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Thanksgiving at River Roast. (River Roast)
Thanksgiving at River Roast. (River Roast)
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Thanksgiving is right around the corner, and if you’re still finalizing plans for the big day, we have everything you need to know about where to get Thanksgiving mains and sides, pies and desserts, and what wine to pair with it all. Plus, read up on the history of the Chicago Thanksgiving Parade.

Looking forward to the rest of the holiday season, we have a guide to 50 holiday concerts and shows to enjoy in the coming weeks, as well as our top 10 picks for theater on our local stages.

Thanksgiving 2025: 70 Chicago restaurants offering dine in or take out holiday meals

Thanksgiving at Di Pescara. (Anjali Pinto)
Thanksgiving at Di Pescara. (Anjali Pinto)

Preparing Thanksgiving dinner can be an enormous hassle, but you can remove much of the stress by picking up a ready-made meal from a Chicago restaurant or even a version where most of the work is done for you and you just have to roast the bird. Read the story by Samantha Nelson here.

Thanksgiving 2025: 35 Chicago restaurants and bakeries offering pies and dessert

Pie from Buck Russell's Bakery & Sandwich Shop. (Ballyhoo Hospitality)
Pie from Buck Russell's Bakery & Sandwich Shop. (Ballyhoo Hospitality)

If you’re in charge of satisfying sweet tooths, you don’t have to stress out about baking. Chicago area restaurants and bakeries are offering Thanksgiving pies that will provide the perfect end to your meal, whether you’re sticking to the classics, looking to dazzle with something novel, or catering to diners with dietary restrictions. Read the story by Samantha Nelson here.

Thanksgiving wines made simple: 3 Chicago pros, 9 picks, 1 easy guide

The Brotte La Marasque Gigondas. (Maison Brotte)
The Brotte La Marasque Gigondas. (Maison Brotte)

When it comes to choosing wine to share with family and friends, it’s hard not to feel overwhelmed by options. The picks in our guide sit between $20 and $35 — not cheap — but a sweet spot where value and character intersect. Read the story by Anna Lee Iijima here.

Vintage Chicago Tribune: Thanksgiving Parade

Shoppers on Christmas Eve in 1935 paused at State and Madison Streets to listen to horse-drawn carolers that were making a tour of the Loop. The carols were sung by musicians on a wagon drawn by the famous six horse team of Wilson & Co. (Chicago Tribune historical photo) dated Dec. 24, 1935.
Shoppers on Christmas Eve in 1935 paused at State and Madison Streets to listen to horse-drawn carolers that were making a tour of the Loop. The carols were sung by musicians on a wagon drawn by the famous six horse team of Wilson & Co. (Chicago Tribune historical photo) dated Dec. 24, 1935.

In 2024, Chicago’s Thanksgiving Parade turned 90. We looked back at milestones of this popular event, which ushers in the holiday season. Read the story by Kori Rumore and Marianne Mather here.

Top 50 holiday concerts and shows in Chicago, from Cirque du Soleil to ‘Holly Dolly Christmas’

The Kinjaz Dance Crew in "'Twas the Night Before" by Cirque du Soleil, coming to the Chicago Theatre. (Kyle Flubacker)
The Kinjaz Dance Crew in "'Twas the Night Before" by Cirque du Soleil, coming to the Chicago Theatre. (Kyle Flubacker)

’Tis the season when Chicago’s stages give way to Ebenezer Scrooges, George Baileys and Nutcracker princes — plus, the sounds of klezmer, flamenco, bluegrass and Motown. Read the story by Emily McClanathan here.

Top 10 holiday shows in Chicago for 2025: Are you Scrooge, George Bailey or Jinkx this year?

Holidays 2023
Audrey Billings, Brandon Dahlquist, Michael Mahler and Dara Cameron in "It's a Wonderful Life: Live in Chicago!" by American Blues Theater in 2023. (Michael Brosilow)
Michael Brosilow/HANDOUT
Audrey Billings, Brandon Dahlquist, Michael Mahler and Dara Cameron in "It's a Wonderful Life: Live in Chicago!" by American Blues Theater in 2023. (Michael Brosilow)

From the many shows on Chicago stages for the holidays, many of them familiar, we make our list of the 10 best bets this year. Read the story by Chris Jones here.