Chicago Weekends: Parks, food and day trips
Curious about what you'll do when you live in Chicago? If you like the idea of hopping along the Riverwalk, seeing shows in converted warehouses, and are daring enough to try kayaking under skyscraper canyons, Chicago is calling you home! This list of fun things to do will take you from beach sunrises to rooftop sunsets and give you a vivid sampling of Chicago's culinary scene and cultural depth.



Anna, Our Local Expert Guiding Your Move
Anna landed in Chicago after a string of moves that included San Diego (goodbye sunshine and beach days), London, Santiago, and a ship at sea. She lives in the Loop for strategic reasons, not just the vibes. She quickly discovered that Midwest nice is a real thing and is adapting. She's even given up being a vegetarian... the constant temptation of Chicago dogs was just too strong. And pepperoni on the tavern style pizza (no, not the deep-dish kind) is a game changer. At Snappy Scout, Anna brings local insight, travel perspective, and a very real understanding of why Illinois surprises people who think they already know it.
Read moreWritten with local insight from Snappy Scout relocation experts
What Will You Do in Chicago?
From weekend adventures to iconic road trips, here's how locals spend their time off.
My Favorite Local Spot in Chicago
La Scarola, an Italian restaurant, bordering West Loop and West Town is one place you cannot skip!


— Anna Shoultz
Illinois Local Expert


Ready to See If Chicago Fits You?
Compare cities, check the routes, or head back to the full Chicago guide for the bigger picture.