Whether sharing cocktails in River North or laughs in West Loop, Chicago brings together charm, wit, and a touch of cheek. MyCheekyDate hosts boutique-style, host-led speed dating events throughout the city — perfectly curated evenings for genuine conversation, connection, and a bit of Windy City sparkle.
DECEMBER 14TH 2025 | SPEED DATING @ RECESS | AGES 32-44
Speed Dating @ Recess - December 14th 2025
Ages: 32-44 | 6PM
838 W Kinzie St, Chicago, IL 60642
Early Bird Admission – Ends 12/09 | $32.95
Regular Admission | $36.00
DECEMBER 20TH 2025 | SATURDAY NIGHT SPEED DATING @ TABU | AGES 25-39
Speed Dating @ Tabu - December 20th 2025
Ages: 25-39 | 7:30PM
401 N Morgan St, Chicago, IL 60642
Early Bird Admission - Ends 12/15 | $35.95
Regular Admission | $39.95
DECEMBER 21ST 2025 | SPEED DATING @ TABU | AGES 36-48
Speed Dating @ Tabu - December 21st 2025
Ages: 36-48 | 6PM
401 N Morgan St, Chicago, IL 60642
Early Bird Admission - Ends 12/16 | $32.95
Regular Admission | $36.00
DECEMBER 27TH 2025 | SATURDAY NIGHT SPEED DATING @ TIME OUT | AGES 25-39
Saturday Night Speed Dating @ Time Out Market Chicago - December 27th 2025
Ages: 25-39 | 7:30PM
916 W Fulton Market, Chicago, IL 60607
Early Bird Admission - Ends 12/22 | $35.95
Regular Admission | $39.95
DECEMBER 28TH 2025 | SPEED DATING @ RECESS | AGES 32-44
Speed Dating @ Recess - December 28th 2025
Ages: 32-44 | 6PM
838 W Kinzie St, Chicago, IL 60642
Early Bird Admission – Ends 12/23 | $32.95
Regular Admission | $36.00
JANUARY 3RD 2026 | SATURDAY NIGHT SPEED DATING @ TABU | AGES 25-39
Saturday Speed Dating @ Tabu - January 3rd 2026
Ages: 25-39 | 7:30PM
401 N Morgan St, Chicago, IL 60642
Early Bird Admission - Ends 12/29 | $35.95
Regular Admission | $39.95
JANUARY 4TH 2026 | SPEED DATING @ TABU | AGES 36-48
Speed Dating @ Tabu - January 4th 2026
Ages: 36-48 | 6PM
401 N Morgan St, Chicago, IL 60642
Early Bird Admission - Ends 12/30 | $32.95
Regular Admission | $36.00
JANUARY 10TH 2026 | SATURDAY NIGHT SPEED DATING @ TIME OUT | AGES 25-39
Saturday Night Speed Dating @ Time Out Market Chicago - January 10th 2026
Ages: 25-39 | 7:30PM
916 W Fulton Market, Chicago, IL 60607
Early Bird Admission - Ends 1/5 | $35.95
Regular Admission | $39.95
JANUARY 11TH 2026 | SPEED DATING @ RECESS | AGES 32-44
Speed Dating @ Recess - January 11th 2026
Ages: 32-44 | 6PM
838 W Kinzie St, Chicago, IL 60642
Early Bird Admission – Ends 1/6 | $32.95
Regular Admission | $36.00
JANUARY 15TH 2026 | SPEED DATING @ UNTITLED SUPPER CLUB | AGES 24-36
Speed Dating @ Untitled Supper Club – January 15th 2026
Ages: 24-36 | 7PM
111 W Kinzie St, Chicago, IL 60654
Early Bird Admission - Ends 1/10 | $32.95
Regular Admission | $36.00
JANUARY 17TH 2026 | SATURDAY NIGHT SPEED DATING @ TABU | AGES 25-39
Saturday Speed Dating @ Tabu - January 17th 2026
Ages: 25-39 | 7:30PM
401 N Morgan St, Chicago, IL 60642
Early Bird Admission - Ends 1/12 | $35.95
Regular Admission | $39.95
JANUARY 18TH 2026 | SPEED DATING @ TABU | AGES 36-48
Speed Dating @ Tabu - January 18th 2026
Ages: 36-48 | 6PM
401 N Morgan St, Chicago, IL 60642
Early Bird Admission - Ends 1/13 | $32.95
Regular Admission | $36.00
JANUARY 24TH 2026 | SATURDAY NIGHT SPEED DATING @ TIME OUT | AGES 25-39
Saturday Night Speed Dating @ Time Out Market Chicago - January 24th 2026
Ages: 25-39 | 7:30PM
916 W Fulton Market, Chicago, IL 60607
Early Bird Admission - Ends 1/19 | $35.95
Regular Admission | $39.95
JANUARY 25TH 2026 | SPEED DATING @ RECESS | AGES 32-44
Speed Dating @ Recess - January 25th 2026
Ages: 32-44 | 6PM
838 W Kinzie St, Chicago, IL 60642
Early Bird Admission – Ends 1/20 | $32.95
Regular Admission | $36.00
JANUARY 31ST 2026 | SATURDAY NIGHT SPEED DATING @ TABU | AGES 25-39
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