Chicago Weekend Activities & Things to Do
Weekend in Chicago
This itinerary focuses on a mix of free parks and cultural experiences with engaging ticketed attractions. Families should plan for walking or using public transportation to save on parking costs, which can be expensive in downtown Chicago. Many attractions are stroller-friendly, but check specific venue notes.
Friday Evening - Family Fun
Friday, March 6Play Garden Fun
Enjoy the expansive and imaginative Play Garden at Maggie Daley Park, featuring climbing structures, slides, and unique play areas designed for children of various ages.
The park is a state-of-the-art collection of architecture, landscape design and art.
Ideal for children aged 3-12. Facilities include restrooms and open space for active play. The Play Garden is open until 9:00 PM.
Easily accessible by public transit (CTA Brown, Orange, Green, Pink, Purple lines to Randolph/Wabash, or numerous bus routes). Parking garages are available nearby but can be expensive. Stroller-friendly paths.
Dinner at Portillo's
Dine at the iconic Portillo's, famous for its Chicago-style hot dogs, Italian beef sandwiches, and chocolate cake shakes. It's a casual and kid-friendly spot with a lively atmosphere.
Great for all ages. Offers a variety of options that appeal to children and adults. Quick service.
Accessible via public transit depending on location. Street parking might be available, but garages are often nearby.
Saturday - Adventure Day
Saturday, March 7Children's Museum Play
Participate in the Chicago Children's Museum's 'Play For All' event.
This initiative invites children and families of all abilities to experience inclusive, multisensory exhibits and programs. The museum offers three floors of hands-on learning, with exhibits like the Tinkering Lab, Kids Town, and Zoom Room. Free for the first 250 registrants, with the museum opening exclusively for these guests before general admission.
Geared towards children aged 1-10 years, with specific areas for toddlers and older kids (main play structure perfect for 3-8 years). Stroller and wheelchair accessible. Food and drink (other than water/coffee) not permitted inside, but snack spots available.
Located at Navy Pier. Public transit (bus routes 29, 65, 66, 124) or taxi/rideshare recommended. Parking at Navy Pier can be expensive.
Navy Pier Lunch
Grab a budget-friendly lunch at one of the many dining options available at Navy Pier, such as McDonald's, Big Bowl Chinese Express, or Lalo's Mexican, offering a variety of choices for families.
Suitable for all ages. Numerous options to satisfy different tastes. Seating available.
Conveniently located within Navy Pier after your Children's Museum visit.
Global Connections Festival
Immerse your family in diverse cultures at Navy Pier's 'Global Connections' series, offering vibrant performances, immersive art, and family-friendly festivities.
This free event celebrates various cultures and is part of a series running through May 2026.
Engaging for all ages with a focus on cultural education and entertainment. Activities designed to be family-friendly.
Located within Navy Pier, easily walkable from the Children's Museum and food court.
Millennium Park Sights
Explore the iconic sights of Millennium Park, including the famous 'Cloud Gate' sculpture (The Bean) for fun reflections and photos, and the interactive Crown Fountain, which displays videos of Chicago residents' faces.
The park provides a lively gathering spot in the heart of the city.
Great for all ages. Open space for kids to run around. The Crown Fountain can be particularly engaging for children. Park hours are 6:00 AM - 9:00 PM.
Walkable from Navy Pier (approx. 15-20 minutes). Accessible by various CTA bus routes and 'L' train lines. Limited street parking, expensive garages. Stroller-friendly.
Sunday - Relaxed Day
Sunday, March 8Lincoln Park Zoo Visit
Spend the morning at the Lincoln Park Zoo, a free-admission zoo open 365 days a year.
Meet and learn about various animals, including bears, penguins, and lions. Explore exhibits like the Farm-in-the-Zoo.
Excellent for all ages, especially children aged 3-12. Buildings and Farm-in-the-Zoo are open from 10:00 AM to 4:30 PM in March. Strollers and wheelchairs are available for rent. Quiet rooms are also available.
Public transportation is highly recommended (CTA buses 22, 36, 151, 156 stop along the zoo's western edge; Brown/Purple Line to Armitage or Red Line to Fullerton, then a mile walk). Zoo parking is expensive ($35-45/day) but is free for the first half hour.
Skate Ribbon Fun
Experience the unique Ice Skating Ribbon at Maggie Daley Park, winding through a scenic landscape.
March 8, 2026, is the last day it's open for the season.
Suitable for children aged 3 and up who can skate. Sessions are 2 hours. Skate aids (plastic penguins/snowmen) are available for $11, first-come, first-served. Reservations are recommended.
Easily accessible by public transit (CTA Brown, Orange, Green, Pink, Purple lines to Randolph/Wabash, or numerous bus routes). Parking garages are nearby but expensive. Stroller-friendly for non-skaters.
Casual Family Dinner
Enjoy a casual, budget-friendly early dinner at a family-favorite spot.
Consider a classic Chicago deep-dish pizza at a place like Pequod's Pizza, which offers a personal pan lunch deal that could work for an early dinner, or explore affordable Middle Eastern fare at Sultan's Market.
Both options are generally family-friendly. Pequod's is known for its caramelized crust deep dish. Sultan's offers quick and affordable falafel and shawarma.
Accessibility depends on the chosen location. Public transit and street parking are typically available in neighborhood areas.
This weekend itinerary for Chicago can be customized using our AI travel planner. Chat with our AI assistant to modify activities, adjust timings, add personal preferences, and get recommendations for restaurants, hotels, and transportation.