5 Great Date Ideas in Chicago, IL

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We’d love to share with you locally chosen date ideas - not your typical list - but curated locally through friends and community posts.   Enjoy! 

  1. Picnic at Montrose Beach or Lincoln Park Zoo

    Consider having a picnic at Montrose Beach or Lincoln Park Zoo, where you can enjoy the beautiful scenery and have a relaxed conversation. 

  2. Color-themed dates (e.g., blue-themed activities)

    Plan a color-themed date, such as visiting the Blue Man Group or a jazz club with "blue" in its name. Explore different cuisines based on countries or colors. For example, visit a Japanese toy store, an izakaya, and a sake bar for a Japanese-themed date.

  3. Long walk from Lincoln Park to the zoo, followed by drinks and dinner

    Take a long walk from Lincoln Park to the zoo, enjoying each other's company and the sights along the way. Afterward, find a cozy spot for drinks and dinner.

  4. Magic Lounge for a magical experience

    Experience the magic of The Magic Lounge, where you can enjoy close-up magic performances and a show featuring phenomenal magicians.

  5. Green Mill for jazz and cocktails

    Immerse yourselves in the jazz scene at the Green Mill, a historic jazz club known for its intimate atmosphere and live performances.

Have fun trying out some of these places - recommended by many great folks on Reddit!

For dating tips, Matchmaker Cassindy and the team at Ancient Wisdom Modern Love are here for you - Dating Guidance by Matchmaker Cassindy

Terrific Dates from the West Coast to the East Coast!

Our team shares here just a few playful, romantic, and delicious dating venues in the cities we work in and travel to often across the country.  We love and enjoy great food – so here are just a few for you.

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Our team is here to support you during the dating process – not just the introduction – we are also your allies to showcase you well, find dating venues that highlight you so that your dates can be successful and enjoyable.

If you are looking for real love and ready to meet someone special, we are ready to chat with you and help you find the “One”.