✨ Chicago Speed Dating | Ages 32–44 | Fancy a Go?

What to Expect

• Meet 8–12 Chicago singles in one evening
• 5-7 minute mini-dates with plenty of variety
• Matches delivered the same day via your MyCheekyDate Smart-Card
• Friendly, attentive host to guide the evening
• Age Group: 32–44

How It Works

After registration, you’ll receive an email inviting you to log in to your MyCheekyDate Smart-Card — a sleek, mobile scorecard that replaces paper and guesswork.
Mark who you fancy meeting again, see their picture to help remind you of your interest, and submit your selections by midnight. Return to our platform after midnight to view your matches — all accessible from mobile, tablet, or desktop. No downloads. No apps. No fuss.

Why Chicago Singles Love It

We believe dating should feel easy, not forced. That’s why we skip the whistles and over-the-top gimmicks. Our “lovely daters” enjoy perks like complimentary events and future discounts for simply being kind, engaging, and genuine. If you’re ready to meet someone special — this is your scene.

The Chicago Connection

Find your match for concerts, foodie festivals, bar crawls, or wellness weekends. Whether you’re new to the city or born and bred, you’ll meet singles who share your spark.

Venue

Recess – 838 W Kinzie St, Chicago, IL 60642
Every venue is chosen for its ambiance, privacy, and comfort — the perfect setting for conversation.

Looking for More?

Explore our Blind-Date Matchmaking Packages ($595–$945) or our Advice Packages for profile and relationship coaching at mycheekydate.com.

Join us for Chicago’s most sophisticated speed dating night — where being lovely has its perks.