10 Chicago Christmas 2026 Ideas: Shows, Food & Bars

4.7 (4,369)

Mon – Fri, 09:00 – 17:00

24 W Randolph St

Dr. Seuss’ How the Grinch Stole Christmas! The Mus plays here December 10 and 11. Elephant-throne lighting frames the 2,253-seat hall. I'd make this my Broadway anchor for a holiday night out. Reviewers praise the clear acoustics and ornate 1926 decor, though some flag long entrance lines and crowded restrooms.

4.8 (668)

Tue – Sun, 11:00 – 16:00

410 S Michigan Ave

Inside the Fine Arts Building, Studebaker Theater pairs restored ornate decor with modern sound systems. The hall opened in 1898 for music and opera. A concert, comedy show or podcast taping could fit a Michigan Avenue holiday evening. Reviewers praise the comfortable seating and vintage elevator operators, while noting dark balcony stairs.

4.9 (2,787)

Mon – Tue, 18:30 – 21:00; Wed – Thu, 19:00 – 22:00; Fri – Sat, 16:30 – 00:00 (+1); Sun, 16:30 – 19:00

182 N Wabash Ave

At 182 N Wabash Avenue, one actor downs five whiskey shots while four sober castmates keep a classic script moving. Craft cocktails can be purchased and delivered to your seat during the 90-minute, 21-and-over show. I think its close-up chaos fits a Chicago holiday evening. Reviewers praise the fast pace, cast, crowd interaction and spontaneous improvisation.

4.9 (1,295)

Mon – Fri, 10:00 – 18:00; Sat, 11:00 – 18:00; Sun, 11:00 – 20:30

4450 N Clark St

Founded by Jackie Taylor, Uptown's Black Ensemble Theater stages original revues celebrating African American music history and culture. Its mission is to eradicate racism through musical theater. I'd add a revue to my holiday plans for the vocals and intimate setting. Reviewers praise the high-energy performances, clear sightlines and excellent singing.

4.7 (720)

Wed – Sat, 12:00 – 20:00; Sun, 11:00 – 17:00

2550 N Lincoln Ave

Apollo Theater brings plays, musicals and comedy to Lincoln Park. Its two performance spaces pair a 440-seat main stage with a 50-seat Studio Theater. I'm drawn to the studio's intimate scale for a holiday theater outing. Audience ratings average 4.7 out of 5 across 720 reviews.

Mon – Fri, 12:00 – 18:00; Sat, 10:00 – 16:00

3145 N Sheffield Ave

Vic Theatre opened in 1912 as an affordable alternative to downtown Chicago stages. Live music and comedy now fill its compact main level and upper tier. I'd add a concert to my holiday plans for the balcony's clear sightlines and comfortable seats. Visitor comments note that age limits vary, so check the requirements for the show you choose.

4.4 (101)

Mon – Fri, Sun, 16:00 – 04:00 (+1); Sat, 12:00 – 05:00 (+1)

742 N Clark St

River North's Clark Street Ale House offers rotating craft taps, a broad bourbon lineup and bar stools with backs. The bar has no kitchen, but food delivery is allowed, and dogs are welcome. I'd use it as a late-night stop during a holiday night out. Reviewers rate it 4.4 out of 5 across 101 reviews.

4.8 (2,074)

Mon – Sat, 09:00 – 21:00; Sun, 11:00 – 18:00

1720 N Marcey St

Lincoln Park's Binny's offers wine, craft beer and spirits alongside glassware and bar accessories, making it a practical stop for assembling a holiday gathering. Shelf notes explain varietals, and staff recommendations can point browsers toward an unexpected bottle. I'd linger for the live-jazz tasting-room setup. Customer ratings average 4.8 out of 5 across 2,074 reviews.

4.4 (257)

Mon – Tue, 16:00 – 00:00 (+1); Wed, 16:00 – 02:00 (+1); Thu – Fri, 14:00 – 02:00 (+1); Sat, 11:00 – 03:00 (+1); Sun, 11:00 – 00:00 (+1)

2158 N Halsted St

Four generations of the Glascott family have run Glascott's Saloon since 1937. The Irish pub pairs Guinness on tap with Greek food. I'd put it on my holiday itinerary for a casual gathering with friends. Game nights draw crowds, too. Customer ratings average 4.4 out of 5 across 257 reviews.

4.2 (4,380)

Mon – Sun, 11:00 – 23:00

61 E Madison St

Pizano's Pizza & Pasta on Madison Street has tin ceilings, red-checked tablecloths and sports memorabilia. The menu pairs deep-dish and ultra-thin cornmeal-crust pizzas with classic Italian pasta. I'd build a downtown holiday dinner around a deep-dish pie. Diners praise the buttery deep-dish crust and ultra-thin pizza.