Chicago Weekend Itinerary Guide

Are you ready to see the best of CHICAGO?

Get this curated guide to create an amazing getaway full of the Windy City’s iconic sights, architecture, and art along with delicious food (especially Italian!), fun cocktail joints, and beautiful views. Only a travel expert like me, who has explored Chicago numerous times, can give you a well-rounded itinerary like this with classic stops and off-the-beaten-track secrets that are what vacation memories are made of.

This digital guide is a super-fun travel plan designed to MAKE THE MOST OF YOUR VACATION DAYS…by someone who gets paid by top magazines to travel and tell others about the best stuff to do and see. It’s everything I wrote about in my One Day in Chicago post, plus so much more!

YOUR ENTIRE TRIP IS MAPPED OUT. THE GUIDE INCLUDES:

• 4 daily itineraries of what to do and see (with the flexibility to skip and add things as you like)
• Daytime activities all ages can enjoy together
• Evening activities for adults including a rooftop bar, speakeasy, and comedy club
• Fantastic low-to-moderately priced restaurants and eateries
• A curated list of great accommodations

SNEAK PEEK @ THE ITINERARY

LIFE JUST GOT EASIER

• No more endless hours sifting through tons of blogs and websites to piece together your trip.
• No more feeling completely overwhelmed by the options and afraid of choosing the wrong route, stop or activity.
• No more missing out on the best experiences (hello: cruising the river, sipping bottomless Aperol spritzes,  and learning fascinating city history for free!).
• No more coming back completely exhausted (you’ll know how much you can actually do in one day).
• No more tourist traps (see hidden gems most tourists miss and avoid cheesy, overpriced attractions).