City Cast Chicago
💗 Your insider’s guide to V-Day in Chicago
February 5, 2025 · — Ava Wojnowski
Hey Chicago! Valentine’s Day is fast approaching and in a city as big as Chicago, it can be difficult to figure out where to go 💗 The City Cast Chicago team covers romantic dinners, themed cocktails, and more.
Looking for even more specials? Read on 👇
What's CITY Talking About?
Settlement Reached in Dexter Reed Lawsuit
In March 2024, Reed was fatally shot and killed after wounding an officer during a traffic stop. Now, the city is set to pay $1.25 million to Reed’s family. The shooting prompted scrutiny over police traffic stops. [Sun-Times]
How Tariff Threat Affects Chicago Brewers
Local breweries are stuck in a holding pattern after President Donald Trump’s 30-day pause on tariffs on Canadian imports. If the cost of Canadian supplies goes up, brewers question how they’ll stay afloat. [Block Club]
- In the meantime, consider checking out and supporting one of Chicago’s many breweries. [City Cast Chicago 🎧]
Chicagoans Take a Stand
Several businesses around Chicago closed on Monday to protest Trump’s immigration policies. Additionally, more than 100 Chicago schools saw “walk-ins” Tuesday morning led by the Chicago Teachers Union. These demonstrations were part of national actions amid heightened fears of deportation. [NBC Chicago, ABC7]
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What To Do
Wednesday, Feb. 5
- 💼 Chicago Job Fair | 11 a.m. to 2 p.m. | Free | The Loop
- 🤣 Chicago: Teachers Gone Bad | 5-6:30 p.m. | Free | Lakeview
- 🍷 Free Wine Tasting | 5-7 p.m. | Free | The Loop
- 💗 Singles Mixer | 7-9 p.m. | $25 | Irving Park
- 📚 Pages & Palettes: A Family Art Show & Children’s Book Fair | 5:30-7 p.m. | Free | Wheaton
- 🎤 Hurricane Wisdom | 7:30 p.m. | $70+ | River North
Thursday, Feb. 6
- 🎭 Chicago Theatre Week Opening | Various Times | $15+ | Citywide
- 🥳 Valentine’s Day Party (13+) | 9 a.m. to 2 p.m. | Free | Hegewisch
- 🌲 Tiny Tot Adventures | 10 a.m. | Free | Dan Ryan Woods
- 💟 Heart Health Screening | 2:30-6:30 p.m. | Free | North Lawndale
- 👃 Valentine’s Perfume Pop-Up | 5-7 p.m. | Varies | West Town
- ♥️ LGBTQ+ Speed Dating | 6:30-8:30 p.m. | $25 | Wicker Park
- 🎤 Nessa Barrett | 7:30 p.m. | 37+ | The Salt Shed
- 🏅 Chicago Comedy Awards | 8 p.m. | $10 | Logan Square
- 🎵 Ivy Ford | 9 p.m. | $15 | South Loop
Good news for Shakira fans! She will be headlining the Sueños Music Festival alongside Peso Pluma, Don Omar, and Grupo Frontera. We just hope it doesn’t get rained out again ☔
Free · Daily