The Best Way To Experience A Weekend In Chicago

If you and your friends are looking for a mix of culture, glam, and relaxation this weekend, here’s the perfect Friday-through-Sunday itinerary to keep things fun and interesting.


Friday: Explore the Art Institute of Chicago & Grab Dinner Downtown

📍 The Art Institute of Chicago | Friday, February 21 | 5:00 PM – 8:00 PM

Start your weekend with a laid-back but inspiring evening at the Art Institute of Chicago. Whether you’re an art lover or just looking for something different, this museum has something for everyone—from world-famous Impressionist paintings to contemporary works.

🔥 Why it’s a great Friday plan:

  • The museum stays open until 8:00 PM, so you don’t have to rush.
  • You can check out legendary pieces like Van Gogh’s “The Bedroom” or Chagall’s stained glass windows.
  • It’s a low-key but interesting way to start the weekend, perfect before grabbing dinner.

Afterward, grab a meal at a nearby restaurant—whether it’s The Gage for upscale pub food or Lou Malnati’s for a deep-dish fix.


Saturday: Get Your Glam on at Junior Council’s Snowball Gala

📍 Palmer House Hilton | Saturday, February 22 | 8:00 PM – Midnight

Saturday is for getting dressed up and partying for a good cause at the Junior Council’s Snowball Gala. It’s one of Chicago’s best winter events, featuring:

Live music & DJs
An open bar & gourmet food
A stunning, historic venue
A massive dance floor

Plus, it’s all for a great cause, benefiting Lurie Children’s Hospital. So, if you’re looking for a reason to break out your best formal wear and dance the night away, this is it.

🎟 Tickets & Info: Check out Junior Council’s website


Sunday: Cozy Up at the Music Box Theatre for a Classic Film

📍 Music Box Theatre | Sunday, February 23 | Afternoon or Evening

After two nights out, Sunday is the perfect time to slow things down. Head to Music Box Theatre, Chicago’s most charming independent cinema, for a classic, indie, or cult-favorite film.

🔥 Why it’s a great Sunday plan:

  • The theater has a vintage, cozy atmosphere, making it ideal for a chill evening.
  • They often screen throwback movies, so you might catch an 80s or 90s classic.
  • You can grab a warm drink, popcorn, or even a craft beer and settle in.

It’s the best way to wind down the weekend without feeling like you wasted it.

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