Adventures in Chicago Group Trip!

Let’s head to Chicago for our first Adventures in Culture and Travel trip! After the planning meeting, we have several details worked out. The group trip will be from Thursday October 2nd through Sunday October 5th, 2025. But for those that prefer spending more or less time there, that’s fine too and you can adjust your dates however you’d like. This is going to be a laid-back style of trip with a lot of flexibility rather than a chaperoned trip where everything is planned out all day every day. The idea is to make this like a fun friends’ trip with a lot of flexibility while also having options for group activities and meals. We’ll plan a group dinner each evening starting Thursday and at least a couple other group activities throughout the trip 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). People will be able to opt in or out of any of the planned activities. Once we have numbers and ideas from the group as to what you want to do, we can start arranging group tours and activities.

Estimated Costs:
-Transportation: Flights currently looking to be between $177-$255 depending on your airline preference and time of day. Amtrak looks to be about $140 round trip. Carpooling is also an option (just note daily parking will be at least $40-50/day in downtown Chicago). My flight is the American Airlines flight leaving Omaha on the 2nd at 9:28am and departing Chicago on the 6th at 7:08am. If you want to be on the same one. I think Patrick is flying in Thursday evening. We can coordinate Ubers or Lyfts to get from the airport to the hotel.

-Hotel: We have some exciting news! We've secured a fantastic rate for everyone at just $199 per night (plus tax). For a 3-night stay, the total will come to approximately $700.88.
Additionally, between now and September 3rd, everyone (except Melissa and myself) who confirms their reservation will be entered into a drawing for a complimentary room upgrade to a suite!
To help us finalize our plans, we ask that everyone reserve their rooms by September 9th. This is also the cutoff date for the discounted rate. Reserving by this date will allow us to confirm the number of attendees for the trip.
Here is the booking link https://book.passkey.com/go/ACTOct02

Again, this is a flexible trip though so you are welcome to choose a hotel independently too if you don’t like the option selected. Then we’d just announce meeting points and times for any planned group activities.
-Chicago CityPass: (currently around $150). The City Pass covers entry to 5 select sites (such as The Art Institute, Field Museum, Hancock Tower, Willis Tower, etc.). Chicago CityPass
-Getting around Chicago: Chicago is a very walkable city so we can get around easily on foot. But we’ll also be using the El (their elevated metro system), and uber/lyft, within Chicago when needed.
-The other primary costs would be food, drink, shopping, tickets beyond what’s included with the City Pass, trip insurance if you want it, and any other activities you want to do (like shows or tours).

The estimated costs should be approximately $1,600-$1,900 depending on how much you opt in or out of and your dining preferences. These costs are each person’s own responsibility. We’ll direct you where to go to make your reservations but the plan is for you to book and pay your own way for the transportation, the hotels, City Pass (if you choose that option), and whatever activities you opt in for. We’re not collecting any money from you or any payment for the trip, rather we’re just in it got a fun trip with you all. The only reason we would is if there’s anything group activity-wise that needs to be pre-paid up front as a group (like group tickets), then we will address that when/if needed.

Feel free to use the discussion board for this post to coordinate with others if you want to carpool or to update arrival times and what activities you prefer. We’ll meet again in a few weeks to discuss more.

I personally love Chicago and am really looking forward to this!