Our Story

Hi, I’m James! On the album page that’s me, lounging on a bed of candy-colored autumn leaves. Chicago Weekend Explorers is my labor of love. I started out arranging group trips for friends and guests from around the globe, showing them my beloved hometown, and over time things grew and grew. Eventually I began to pour so much of myself into scouting out new and fun things to get up to, I came up with Chicago Weekend Explorers: a tour company dedicated to maximizing the precious few weekend hours we all cherish so much. I feel blessed to be from such a fantastic city and I hope to share it with you!

Chicagoland and beyond!

Everyone at Chicago Weekend Explorers is constantly on the hunt for fun things going on in Chicago, and once we find them, we love sharing them with you. We started out focusing purely on the Chicago area, but we have since grown to include a few hiking and camping tours in Colorado and Arizona, and we are prepping our first foray into Mexico for The Day of the Dead and other fun festivals and events! We make a supreme effort to get into the sublime details of it all; we assume you can find the standard issue Chicago tourist haunts without our help. Check our constantly updated roster of tours and excursions to see what our latest inspiration is!

Chicagoland and all it offers

We design our tours to go beyond the typical, and to bring you the best Chicago (and occasionally further afield) has to offer! Local architectural gems beyond Frank Lloyd Wright; caves, waterfalls, and exquisite hikes within striking distance; and a rich understanding of  Chicago’s history – we try to cover a lot of ground. Check our constantly updated roster of tours and excursions to see what the latest inspiration is, and be prepared for a fantastic experience!