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Open the guide and bookmark your favorite finds right away
Start sketching out your trip with the included itineraries
Book your tickets and tag me on instagram so I can celebrate you!
Because that’s where the city really comes alive — in the corner cafés where the barista remembers your order, in the quiet parks tucked between brownstones, in the late-night spots that only locals know to seek out.
That’s the Chicago I built this guide around: not the polished highlight reel, but the lived-in version that lingers in your memory long after you’ve left.
Planning a weekend trip shouldn’t feel like juggling a dozen tabs and scraps of paper. This free template makes it simple to map out your days, organize meals and activities, and keep track of the little details that make a trip feel smooth instead of stressful.
Whether you’re heading to Chicago or anywhere else, it’s designed to help you spend less time planning and more time actually enjoying your weekend away.