AI
Exploring the Hidden Chicago date idea illustration

Don't like the image? Click here to regenerate

Exploring the Hidden Chicago

Duration: 3-4 hours
Budget: $20-$30

This date idea is perfect for the adventurous couple who are up for an exciting and physical evening exploring hidden gems of Chicago, even on a tight budget.

Add to favorites
  • Get ready to explore the enchanting city of Chicago. You'll go from exploring hidden art murals to trying out city's local food, all while admiring the famous skyline.
  • Your adventure begins by hitting the hidden art murals in Pilsen neighborhood. This is followed by a walk or cycle along The 606, an elevated, 2.7-mile-long trail lined with art installations, observation points, and native plants.
  • Just as the sun is setting, head to any rooftop where you can enjoy a bring-your-own-picnic and the city's skyline. End your date with a visit to Navy Pier for a free dazzling fireworks show.

Preparation steps:

  • Wear something comfortable that you don't mind getting a bit dirty. Athletic shoes would be perfect for the walking and cycling.
  • Pack light snacks, water, and your favorite drinks for the rooftop picnic. Don't forget a blanket to sit on.
  • Bring your smartphones with fully charged batteries for taking lots of pictures.

Some tips:

  • Start your adventure early so you can make the most of your time.
  • If you're unfamiliar with the city, consider using a navigation app or a map to help you reach your sketched destinations.
  • Be sure to check out the exact timing of the weekly Navy Pier fireworks show in September.

Recommended locations:

Looking for a custom romantic story?

Discover the magic of our AI Story Generator where you and your partner become the main characters in your own love story.


Write a Story

Try it for free