Chicago with kids

Castle

Sat, Oct 17 · 10 AM–5 PM · Chicago Children’s Museum, 700 E. Grand Ave., Chicago, IL

Price: see link

BOO! at the Zoo

Sat, Oct 17 · 10 AM–6 PM · Brookfield Zoo Chicago, 3300 Golf Rd, Brookfield, IL

Price: see link

Mini Zoom Room

Sat, Oct 17 · 10 AM–5 PM · Chicago Children’s Museum, 700 E. Grand Ave., Chicago, IL

Price: see link

ClarkeToberfest: A Weekend of Fall Festivities at the Harley Clarke Mansion

Sat, Oct 17 · 3 PM–10 PM · The Harley Clarke Mansion, 2603 Sheridan Road, Evanston, IL

Clarketoberfest at the Harley Clarke Mansion Oct. 16–18 brings three days of FREE fall fun, beer, food by Hatchet Burger, dancing, family festivities, and live music – including kid-favorite Jeanie B!

Free

Scott Green Lies To Your Kids

Sat, Oct 17 · 6 PM–7 PM · The iO Theater, 1501 N Kingsbury St, Chicago, IL 60642, USA,, The iO Theater, 1501 N Kingsbury St, Chicago, IL 60642, USA,, IL

Price: see link

Baby Wants Candy! The Original Completely Improvised Musical

Sat, Oct 17 · 7:30 PM–8:30 PM · The Second City, 1616 N. Wells St., Chicago

$25

Castle

Sun, Oct 18 · 10 AM–5 PM · Chicago Children’s Museum, 700 E. Grand Ave., Chicago, IL

Price: see link

BOO! at the Zoo

Sun, Oct 18 · 10 AM–6 PM · Brookfield Zoo Chicago, 3300 Golf Rd, Brookfield, IL

Price: see link

Mini Zoom Room

Sun, Oct 18 · 10 AM–5 PM · Chicago Children’s Museum, 700 E. Grand Ave., Chicago, IL

Price: see link

ClarkeToberfest: A Weekend of Fall Festivities at the Harley Clarke Mansion

Sun, Oct 18 · 12 PM–7 PM · The Harley Clarke Mansion, 2603 Sheridan Road, Evanston, IL

Clarketoberfest at the Harley Clarke Mansion Oct. 16–18 brings three days of FREE fall fun, beer, food by Hatchet Burger, dancing, family festivities, and live music – including kid-favorite Jeanie B!

Free

Grace Spee: The Feminine Gothic Narrative in Survival Horror

Sun, Oct 18 · 2 PM–5 PM · Chicago Gamespace, 2418 W Bloomingdale Ave Apt 101, Chicago, IL

$8

Homeschool Days at PEPPA PIG World of Play Chicago

Mon, Oct 19 · 10 AM–5 PM · Peppa Pig World of Play Chicago, 5 Woodfield Mall, Schaumburg

Price: see link

Castle

Mon, Oct 19 · 10 AM–5 PM · Chicago Children’s Museum, 700 E. Grand Ave., Chicago, IL

Price: see link

BOO! at the Zoo

Mon, Oct 19 · 10 AM–6 PM · Brookfield Zoo Chicago, 3300 Golf Rd, Brookfield, IL

Price: see link

Mini Zoom Room

Mon, Oct 19 · 10 AM–5 PM · Chicago Children’s Museum, 700 E. Grand Ave., Chicago, IL

Price: see link

Homeschool Days at PEPPA PIG World of Play Chicago

Tue, Oct 20 · 10 AM–5 PM · Peppa Pig World of Play Chicago, 5 Woodfield Mall, Schaumburg

Price: see link

Castle

Tue, Oct 20 · 10 AM–5 PM · Chicago Children’s Museum, 700 E. Grand Ave., Chicago, IL

Price: see link

BOO! at the Zoo

Tue, Oct 20 · 10 AM–6 PM · Brookfield Zoo Chicago, 3300 Golf Rd, Brookfield, IL

Price: see link

Homeschool Days at PEPPA PIG World of Play Chicago

Wed, Oct 21 · 10 AM–5 PM · Peppa Pig World of Play Chicago, 5 Woodfield Mall, Schaumburg

Price: see link

Castle

Wed, Oct 21 · 10 AM–5 PM · Chicago Children’s Museum, 700 E. Grand Ave., Chicago, IL

Price: see link

BOO! at the Zoo

Wed, Oct 21 · 10 AM–6 PM · Brookfield Zoo Chicago, 3300 Golf Rd, Brookfield, IL

Price: see link

Mini Zoom Room

Wed, Oct 21 · 10 AM–5 PM · Chicago Children’s Museum, 700 E. Grand Ave., Chicago, IL

Price: see link

Homeschool Days at PEPPA PIG World of Play Chicago

Thu, Oct 22 · 10 AM–5 PM · Peppa Pig World of Play Chicago, 5 Woodfield Mall, Schaumburg

Price: see link

Castle

Thu, Oct 22 · 10 AM–5 PM · Chicago Children’s Museum, 700 E. Grand Ave., Chicago, IL

Price: see link

BOO! at the Zoo

Thu, Oct 22 · 10 AM–6 PM · Brookfield Zoo Chicago, 3300 Golf Rd, Brookfield, IL

Price: see link

Mini Zoom Room

Thu, Oct 22 · 10 AM–5 PM · Chicago Children’s Museum, 700 E. Grand Ave., Chicago, IL

Price: see link

Homeschool Days at PEPPA PIG World of Play Chicago

Fri, Oct 23 · 10 AM–5 PM · Peppa Pig World of Play Chicago, 5 Woodfield Mall, Schaumburg

Price: see link

Castle

Fri, Oct 23 · 10 AM–5 PM · Chicago Children’s Museum, 700 E. Grand Ave., Chicago, IL

Price: see link

BOO! at the Zoo

Fri, Oct 23 · 10 AM–6 PM · Brookfield Zoo Chicago, 3300 Golf Rd, Brookfield, IL

Price: see link

Mini Zoom Room

Fri, Oct 23 · 10 AM–5 PM · Chicago Children’s Museum, 700 E. Grand Ave., Chicago, IL

Price: see link

Castle

Sat, Oct 24 · 10 AM–5 PM · Chicago Children’s Museum, 700 E. Grand Ave., Chicago, IL

Price: see link

BOO! at the Zoo

Sat, Oct 24 · 10 AM–6 PM · Brookfield Zoo Chicago, 3300 Golf Rd, Brookfield, IL

Price: see link

Mini Zoom Room

Sat, Oct 24 · 10 AM–5 PM · Chicago Children’s Museum, 700 E. Grand Ave., Chicago, IL

Price: see link

Spooktacular: Lincoln Avenue

Sat, Oct 24 · 1 PM–4 PM · Lincoln Avenue, Lincoln Avenue, between Wrightwood and Webster, Chicago

Get ready for two days of trick-or-treating fun in Lincoln Park!

Free

Magic Makers: Family Comedy Magic Show

Sat, Oct 24 · 3 PM–4 PM · The Checkout, 4116 North Clark Street, Chicago

Magic Makers: Family Comedy Magic Show What happens when a magician opens a toolbox and starts making things up?

$24.11

Scott Green Lies To Your Kids

Sat, Oct 24 · 6 PM–7 PM · The iO Theater, 1501 N Kingsbury St, Chicago, IL 60642, USA,, The iO Theater, 1501 N Kingsbury St, Chicago, IL 60642, USA,, IL

Price: see link

Baby Wants Candy! The Original Completely Improvised Musical

Sat, Oct 24 · 7:30 PM–8:30 PM · The Second City, 1616 N. Wells St., Chicago

$25

Castle

Sun, Oct 25 · 10 AM–5 PM · Chicago Children’s Museum, 700 E. Grand Ave., Chicago, IL

Price: see link

BOO! at the Zoo

Sun, Oct 25 · 10 AM–6 PM · Brookfield Zoo Chicago, 3300 Golf Rd, Brookfield, IL

Price: see link

Mini Zoom Room

Sun, Oct 25 · 10 AM–5 PM · Chicago Children’s Museum, 700 E. Grand Ave., Chicago, IL

Price: see link

BOO-seum Bash

Sun, Oct 25 · 10 AM–1 PM · Peggy Notebaert Nature Museum, 2430 N. Cannon Dr., Chicago, IL

Trick or Treat! It’s time to have some merry mischief at the museum!

Price: see link

Lincoln Scared Ravenswoooood

Sun, Oct 25 · 11 AM–1 PM · The Perfect Cup, 4700 N Damen, Chicago

Trick-or-Treat with your kids this year in Lincoln Square Ravenswood!

Price: see link

Spooktacular: Clark Street

Sun, Oct 25 · 1 PM–4 PM · Clark Street, Clark Street, between Armitage and Diversey and Diversey from Orchard to Lakeview, Chicago

Get ready for two days of trick-or-treating fun in Lincoln Park!

Price: see link

Grace Spee: The Feminine Gothic Narrative in Survival Horror

Sun, Oct 25 · 2 PM–5 PM · Chicago Gamespace, 2418 W Bloomingdale Ave Apt 101, Chicago, IL

$8

Homeschool Days at PEPPA PIG World of Play Chicago

Mon, Oct 26 · 10 AM–5 PM · Peppa Pig World of Play Chicago, 5 Woodfield Mall, Schaumburg

Price: see link

Castle

Mon, Oct 26 · 10 AM–5 PM · Chicago Children’s Museum, 700 E. Grand Ave., Chicago, IL

Price: see link

Mini Zoom Room

Mon, Oct 26 · 10 AM–5 PM · Chicago Children’s Museum, 700 E. Grand Ave., Chicago, IL

Price: see link

Homeschool Days at PEPPA PIG World of Play Chicago

Tue, Oct 27 · 10 AM–5 PM · Peppa Pig World of Play Chicago, 5 Woodfield Mall, Schaumburg

Price: see link

Castle

Tue, Oct 27 · 10 AM–5 PM · Chicago Children’s Museum, 700 E. Grand Ave., Chicago, IL

Price: see link

Homeschool Days at PEPPA PIG World of Play Chicago

Wed, Oct 28 · 10 AM–5 PM · Peppa Pig World of Play Chicago, 5 Woodfield Mall, Schaumburg

Price: see link

Castle

Wed, Oct 28 · 10 AM–5 PM · Chicago Children’s Museum, 700 E. Grand Ave., Chicago, IL

Price: see link

Homeschool Days at PEPPA PIG World of Play Chicago

Thu, Oct 29 · 10 AM–5 PM · Peppa Pig World of Play Chicago, 5 Woodfield Mall, Schaumburg

Price: see link

Castle

Thu, Oct 29 · 10 AM–5 PM · Chicago Children’s Museum, 700 E. Grand Ave., Chicago, IL

Price: see link

Homeschool Days at PEPPA PIG World of Play Chicago

Fri, Oct 30 · 10 AM–5 PM · Peppa Pig World of Play Chicago, 5 Woodfield Mall, Schaumburg

Price: see link

Castle

Fri, Oct 30 · 10 AM–5 PM · Chicago Children’s Museum, 700 E. Grand Ave., Chicago, IL

Price: see link

Castle

Sat, Oct 31 · 10 AM–5 PM · Chicago Children’s Museum, 700 E. Grand Ave., Chicago, IL

Price: see link

Baby Wants Candy! The Original Completely Improvised Musical

Sat, Oct 31 · 7:30 PM–8:30 PM · The Second City, 1616 N. Wells St., Chicago

$25

Castle

Sun, Nov 1 · 10 AM–5 PM · Chicago Children’s Museum, 700 E. Grand Ave., Chicago, IL

Price: see link

Día de los Muertos at Navy Pier

Sun, Nov 1 · 1 PM–10 PM · Navy Pier, Chicago

Join us at Navy Pier on Saturday, November 1 for Día de los Muertos, featuring art, cultural experiences and activities celebrating this meaningful tradition.

Free

Grace Spee: The Feminine Gothic Narrative in Survival Horror

Sun, Nov 1 · 2 PM–5 PM · Chicago Gamespace, 2418 W Bloomingdale Ave Apt 101, Chicago, IL

$8

Homeschool Days at PEPPA PIG World of Play Chicago

Mon, Nov 2 · 10 AM–5 PM · Peppa Pig World of Play Chicago, 5 Woodfield Mall, Schaumburg

Price: see link

Castle

Mon, Nov 2 · 10 AM–5 PM · Chicago Children’s Museum, 700 E. Grand Ave., Chicago, IL

Price: see link

Homeschool Days at PEPPA PIG World of Play Chicago

Tue, Nov 3 · 10 AM–5 PM · Peppa Pig World of Play Chicago, 5 Woodfield Mall, Schaumburg

Price: see link

Castle

Tue, Nov 3 · 10 AM–5 PM · Chicago Children’s Museum, 700 E. Grand Ave., Chicago, IL

Price: see link

Homeschool Days at PEPPA PIG World of Play Chicago

Wed, Nov 4 · 10 AM–5 PM · Peppa Pig World of Play Chicago, 5 Woodfield Mall, Schaumburg

Price: see link

Castle

Wed, Nov 4 · 10 AM–5 PM · Chicago Children’s Museum, 700 E. Grand Ave., Chicago, IL

Price: see link

Homeschool Days at PEPPA PIG World of Play Chicago

Thu, Nov 5 · 10 AM–5 PM · Peppa Pig World of Play Chicago, 5 Woodfield Mall, Schaumburg

Price: see link

Castle

Thu, Nov 5 · 10 AM–5 PM · Chicago Children’s Museum, 700 E. Grand Ave., Chicago, IL

Price: see link

Homeschool Days at PEPPA PIG World of Play Chicago

Fri, Nov 6 · 10 AM–5 PM · Peppa Pig World of Play Chicago, 5 Woodfield Mall, Schaumburg

Price: see link

Castle

Fri, Nov 6 · 10 AM–5 PM · Chicago Children’s Museum, 700 E. Grand Ave., Chicago, IL

Price: see link

Castle

Sat, Nov 7 · 10 AM–5 PM · Chicago Children’s Museum, 700 E. Grand Ave., Chicago, IL

Price: see link

2026 Chicago Toy & Game Fair Tickets

Sat, Nov 7 · 10 AM–6 PM · Donald E. Stephens Convention Center, 5555 North River Road, Rosemont

The Chicago Toy & Game Fair (CHITAG) returns to the Donald E.

Price: see link

Baby Wants Candy! The Original Completely Improvised Musical

Sat, Nov 7 · 7:30 PM–8:30 PM · The Second City, 1616 N. Wells St., Chicago

$25

Castle

Sun, Nov 8 · 10 AM–5 PM · Chicago Children’s Museum, 700 E. Grand Ave., Chicago, IL

Price: see link

2026 Chicago Toy & Game Fair Tickets

Sun, Nov 8–9 · Donald E. Stephens Convention Center, 5555 North River Road, Rosemont

The Chicago Toy & Game Fair (CHITAG) returns to the Donald E.

Price: see link

Grace Spee: The Feminine Gothic Narrative in Survival Horror

Sun, Nov 8 · 2 PM–5 PM · Chicago Gamespace, 2418 W Bloomingdale Ave Apt 101, Chicago, IL

$8

Vince Staples – Cry Baby Tour

Sun, Nov 8 · 7:30 PM–10:30 PM · Riviera Theatre, 4746 N Racine Ave, Chicago, IL

Vince Staples will perform live in Chicago on Sunday, November 8, 2026, at the Riviera Theatre.

Price: see link

Homeschool Days at PEPPA PIG World of Play Chicago

Mon, Nov 9 · 10 AM–5 PM · Peppa Pig World of Play Chicago, 5 Woodfield Mall, Schaumburg

Price: see link

Castle

Mon, Nov 9 · 10 AM–5 PM · Chicago Children’s Museum, 700 E. Grand Ave., Chicago, IL

Price: see link

Homeschool Days at PEPPA PIG World of Play Chicago

Tue, Nov 10 · 10 AM–5 PM · Peppa Pig World of Play Chicago, 5 Woodfield Mall, Schaumburg

Price: see link

Castle

Tue, Nov 10 · 10 AM–5 PM · Chicago Children’s Museum, 700 E. Grand Ave., Chicago, IL

Price: see link

Homeschool Days at PEPPA PIG World of Play Chicago

Wed, Nov 11 · 10 AM–5 PM · Peppa Pig World of Play Chicago, 5 Woodfield Mall, Schaumburg

Price: see link

Castle

Wed, Nov 11 · 10 AM–5 PM · Chicago Children’s Museum, 700 E. Grand Ave., Chicago, IL

Price: see link

Homeschool Days at PEPPA PIG World of Play Chicago

Thu, Nov 12 · 10 AM–5 PM · Peppa Pig World of Play Chicago, 5 Woodfield Mall, Schaumburg

Price: see link

Castle

Thu, Nov 12 · 10 AM–5 PM · Chicago Children’s Museum, 700 E. Grand Ave., Chicago, IL

Price: see link

Homeschool Days at PEPPA PIG World of Play Chicago

Fri, Nov 13 · 10 AM–5 PM · Peppa Pig World of Play Chicago, 5 Woodfield Mall, Schaumburg

Price: see link

Castle

Fri, Nov 13 · 10 AM–5 PM · Chicago Children’s Museum, 700 E. Grand Ave., Chicago, IL

Price: see link

Castle

Sat, Nov 14 · 10 AM–5 PM · Chicago Children’s Museum, 700 E. Grand Ave., Chicago, IL

Price: see link

Scott Green Lies To Your Kids

Sat, Nov 14 · 6 PM–7 PM · The iO Theater, 1501 N Kingsbury St, Chicago, IL 60642, USA,, The iO Theater, 1501 N Kingsbury St, Chicago, IL 60642, USA,, IL

Price: see link

Baby Wants Candy! The Original Completely Improvised Musical

Sat, Nov 14 · 7:30 PM–8:30 PM · The Second City, 1616 N. Wells St., Chicago

$25

Castle

Sun, Nov 15 · 10 AM–5 PM · Chicago Children’s Museum, 700 E. Grand Ave., Chicago, IL

Price: see link

Grace Spee: The Feminine Gothic Narrative in Survival Horror

Sun, Nov 15 · 2 PM–5 PM · Chicago Gamespace, 2418 W Bloomingdale Ave Apt 101, Chicago, IL

$8

Manchester Orchestra – Chicago, IL – I’m Like a Virgin Losing a Child 20th Anniversary Tour

Sun, Nov 15 · 7 PM–10 PM · The Vic Theatre, 3145 N. Sheffield, Chicago, IL

Manchester Orchestra will perform live at The Vic Theatre in Chicago on Sunday, November 15, 2026.

Price: see link

Homeschool Days at PEPPA PIG World of Play Chicago

Mon, Nov 16 · 10 AM–5 PM · Peppa Pig World of Play Chicago, 5 Woodfield Mall, Schaumburg

Price: see link

Castle

Mon, Nov 16 · 10 AM–5 PM · Chicago Children’s Museum, 700 E. Grand Ave., Chicago, IL

Price: see link

Homeschool Days at PEPPA PIG World of Play Chicago

Tue, Nov 17 · 10 AM–5 PM · Peppa Pig World of Play Chicago, 5 Woodfield Mall, Schaumburg

Price: see link

Castle

Tue, Nov 17 · 10 AM–5 PM · Chicago Children’s Museum, 700 E. Grand Ave., Chicago, IL

Price: see link

Skilla Baby – Chicago, IL – The Price of Fame Tour

Tue, Nov 17 · 8 PM–11 PM · House of Blues

Detroit rap heavyweight Skilla Baby is bringing his headlining “The Price of Fame Tour” to the House of Blues in Chicago.

Price: see link

Homeschool Days at PEPPA PIG World of Play Chicago

Wed, Nov 18 · 10 AM–5 PM · Peppa Pig World of Play Chicago, 5 Woodfield Mall, Schaumburg

Price: see link

Castle

Wed, Nov 18 · 10 AM–5 PM · Chicago Children’s Museum, 700 E. Grand Ave., Chicago, IL

Price: see link

Homeschool Days at PEPPA PIG World of Play Chicago

Thu, Nov 19 · 10 AM–5 PM · Peppa Pig World of Play Chicago, 5 Woodfield Mall, Schaumburg

Price: see link

Castle

Thu, Nov 19 · 10 AM–5 PM · Chicago Children’s Museum, 700 E. Grand Ave., Chicago, IL

Price: see link

Homeschool Days at PEPPA PIG World of Play Chicago

Fri, Nov 20 · 10 AM–5 PM · Peppa Pig World of Play Chicago, 5 Woodfield Mall, Schaumburg

Price: see link

Castle

Fri, Nov 20 · 10 AM–5 PM · Chicago Children’s Museum, 700 E. Grand Ave., Chicago, IL

Price: see link