Explore the Windy City with this Spoonful of Sugar ready-to-go itinerary — perfect for a 7-day Chicago adventure that lets you truly settle in. This week-long guide combines all the iconic highlights with plenty of off-the-beaten-path moments, leisurely neighborhood explorations, and even a bonus day trip outside the city.
✨Great if you have more time and want the full Chicago immersion experience — from famous sights to charming detours — without overstuffing the schedule!
Auntie’s Spoonful of Sugar itineraries are designed for travelers who love structure with a side of spontaneity. You can expect thoughtful, low-stress planning in one beautiful PDF download — no customization required.
What you’ll get:
7-Day Chicago Itinerary PDF with curated daily plans, meal ideas, and transit tips
Auntie’s original Ways to Wander walking route to explore Chicago on foot
Choose Your Aunt-venture Guide with a list of what to book and decisions to make
Auntie’s Tips & Tricks for Traveling in Chicago to help you feel confident before you go
Perfect for first-timers, solo wanderers, couples, or anyone dreaming of Chicago with ease and style.
Explore the Windy City with this Spoonful of Sugar ready-to-go itinerary — perfect for a 7-day Chicago adventure that lets you truly settle in. This week-long guide combines all the iconic highlights with plenty of off-the-beaten-path moments, leisurely neighborhood explorations, and even a bonus day trip outside the city.
✨Great if you have more time and want the full Chicago immersion experience — from famous sights to charming detours — without overstuffing the schedule!
Auntie’s Spoonful of Sugar itineraries are designed for travelers who love structure with a side of spontaneity. You can expect thoughtful, low-stress planning in one beautiful PDF download — no customization required.
What you’ll get:
7-Day Chicago Itinerary PDF with curated daily plans, meal ideas, and transit tips
Auntie’s original Ways to Wander walking route to explore Chicago on foot
Choose Your Aunt-venture Guide with a list of what to book and decisions to make
Auntie’s Tips & Tricks for Traveling in Chicago to help you feel confident before you go
Perfect for first-timers, solo wanderers, couples, or anyone dreaming of Chicago with ease and style.
