Your Chicago Holiday Guide: Festive Fun This Weekend!

Chicago is buzzing with holiday spirit this weekend, offering a rich tapestry of events from musical performances to family-friendly outings. Whether you’re seeking a classic sing-a-long, unique local shopping, or vibrant concerts, the city has something special for everyone to enjoy as the festive season kicks into full gear.

Unwrap Chicago’s Holiday Magic

Melodies of the Season: Concerts & Live Performances

Get into the festive groove with a variety of musical acts gracing Chicago stages:

• Pentatonix: Christmas in the City Tour – The acclaimed a cappella group brings their holiday harmonies to the Chicago area. Catch them performing classics like “Hallelujah” and “12 Days of Christmas.”
  When: 7:30 p.m. Dec. 2
  Where: Allstate Arena, 6920 N. Mannheim Road, Rosemont
  Tickets: From $52.50 at rosemont.com
• Straight No Chaser: Holiday Road Tour – Celebrating over 25 years, this Indiana University-formed a cappella group performs Christmas favorites.
  When: 3 p.m. Nov. 29
  Where: The Chicago Theatre, 175 N. State St.
  Tickets: From $57.60 at msg.com
• Sleeping At Last: Home for the Holidays – Ryan O’Neal, known as Sleeping At Last, joins the Chicago Philharmonic for a “moving and nostalgic evening” featuring Christmas songs and more.
  When: 7:30 p.m. Nov. 29
  Where: Auditorium Theatre, 50 E. Ida B. Wells Drive
  Tickets: From $53 at auditoriumtheatre.org
• Erykah Badu: Mama’s Gun 25th Anniversary – Experience two nights with the neo-soul icon as she celebrates 25 years of her acclaimed album. Known for her “Afrofuturistic universe” and “cosmic wisdom.”
  When: 8 p.m. Dec. 2-3
  Where: The Chicago Theatre, 175 N. State St.
  Tickets: From $105.15 at msg.com
• “Viva El Palenque” – Enjoy a joint appearance by two classic Sinaloan bands, Banda El Recodo and La Arrolladora Banda El Limón, both entertaining crowds for decades with traditional Mexican music.
  When: 8 p.m. Nov. 29
  Where: Allstate Arena, 6920 N. Mannheim Road, Rosemont
  Tickets: From $82.70 at rosemont.com

Family Favorites & Enduring Traditions

Create lasting memories with these beloved Chicago holiday traditions:

• CTA Holiday Train and Bus – Keep an eye out for Santa on the festively decorated “L” trains and buses, a tradition over 30 years old. Enjoy photo opportunities with Santa and know that this initiative also helps deliver over 400 food baskets to community organizations.
  When: Through Dec. 22 on various routes
  Fares: Normal rates apply. View schedule at transitchicago.com
• “The Sound of Music” Sing-A-Long – Join the annual holiday tradition at the Music Box Theatre, singing along with Julie Andrews and Christopher Plummer in this Rodgers and Hammerstein classic. Be warned, it sells out quickly!
  When: Through Dec. 4
  Where: Music Box Theatre, 3733 N. Southport Ave.
  Tickets: From $12 at musicboxtheatre.com

Explore & Experience Chicago: Beyond the Stage

Beyond concerts and classic films, discover more ways to enjoy the city:

• Small Business Saturday – Support local businesses across Chicago’s neighborhoods on Nov. 30. Chambers of commerce from Bronzeville to Rogers Park are organizing special perks for shoppers. For a market experience, check out the Holiday Gift Market at the Salt Shed, featuring artisans and vintage vendors.
  When: Nov. 30 (Salt Shed market 11 a.m.-5 p.m.)
  Where: City-wide, and Salt Shed, 1357 N. Elston Ave.
  Cost: Salt Shed market is free with RSVP at ticketweb.com
• City of Chicago Ice Rinks Open – Lace up your skates! Nine Chicago Park District ice rinks, including the famous Maggie Daley Skating Ribbon, are opening this weekend (weather permitting). The Morgan Park Sports Center also offers indoor skating.
  When: Starting this weekend
  Where: Various locations throughout Chicago
  Details: chicagoparkdistrict.com
• Community Bonfire at Maggie Daley Park – Warm up by the fire, meet neighbors, and learn about local wildlife. Don’t forget to bring your own marshmallows – roasting sticks will be provided! A brief campfire building lesson starts at 5 p.m.
  When: 5-7 p.m. Dec. 2
  Where: Maggie Daley Park, 337 E. Randolph St.
  Cost: Free. Details at chicagoparkdistrict.com

Frequently Asked Questions About Chicago Holiday Events

• What are the dates for the CTA Holiday Train?
  The CTA Holiday Train and Bus run through December 22nd, bringing festive cheer and delivering food baskets across the city.
• Are there any free holiday events this weekend in Chicago?
  Yes! The Community Bonfire at Maggie Daley Park on December 2nd is free, and the Holiday Gift Market at the Salt Shed on November 30th offers free RSVP.
• Where can I go ice skating in Chicago this winter?
  The City of Chicago offers nine Park District ice rinks, including the popular Maggie Daley Skating Ribbon, opening this weekend. For an indoor option, consider the Morgan Park Sports Center.
• Is the “Sound of Music” Sing-A-Long good for families?
  Absolutely! It’s an annual, family-friendly holiday tradition at the Music Box Theatre. However, tickets tend to sell out quickly, so it’s wise to book in advance.
• What is Small Business Saturday and when is it?
  Small Business Saturday is on November 30th. It’s an initiative encouraging holiday shoppers to support local businesses across various Chicago neighborhoods, often with special perks and markets like the one at the Salt Shed.

Embrace the festive energy of Chicago this weekend by diving into these unique local experiences. Don’t forget to check specific event details and ticket availability to make the most of your holiday celebrations!

Unwrap Chicago Holiday Magic This Weekend