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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JUNE 20TH 2026 | SATURDAY NIGHT SPEED DATING @ TABU | AGES 27-42
Saturday Night Speed Dating @ Tabu - June 20th 2026
Ages: 27-42 | 7:30PM
401 N Morgan St, Chicago, IL 60642
Early Bird Admission - Ends 06/15 | $32.95
Regular Admission | $36
JUNE 21ST 2026 | SPEED DATING @ RECESS | AGES 36-48
Speed Dating @ Recess - June 21st 2026
Ages: 36-48 | 6PM
838 W Kinzie St, Chicago, IL 60642
Early Bird Admission – Ends 06/16 | $32.95
Regular Admission | $36.00
JUNE 27TH 2026 | SATURDAY NIGHT SPEED DATING @ TABU | AGES 25-39
Saturday Night Speed Dating @ Tabu - June 27th 2026
Ages: 25-39 | 7:30PM
401 N Morgan St, Chicago, IL 60642
Early Bird Admission - Ends 06/22 | $32.95
Regular Admission | $36
JUNE 28TH 2026 | SPEED DATING @ TABU | AGES 32-44
Speed Dating @ Tabu - June 28th 2026
Ages: 32-44 | 5PM
401 N Morgan St, Chicago, IL 60642
Early Bird Admission - Ends 06/23 | $32.95
Regular Admission | $36.00
JULY 1ST 2026 | SPEED DATING @ RECESS | AGES 25-39
Speed Dating @ Recess - July 1st 2026
Ages: 25-39 | 7:30PM
838 W Kinzie St, Chicago, IL 60642
Early Bird Admission – Ends 06/26 | $32.95
Regular Admission | $36.00
JULY 11TH 2026 | SATURDAY NIGHT SPEED DATING @ TABU | AGES 25-39
Saturday Night Speed Dating @ Tabu - July 11th 2026
Ages: 25-39 | 7:30PM
401 N Morgan St, Chicago, IL 60642
Early Bird Admission - Ends 07/06 | $32.95
Regular Admission | $36
JULY 12TH 2026 | SPEED DATING @ TABU | AGES 32-44
Speed Dating @ Tabu - July 12th 2026
Ages: 32-44 | 5PM
401 N Morgan St, Chicago, IL 60642
Early Bird Admission - Ends 07/07 | $32.95
Regular Admission | $36.00
JULY 15TH 2026 | SPEED DATING @ RECESS | AGES 25-39
Speed Dating @ Recess - July 15th 2026
Ages: 25-39 | 7:30PM
838 W Kinzie St, Chicago, IL 60642
Early Bird Admission – Ends 07/10 | $32.95
Regular Admission | $36.00
JULY 18TH 2026 | SATURDAY NIGHT SPEED DATING @ TABU | AGES 27-42
Saturday Night Speed Dating @ Tabu - July 18th 2026
Ages: 27-42 | 7:30PM
401 N Morgan St, Chicago, IL 60642
Early Bird Admission - Ends 07/13 | $32.95
Regular Admission | $36
JULY 19TH 2026 | SPEED DATING @ RECESS | AGES 36-48
Speed Dating @ Recess - July 19th 2026
Ages: 36-48 | 6PM
838 W Kinzie St, Chicago, IL 60642
Early Bird Admission – Ends 07/14 | $32.95
Regular Admission | $36.00
JULY 25TH 2026 | SATURDAY NIGHT SPEED DATING @ TABU | AGES 25-39
Saturday Night Speed Dating @ Tabu - July 25th 2026
Ages: 25-39 | 7:30PM
401 N Morgan St, Chicago, IL 60642
Early Bird Admission - Ends 07/20 | $32.95
Regular Admission | $36
JULY 26TH 2026 | SPEED DATING @ TABU | AGES 32-44
Speed Dating @ Tabu - July 26th 2026
Ages: 32-44 | 5PM
401 N Morgan St, Chicago, IL 60642
Early Bird Admission - Ends 07/21 | $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. 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.