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. I absolutely LOVE food, bakeries, restaurants, rooftops, patios, parks, shows, comedy, hiking, and am open to any other adventures. So far, these are the places and events I would love to check out, and am open to other ideas.

• Stand-up Comedy!!

  • Robby Hoffman if she ever tours Chicago (check out her Netflix special)

  • I’ve already seen a ton of different comedians live, but am open to seeing them again or others who are not listed here, so just let me know if you have a show in mind!

• Aire Ancient Baths

• Chicago architecture river tour

• Alamo Drafthouse (a meal at the movies)

• Rooftop Cinema Club (outdoor rooftop movies)

• 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

  • I also love omakase w/ sake pairings and sushi in general!

  • Would also love to try an elevated dim sum restaurant or a more traditional spot with carts!!

  • Hot pot too! But please be ready to EAT if you take me here. It defeats the purpose if you can’t eat much, because the point is to load up!!

  • Also deep dish and Detroit style pizza, but with vegan cheese options because I’m lactose intolerant.

  • In general, I love rooftops and patios with a view :)