City Cast Chicago
✈️ Your expert guide to O’Hare and Midway
December 23, 2025 · — Emmi Mack
Okay, Chicago! This is your last newsletter before Christmas.
Let’s review:
- Here’s what movies to watch
- Here’s what live shows to see
- Here’s where to drink
- Here are even more winter festivities
- Here’s where to shop last minute
- And, if you’re really a procrastinator, here are Christmas trees to consider
NOW GO!
What's CITY Talking About
A Deeper Dive Into the City's 2026 Budget
The counterproposal to Mayor Brandon Johnson’s budget passed through City Council. Here are some highlights:
- A higher shopping bag fee
- Increased property taxes for libraries
- A new flat fee on retail liquor sales
- Legalized video gambling
- The sale of city debt to outside collectors [Block Club]
The Best Rejected License Plates from 2025
ICUP — the four letters tell a story. Unfortunately, Illinois’ Secretary of State isn’t interested in hearing it. The office released a slate of rejected plate requests from 2025. In addition to ICUP, the list includes BDASMOM, BBL, BLUBALN, IBPOOPN, and TYPESHT. [WTTW]
- Hmm: But what about ASSMAN? [YouTube: Seinfeld]
City Keeps Partnering With Developer Who Owes Taxpayers Millions
After a risky venture with developer Allison S. Davis, city pension funds lost a combined $54 million. Davis also owes taxpayers $6 million from a mortgage on that project after former Mayor Richard M. Daley gave him an interest-free loan. Davis owes $270,000 in property taxes, too. So why is Mayor Brandon Johnson still doing business with this guy? [Sun-Times]
How to Kill Time at Midway and O’Hare
Chicago’s airports are bustling with record travel. Luckily, we’ve got tips on where to eat, shop, and more once you’re there. Axios’ Justin Kaufmann, who’s covering the massive renovations at O’Hare, shares his expertise on today’s podcast. [City Cast Chicago 🎧]
Sponsored Content
Chicago Vows From Lake to Loop
Whether it’s lakeshore calm or downtown energy, Chicago gives you unforgettable places to say “I do.” Simply Eloped plans small, meaningful elopements and vow renewals across the city. We take care of every detail; you get the kind of day big weddings can’t deliver.
What To Do
Tuesday, Dec. 23
- 🥚 Eggnog-palooza | Fitzgeralds Sidebar | Berwyn
- 😱 “Home Alone” double feature | West Lawn Branch
- 🎨 Bob Ross Painting Night | Nighthawk | Albany Park
- 🛼 Elf Holiday Brunch | MLK Skating and Bowling Center | Auburn Gresham
- 🏀 Mayor’s Holiday Basketball Tournament | Broadway Armory Park | Edgewater
- 🖼️ The Exhibit House | The Water Tower Place | Loop
Wednesday, Dec. 24
- 🎷 Alexander McLean Project - Christmas Eve Celebration | Jazz Showcase | South Loop
- 🛼 Christmas Eve Remix | MLK Skating and Bowling Center | Auburn Gresham
- 🎥 “It’s a Wonderful Life” | Alamo Drafthouse | Wrigleyville
- 🍳 Christmas Eve Brunch with Santa | I|O Godfrey | River North
- 🕎 Matzo Bash | Joy District | River North
- 🎶 Christmas Eve Queen! | Metro | Wrigleyville
Thursday, Dec. 25
- 🍽️ Holiday Meal and Celebration | Center on Halsted | Northalsted
- ☕ Clock That Tea | Uptown Taproom
- 🎅 Christmas movies | ChiTown Drive-In | Pilsen
- 🛳️ Dinner Cruise | Navy Pier
- 🤶 Christmas Carnival Character Bash | MLK Skating and Bowling Center | Auburn Gresham
- 🌸 Winter Flower Show | Lincoln Park Conservatory
- 🤫 Santa's Secret | Pioneer Court | Streeterville
- ⭐️ Stars & Garters After Dark | Stars & Garters | Wrigleyville
If our many events lists, holiday guides, and daily conversations have helped you out this busy season, please show us some love in the Reader’s Best of Chicago awards. Our newsletter and podcast are both nominated 😁
Also, I want to wish you a happy holidays before signing off the rest of this week. Hey Chicago will be back in your inbox for a few days next week though, so look out!
Free · Daily