Weekend in Chicago
This weekend itinerary offers Chicago families a smart mix of free outdoor festivities and exciting indoor attractions. We've balanced engaging community events with worthwhile paid experiences, keeping budget in mind while ensuring memorable adventures for children aged 3-12. Expect fall fun, creative play, and delicious, family-friendly food options throughout the city.
Friday Evening - Fall Festival Fun
Friday, October 3Lincoln Park Fall Fest
Kick off the weekend at the free and family-friendly Fall Fest at Lincoln Park Zoo.
Stroll through seasonally decorated gardens, enjoy free musical entertainment, watch professional pumpkin carvers, and visit the pumpkin patch. There are also fall-themed animal enrichment activities. Ticketed attractions like rides are available if you choose.
Perfect for energetic kids, with plenty of space to run around. Enjoy the festive atmosphere. Bathrooms are readily available throughout the zoo. Stroller-friendly paths make it easy for younger children. Plan for approximately 1.5-2 hours. Kids will love seeing the animals and the fall decorations.
Accessible via public transit (CTA buses drop near the zoo entrance). Limited paid street parking and zoo parking garage available, which can be busy on weekends. Consider ridesharing or public transport to avoid parking hassle.
Highwood Pumpkin Fest
Head north to the Great Highwood Pumpkin Festival, a vibrant, family-friendly event featuring live music, a variety of food and artisan vendors, and a carnival.
Kids can enjoy a children's costume contest, pumpkin pie eating contests, and trick-or-treating at various locations. This evening visit provides a lively atmosphere for an early dinner.
This festival offers a bustling, energetic evening for families. Kids will be thrilled by the carnival rides (additional cost), the chance to see costumes, and possibly even participate in trick-or-treating or a pie-eating contest. Food trucks and vendors will offer numerous kid-friendly dinner options. Bathrooms are available. Plan for 2-3 hours.
Highwood is a suburb north of Chicago. Driving is recommended for ease with children; parking will be available but may be busy around the festival area. Metra train (Union Pacific North Line) to Highwood station is an option, then a short walk.
Saturday - Navy Pier Adventure Day
Saturday, October 4Children's Museum Play For All
Experience 'Play For All' at the Chicago Children's Museum, an inclusive event welcoming families of all abilities.
The museum opens an exclusive hour early at 10 AM for registrants, before opening to the general public at 11 AM. Explore three floors of interactive exhibits, including a dinosaur expedition, a three-story schooner, and the Cardboard Lab.
This is a fantastic free opportunity for kids aged 0-10, with many exhibits perfect for the 3-12 age range. The Cardboard Lab is great for creative tinkering (ages 2+). Bathrooms are available on all floors, and the museum is very stroller-friendly. Arrive early as it's free for the first 250 registrants. Plan for 2-3 hours of engaging play.
Navy Pier is well-served by CTA buses. Parking is available in the Navy Pier garages, but it can be expensive. Consider public transportation or ridesharing to save on parking costs.
Navy Pier Spooky Saturday & Lunch
After enjoying the Children's Museum, immerse yourselves in Navy Pier's 'Slightly Spooky Saturday.
' This free event runs from 12 PM to 6 PM and features trick-or-treating throughout the Pier, complimentary workshops, live performances, and giveaways. Enjoy lunch from one of the many family-friendly food vendors or restaurants at Navy Pier.
A perfect follow-up to the museum visit. Kids will love dressing up in costumes (encouraged!) and collecting treats. The workshops and performances add extra entertainment. There are numerous casual dining options at Navy Pier, offering kid-friendly meals. Bathrooms are plentiful. Plan for 2-3 hours for the event and lunch.
Stay at Navy Pier from the Children's Museum visit. Easily walkable with strollers. Consider a rest or snack break to pace yourselves through the event's duration.
Lincoln Park Zoo Stroll
Return to Lincoln Park Zoo for an afternoon stroll.
Enjoy the free animal exhibits and explore more of the beautiful park grounds. It's a relaxed way to enjoy the fall weather and observe wildlife, perfect for unwinding after the bustling Navy Pier.
Great for kids to burn off some energy while observing animals. The Wild Sapling Play Forest is an excellent free playground within the zoo for adventurous play. Bathrooms are easily accessible. Stroller-friendly paths. Plan for 1.5-2 hours.
From Navy Pier, you can take a rideshare or a CTA bus (e.g., 29 State, transfer to 151 Sheridan) to reach Lincoln Park. Parking is available at the zoo's garage or nearby street parking, but it can be challenging on a Saturday afternoon.
Pizza & Ice Cream Treat
Enjoy an early, casual dinner at a family-friendly pizza place in the Lincoln Park neighborhood, followed by a sweet treat like ice cream.
This allows for an early bedtime after a full day of adventures.
Chicago deep-dish pizza is a family favorite! Many pizzerias offer kids' menus or smaller portions. Finish with an ice cream cone for a perfect end to a fun-filled day. Good for all ages. Restrooms available.
Walkable from Lincoln Park Zoo to many neighborhood spots, or a short rideshare depending on your chosen restaurant. Street parking may be available but can be competitive.
Sunday - Creative & Relaxed Day
Sunday, October 5Wicker Park Farmers Market
Enjoy a relaxed Sunday morning browsing the vibrant Wicker Park Farmers Market.
Discover fresh seasonal produce, artisanal cheeses, baked goods, and prepared foods. The market often features live music, creating a pleasant atmosphere for families to explore and grab some affordable breakfast or brunch items.
A great way to start Sunday at a relaxed pace. Kids can enjoy the sights and sounds, and you can pick up some fresh, healthy snacks. There's often space for kids to move around. Stroller friendly. Plan for 1-1.5 hours.
Located right by the Damen CTA Blue Line station. Street parking is available but can be challenging on Sundays; consider public transit.
Pumpkin Painting Party
Unleash your family's creativity at the Peggy Notebaert Nature Museum's Pumpkin Painting Party.
Each family can paint a pumpkin to take home, making for a memorable fall souvenir. After the activity, explore the museum's exhibits focusing on local nature and environmental science, including the popular Judy Istock Butterfly Haven.
This hands-on activity is perfect for children aged 3-12, fostering creativity and providing a fun seasonal craft. The museum also offers engaging exhibits for curious young minds. Restrooms are available. Plan for 2-2.5 hours, including time for painting and exploring the museum.
Accessible via CTA buses (e.g., 151 Sheridan). Limited paid parking available in the nearby area. Can be combined with a walk in Lincoln Park.
Park Play & Treat
Wind down the weekend with some active play at a nearby park or playground in Lincoln Park, allowing kids to get their last wiggles out.
Afterward, grab a simple, affordable treat like hot chocolate or a cookie to enjoy together before heading home and preparing for the week ahead.
Oz Park, with its Wizard of Oz-themed statues and playground, is a unique and engaging spot for kids. It's a great, free way to end the weekend on a relaxed note. Restrooms are available near the playground. Perfect for all ages. Plan for 1-1.5 hours.
Easily walkable from the Peggy Notebaert Nature Museum. Street parking is available but can be competitive.
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