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Art Trails, Taste Tests, and Gentle Thoughts - Chicago

Uncover hidden art as you explore the city, treat each other to surprise bites, and wrap it all up with words meant just for each other. A date that blends creativity, connection, and a little Chicago charm.

Regular price
$35.00 USD
Unit price
 per 
Art Trails, Taste Tests, and Gentle Thoughts - Chicago
  • Type: Physical

  • Physical

    Your physical package includes an information booklet with tips and 3 separate booklets, each detailing a unique stop on your unforgettable mystery date.

  • Digital

    Your digital copy will be emailed as a PDF, containing a downloadable information guide and 3 booklets with all the details for your exciting mystery date.

What to expect

  • Stop 1: City Strokes

    Wander through alleyways alive with color and clues. Let the murals guide your steps as you uncover hidden gems — and maybe learn something new along the way. Drive time to second stop is about 20 minutes.

  • Stop 2: Bite Surprise

    This next stop is buzzing with local flavor — but the twist is, your partner's ordering for you. Trust the pick, take the bite, and enjoy the moment. Drive time to third stop is about 5 minutes.

  • Stop 3: Windy Words

    Settle into a quiet spot beneath the city skyline. With the day fresh in your mind, take a moment to turn your thoughts into something meaningful to share.

Frequently Asked Questions

How long will it take?

Your adventure will take about 2-4 hours, depending on how much time you choose to spend at each stop. Enjoy the journey at your own pace!

When can we use the date?

This date can be used Monday-Friday and any month of the year.

When should we go?

We recommend going around 10am-11am as a general estimate for an afternoon date or 2pm-3pm for an evening date (beware of traffic!)

Can I bring my dog?

We love our furry friends but unfortunately this date is not pet friendly. Check out our other dates to find one that is for another time!

How much will it cost?

First Stop: Paid Parking

Second Stop: Paid Parking

Third Stop: Paid Parking

Additional costs such as food, gas, and the supplies are not included