Plan your perfect Chicago weekend
Pick your vibe and we’ll build a ready-to-go itinerary from this weekend’s real events and our favourite local spots — then share it or email it to whoever you’re going with.
Popular Chicago weekend plans
Ready-made itineraries to steal — or tweak with your own vibe above.
A Foodie Weekend in Chicago: Where to Eat & Drink
For people who plan trips around meals — a delicious Chicago weekend of markets, restaurants, and bars.
★ Editor’s pickA Free Weekend in Chicago: Best Things to Do for $0
You don’t need to spend a cent — the best free things to do in Chicago this weekend.
★ Editor’s pickDate Night in Chicago: The Perfect Weekend Plan
A romantic Chicago weekend itinerary — great food, a little culture, and somewhere to linger after dark.
★ Editor’s pickFirst Time in Chicago? The Perfect Weekend Itinerary
New to Chicago? Hit the icons, the culture, and the local flavour in one well-paced weekend.
★ Editor’s pickThe Best Outdoor Weekend in Chicago
Fresh air, green space, and waterfront views — an outdoorsy Chicago weekend plan.
★ Editor’s pickThings to Do in Chicago With Kids This Weekend
A family-friendly Chicago weekend — parks, hands-on fun, and easy stops that work with little ones.