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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SEPTEMBER 19TH 2026 | SATURDAY NIGHT SPEED DATING @ RECESS | AGES 29-42
Saturday Night Speed Dating @ Recess - September 19th 2026
Ages: 29-42 | 7:30PM
838 W Kinzie St, Chicago, IL 60642
Early Bird Admission - Ends 09/14 | $32.95
Regular Admission | $36
SEPTEMBER 20TH 2026 | SPEED DATING @ RECESS | AGES 32-44
Saturday Night Speed Dating @ Recess - September 20th 2026
Ages: 32-44 | 6PM
838 W Kinzie St, Chicago, IL 60642
Early Bird Admission - Ends 09/15 | $32.95
Regular Admission | $36
SEPTEMBER 23RD 2026 | SPEED DATING @ RECESS | AGES 25-39
Saturday Night Speed Dating @ Recess - September 23rd 2026
Ages: 25-39 | 7PM
838 W Kinzie St, Chicago, IL 60642
Early Bird Admission - Ends 09/18 | $32.95
Regular Admission | $36
SEPTEMBER 26TH 2026 | SATURDAY NIGHT SPEED DATING @ RECESS | AGES 25-39
Saturday Night Speed Dating @ Recess - September 26th 2026
Ages: 25-39 | 7:30PM
838 W Kinzie St, Chicago, IL 60642
Early Bird Admission - Ends 09/21 | $32.95
Regular Admission | $36
SEPTEMBER 27TH 2026 | SPEED DATING @ RECESS | AGES 36-48
Saturday Night Speed Dating @ Recess - September 27th 2026
Ages: 36-48 | 6PM
838 W Kinzie St, Chicago, IL 60642
Early Bird Admission - Ends 09/22 | $32.95
Regular Admission | $36
OCTOBER 3RD 2026 | SATURDAY NIGHT SPEED DATING @ RECESS | AGES 29-42
Saturday Night Speed Dating @ Recess - October 3rd 2026
Ages: 29-42| 7:30PM
838 W Kinzie St, Chicago, IL 60642
Early Bird Admission - Ends 09/28 | $32.95
Regular Admission | $36
OCTOBER 4TH 2026 | SPEED DATING @ RECESS | AGES 32-44
Speed Dating @ Recess - October 4th 2026
Ages: 32-44| 6PM
838 W Kinzie St, Chicago, IL 60642
Early Bird Admission - Ends 09/29 | $32.95
Regular Admission | $36
OCTOBER 10TH 2026 | SATURDAY NIGHT SPEED DATING @ RECESS | AGES 25-39
Saturday Night Speed Dating @ Recess - October 10th 2026
Ages: 25-39| 7:30PM
838 W Kinzie St, Chicago, IL 60642
Early Bird Admission - Ends 10/05 | $32.95
Regular Admission | $36
OCTOBER 11TH 2026 | SPEED DATING @ RECESS | AGES 36-48
Speed Dating @ Recess - October 11th 2026
Ages: 36-48| 6PM
838 W Kinzie St, Chicago, IL 60642
Early Bird Admission - Ends 10/06 | $32.95
Regular Admission | $36
OCTOBER 14TH 2026 | SPEED DATING @ RECESS | AGES 29-42
Speed Dating @ Recess - October 14th 2026
Ages: 29-42| 7PM
838 W Kinzie St, Chicago, IL 60642
Early Bird Admission - Ends 10/09 | $32.95
Regular Admission | $36
OCTOBER 17TH 2026 | SATURDAY NIGHT SPEED DATING @ RECESS | AGES 29-42
Saturday Night Speed Dating @ Recess - October 17th 2026
Ages: 29-42| 7:30PM
838 W Kinzie St, Chicago, IL 60642
Early Bird Admission - Ends 10/12 | $32.95
Regular Admission | $36
OCTOBER 18TH 2026 | SPEED DATING @ RECESS | AGES 32-44
Speed Dating @ Recess - October 18th 2026
Ages: 32-44| 6PM
838 W Kinzie St, Chicago, IL 60642
Early Bird Admission - Ends 10/13 | $32.95
Regular Admission | $36
OCTOBER 24TH 2026 | SATURDAY NIGHT SPEED DATING @ RECESS | AGES 25-39
Saturday Night Speed Dating @ Recess - October 24th 2026
Ages: 25-39| 7:30PM
838 W Kinzie St, Chicago, IL 60642
Early Bird Admission - Ends 10/19 | $32.95
Regular Admission | $36
OCTOBER 25TH 2026 | SPEED DATING @ RECESS | AGES 36-48
Speed Dating @ Recess - October 25th 2026
Ages: 36-48| 6PM
838 W Kinzie St, Chicago, IL 60642
Early Bird Admission - Ends 10/20 | $32.95
Regular Admission | $36
OCTOBER 28TH 2026 | SPEED DATING @ RECESS | AGES 29-42
Speed Dating @ Recess - October 28th 2026
Ages: 29-42| 7PM
838 W Kinzie St, Chicago, IL 60642
Early Bird Admission - Ends 10/23 | $32.95
Regular Admission | $36
OCTOBER 31ST 2026 | SATURDAY NIGHT SPEED DATING @ RECESS | AGES 29-42
Saturday Night Speed Dating @ Recess - October 31st 2026
Ages: 29-42| 7:30PM
838 W Kinzie St, Chicago, IL 60642
Early Bird Admission - Ends 10/26 | $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.