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? Explore matchmaking in this city.
JANUARY 31ST 2026 | SATURDAY NIGHT SPEED DATING @ TABU | AGES 25-39
*MEN SOLD OUT - Gentlemen, Wait List tickets available for purchase.*
Saturday Speed Dating @ Tabu - January 31st 2026
Ages: 25-39 | 7:30PM
401 N Morgan St, Chicago, IL 60642
Early Bird Admission - Ends 1/26 | $35.95
Regular Admission | $39.95
FEBRUARY 7TH 2026 | SATURDAY NIGHT SPEED DATING @ RECESS | AGES 25-39
*MEN SOLD OUT - Gentlemen, Wait List tickets available for purchase.*
Saturday Night Speed Dating @ Recess - February 7th 2026
Ages: 25-39 | 7:30PM
838 W Kinzie St, Chicago, IL 60642
Early Bird Admission - Ends 2/2 | $35.95
Regular Admission | $39.95
FEBRUARY 8TH 2026 | SPEED DATING @ TABU | AGES 36-48
Speed Dating @ Tabu - February 8th 2026
Ages: 36-48 | 6PM
401 N Morgan St, Chicago, IL 60642
Early Bird Admission - Ends 2/3 | $32.95
Regular Admission | $36.00
FEBRUARY 15TH 2026 | SPEED DATING @ RECESS | AGES 32-44
Speed Dating @ Recess - February 15th 2026
Ages: 32-44 | 6PM
838 W Kinzie St, Chicago, IL 60642
Early Bird Admission – Ends 2/10 | $32.95
Regular Admission | $36.00
FEBRUARY 21ST 2026 | SATURDAY NIGHT SPEED DATING @ RECESS | AGES 25-39
Saturday Night Speed Dating @ Recess - February 21st 2026
Ages: 25-39 | 7:30PM
838 W Kinzie St, Chicago, IL 60642
Early Bird Admission - Ends 2/16 | $35.95
Regular Admission | $39.95
FEBRUARY 22ND 2026 | SPEED DATING @ TABU | AGES 36-48
Speed Dating @ Tabu - February 22nd 2026
Ages: 36-48 | 6PM
401 N Morgan St, Chicago, IL 60642
Early Bird Admission - Ends 2/22 | $32.95
Regular Admission | $36.00
FEBRUARY 28TH 2026 | SATURDAY NIGHT SPEED DATING @ TABU | AGES 25-39
Saturday Night Speed Dating @ Tabu - February 28th 2026
Ages: 25-39 | 7:30PM
401 N Morgan St, Chicago, IL 60642
Early Bird Admission - Ends 2/16 | $35.95
Regular Admission | $39.95
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.