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5 Things to Do Around Chicago This Weekend

Celebrate that you finally made it through the week with five awesome events around Chicago this week! Every week we at Dream Town scour the city and handpick five things we’re excited about.

From culture and history, to weird culture and history, to checking out some art and theatre; you’ll have no shortage of things to talk about next Monday.


The annual One of a Kind Show and Sale Chicago is an extraordinary holiday shopping event featuring fine arts and crafts from a juried selection of North America’s most talented artists. The four-day show is scheduled during one of the busiest weekends of the year and provides an outstanding opportunity for exhibiting artists to sell to tens of thousands of enthusiastic shoppers in an ideal environment.

  • When: Thur Dec 1 – Sun Dec 4
  • Where: 222 Merchandise Mart Plaza
  • Hours: Thur-Fri 11am – 8pm, Sat 10am – 7pm, Sun 10am – 5pm
  • Admission: starts at $12
  • More Info:


The Navy Pier Winter WonderFest has all the family fun to keep you warm this winter, with ice skating and a plethora of adrenaline-pumping rides including the Arctic Plunge, Snowman Bouncer, and Ice Line Express. The centerpiece of the event is the Chicago Blackhawks indoor ice-skating rink, which grants visitors 170,000 square feet of smooth ice to carve up to their hearts’ content.

  • When: Fri Dec 2 – Sun Jan 8
  • Where: Navy Pier (600 E Grand Ave)
  • Hours: Mon – Thur 10am – 5pm, Fri-Sat 10am –10pm, Sun 10am – 8pm
  • Admission: starts at $10
  • More Info:


The works of William Shakespeare have been a fertile literary source for movies–the richness of his imagery, the durability of his stories, and the universality of his characters have stimulated the imaginations of countless actors and filmmakers. Enjoy a carefully curated series of ten film adaptations of the Bard’s plays and rediscover why his work remains timeless centuries after his death.

  • When: Sat Dec 3 – Thur Jan 5
  • Where: Siskel Film Center (164 N State St)
  • Hours: see schedule
  • Admission: starts at $6 for members and $11 for non-members
  • More Info:


Stay on your toes this holiday season at the annual Dance Along Nutcracker at the Chicago Cultural Center. Taking place under the majestic Tiffany stained-glass dome in Preston Bradley Hall, this event invites dancers of all ages and abilities to join professional members of Ballet Chicago in celebrating the beloved Tchaikovsky classic. One hour before each performance, participants will be taught basic ballet positions and movements.

  • When: Sun Dec 4
  • Where: Chicago Cultural Center (78 E Washington St)
  • Hours: 12pm and 3pm
  • Admission: Free
  • More Info:


Acclaimed cabaret singer David Edelfelt, accompanied by pianist Beckie Menzie, presents this spectacular evening of both traditional holiday songs and newer gems. Hailed as “a consummate song interpreter,” Edelfelt has entertained and delighted Chicago audiences with his rich vocals and stage presence, and has updated his usual repertoire with some new surprises.

  • When: Fri Dec 2 / Sun Dec 4
  • Where: Fri–Skokie Theater (7924 N Lincoln Ave, Skokie) / Sun–Davenport’s (1383 Milwaukee Ave, Chicago)
  • Hours: Fri 8pm / Sun 7pm
  • Admission: Fri $25 / Sun $20 cover + 2-drink minimum
  • More Info:

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