Chicago Trip Planning Meeting

This is a planning meeting for those interested in joining us for a fun laid-back Chicago trip together. The trip is October 2nd through October 5th, 2025 but for those that prefer spending more or less time there, you can adjust your dates however you’d like. This meeting is a good way for those who are interested to contribute to the planning or just meet others who are going. We have some details already in mind and a group block set up for the hotel. The hotel is the Fairfield Inn & Suites Downtown/River North. The hotel is $700.88 total per room for the three nights (taxes and breakfast included). Book by September 9th as this is the cutoff date for the discounted rate. That rate will be honored if you want to arrive earlier or leave later too. Additionally, everyone who confirms their reservation between now and September 3rd (except Patrick and Melissa), will be entered into a drawing for a complimentary room upgrade to a suite! Here is the booking link Fairfield reservation link.

This trip is going to have a lot of flexibility rather than being a chaperoned-style trip, while still incorporating a few options for group activities. You are responsible for reserving your own room and booking your own transportation to/from Chicago. We can do a group dinner each evening starting Thursday and at least a couple other group activities depending on what people want to do (possibilities include an architecture river cruise, guided tour of the Art Institute of Chicago, Chicago Theatre Tour, Second City, etc).

Here’s a general itinerary idea to get us started (subject to change based on the group’s interests):
-10/02/25 (Thurs) 7:00pm: Gather for a group dinner
-10/03/25 1:00pm: Guided tour of The Art Institute of Chicago. 5:00pm: Group dinner in Old Town. 7:00pm or 8:00pm:
Second City Comedy Show
-10/04/25 4:00pm or 5:30 (sunset):
Architecture River Cruise. 7:30pm:
Group dinner. 9pm: Blues or Jazz club
-10/05/25 12:00: group lunch (deep dish)

You are still welcome to join for the trip if you can’t make it to this meeting. Check out the event post for the trip for more details and follow the comments to keep updated on ideas. Feel free to submit ideas for consideration. We will list the meeting location once we have an idea how many are attending.