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 Luvo Matchmaking, a founder-led experience built from these same real-world communities.
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MAY 2ND 2026 | SATURDAY NIGHT SPEED DATING @ RECESS | AGES 25-39
Saturday Night Speed Dating @ Recess - May 2nd 2026
Ages: 25-39 | 7:30PM
838 W Kinzie St, Chicago, IL 60642
Early Bird Admission - Ends 4/27 | $32.95
Regular Admission | $36
MAY 9TH 2026 | SATURDAY NIGHT SPEED DATING @ TABU | AGES 27-42
Saturday Night Speed Dating @ Tabu - May 9th 2026
Ages: 27-42 | 7:30PM
401 N Morgan St, Chicago, IL 60642
Early Bird Admission - Ends 05/04 | $32.95
Regular Admission | $36
MAY 10TH 2026 | SPEED DATING @ RECESS | AGES 36-48
Speed Dating @ Recess - May 10th 2026
Ages: 36-48 | 6PM
838 W Kinzie St, Chicago, IL 60642
Early Bird Admission – Ends 05/05 | $32.95
Regular Admission | $36.00
MAY 16TH 2026 | SATURDAY NIGHT SPEED DATING @ TABU | AGES 25-39
Saturday Night Speed Dating @ Tabu - May 16th 2026
Ages: 25-39 | 7:30PM
401 N Morgan St, Chicago, IL 60642
Early Bird Admission - Ends 05/11 | $32.95
Regular Admission | $36
MAY 17TH 2026 | SPEED DATING @ TABU | AGES 32-44
Speed Dating @ Tabu - May 17th 2026
Ages: 32-44 | 5PM
401 N Morgan St, Chicago, IL 60642
Early Bird Admission - Ends 05/12 | $32.95
Regular Admission | $36.00
MAY 23RD 2026 | SATURDAY NIGHT SPEED DATING @ TABU | AGES 27-42
Saturday Night Speed Dating @ Tabu - May 23rd 2026
Ages: 27-42 | 7:30PM
401 N Morgan St, Chicago, IL 60642
Early Bird Admission - Ends 05/18 | $32.95
Regular Admission | $36
MAY 24TH 2026 | SPEED DATING @ RECESS | AGES 36-48
Speed Dating @ Recess - May 24th 2026
Ages: 36-48 | 6PM
838 W Kinzie St, Chicago, IL 60642
Early Bird Admission – Ends 05/19 | $32.95
Regular Admission | $36.00
MAY 30TH 2026 | SATURDAY NIGHT SPEED DATING @ TABU | AGES 25-39
Saturday Night Speed Dating @ Tabu - May 30th 2026
Ages: 25-39 | 7:30PM
401 N Morgan St, Chicago, IL 60642
Early Bird Admission - Ends 05/25 | $32.95
Regular Admission | $36
MAY 31ST 2026 | SPEED DATING @ TABU | AGES 32-44
Speed Dating @ Tabu - May 31st 2026
Ages: 32-44 | 5PM
401 N Morgan St, Chicago, IL 60642
Early Bird Admission - Ends 05/26 | $32.95
Regular Admission | $36.00
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.