Chicago Date Ideas

I just moved here summer of 2025, so I don’t know much about the city yet! I haven’t had a ton of time to explore and will gradually be adding more onto this page. So far, these are the places and events I would love to check out, and I’m also open to other ideas:

• Restaurants:

  • Filipino dinner tasting menu at Kasama

  • Bavette’s Steakhouse

  • Lula Cafe

  • Daisies

  • Cindy’s Rooftop (mainly for the view)

  • Afternoon Tea Party at Kale My Name (a vegan spot)

  • Alice & Friends Vegan Kitchen

• Aire Ancient Baths

• Chicago architecture river tour

• Rooftop Cinema Club (outdoor rooftop movies)

• Alamo Drafthouse (a meal at the movies)

• Hamilton: March 4-April 26, 2026

• Standup Comedy: I’ve already seen a ton of different comedians live, but one I haven’t seen and am currently obsessed with is Robby Hoffman. Of course also open to seeing others, so just let me know if you have a show in mind!