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May 2026
Dates
Events
Monday, April 6, 2026 - Thursday, May 14, 2026
12:00 AM to 11:45 PM
S2 Credit Recovery (Session 2)

District-wide
Thursday, April 30, 2026
All Day
Administrative Grade Review

District-wide
Friday, May 1, 2026
All Day
4th Quarter Progress Report Distribution

District-wide
Friday, May 1, 2026
All Day
AI Foundations Badge (Self-Paced)

Virtual
Friday, May 1, 2026 - Saturday, May 30, 2026
12:00 AM to 11:45 PM
All-City Visual Arts Exhibition at Design Museum of Chicago
Design Museum of Chicago
72 E Randolph, Chicago, IL 60601
Friday, May 1, 2026
All Day
All-City Visual Arts Exhibition Opening (Time TBD)
Design Museum of Chicago
72 E Randolph, Chicago, IL 60601
Friday, May 1, 2026
All Day
Pay Period 09

District Wide
Friday, May 1, 2026
3:00 PM to 3:45 PM
Galileo Prospective Parent Open House and Tour
Galileo Scholastic Academy
820 S Carpenter
Tuesday, May 5, 2026 - Friday, May 8, 2026
10:00 AM to 1:00 PM
RE•VER•BER•ATE Festival at Chicago Cultural Center (10am-1pm)
Chicago Cultural Center
78 E Washington St, Chicago, IL 60602
Tuesday, May 5, 2026
4:00 PM to 5:00 PM
Tech Tuesday: Media Literacy First: Preparing Students in Grades 3–12 for the Age of AI
Virtual for CPS
Virtual for CPS
Wednesday, May 6, 2026
9:00 AM to 12:00 PM
Aspen Registration Enrollment & Parent Portal Training (2025-2026)
Colman Training Center (In Person)
4655 S. Dearborn St, Chicago, IL
Wednesday, May 6, 2026
11:00 AM to 1:00 PM
Ally Insider: Discover What's New!

Virtual
Wednesday, May 6, 2026
5:00 PM to 7:00 PM
Senn Future Bulldog Night
Senn High School
5900 N Glenwood Ave
Thursday, May 7, 2026
1:00 PM to 4:00 PM
NextGen Town Hall Cohort 3

Districtwide
Friday, May 8, 2026
All Day
12th Grade ONLY Semester Two Preliminary

District-wide
Friday, May 8, 2026 - Thursday, June 4, 2026
12:00 AM to 5:00 PM
Grade Posting Window for 4th Quarter Report Cards

District-wide
Friday, May 8, 2026 - Thursday, June 4, 2026
12:00 AM to 5:00 PM
Grade Posting Window for 4th Quarter Report Cards

District-wide
Friday, May 8, 2026
12:30 PM to 2:30 PM
Lead Coach PL - Leadership Learning

Virtual
Monday, May 11, 2026
All Day
The deadline to submit requests to waive graduation requirements.

District-wide
Monday, May 11, 2026
11:00 AM to 12:00 PM
Star 360 EOY Ready

Virtual
Monday, May 11, 2026
2:00 PM to 3:00 PM
Star 360 EOY Data Analysis Workshop & Reflection

Virtual
Tuesday, May 12, 2026
4:00 PM to 5:00 PM
Tech Tuesday: Personalize Gemini with Gems
Virtual for CPS
Virtual for CPS
Wednesday, May 13, 2026
9:00 AM to 12:00 PM
Aspen Registration Enrollment & Parent Portal Training (2025-2026)
Colman Training Center (In Person)
4655 S. Dearborn St, Chicago, IL
Wednesday, May 13, 2026
10:30 AM to 3:30 PM
May Board Agenda Review Committee Meeting
CPS Loop Office, Garden Level, Board Room
42 W. Madison St. Chicago, IL 60602
Wednesday, May 13, 2026
12:00 PM to 1:00 PM
Languishing, Flourishing and Your Mental Health
Go to Webinar
Virtual
Wednesday, May 13, 2026
4:30 PM to 6:30 PM
Language with Intention: Applying WIDA Standards Series, Session 4 of 4
Saucedo Elementary School - Room 104
2850 S. 25th Blvd, Chicago, IL 60623
Thursday, May 14, 2026
All Day
S2 Credit Recovery (Evening/Saturday School) End

District-wide
Thursday, May 14, 2026
9:00 AM to 4:00 PM
Data Analysis

Districtwide
Friday, May 15, 2026
All Day
Pay Period 10

District Wide
Friday, May 15, 2026
12:00 AM to 5:00 PM
Teacher Grade Posting deadline for Benchmark Grades

District-wide
Friday, May 15, 2026
12:00 AM to 5:00 PM
Teacher Grade Posting deadlines for Benchmark Grades

District-wide
Friday, May 15, 2026
9:00 AM to 4:30 PM
Take the Lead 2026 - Day 5 of 5 - Executing Strategy - Essential Roles of Leadership

Districtwide
Saturday, May 16, 2026
10:00 AM to 12:00 PM
In-Person Teacher Job Fair
Avalon Park Fine & Performing Arts School
8045 S. Kenwood Ave.
Sunday, May 17, 2026
12:00 PM to 4:00 PM
All-City Performing Arts Showcase
Jones College Preparatory HS
700 S State St, Chicago, IL 60605
Monday, May 18, 2026
All Day
Deadline for completion for the Learn, Plan, Succeed and FAA

District-wide
Tuesday, May 19, 2026
All Day
(Tentative) Q4 Preliminary Summer Bridge Eligibility report availability.

District-wide
Tuesday, May 19, 2026
All Day
Q4 Preliminary Summer Bridge Eligibility Forecast report availability.^

District-wide
Tuesday, May 19, 2026
4:15 PM to 5:30 PM
May Monthly Instructional Team Coach PL

Virtual
Wednesday, May 20, 2026
9:00 AM to 12:00 PM
Aspen Registration Enrollment & Parent Portal Training (2025-2026)
Colman Training Center (In Person)
4655 S. Dearborn St, Chicago, IL
Wednesday, May 20, 2026
2:00 PM to 3:00 PM
TechCo Webinar

Virtual
Wednesday, May 20, 2026
4:00 PM to 5:30 PM
ACT Mini Instructional Leadership Team Institute (ILTI)

Virtual
Thursday, May 21, 2026
All Day
High School Graduations Begin

District-wide
Thursday, May 21, 2026
4:00 PM to 5:30 PM
IAR Mini Instructional Leadership Team Institute (ILTI)

Virtual
Thursday, May 21, 2026
4:30 PM to 6:30 PM
Beyond Naming: Defining and Distinguishing 2D and 3D Shapes
Garfield Park Office - Gym
2651 W. Washington Blvd. Chicago, IL 60612
Thursday, May 21, 2026
6:00 PM to 7:30 PM
Office for Students with Disabilities (OSD) Family Advisory Board (FAB) Meeting
Virtual
Virtual
Thursday, May 21, 2026
7:30 PM to 9:00 PM
ART on THE MART Exhibition Opening
Viewing: Chicago Riverwalk between
W Wacker and N Franklin on the Riverwalk
Friday, May 22, 2026
All Day
(Tentative) Q4 Final Summer Bridge Eligibility Forecast report availability^

District-wide
Friday, May 22, 2026
All Day
(Tentative) Q4 Final Summer Bridge Eligibility report availability^

District-wide
Friday, May 22, 2026
12:30 PM to 2:30 PM
Lead Coach PL - Content Learning

Virtual
Monday, May 25, 2026
All Day
Memorial Day; No Classes

Districtwide
Tuesday, May 26, 2026
12:30 PM to 1:30 PM
Star 360 EOY Data Analysis Workshop & Reflection

Virtual
Wednesday, May 27, 2026
12:00 AM to 5:00 PM
8th Grade Posting deadline for all classes and subjects (5 p.m.)

District-wide
Wednesday, May 27, 2026
9:00 AM to 12:00 PM
Aspen Registration Enrollment & Parent Portal Training (2025-2026) Virtual
Colman Training Center (In Person)
4655 S. Dearborn St, Chicago, IL
Wednesday, May 27, 2026
9:00 AM to 4:30 PM
Equip for New CPS Leaders Cohort (Day 3 of 4)

Districtwide
Thursday, May 28, 2026
All Day
Summer Bridge Parent Letter Notification

District-wide
Thursday, May 28, 2026
All Day
Summer Bridge Parent Letter Notification

District-wide
Thursday, May 28, 2026
10:30 AM to 3:30 PM
May School Board Meeting
CPS Loop Office, Garden Level, Board Room
42 W. Madison St. Chicago, IL 60602
Friday, May 29, 2026 - Monday, June 1, 2026
12:00 AM to 5:00 PM
Administrative Grade Review Window Deadline (5 p.m.)

District-wide
Friday, May 29, 2026
All Day
Elementary School Graduations Begin

District-wide
Friday, May 29, 2026
All Day
Pay Period 11

District Wide
Friday, May 29, 2026
12:00 AM to 5:00 PM
Teacher Grade Posting deadline for all classes and all subjects

District-wide
Friday, May 29, 2026
9:00 AM to 4:00 PM
Critical Thinking

Districtwide
Friday, May 29, 2026
9:00 AM to 5:00 PM
EOY Choice Board Due - School-Based New Teacher Mentor

Virtual