The Lincoln Park Zoo makes for a great first date, and not just because it’s free (but also, that’s pretty cool). Much like a festival, the zoo itself provides plenty of conversation starters, so you probably won’t have to worry about awkward silence. Plus, it’s in Lincoln Park, which is a great neighborhood for grabbing lunch or dinner after you’re done staring at wild animals together.
Learn about our tallest and most impressive buildings
Any kind of Downtown tours have the reputation that they’re for tourists, but that’s a shame. There’s plenty for Chicagoans to learn about their city, and an architecture walking tour makes for an awesome date. For starters, you’re not piling onto a bus or a boat, so you’re not trapped. And secondly, Chicago’s architecture is awesome, period. This is the perfect option if you want to impress your date with how cultured you are, but don’t want to sit in a dark theater or walk through a museum for two hours.
Hit up any of the many festivals in town
Chicago has an unbelievable number of festivals and markets throughout the summer months, and these events make for a perfect date: There’s plenty to see if conversation dwindles, but there’s also ample opportunity to talk as you wander through if the chemistry is really working in your favor. Whether you want to eat and drink in a zoo or listen to gospel music, there’s a festival for you.
Dive under the covers at a blanket fort party
If you’re in the mood for partying in your super badass Avengers pajamas, Blanket Fort is a new variety show in the Flat Iron Arts Building that combines pajamas and a BYOP (bring your own pillow) policy with improv, sketch, music, stand-up, and other weirdness every second Sunday of the month. Admission is just $5.