From candlelit corners in River North to the creative buzz of Wicker Park, Chicago brings warmth, confidence, and unmistakable chemistry. MyCheekyDate hosts boutique-style, host-led speed dating events across the city — designed for real conversation, laughter, and easy connection. Curious about the local dating vibe? Explore Cheeky Thoughts: Chicago Edition. Prefer curated one-to-one introductions? Curated Introduction Packages are also available in Chicago.
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Welcome to MyCheekyDate — where great rooms aren’t accidental… they’re cultivated. ✨
MARCH 15TH 2026 | SPEED DATING @ RECESS | AGES 32-44
Speed Dating @ Recess - March 15th 2026
Ages: 32-44 | 6PM
838 W Kinzie St, Chicago, IL 60642
Early Bird Admission – Ends 3/10 | $32.95
Regular Admission | $36.00
MARCH 21ST 2026 | SATURDAY NIGHT SPEED DATING @ TABU | AGES 25-39
Saturday Night Speed Dating @ Tabu - March 21st 2026
Ages: 25-39 | 7:30PM
401 N Morgan St, Chicago, IL 60642
Early Bird Admission - Ends 3/16 | $32.95
Regular Admission | $36
MARCH 22ND 2026 | SPEED DATING @ TABU | AGES 32-44
Speed Dating @ Tabu - March 22nd 2026
Ages: 32-44 | 5PM
401 N Morgan St, Chicago, IL 60642
Early Bird Admission - Ends 3/17 | $32.95
Regular Admission | $36.00
MARCH 28TH 2026 | SATURDAY NIGHT SPEED DATING @ TABU | AGES 27-42
Saturday Night Speed Dating @ Tabu - March 28th 2026
Ages: 27-42 | 7:30PM
401 N Morgan St, Chicago, IL 60642
Early Bird Admission - Ends 3/23 | $32.95
Regular Admission | $36
APRIL 4TH 2026 | SATURDAY NIGHT SPEED DATING @ TABU | AGES 25-39
Saturday Night Speed Dating @ Tabu - April 4th 2026
Ages: 25-39 | 7:30PM
401 N Morgan St, Chicago, IL 60642
Early Bird Admission - Ends 3/30 | $32.95
Regular Admission | $36
APRIL 5TH 2026 | SPEED DATING @ TABU | AGES 32-44
Speed Dating @ Tabu - April 5th 2026
Ages: 32-44 | 5PM
401 N Morgan St, Chicago, IL 60642
Early Bird Admission - Ends 3/31 | $32.95
Regular Admission | $36.00
APRIL 11TH 2026 | SATURDAY NIGHT SPEED DATING @ TABU | AGES 27-42
Saturday Night Speed Dating @ Tabu - April 11th 2026
Ages: 27-42 | 7:30PM
401 N Morgan St, Chicago, IL 60642
Early Bird Admission - Ends 4/6 | $35.95
Regular Admission | $39.95
APRIL 12TH 2026 | SPEED DATING @ RECESS | AGES 36-48
Speed Dating @ Recess - April 12th 2026
Ages: 36-48 | 6PM
838 W Kinzie St, Chicago, IL 60642
Early Bird Admission – Ends 4/7 | $32.95
Regular Admission | $36.00
APRIL 18TH 2026 | SATURDAY NIGHT SPEED DATING @ TABU | AGES 25-39
Saturday Night Speed Dating @ Tabu - April 18th 2026
Ages: 25-39 | 7:30PM
401 N Morgan St, Chicago, IL 60642
Early Bird Admission - Ends 4/13 | $32.95
Regular Admission | $36
APRIL 19TH 2026 | SPEED DATING @ TABU | AGES 32-44
Speed Dating @ Tabu - April 19th 2026
Ages: 32-44 | 5PM
401 N Morgan St, Chicago, IL 60642
Early Bird Admission - Ends 4/14 | $32.95
Regular Admission | $36.00
APRIL 25TH 2026 | SATURDAY NIGHT SPEED DATING @ TABU | AGES 27-42
Saturday Night Speed Dating @ Tabu - April 25th 2026
Ages: 27-42 | 7:30PM
401 N Morgan St, Chicago, IL 60642
Early Bird Admission - Ends 4/20 | $32.95
Regular Admission | $36
APRIL 26TH 2026 | SPEED DATING @ RECESS | AGES 36-48
Speed Dating @ Recess - April 26th 2026
Ages: 36-48 | 6PM
838 W Kinzie St, Chicago, IL 60642
Early Bird Admission – Ends 4/21 | $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.
As one of the world’s longest-running speed dating companies, we’ve produced tens of thousands of events internationally, with Chicago evenings following the same proven, host-led format used in major cities worldwide.
Events are ticketed through Eventbrite, with clear expectations, transparent policies, and a calm, welcoming flow designed to help guests actually connect.