From River North to Wicker Park, Chicago brings warmth, confidence, and chemistry. MyCheekyDate hosts boutique, host-led speed dating events designed for real conversation and connection. Curious about the local dating vibe? Explore Cheeky Thoughts: Chicago Edition. Prefer something more curated? Curated Introduction Packages are available in Chicago, while those seeking a more private, premium approach can explore Luxury Matchmaking, a founder-led experience built from these same real-world communities.

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OCTOBER 31ST 2026 | SATURDAY NIGHT SPEED DATING @ RECESS | AGES 25-39

Speed Dating @ Recess - October 31st 2026

Ages: 25-39 | 7:30PM

838 W Kinzie St, Chicago, IL 60642

Early Bird Admission - Ends 10/23 | $32.95

Regular Admission | $36


NOVEMBER 1ST 2026 | SPEED DATING @ RECESS | AGES 32-44

Speed Dating @ Recess - November 1st 2026

Ages: 32-44 | 6PM

838 W Kinzie St, Chicago, IL 60642

Early Bird Admission - Ends 10/27 | $32.95

Regular Admission | $36


NOVEMBER 7TH 2026 | SATURDAY NIGHT SPEED DATING @ RECESS | AGES 25-39

Saturday Night Speed Dating @ Recess - November 7th 2026

Ages: 25-39| 7:30PM

838 W Kinzie St, Chicago, IL 60642

Early Bird Admission - Ends 11/02 | $32.95

Regular Admission | $36


NOVEMBER 8TH 2026 | SPEED DATING @ RECESS | AGES 36-48

Speed Dating @ Recess - November 8th 2026

Ages: 36-48| 6PM

838 W Kinzie St, Chicago, IL 60642

Early Bird Admission - Ends 11/03 | $32.95

Regular Admission | $36


NOVEMBER 14TH 2026 | SATURDAY NIGHT SPEED DATING @ RECESS | AGES 29-42

Saturday Night Speed Dating @ Recess - November 14th 2026

Ages: 29-42| 7:30PM

838 W Kinzie St, Chicago, IL 60642

Early Bird Admission - Ends 11/09 | $32.95

Regular Admission | $36


NOVEMBER 15TH 2026 | SPEED DATING @ RECESS | AGES 32-44

Speed Dating @ Recess - November 15th 2026

Ages: 32-44| 6PM

838 W Kinzie St, Chicago, IL 60642

Early Bird Admission - Ends 11/10 | $32.95

Regular Admission | $36


NOVEMBER 21ST 2026 | SATURDAY NIGHT SPEED DATING @ RECESS | AGES 25-39

Saturday Night Speed Dating @ Recess - November 7th 2026

Ages: 25-39| 7:30PM

838 W Kinzie St, Chicago, IL 60642

Early Bird Admission - Ends 11/02 | $32.95

Regular Admission | $36


NOVEMBER 22ND 2026 | SPEED DATING @ RECESS | AGES 36-48

Speed Dating @ Recess - November 22nd 2026

Ages: 36-48| 6PM

838 W Kinzie St, Chicago, IL 60642

Early Bird Admission - Ends 11/17 | $32.95

Regular Admission | $36


NOVEMBER 28TH 2026 | SATURDAY NIGHT SPEED DATING @ RECESS | AGES 29-42

Saturday Night Speed Dating @ Recess - November 28th 2026

Ages: 29-42 | 7:30PM

838 W Kinzie St, Chicago, IL 60642

Early Bird Admission - Ends 11/23 | $32.95

Regular Admission | $36


NOVEMBER 29TH 2026 | SPEED DATING @ RECESS | AGES 32-44

Speed Dating @ Recess - November 29th 2026

Ages: 32-44| 6PM

838 W Kinzie St, Chicago, IL 60642

Early Bird Admission - Ends 11/24 | $32.95

Regular Admission | $36


Chicago Speed Dating, Hosted with Experience

MyCheekyDate hosts professionally organized speed dating events in Chicago, bringing together local singles for structured, in-person conversations — no swiping, no guesswork. With over 1,700 events hosted in Chicago and more than 26,000 across 50+ cities, each evening follows a proven, host-led format refined over nearly two decades.

Events take place in neighborhoods like the West Loop at venues such as Recess and Tabu, creating a relaxed, social setting. To keep things balanced, we monitor attendance and may occasionally adjust the schedule in advance — a deliberate choice to protect the experience. Your ticket always remains valid for a future Chicago event, and if you prefer not to attend a rescheduled event, you may request a refund. It’s all part of the Cheeky Guarantee - keeping things flexible and centered around a genuinely good night out.


“Always have a great time at these events. From the host to the daters, everyone is just so welcoming.”
— Verified Trustpilot Review

Learn more about how our events work, what to expect, and how we support our guests:

Considering a more personalized approach? See whether matchmaking is worth it in Chicago.

The Cheeky Guarantee
If MyCheekyDate reschedules or cancels your event, you may request a full refund to your original payment method. Simply contact us directly and we’ll take care of your refund from there and make sure it gets processed. If your own plans change, your ticket remains valid as flexible credit and never expires, so you’re always welcome to reschedule for another event.