Holiday in Chicago

Saturday, Oct 3

Violet Ultra’s Le Voulez Boo

The Newport Theater

Join Trae Crowder for a night of comedy at Cap City Comedy Club. A great event for fans of stand-up humor.

Saturday, Oct 3

Oktoberfest

The Boss Bar

Join us for an epic Oktoberfest celebration with food and drinks at The Boss Bar. Great for beer lovers.

Monday, Oct 5

Creepin’ It Real: A Spooky Sketch Show

UP Comedy Club

Enjoy a Halloween themed sketch comedy show in Chicago. Perfect for fans of spooky humor and comedy lovers alike.

Saturday, Oct 10

Raks Inferno: Halloween Cirque Burlesque

The Newport Theater

Experience Raks Inferno, a Halloween burlesque circus at The Newport Theater. Enjoy spectacular performances in a unique setting.

Thursday, Oct 29

Italoween

The California Clipper

Celebrate Italoween with Nolia & Pen Pals, featuring Italo Disco and more. A great night for dance music fans.

Friday, Oct 30

Halloween Party at Howl at the Moon

Howl at the Moon Chicago

Join the Halloween weekend party at Howl at the Moon with live music and a costume contest. A lively night for partygoers.

Friday, Oct 30

Halloween Party at Howl at the Moon Chicago

Howl at the Moon Chicago

Celebrate Halloween with live music and a costume contest at Howl at the Moon Chicago. A lively night for party-goers.

Saturday, Oct 31

Slightly Spooky Saturday

Navy Pier

Celebrate Halloween with trick-or-treating and live entertainment at Navy Pier. A festive event for families.

Sunday, Nov 1

The Rocky Horror Picture Show

The Chicago Theatre

See The Rocky Horror Picture Show at The Chicago Theatre for a spooktacular night. Perfect for fans of cult classic cinema.

Sunday, Nov 1

I|O Godfrey Halloween 2026

IO Godfrey Rooftop Lounge

Join the Halloween celebration at IO Godfrey Rooftop Lounge in Chicago. A must for fans of themed nightlife and music.

Sunday, Nov 1

Do The Needful - Live on Halloween

Skylark

Enjoy a vibrant Bollywood performance by Do The Needful this Halloween. Perfect for music lovers and dance enthusiasts.

Sunday, Nov 1

SATURDAY OCTOBER 31: GOOFAZZ HALLOWEEN COMEDY SHOW

The Comedy Bar

Join the Goofazz Halloween Comedy Show for a night of laughs and costumes at The Comedy Bar in Chicago.

Sunday, Nov 1

HALLOWEEN LATE NIGHT TIL 5AM with DJ N. Harmonix + Devinci Spinns

Hopsmith Chicago

Dance from 9 PM to 5 AM at Hopsmith Tavern with DJs N. Harmonix and Devinci Spinns. Perfect for Halloween party-goers.

Sunday, Nov 1

Brandon Good's Halloween Spooktackular with Roxy Swain as Dolly Parton

Broken Hearts

Enjoy a lively Halloween night with Brandon Good and Roxy Swain performing as Dolly Parton. Great for country music fans.

Tuesday, Nov 3

HERE: for the holidays

The Newport Theater

Celebrate the night before the Midterm Elections with a special event. Great for those looking to engage in the holiday spirit.

Saturday, Nov 21

River North Pole - A family fun indoor event with Santa and Mrs. Claus!

Trump International Hotel & Tower® Chicago

Join us for a family fun day with Santa and Mrs. Claus at the River North Pole event.

Thursday, Nov 26

Thanksgiving

Mother Hubbard's Sports Pub

Celebrate Thanksgiving with a feast at Mother Hubbard's Sports Pub with friends and family.

Thursday, Nov 26

Thanksgiving Dinner Buffet in the Grand Ballroom

Trump International Hotel & Tower® Chicago

Experience a memorable Thanksgiving dinner buffet at Trump International Hotel & Tower in Chicago.

Friday, Nov 27

Thanksgiving Feast for 10 People at Home

Fairmont Chicago, Millennium Park

Enjoy a luxurious Thanksgiving feast prepared by our culinary team. Perfect for families celebrating the holiday at home.

Friday, Nov 27

Rudolph Runs Wild

The Second City

Enjoy a festive interactive show with family-friendly comedy and songs. Perfect for kids and adults looking for holiday fun.

Saturday, Dec 5

Godfrey Holiday Cocktail Fest - Cocktail Tasting

IO Godfrey Rooftop Lounge

Enjoy a variety of seasonal cocktails at this unique tasting event. Perfect for cocktail lovers and holiday enthusiasts.

Thursday, Dec 10

Caroline & Laura's Holiday Spectacular!

The Newport Theater

Join Caroline & Laura for their 10th Holiday Spectacular at The Newport Theater. A festive event filled with music and fun.

Monday, Dec 14

Jamie Shriner: Home for the Holidays 12/13/26

The Lincoln Lodge

Join Jamie Shriner for a holiday-themed comedy show at The Lincoln Lodge. Perfect for holiday fun.