Butch McGuires | Check it out

20 W. Division Street
312.337.9080
Sun-Fri until 4am
Sat until 5am

Butch McGuires is a year-round Chicago staple, but during the holiday season this pub becomes something spectacular. The college pennants that typically hang from the ceilings are replaced by an inordinate amount of christmas lights, ornaments, and bells. A double-decker toy train — presumably the Polar Express! — encircles the front room dangling above the bar. Patrons of Butch’s are always a fun time, but during the holidays you’re sure to make a few new friends, and have a few too many pints.

Glascott’s Groggery | Check it out

2158 N. Halsted St.
773.281.1205
Sun-Fri until 2am
Sat until 3am

Pass by Glascott’s during the winter months and you’re bound to crack a smile, no matter how bah-humbug you’re feeling. Massive wreaths adorn each of the bar’s large windows, while holly and lights add extra holiday cheer. Glascott’s is the perfect place to bring the out-of-town cousins for a few drinks… or to get away from the fam when you’ve hit your limit!

River Shannon | Check it out

425 W. Armitage
312.944.5087
Sun-Fri until 2am
Sat until 3am

This festive drinkery has occupied its corner spot in Lincoln Park since 1946, and continues to bring in the crowds, including everyone from stock brokers to college students. River Shannon is of the mindset “go big or go home”… that’s why no matter what the holiday, the decorations are sure to stand out above the rest. Halloween is our favorite here — but Christmas is no exception. Stop by for a pint and enjoy the festive decor and friendly atmosphere.

Simon’s Tavern | Check it out

5210 N. Clark St.
773.878.0894
Sun-Fri until 2am
Sat until 3am

Following in its Swedish heritage, Simon’s still serves glögg during the holidays (hot port wine blended with raisins, Swedish vodka, and other spices). A large fireplace warms the bar, and festive decorations (and a super friendly staff) make the place feel like home. Simon’s has been around since 1934… we tend to take that as a good sign!

Palm Court at the Drake Hotel | Check it out

140 E. Walton St.
312.787.2200
Sun-Thurs until 12am
Fri-Sat until 1am

If you’re looking for a holiday drinking spot that’s a little more demure, Palm Court at the Drake beckons. Though mostly known for its elegant high tea, this spot also serves up cocktails and wine to both tourists and locals alike throughout those blustery winter evenings. Dress to impress, and look forward to majestic decor and a cosmopolitan yet nostalgic night on the town.