Wondering where to take your valentine? We’re sharing romantic spots that remind us where people, real and fictional, have found love and community in the city.
The Obama Kissing Rock in Hyde Park has a plaque marking where the former president and first lady smooched for the first time after some Baskin-Robbins ice cream.
O'Hare Gate B5 is where U.S. Secretary of Transportation Pete Buttigieg proposed to his now-husband.
The Art Institute is where this newsletter writer’s parents got engaged!
Hollywood Beach, Jackson Park’s Wooded Island, and the old Belmont Rocks have been meetup spots for queer Chicagoans for decades.
Leather Archives & Museum in Rogers Park has all types of history on BDSM culture, leather, kink, and fetish.Next week, we’ll share some last-minute Valentine’s Day date ideas!
Get to Know These Romantic Spots
Sidney Madden
Transportation Secretary Pete Buttigieg proposed to his husband Chasten at O’Hare. (Chris Rycroft / Wikimedia Commons)
Share article
Stay connected to City Cast Chicago and get ready to join the local conversation.
Neighborhood Guides
Your Guide to May 2026
May kicked off with a May Day jolt, and I expect the energy will stay high.
Where to Read in Chicago
It’s National Library Week through April 25 — which is coincidentally Independent Bookstore Day! There’s an official crawl across Chicago...
Celebrate 420 at These Chicago Dispensaries
It’s been a little over 6 years since recreational marijuana was legalized in Illinois. At the time, Gov. JB Pritzker called it the “most...
Is Avondale Really That Cool?
We investigated Avondale ourselves, and think that Time Out might be onto something.
Get to Know Bronzeville
Check out this guide on what to see, eat, and do in this historic Chicago neighborhood.
Walk Around the Bottom of Western With Me!
My stroll to the bottom of Western Avenue took me through West Morgan Park, Kennedy Park, and Beverly Woods.
Wander Through Ford City Mall With Me
Once a haven for young mall rats, Ford City Mall may soon become an industrial park. But it's not gone yet.
Scooter Another Mile Along Western With Me
Today, we’re zooming into the Tri-Taylor Historic District, starting on Madison Street and scooting to Roosevelt Road.
The latest in Chicago
Take This Week's Chicago News Trivia Quiz
How closely were you paying attention to this week's current events? Test yourself in our weekly trivia quiz.
Chicago’s Indoor/Outdoor Bars
Here are some of our favorite bars that offer outdoor patios to grab a drink.
Jim’s and the History of the Maxwell Street Polish
After nearly 90 years in the Maxwell Street Area, Jim’s Original is moving to Pilsen. The stand popularized the Maxwell Street Polish.
New Spots To Dine & Drink in Chicago
Chicago has no shortage of good places to eat around town. Here are some of the bar, restaurant, and café openings we're watching.
Chicago Bridges Quiz
Think you know Chicago bridges? Test your knowledge!
Welcome to The Belmont and Decibel — AKA New Berlin
Decibel is now open in the former Berlin space on Belmont. Comparisons are inevitable.
Chicago Was — Is? — a Magic Town
The Hand & The Eye is a new venue marketing Chicago-style magic. But what is Chicago-style magic?
The End of an Era For Lincolnwood Town Center
Lincolnwood Town Center shuts down April 30 — depending who you ask. I went to the mall to check things out for myself.
