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Up the Auntie with this personally prepared 3-day Chicago itinerary — personalized to match your group’s interests! Perfect for a quick escape, this plan makes the most of your short stay in the Windy City with curated daily highlights, personalized accommodation picks, and Auntie’s signature walking routes. Once Auntie has everything she needs, she'll get to work and send everything your way! (Typical turnaround time is 5-7 business days after you provide your details.)
✨Great for travelers with limited time who want a custom feel without overcomplicating a short trip!
Up the Auntie itineraries include:
Detailed, partially customized 3-day Chicago itinerary with Auntie’s curated suggestions for transit, meals, and activities for each day based on the needs and interest of your group plus all your transport and accommodation details neatly organized for you
Auntie’s original Ways to Wander walking route to explore Chicago on foot
Three personalized accommodation recommendations based on your travel needs, group size, budget, and priorities
Choose Your Aunt-Venture Checklist of what to book with links to make booking super easy
Auntie’s Tips & Tricks for Traveling in Chicago to help you feel confident before you go
Auntie’s custom packing list including recommended gear
Custom trip name
The perfect balance of personalization and ease — a trip that feels genuinely yours, without the full custom price tag.
Up the Auntie with this personally prepared 3-day Chicago itinerary — personalized to match your group’s interests! Perfect for a quick escape, this plan makes the most of your short stay in the Windy City with curated daily highlights, personalized accommodation picks, and Auntie’s signature walking routes. Once Auntie has everything she needs, she'll get to work and send everything your way! (Typical turnaround time is 5-7 business days after you provide your details.)
✨Great for travelers with limited time who want a custom feel without overcomplicating a short trip!
Up the Auntie itineraries include:
Detailed, partially customized 3-day Chicago itinerary with Auntie’s curated suggestions for transit, meals, and activities for each day based on the needs and interest of your group plus all your transport and accommodation details neatly organized for you
Auntie’s original Ways to Wander walking route to explore Chicago on foot
Three personalized accommodation recommendations based on your travel needs, group size, budget, and priorities
Choose Your Aunt-Venture Checklist of what to book with links to make booking super easy
Auntie’s Tips & Tricks for Traveling in Chicago to help you feel confident before you go
Auntie’s custom packing list including recommended gear
Custom trip name
The perfect balance of personalization and ease — a trip that feels genuinely yours, without the full custom price tag.
