the crawl start?
Chicago IL. Exact address with ticket purchase.
What is the weather like?
Chicago IL in December averages 18 to 28 degrees at night. Cold Windy City winter with lake effect wind. Full winter gear required.
Is there a dress code?
Ugly sweaters are the theme. The more outrageous the better.
What is included?
Welcome drink, wristband, drink specials, holiday gear, ugly sweater contest.
Group bookings?
Ten or more get priority entry. Contact pubcrawls.com.
Age requirement?
21 and over with valid ID.
Can I buy at the door?
Subject to availability. Buy in advance.
Is the event walkable?
Yes. All venues are within walking distance on the route.
